730:
aqueous solution of a β-lactam antibiotic can denote β-lactamase hydrolysis of amide bonds in the β-lactam ring. This is often observed with a chromogenic β-lactamase substrate like ceftriaxone, merapenem, or nitrocefin, that undergoes a distinctive color change from yellow to red as the amide bond in the β-lactam ring is hydrolyzed by β-lactamase. This color change is a visual indicator of the presence and activity of β-lactamase enzymes, which are responsible for conferring resistance to β-lactam antibiotics in many bacterial species. The hydrolysis of the β-lactam ring by β-lactamase enzymes renders the antibiotic ineffective, thereby allowing the bacteria to survive in the presence of the antibiotic. Some β-lactam antibiotics like ceftriaxone and meropenem are known to be relatively unstable in solution, especially when stored for extended periods, and degrade in an aqueous solution even without the presence of β-lactamase. For ceftriaxone, the color of solutions can range from light yellow to amber, depending on the length of storage, concentration, and diluent used. A study found that meropenem concentrations dropped to 90% of the initial concentration at 7.4 hours at 22°C and 5.7 hours at 33°C, indicating degradation over time.
772:
1006:
411:
51:
389:
402:
669:
679:
946:
until the β-carbon of β-lactam is reached, at which point numbering continues counterclockwise around the lactam ring to number the remaining to carbons. For example, the nitrogen atom of all bicyclic β-lactams fused to five-membered rings is labelled position 4, as it is in penams, while in cephems, the nitrogen is position 5.
721:
harbor some level of β-lactamase expression. In this case, failure to use the most appropriate β-lactam antibiotic therapy at the onset of treatment could result in selection for bacteria with higher levels of β-lactamase expression, thereby making further efforts with other β-lactam antibiotics more difficult.
716:
such as boronic acids are being studied in which they irreversibly bind to the active site of β-lactamases. This is a benefit over clavulanic acid and similar β-lactam competitors, because they cannot be hydrolysed, and therefore rendered useless. Extensive research is currently being done to develop
1009:
This figure outlines the different methods of β-lactam closure among the various classes of β-lactam compounds. Penams and cephems are cyclized oxidatively (first row); clavams and carbapenems are closed by ATP-utilizing amidation (second and third row); and some monobactams may be closed by a third
724:
In the context of medical pharmacology, penicillins, cephalosporins, and carbapenems, while all have the β-lactam ring that serves as the fundamental structure, also have an auxiliary ring that carries a carboxylate group that is positioned on the same side as the carbonyl group within the β-lactam
729:
of the β-lactam ring, thereby eliminating the antimicrobial activity of these antibiotics. This resistance mechanism underscores the importance of the structural integrity of the β-lactam ring for the antibiotic's function. The color change from colorless or light yellow to amber or even red in an
1021:
While the ring closure in penams and cephems is between positions 1 and 4 of the β-lactam and is oxidative, the clavams and carbapenems have their rings closed between positions 1 and 2 of the ring. β-lactam synthetases are responsible for these cyclizations, and the carboxylate of the open-ring
945:
By convention, the bicyclic β-lactams are numbered starting with the position occupied by sulfur in the penams and cephems, regardless of which atom it is in a given class. That is, position 1 is always adjacent to the β-carbon of β-lactam ring. The numbering continues clockwise from position one
708:
so that the amoxicillin is not affected by the β-lactamase enzymes. Another β-lactam/β-lactamase inhibitor combination is piperacillin/tazobactam with a broad spectrum of antibacterial activity that includes gram-positive and -negative aerobic and anaerobic bacteria. The addition of tazobactam to
720:
However, in all cases where infection with β-lactamase-producing bacteria is suspected, the choice of a suitable β-lactam antibiotic should be carefully considered prior to treatment. In particular, choosing appropriate β-lactam antibiotic therapy is of utmost importance against organisms which
539:. Inhibition of cross-linkage by β-lactams causes a build-up of peptidoglycan precursors, which triggers the digestion of existing peptidoglycan by autolytic hydrolases without the production of new peptidoglycan. As a result, the bactericidal action of β-lactam antibiotics is further enhanced.
738:
As a response to the use of β-lactams to control bacterial infections, some bacteria have evolved penicillin binding proteins with novel structures. β-Lactam antibiotics cannot bind as effectively to these altered PBPs, and, as a result, the β-lactams are less effective at disrupting cell wall
419:
In the absence of β-lactam antibiotics (left), the cell wall plays an important role in bacterial reproduction. Bacteria attempting to grow and divide in the presence of β-lactam antibiotics (right) fail to do so, and instead shed their cell walls, forming osmotically fragile
492:
residue of the PBP active site. This irreversible inhibition of the PBPs prevents the final crosslinking (transpeptidation) of the nascent peptidoglycan layer, disrupting cell wall synthesis. β-Lactam antibiotics block not only the division of bacteria, including
196:
biosynthesis in the bacterial organism and are the most widely used group of antibiotics. Until 2003, when measured by sales, more than half of all commercially available antibiotics in use were β-lactam compounds. The first β-lactam antibiotic discovered,
617:
By definition, all β-lactam antibiotics have a β-lactam ring in their structure. The effectiveness of these antibiotics relies on their ability to reach the PBP intact and their ability to bind to the PBP. Hence, there are two main modes of
1029:
The biosynthesis of the β-lactam ring of tabtoxin mirrors that of the clavams and carbapenems. The closure of the lactam ring in the other monobactams, such as sulfazecin and the nocardicins, may involve a third mechanism involving
725:
ring, and, as such, this structural configuration is critical to their antimicrobial activity. Bacterial resistance to these antibiotics primarily occurs through the production of β-lactamases, enzymes that hydrolyze the
348:
will occur in approximately 0.01% of patients. There is perhaps a 5–10% cross-sensitivity between penicillin-derivatives, cephalosporins, and carbapenems; but this figure has been challenged by various investigators.
961:
To date, two distinct methods of biosynthesizing the β-lactam core of this family of antibiotics have been discovered. The first pathway discovered was that of the penams and cephems. This path begins with a
688:
The production of a β-lactamase by a bacterium does not necessarily rule out all treatment options with β-lactam antibiotics. In some instances, β-lactam antibiotics may be co-administered with a
1457:
Pichichero ME (April 2005). "A review of evidence supporting the
American Academy of Pediatrics recommendation for prescribing cephalosporin antibiotics for penicillin-allergic patients".
1841:
Nangia A, Biradha K, Desiraju GR (1996). "Correlation of biological activity in β-lactam antibiotics with
Woodward and Cohen structural parameters—a Cambridge database study".
352:
Nevertheless, the risk of cross-reactivity is sufficient to warrant the contraindication of all β-lactam antibiotics in patients with a history of severe allergic reactions (
535:
Under normal circumstances, peptidoglycan precursors signal a reorganisation of the bacterial cell wall and, as a consequence, trigger the activation of autolytic cell wall
360:) to any β-lactam antibiotic. Rarely, allergic reactions have been triggered by exposure from kissing and sexual contact with a partner who is taking these antibiotics.
2808:
581:) of the pyramid formed by the nitrogen atom of the β-lactam as the apex and the three adjacent carbon atoms as the base. The second is called "Cohen's parameter",
332:
Immunologically mediated adverse reactions to any β-lactam antibiotic may occur in up to 10% of patients receiving that agent (a small fraction of which are truly
1018:
to the cephem core. As with the penams, the variety of cephalosporins and cephamycins come from different transamidations, as is the case for the penicillins.
2655:"The mechanism for isopenicillin N synthase from density-functional modeling highlights the similarities with other enzymes in the 2-His-1-carboxylate family"
3822:
86:
392:
Penicillin and most other β-lactam antibiotics act by inhibiting penicillin-binding proteins, which normally catalyze cross-linking of bacterial cell walls.
2545:
450:
organisms, being the outermost and primary component of the wall. The final transpeptidation step in the synthesis of the peptidoglycan is facilitated by
2285:
1152:(Report). U.S. Department of Health and Human Services; Food and Drug Administration; Center for Drug Evaluation and Research (CDER). April 2013.
573:
Two structural features of β-lactam antibiotics have been correlated with their antibiotic potency. The first is known as "Woodward's parameter",
476:
residues on the precursor NAM/NAG-peptide subunits of the nascent peptidoglycan layer. The structural similarity between β-lactam antibiotics and
2801:
1700:
Fisher JF, Meroueh SO, Mobashery S (2005). "Bacterial resistance to β-lactam antibiotics: compelling opportunism, compelling opportunity".
2682:
1068:
748:
461:(PBPs). PBPs vary in their affinity for penicillin and other β-lactam antibiotics. The number of PBPs varies between bacterial species.
2506:
2390:
2310:
2969:
1572:
Miyachiro MM, Contreras-Martel C, Dessen A (2019). "Penicillin-Binding
Proteins (PBPS) and Bacterial Cell Wall Elongation Complexes".
242:
and treatment of bacterial infections caused by susceptible organisms. At first, β-lactam antibiotics were mainly active only against
2794:
1380:"Penetration of drugs through the blood-cerebrospinal fluid/blood-brain barrier for treatment of central nervous system infections"
709:
piperacillin has enhanced its stability against a wide range of β-lactamase enzymes including some
Extended-Spectrum β-lactamases.
2368:
2229:"Characterization of Interactions between CTX-M-15 and Clavulanic Acid, Desfuroylceftiofur, Ceftiofur, Ampicillin, and Nitrocefin"
2763:
Townsend CA, Brown AM, Nguyen LT (1983). "Nocardicin A: stereochemical and biomimetic studies of monocyclic β-lactam formation".
266:
2909:
2898:
547:
Another possibility that has been proposed to account for much of the cytotoxicity of β-lactams focuses on the oxidation of the
1026:. In clavams, the β-lactam is formed prior to the second ring; in carbapenems, the β-lactam ring is closed second in sequence.
17:
4047:
2345:
2131:"Beyond susceptible and resistant Part I: treatment of infections due to Gram-negative organisms with inducible B-lactamases"
1589:
704:(a β-lactamase inhibitor). The clavulanic acid is designed to overwhelm all β-lactamase enzymes, and effectively serve as an
1356:
484:-alanine facilitates their binding to the active site of PBPs. The β-lactam nucleus of the molecule irreversibly binds to (
1015:
831:
2528:
1048:
2546:
https://web.archive.org/web/20240222172948/https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/0550585s063lbl.pdf
1547:
1099:
646:
1153:
1444:
4091:
4064:
1623:"Morphological and ultrastructural changes in bacterial cells as an indicator of antibacterial mechanism of action"
2786:
1923:
Cohen NC (February 1, 1983). ".beta.-Lactam antibiotics: geometrical requirements for antibacterial activities".
1053:
782:
364:
1043:
766:
222:, an enzyme that attacks the β-lactam ring. To overcome this resistance, β-lactam antibiotics can be given with
3966:
3852:
622:
to β-lactams: enzymatic hydrolysis of the β-lactam ring and possession of altered penicillin-binding proteins.
2278:
1678:
1436:
780:
779:
645:
the β-lactam ring of the antibiotic, rendering the antibiotic ineffective. (An example of such an enzyme is
321:
3018:
783:
776:
247:
2178:
Kim D, Kim S, Kwon Y, Kim Y, Park H, Kwak K, Lee H, Lee JH, Jang KM, Kim D, Lee SH, Kang LW (March 2023).
3877:
3797:
2924:
2858:
658:
458:
257:
In uninflamed (normal) brain meninges, the penetration of beta-lactam antibiotics is low, at 0.15 of AUC
556:
555:
could cause cytotoxicity. Bacterial cytotoxicity could arise from incomplete repair of closely spaced
103:
3802:
2929:
953:; the nitrogen atom is position 1, the carbonyl carbon is 2, the α-carbon is 3, and the β-carbon 4.
2825:
1735:
Kasten B, Reski R (January 1, 1997). "β-Lactam antibiotics inhibit chloroplast division in a moss (
995:
777:
753:
649:, discovered in 2009.) The genes encoding these enzymes may be inherently present on the bacterial
619:
551:
nucleotide in the bacterial nucleotide pool. The incorporation of oxidized guanine nucleotide into
314:
215:
115:
3731:
713:
689:
223:
4052:
3867:
3827:
2934:
2842:
1141:
Yao, JDC, Moellering, RC Jr. (2007). "Antibacterial agents". In Murray, PR, et al. (eds.).
3891:
3842:
3832:
3587:
3359:
2017:
1023:
781:
357:
251:
3620:
3452:
3271:
2654:
4096:
3872:
3857:
3837:
1073:
283:
239:
757:. Altered PBPs do not necessarily rule out all treatment options with β-lactam antibiotics.
3956:
3862:
3807:
2717:
2420:
1881:
1794:
1783:"Oxidation of the guanine nucleotide pool underlies cell death by bactericidal antibiotics"
1752:
1459:
1292:
963:
778:
525:
341:
8:
3847:
3817:
3666:
3628:
775:
705:
446:. The peptidoglycan layer is important for cell wall structural integrity, especially in
435:
2721:
2424:
1885:
1798:
1756:
1657:
1296:
2493:
2441:
2408:
2364:
2337:
2255:
2228:
2204:
2179:
2155:
2130:
2106:
2073:
2054:
1992:
1967:
1815:
1782:
1670:
1603:
1539:
1484:
1404:
1379:
1313:
1276:
1252:
1219:
1200:
203:
2595:
2558:
2469:"Stability of Meropenem After Reconstitution for Administration by Prolonged Infusion"
2326:"Laboratory Diagnosis of Infection Due to Bacteria, Fungi, Parasites, and Rickettsiae"
1764:
3382:
3088:
2863:
2745:
2740:
2705:
2674:
2635:
2600:
2498:
2446:
2432:
2384:
2341:
2325:
2304:
2260:
2209:
2160:
2111:
2093:
2046:
2038:
1997:
1948:
1940:
1905:
1897:
1854:
1820:
1717:
1662:
1607:
1595:
1585:
1531:
1523:
1476:
1440:
1409:
1348:
1318:
1257:
1192:
1150:
Non-Penicillin Beta Lactam Drugs: A CGMP Framework for
Preventing Cross-Contamination
1111:
991:
451:
98:
2586:
2058:
1543:
1488:
1243:
1204:
410:
50:
3970:
3121:
2919:
2816:
2772:
2735:
2725:
2666:
2627:
2590:
2582:
2488:
2480:
2436:
2428:
2333:
2250:
2240:
2199:
2191:
2150:
2142:
2101:
2085:
2030:
1987:
1979:
1932:
1889:
1846:
1810:
1802:
1760:
1709:
1674:
1652:
1642:
1634:
1577:
1515:
1468:
1399:
1391:
1308:
1300:
1247:
1239:
1184:
1031:
333:
568:
3758:
3202:
3029:
1519:
701:
672:
662:
593:. This distance is thought to correspond to the distance between the carboxylate-
302:
227:
121:
2833:
2829:
2195:
1874:
Philosophical
Transactions of the Royal Society of London B: Biological Sciences
1581:
1340:
4058:
2988:
2710:
Proceedings of the
National Academy of Sciences of the United States of America
1304:
999:
967:
634:
521:
498:
291:
219:
2631:
2146:
1638:
1281:
isolate (IMI 15378) reveals sequence divergence of penicillin synthesis genes"
1188:
4085:
3952:
3811:
3426:
3254:
3166:
3160:
3106:
3102:
3072:
3067:
3062:
3057:
3047:
2983:
2954:
2944:
2532:
2484:
2097:
2042:
2034:
2015:
Gin A, Dilay L, Karlowsky JA, Walkty A, Rubinstein E, Zhanel GG (June 2007).
1944:
1901:
1858:
1527:
1005:
638:
598:
494:
447:
439:
243:
169:
91:
60:
2730:
1806:
1119:
3721:
3638:
3481:
3339:
3324:
3130:
2959:
2678:
2639:
2502:
2468:
2450:
2264:
2213:
2164:
2115:
2050:
2001:
1893:
1824:
1721:
1666:
1599:
1535:
1503:
1480:
1472:
1413:
1352:
1322:
1261:
1196:
1149:
1115:
838:
594:
431:
2749:
2604:
1952:
1909:
1275:
Pathak A, Nowell RW, Wilson CG, Ryan MJ, Barraclough TG (September 2020).
1014:
The biosynthesis of cephems branch off at isopenicillin N by an oxidative
4033:
4011:
3980:
3974:
3900:
3780:
3770:
3656:
3648:
3633:
3547:
3517:
3512:
3507:
3502:
3497:
3476:
3465:
3437:
3431:
3387:
3349:
3329:
3314:
3262:
3140:
3097:
3038:
3004:
2979:
2949:
2939:
2817:
2245:
1983:
1850:
1781:
Foti JJ, Devadoss B, Winkler JA, Collins JJ, Walker GC (April 20, 2012).
1395:
918:
860:
849:
740:
697:
682:
586:
509:
505:
421:
368:
345:
295:
189:
3908:
Insert into bacterial cell wall causing perforation and depolarization:
2776:
1936:
1502:
Liccardi G, Caminati M, Senna G, Calzetta L, Rogliani P (October 2017).
717:
tailored boronic acids to target different isozymes of beta-lactamases.
388:
157:
64:
4021:
4016:
3984:
3960:
3931:
3909:
3775:
3748:
3698:
3679:
3610:
3600:
3562:
3552:
3542:
3527:
3522:
3470:
3441:
3407:
3397:
3377:
3334:
3304:
3299:
3289:
3258:
3184:
3156:
3135:
3111:
3052:
3043:
2884:
2018:"Piperacillin–tazobactam: a β-lactam/β-lactamase inhibitor combination"
1078:
971:
938:
891:
853:
726:
650:
642:
473:
310:
198:
185:
181:
173:
161:
153:
56:
41:
2670:
2089:
1713:
1647:
134:
4028:
3914:
3765:
3743:
3716:
3711:
3706:
3684:
3674:
3605:
3576:
3567:
3537:
3492:
3416:
3411:
3402:
3392:
3372:
3344:
3319:
3309:
3294:
3284:
3279:
3239:
3234:
3227:
3216:
3206:
3197:
3078:
2999:
2994:
2821:
1063:
929:
693:
536:
529:
513:
501:
485:
443:
353:
287:
193:
1175:
Elander RP (2003). "Industrial production of β-lactam antibiotics".
733:
4004:
3595:
3571:
3557:
3532:
3487:
3460:
3421:
3367:
3222:
3211:
1622:
1058:
914:
903:
876:
590:
578:
372:
306:
2467:
Fawaz S, Barton S, Whitney L, Swinden J, Nabhani-Gebara S (2019).
826:β-Lactams are classified according to their core ring structures.
668:
401:
925:
887:
654:
548:
517:
337:
3754:
3250:
2556:
2227:
Ahmadvand P, Avillan JJ, Lewis JA, Call DR, Kang C (May 2022).
1571:
907:
864:
739:
synthesis. Notable examples of this mode of resistance include
631:
320:
Pain and inflammation at the injection site is also common for
177:
678:
601:
of the PBP enzyme. The best antibiotics are those with higher
3739:
3188:
2888:
1872:
Woodward RB (May 16, 1980). "Penems and related substances".
1501:
987:
950:
880:
842:
286:
for the β-lactam antibiotics include diarrhea, nausea, rash,
165:
1576:. Subcellular Biochemistry. Vol. 93. pp. 273–289.
625:
269:
of cerebrosopinal fluid against area under curve of serum).
63:(bottom) the 2 most common groups of β-lactam antibiotics .
2618:
Dalhoff A, Janjic N, Echols R (2006). "Redefining penems".
1574:
Macromolecular
Protein Complexes II: Structure and Function
1780:
1140:
2466:
2226:
1620:
1100:"Appropriate prescribing of oral beta-lactam antibiotics"
552:
2652:
2074:"Class D β-Lactamases: a reappraisal after five decades"
2330:
Principles and
Practice of Pediatric Infectious Disease
2014:
559:
lesions in the DNA resulting in double-strand breaks.
2557:
Ubukata K, Nonoguchi R, Matsuhashi M, Konno M (1989).
2072:
Leonard DA, Bonomo RA, Powers RA (November 19, 2013).
1843:
Journal of the
Chemical Society, Perkin Transactions 2
1699:
1277:"Comparative genomics of Alexander Fleming's original
1274:
1217:
3823:
Benzathine benzylpenicillin/procaine benzylpenicillin
1840:
1049:
ATC code J01C Beta-lactam antibacterials, penicillins
585:, and is the distance between the carbon atom of the
2323:
872:β-Lactams fused to unsaturated five-membered rings:
383:
2762:
2617:
2071:
899:β-Lactams fused to unsaturated six-membered rings:
2703:
2359:
2357:
2135:Journal of Pediatric Pharmacology and Therapeutics
2016:
1508:Current Opinion in Allergy and Clinical Immunology
990:cyclized (two cyclizations by a single enzyme) to
998:(IPNS) to form the penam core structure. Various
949:The numbering of monobactams follows that of the
734:Possession of altered penicillin-binding proteins
4083:
2706:"β-lactam synthetase: a new biosynthetic enzyme"
1377:
937:β-Lactams not fused to any other ring are named
160:ring in their chemical structure. This includes
2462:
2460:
2402:
2400:
2354:
1567:
1565:
774:
605:values (more reactive to hydrolysis) and lower
192:. Most β-lactam antibiotics work by inhibiting
2180:"Structural Insights for β-Lactam Antibiotics"
1836:
1834:
1338:
1334:
1332:
1220:"Fleming's penicillin producing strain is not
1054:ATC code J01D Other beta-lactam antibacterials
2802:
2177:
1456:
2653:Lundberg M, Siegbahn PE, Morokuma K (2008).
2567:gene, which encodes a methicillin-resistant
2457:
2409:"Metallo-β-lactamase structure and function"
2397:
2220:
2171:
2128:
1614:
1562:
1097:
2550:
1965:
1831:
1776:
1774:
1734:
1621:Cushnie TP, O'Driscoll NH, Lamb AJ (2016).
1378:Nau R, Sörgel F, Eiffert H (October 2010).
1371:
1329:
1268:
1218:Houbraken J, Frisvad JC, Samson RA (2011).
1211:
1145:(9th ed.). Washington D.C.: ASM Press.
1091:
1069:Discovery and development of cephalosporins
1002:lead to the different natural penicillins.
327:
238:β-Lactam antibiotics are indicated for the
2809:
2795:
516:. In contrast, they have no effect on the
497:, but also the division of cyanelles, the
254:organisms has increased their usefulness.
218:to β-lactam antibiotics by synthesizing a
49:
3930:Inhibits PG elongation and crosslinking:
2739:
2729:
2594:
2492:
2440:
2254:
2244:
2203:
2154:
2105:
1991:
1968:"Three decades of β-lactamase inhibitors"
1814:
1656:
1646:
1403:
1312:
1251:
665:may be induced by exposure to β-lactams.
626:Enzymatic hydrolysis of the β-lactam ring
277:
2765:Journal of the American Chemical Society
2406:
1871:
1771:
1004:
924:β-Lactams containing 3,6-dihydro-2H-1,3-
902:β-Lactams containing 3,6-dihydro-2H-1,3-
770:
677:
667:
387:
246:bacteria, yet the recent development of
2704:Bachmann BO, Li R, Townsend CA (1998).
2685:from the original on September 22, 2017
2023:Expert Review of Anti-infective Therapy
1427:
1425:
1423:
1174:
913:β-Lactams containing 1,2,3,4-tetrahydro
367:may occur after initial treatment of a
14:
4084:
2509:from the original on February 27, 2024
2389:: CS1 maint: archived copy as title (
2371:from the original on February 22, 2024
2309:: CS1 maint: archived copy as title (
2291:from the original on February 16, 2022
1359:from the original on December 15, 2020
1177:Applied Microbiology and Biotechnology
1156:from the original on December 13, 2019
612:
464:β-Lactam antibiotics are analogues of
378:
2790:
2571:-specific penicillin-binding protein"
2332:. W.B. Saunders. pp. 1341–1352.
2324:Christenson JC, Korgenski EK (2008).
1922:
1681:from the original on October 7, 2017
1627:Cellular and Molecular Life Sciences
1504:"Anaphylaxis and intimate behaviour"
1420:
1098:Holten KB, Onusko EM (August 2000).
886:β-Lactams containing 2,3-dihydro-1H-
589:and the oxygen atom of the β-lactam
542:
532:of plastid division in land plants.
1550:from the original on April 25, 2023
970:(ACVS), which generates the linear
438:by inhibiting the synthesis of the
324:administered β-lactam antibiotics.
250:antibiotics active against various
27:Class of broad-spectrum antibiotics
24:
2338:10.1016/B978-0-7020-3468-8.50292-3
1433:Australian Medicines Handbook 2004
647:New Delhi metallo-beta-lactamase 1
272:
25:
4108:
3955:subunit synthesis and transport:
609:values (better binding to PBPs).
384:Inhibition of cell wall synthesis
2559:"Expression and inducibility in
2433:10.1111/j.1749-6632.2012.06796.x
994:intermediate isopenicillin N by
875:β-Lactams containing 2,3-dihydro
409:
400:
201:, was isolated from a strain of
2756:
2697:
2646:
2611:
2587:10.1128/jb.171.5.2882-2885.1989
2539:
2521:
2317:
2271:
2122:
2065:
2008:
1959:
1916:
1865:
1728:
1693:
1495:
1244:10.5598/imafungus.2011.02.01.12
1143:Manual of Clinical Microbiology
964:nonribosomal peptide synthetase
956:
760:
3853:Imipenem/cilastatin/relebactam
1925:Journal of Medicinal Chemistry
1450:
1168:
1134:
786:The β-lactam core structures.
630:If the bacterium produces the
233:
13:
1:
2529:"Ceftriaxone: Package Insert"
2078:Accounts of Chemical Research
1972:Clinical Microbiology Reviews
1765:10.1016/S0176-1617(97)80193-9
1437:Australian Medicines Handbook
1384:Clinical Microbiology Reviews
1339:Pandey N, Cascella M (2020).
1084:
863:rings are named oxapenams or
1966:Drawz SM, Bonomo RA (2010).
1520:10.1097/ACI.0000000000000386
1044:List of β-lactam antibiotics
767:List of β-lactam antibiotics
700:(a β-lactam antibiotic) and
375:with a β-lactam antibiotic.
7:
3878:Ticarcillin/clavulanic acid
3798:Amoxicillin/clavulanic acid
2935:Phenoxymethylpenicillin (V)
2925:Benzathine benzylpenicillin
2407:Palzkill T (January 2013).
2196:10.4062/biomolther.2023.008
1745:Journal of Plant Physiology
1582:10.1007/978-3-030-28151-9_8
1164:– via US FDA website.
1037:
1022:substrates is activated by
751:) and penicillin-resistant
659:plasmid-mediated resistance
459:penicillin binding proteins
365:Jarisch–Herxheimer reaction
10:
4113:
1305:10.1038/s41598-020-72584-5
1032:inversion of configuration
764:
566:
562:
104:Penicillin binding protein
4042:
3994:
3944:
3923:
3899:
3890:
3803:Ampicillin/flucloxacillin
3790:
3730:
3697:
3665:
3647:
3619:
3586:
3451:
3358:
3270:
3249:
3183:
3149:
3120:
3087:
3028:
3017:
2968:
2930:Procaine benzylpenicillin
2908:
2897:
2883:
2841:
2632:10.1016/j.bcp.2005.12.003
2147:10.5863/1551-6776-16.1.23
1639:10.1007/s00018-016-2302-2
1341:"Beta lactam antibiotics"
1189:10.1007/s00253-003-1274-y
1104:American Family Physician
524:. This is supporting the
430:β-Lactam antibiotics are
305:include fever, vomiting,
133:
128:
114:
109:
97:
85:
77:
72:
48:
39:
34:
2620:Biochemical Pharmacology
2485:10.1177/0018578718779009
2035:10.1586/14787210.5.3.365
996:isopenicillin N synthase
754:Streptococcus pneumoniae
577:, and is the height (in
520:of the highly developed
328:Allergy/hypersensitivity
315:pseudomembranous colitis
4092:Beta-lactam antibiotics
3868:Piperacillin/tazobactam
3828:Cefepime/enmetazobactam
2731:10.1073/pnas.95.16.9082
2575:Journal of Bacteriology
1807:10.1126/science.1219192
1741:Lycopersicon esculentum
1222:Penicillium chrysogenum
653:or may be acquired via
557:8-oxo-2'-deoxyguanosine
248:broad-spectrum β-lactam
214:Bacteria often develop
3959:synthesis inhibition (
3843:Ceftolozane/tazobactam
3833:Cefoperazone/sulbactam
3732:β-lactamase inhibitors
1894:10.1098/rstb.1980.0042
1473:10.1542/peds.2004-1276
1431:Rossi S (ed.) (2004).
1011:
986:-valine (ACV). ACV is
823:
714:β-lactamase inhibitors
685:
675:
508:, and the division of
472:-alanine—the terminal
393:
358:interstitial nephritis
284:adverse drug reactions
278:Adverse drug reactions
224:β-lactamase inhibitors
18:Beta-lactam antibiotic
3873:Sulbactam/durlobactam
3858:Meropenem/vaborbactam
3838:Ceftazidime/avibactam
2970:β-lactamase resistant
2910:β-lactamase sensitive
2561:Staphylococcus aureus
2129:Macdougall C (2011).
1739:) but not in tomato (
1737:Physcomitrella patens
1074:History of penicillin
1008:
848:β-Lactams containing
837:β-Lactams containing
834:five-membered rings:
785:
745:Staphylococcus aureus
690:β-lactamase inhibitor
681:
671:
391:
3863:Panipenem/betamipron
3808:Ampicillin/sulbactam
2920:Benzylpenicillin (G)
2854:cell wall by binding
2246:10.3390/ijms23095229
1984:10.1128/CMR.00037-09
1851:10.1039/p29960000943
1396:10.1128/CMR.00007-10
1291:(1): Article 15705.
1010:method (fourth row).
620:bacterial resistance
526:endosymbiotic theory
265:ratio (the ratio of
143:β-Lactam antibiotics
3848:Imipenem/cilastatin
3818:Aztreonam/avibactam
3629:Ceftaroline fosamil
2777:10.1021/ja00342a047
2722:1998PNAS...95.9082B
2425:2013NYASA1277...91P
2184:Biomol Ther (Seoul)
1937:10.1021/jm00356a027
1886:1980RSPTB.289..239W
1799:2012Sci...336..315F
1757:1997JPPhy.150..137K
1297:2020NatSR..1015705P
859:β-Lactams fused to
830:β-Lactams fused to
661:), and β-lactamase
613:Modes of resistance
569:β-Lactam reactivity
442:layer of bacterial
379:Mechanism of action
209:Penicillium notatum
150:-lactam antibiotics
81:Bacterial infection
35:β-Lactam antibiotic
4069:Never to phase III
4001:Hydrolyze NAM-NAG
3089:Carboxypenicillins
2852:layer of bacterial
2848:(inhibit synthesis
1285:Scientific Reports
1012:
824:
686:
676:
641:, the enzyme will
394:
371:infection such as
204:Penicillium rubens
55:Core structure of
4079:
4078:
3940:
3939:
3886:
3885:
3693:
3692:
3475:Antipseudomonal (
3383:Cefuroxime axetil
3179:
3178:
3175:
3174:
3122:Ureidopenicillins
3013:
3012:
2877:
2870:
2866:
2856:to and inhibiting
2716:(16): 9082–9086.
2671:10.1021/bi701577q
2535:on April 2, 2023.
2473:Hospital Pharmacy
2347:978-0-7020-3468-8
2090:10.1021/ar300327a
2084:(11): 2407–2415.
1880:(1036): 239–250.
1793:(6079): 315–319.
1714:10.1021/cr030102i
1633:(23): 4471–4492.
1591:978-3-030-28150-2
1034:at the β-carbon.
985:
981:
977:
696:(FGP) is made of
543:Guanine oxidation
528:and indicates an
454:
140:
139:
99:Biological target
73:Class identifiers
16:(Redirected from
4104:
3897:
3896:
3268:
3267:
3124:(4th generation)
3091:(4th generation)
3032:(3rd generation)
3030:Aminopenicillins
3026:
3025:
2973:(2nd generation)
2913:(1st generation)
2906:
2905:
2895:
2894:
2881:
2880:
2876:
2868:
2864:
2850:of peptidoglycan
2846:
2811:
2804:
2797:
2788:
2787:
2781:
2780:
2760:
2754:
2753:
2743:
2733:
2701:
2695:
2694:
2692:
2690:
2665:(3): 1031–1042.
2650:
2644:
2643:
2626:(7): 1085–1095.
2615:
2609:
2608:
2598:
2554:
2548:
2543:
2537:
2536:
2531:. Archived from
2525:
2519:
2518:
2516:
2514:
2496:
2464:
2455:
2454:
2444:
2413:Ann N Y Acad Sci
2404:
2395:
2394:
2388:
2380:
2378:
2376:
2361:
2352:
2351:
2321:
2315:
2314:
2308:
2300:
2298:
2296:
2290:
2283:
2275:
2269:
2268:
2258:
2248:
2224:
2218:
2217:
2207:
2175:
2169:
2168:
2158:
2126:
2120:
2119:
2109:
2069:
2063:
2062:
2020:
2012:
2006:
2005:
1995:
1963:
1957:
1956:
1920:
1914:
1913:
1869:
1863:
1862:
1838:
1829:
1828:
1818:
1778:
1769:
1768:
1732:
1726:
1725:
1702:Chemical Reviews
1697:
1691:
1690:
1688:
1686:
1660:
1650:
1618:
1612:
1611:
1569:
1560:
1559:
1557:
1555:
1499:
1493:
1492:
1454:
1448:
1429:
1418:
1417:
1407:
1375:
1369:
1368:
1366:
1364:
1336:
1327:
1326:
1316:
1272:
1266:
1265:
1255:
1215:
1209:
1208:
1183:(5–6): 385–392.
1172:
1166:
1165:
1163:
1161:
1146:
1138:
1132:
1131:
1129:
1127:
1118:. Archived from
1095:
983:
979:
978:-α-aminoadipyl)-
975:
928:rings are named
917:rings are named
906:rings are named
890:rings are named
879:rings are named
852:rings are named
841:rings are named
773:
483:
479:
471:
467:
457:, also known as
455:-transpeptidases
452:
413:
404:
342:amoxicillin rash
267:area under curve
124:
53:
32:
31:
21:
4112:
4111:
4107:
4106:
4105:
4103:
4102:
4101:
4082:
4081:
4080:
4075:
4074:
4059:Clinical trials
4038:
3990:
3936:
3919:
3882:
3786:
3759:Clavulanic acid
3726:
3689:
3661:
3643:
3615:
3582:
3447:
3354:
3261:
3257:
3253:
3245:
3203:Antipseudomonal
3171:
3145:
3116:
3083:
3020:
3009:
2972:
2964:
2912:
2900:
2873:transpeptidases
2872:
2862:
2857:
2855:
2853:
2851:
2849:
2847:
2845:
2837:
2815:
2785:
2784:
2761:
2757:
2702:
2698:
2688:
2686:
2651:
2647:
2616:
2612:
2555:
2551:
2544:
2540:
2527:
2526:
2522:
2512:
2510:
2465:
2458:
2405:
2398:
2382:
2381:
2374:
2372:
2365:"Archived copy"
2363:
2362:
2355:
2348:
2322:
2318:
2302:
2301:
2294:
2292:
2288:
2281:
2279:"Archived copy"
2277:
2276:
2272:
2225:
2221:
2176:
2172:
2127:
2123:
2070:
2066:
2013:
2009:
1964:
1960:
1921:
1917:
1870:
1866:
1839:
1832:
1779:
1772:
1733:
1729:
1698:
1694:
1684:
1682:
1619:
1615:
1592:
1570:
1563:
1553:
1551:
1500:
1496:
1455:
1451:
1430:
1421:
1376:
1372:
1362:
1360:
1337:
1330:
1273:
1269:
1216:
1212:
1173:
1169:
1159:
1157:
1148:
1139:
1135:
1125:
1123:
1122:on June 6, 2011
1096:
1092:
1087:
1040:
1000:transamidations
959:
818:A carbacephem.
784:
771:
769:
763:
736:
702:clavulanic acid
692:. For example,
673:Clavulanic acid
663:gene expression
628:
615:
571:
565:
545:
522:vascular plants
491:
481:
477:
469:
465:
428:
427:
426:
425:
416:
415:
414:
406:
405:
386:
381:
356:, anaphylaxis,
340:reactions, see
330:
303:adverse effects
280:
275:
273:Adverse effects
264:
260:
236:
228:clavulanic acid
156:that contain a
120:
68:
28:
23:
22:
15:
12:
11:
5:
4110:
4100:
4099:
4094:
4077:
4076:
4073:
4072:
4071:
4070:
4067:
4056:
4050:
4044:
4043:
4040:
4039:
4037:
4036:
4031:
4026:
4025:
4024:
4019:
4009:
4008:
4007:
3998:
3996:
3992:
3991:
3989:
3988:
3978:
3964:
3948:
3946:
3942:
3941:
3938:
3937:
3935:
3934:
3927:
3925:
3921:
3920:
3918:
3917:
3912:
3905:
3903:
3894:
3888:
3887:
3884:
3883:
3881:
3880:
3875:
3870:
3865:
3860:
3855:
3850:
3845:
3840:
3835:
3830:
3825:
3820:
3815:
3805:
3800:
3794:
3792:
3788:
3787:
3785:
3784:
3778:
3773:
3768:
3764:non-β-lactam (
3762:
3752:
3746:
3736:
3734:
3728:
3727:
3725:
3724:
3719:
3714:
3709:
3703:
3701:
3695:
3694:
3691:
3690:
3688:
3687:
3682:
3677:
3671:
3669:
3663:
3662:
3660:
3659:
3653:
3651:
3645:
3644:
3642:
3641:
3636:
3631:
3625:
3623:
3621:5th generation
3617:
3616:
3614:
3613:
3608:
3603:
3598:
3592:
3590:
3588:4th generation
3584:
3583:
3581:
3580:
3574:
3565:
3560:
3555:
3550:
3545:
3540:
3535:
3530:
3525:
3520:
3515:
3510:
3505:
3500:
3495:
3490:
3485:
3479:
3473:
3468:
3463:
3457:
3455:
3453:3rd generation
3449:
3448:
3446:
3445:
3435:
3429:
3424:
3419:
3414:
3405:
3400:
3395:
3390:
3385:
3380:
3375:
3370:
3364:
3362:
3360:2nd generation
3356:
3355:
3353:
3352:
3347:
3342:
3337:
3332:
3327:
3322:
3317:
3312:
3307:
3302:
3297:
3292:
3287:
3282:
3276:
3274:
3272:1st generation
3265:
3255:Cephalosporins
3247:
3246:
3244:
3243:
3237:
3231:
3225:
3220:
3214:
3209:
3200:
3193:
3191:
3181:
3180:
3177:
3176:
3173:
3172:
3170:
3169:
3164:
3153:
3151:
3147:
3146:
3144:
3143:
3138:
3133:
3127:
3125:
3118:
3117:
3115:
3114:
3109:
3100:
3094:
3092:
3085:
3084:
3082:
3081:
3076:
3070:
3065:
3060:
3055:
3050:
3041:
3035:
3033:
3023:
3015:
3014:
3011:
3010:
3008:
3007:
3002:
2997:
2992:
2989:Flucloxacillin
2986:
2976:
2974:
2966:
2965:
2963:
2962:
2957:
2952:
2947:
2942:
2937:
2932:
2927:
2922:
2916:
2914:
2903:
2892:
2878:
2839:
2838:
2820:active on the
2818:Antibacterials
2814:
2813:
2806:
2799:
2791:
2783:
2782:
2771:(4): 919–927.
2755:
2696:
2645:
2610:
2549:
2538:
2520:
2479:(3): 190–196.
2456:
2396:
2353:
2346:
2316:
2270:
2219:
2190:(2): 141–147.
2170:
2121:
2064:
2029:(3): 365–383.
2007:
1978:(1): 160–201.
1958:
1931:(2): 259–264.
1915:
1864:
1845:(5): 943–953.
1830:
1770:
1751:(1): 137–140.
1727:
1708:(2): 395–424.
1692:
1613:
1590:
1561:
1514:(5): 350–355.
1494:
1467:(4): 1048–57.
1449:
1419:
1370:
1328:
1267:
1210:
1167:
1133:
1089:
1088:
1086:
1083:
1082:
1081:
1076:
1071:
1066:
1061:
1056:
1051:
1046:
1039:
1036:
1016:ring expansion
968:ACV synthetase
958:
955:
943:
942:
935:
934:
933:
922:
911:
897:
896:
895:
884:
870:
869:
868:
857:
846:
810:A monobactam.
806:A carbapenem.
794:A carbapenam.
762:
759:
735:
732:
637:or the enzyme
627:
624:
614:
611:
564:
561:
544:
541:
499:photosynthetic
489:
418:
417:
408:
407:
399:
398:
397:
396:
395:
385:
382:
380:
377:
329:
326:
309:, dermatitis,
292:superinfection
279:
276:
274:
271:
262:
258:
235:
232:
211:at the time).
170:cephalosporins
138:
137:
131:
130:
126:
125:
118:
112:
111:
110:External links
107:
106:
101:
95:
94:
89:
83:
82:
79:
75:
74:
70:
69:
61:cephalosporins
54:
46:
45:
37:
36:
26:
9:
6:
4:
3:
2:
4109:
4098:
4095:
4093:
4090:
4089:
4087:
4068:
4066:
4063:
4062:
4060:
4057:
4054:
4051:
4049:
4046:
4045:
4041:
4035:
4032:
4030:
4027:
4023:
4020:
4018:
4015:
4014:
4013:
4010:
4006:
4003:
4002:
4000:
3999:
3997:
3993:
3986:
3982:
3979:
3976:
3972:
3968:
3965:
3962:
3958:
3954:
3950:
3949:
3947:
3945:Intracellular
3943:
3933:
3929:
3928:
3926:
3922:
3916:
3913:
3911:
3907:
3906:
3904:
3902:
3898:
3895:
3893:
3889:
3879:
3876:
3874:
3871:
3869:
3866:
3864:
3861:
3859:
3856:
3854:
3851:
3849:
3846:
3844:
3841:
3839:
3836:
3834:
3831:
3829:
3826:
3824:
3821:
3819:
3816:
3813:
3812:Sultamicillin
3809:
3806:
3804:
3801:
3799:
3796:
3795:
3793:
3789:
3782:
3779:
3777:
3774:
3772:
3769:
3767:
3763:
3760:
3756:
3753:
3750:
3747:
3745:
3741:
3738:
3737:
3735:
3733:
3729:
3723:
3720:
3718:
3715:
3713:
3710:
3708:
3705:
3704:
3702:
3700:
3696:
3686:
3683:
3681:
3678:
3676:
3673:
3672:
3670:
3668:
3664:
3658:
3655:
3654:
3652:
3650:
3646:
3640:
3637:
3635:
3632:
3630:
3627:
3626:
3624:
3622:
3618:
3612:
3609:
3607:
3604:
3602:
3599:
3597:
3594:
3593:
3591:
3589:
3585:
3578:
3575:
3573:
3569:
3566:
3564:
3561:
3559:
3556:
3554:
3551:
3549:
3546:
3544:
3541:
3539:
3536:
3534:
3531:
3529:
3526:
3524:
3521:
3519:
3516:
3514:
3511:
3509:
3506:
3504:
3501:
3499:
3496:
3494:
3491:
3489:
3486:
3483:
3480:
3478:
3474:
3472:
3469:
3467:
3464:
3462:
3459:
3458:
3456:
3454:
3450:
3443:
3439:
3436:
3433:
3430:
3428:
3427:Cefbuperazone
3425:
3423:
3420:
3418:
3415:
3413:
3409:
3406:
3404:
3401:
3399:
3396:
3394:
3391:
3389:
3386:
3384:
3381:
3379:
3376:
3374:
3371:
3369:
3366:
3365:
3363:
3361:
3357:
3351:
3348:
3346:
3343:
3341:
3338:
3336:
3333:
3331:
3328:
3326:
3323:
3321:
3318:
3316:
3313:
3311:
3308:
3306:
3303:
3301:
3298:
3296:
3293:
3291:
3288:
3286:
3283:
3281:
3278:
3277:
3275:
3273:
3269:
3266:
3264:
3260:
3256:
3252:
3248:
3241:
3238:
3236:
3232:
3229:
3226:
3224:
3221:
3218:
3215:
3213:
3210:
3208:
3204:
3201:
3199:
3196:Carbapenems (
3195:
3194:
3192:
3190:
3186:
3182:
3168:
3167:Sulbenicillin
3165:
3162:
3161:Pivmecillinam
3158:
3155:
3154:
3152:
3148:
3142:
3139:
3137:
3134:
3132:
3129:
3128:
3126:
3123:
3119:
3113:
3110:
3108:
3107:Carindacillin
3104:
3103:Carbenicillin
3101:
3099:
3096:
3095:
3093:
3090:
3086:
3080:
3077:
3074:
3073:Talampicillin
3071:
3069:
3068:Metampicillin
3066:
3064:
3063:Lenampicillin
3061:
3059:
3058:Bacampicillin
3056:
3054:
3051:
3049:
3048:Pivampicillin
3045:
3042:
3040:
3037:
3036:
3034:
3031:
3027:
3024:
3022:
3016:
3006:
3003:
3001:
2998:
2996:
2993:
2990:
2987:
2985:
2984:Dicloxacillin
2981:
2978:
2977:
2975:
2971:
2967:
2961:
2958:
2956:
2955:Clometocillin
2953:
2951:
2948:
2946:
2945:Pheneticillin
2943:
2941:
2938:
2936:
2933:
2931:
2928:
2926:
2923:
2921:
2918:
2917:
2915:
2911:
2907:
2904:
2902:
2896:
2893:
2890:
2886:
2882:
2879:
2874:
2860:
2844:
2840:
2835:
2831:
2827:
2823:
2819:
2812:
2807:
2805:
2800:
2798:
2793:
2792:
2789:
2778:
2774:
2770:
2766:
2759:
2751:
2747:
2742:
2737:
2732:
2727:
2723:
2719:
2715:
2711:
2707:
2700:
2684:
2680:
2676:
2672:
2668:
2664:
2660:
2656:
2649:
2641:
2637:
2633:
2629:
2625:
2621:
2614:
2606:
2602:
2597:
2592:
2588:
2584:
2581:(5): 2882–5.
2580:
2576:
2572:
2570:
2566:
2562:
2553:
2547:
2542:
2534:
2530:
2524:
2508:
2504:
2500:
2495:
2490:
2486:
2482:
2478:
2474:
2470:
2463:
2461:
2452:
2448:
2443:
2438:
2434:
2430:
2426:
2422:
2419:(1): 91–104.
2418:
2414:
2410:
2403:
2401:
2392:
2386:
2370:
2366:
2360:
2358:
2349:
2343:
2339:
2335:
2331:
2327:
2320:
2312:
2306:
2287:
2280:
2274:
2266:
2262:
2257:
2252:
2247:
2242:
2238:
2234:
2233:Int J Mol Sci
2230:
2223:
2215:
2211:
2206:
2201:
2197:
2193:
2189:
2185:
2181:
2174:
2166:
2162:
2157:
2152:
2148:
2144:
2140:
2136:
2132:
2125:
2117:
2113:
2108:
2103:
2099:
2095:
2091:
2087:
2083:
2079:
2075:
2068:
2060:
2056:
2052:
2048:
2044:
2040:
2036:
2032:
2028:
2024:
2019:
2011:
2003:
1999:
1994:
1989:
1985:
1981:
1977:
1973:
1969:
1962:
1954:
1950:
1946:
1942:
1938:
1934:
1930:
1926:
1919:
1911:
1907:
1903:
1899:
1895:
1891:
1887:
1883:
1879:
1875:
1868:
1860:
1856:
1852:
1848:
1844:
1837:
1835:
1826:
1822:
1817:
1812:
1808:
1804:
1800:
1796:
1792:
1788:
1784:
1777:
1775:
1766:
1762:
1758:
1754:
1750:
1746:
1742:
1738:
1731:
1723:
1719:
1715:
1711:
1707:
1703:
1696:
1680:
1676:
1672:
1668:
1664:
1659:
1654:
1649:
1644:
1640:
1636:
1632:
1628:
1624:
1617:
1609:
1605:
1601:
1597:
1593:
1587:
1583:
1579:
1575:
1568:
1566:
1549:
1545:
1541:
1537:
1533:
1529:
1525:
1521:
1517:
1513:
1509:
1505:
1498:
1490:
1486:
1482:
1478:
1474:
1470:
1466:
1462:
1461:
1453:
1446:
1445:0-9578521-4-2
1442:
1438:
1434:
1428:
1426:
1424:
1415:
1411:
1406:
1401:
1397:
1393:
1390:(4): 858–83.
1389:
1385:
1381:
1374:
1358:
1354:
1350:
1346:
1342:
1335:
1333:
1324:
1320:
1315:
1310:
1306:
1302:
1298:
1294:
1290:
1286:
1282:
1280:
1271:
1263:
1259:
1254:
1249:
1245:
1241:
1237:
1233:
1229:
1227:
1223:
1214:
1206:
1202:
1198:
1194:
1190:
1186:
1182:
1178:
1171:
1155:
1151:
1144:
1137:
1121:
1117:
1113:
1110:(3): 611–20.
1109:
1105:
1101:
1094:
1090:
1080:
1077:
1075:
1072:
1070:
1067:
1065:
1062:
1060:
1057:
1055:
1052:
1050:
1047:
1045:
1042:
1041:
1035:
1033:
1027:
1025:
1019:
1017:
1007:
1003:
1001:
997:
993:
989:
973:
969:
965:
954:
952:
947:
940:
936:
931:
927:
923:
920:
916:
912:
909:
905:
901:
900:
898:
893:
889:
885:
882:
878:
874:
873:
871:
866:
862:
858:
855:
851:
847:
844:
840:
836:
835:
833:
829:
828:
827:
822:An oxacephem.
821:
817:
813:
809:
805:
801:
798:An oxapenam.
797:
793:
789:
768:
758:
756:
755:
750:
746:
742:
731:
728:
722:
718:
715:
710:
707:
703:
699:
695:
691:
684:
680:
674:
670:
666:
664:
660:
656:
652:
648:
644:
640:
639:penicillinase
636:
633:
623:
621:
610:
608:
604:
600:
599:oxyanion hole
596:
592:
588:
584:
580:
576:
570:
560:
558:
554:
550:
540:
538:
533:
531:
527:
523:
519:
515:
511:
507:
503:
500:
496:
495:cyanobacteria
487:
475:
462:
460:
456:
449:
448:gram-positive
445:
441:
440:peptidoglycan
437:
433:
423:
412:
403:
390:
376:
374:
370:
366:
361:
359:
355:
350:
347:
343:
339:
335:
325:
323:
318:
316:
312:
308:
304:
299:
297:
293:
289:
285:
270:
268:
255:
253:
252:gram-negative
249:
245:
244:gram-positive
241:
231:
229:
225:
221:
217:
212:
210:
206:
205:
200:
195:
191:
187:
183:
179:
175:
171:
167:
164:derivatives (
163:
159:
155:
151:
149:
144:
136:
132:
127:
123:
119:
117:
113:
108:
105:
102:
100:
96:
93:
90:
88:
84:
80:
76:
71:
66:
62:
58:
52:
47:
44:
43:
38:
33:
30:
19:
4097:Nephrotoxins
3983:inhibitors (
3973:inhibitors (
3901:Lipopeptides
3892:Polypeptides
3791:Combinations
3722:Nocardicin A
3639:Ceftobiprole
3482:Cefoperazone
3340:Cefaloridine
3325:Cefaloglycin
3263:Carbacephems
3131:Piperacillin
2960:Penamecillin
2861:, a group of
2768:
2764:
2758:
2713:
2709:
2699:
2687:. Retrieved
2662:
2659:Biochemistry
2658:
2648:
2623:
2619:
2613:
2578:
2574:
2568:
2564:
2560:
2552:
2541:
2533:the original
2523:
2513:February 22,
2511:. Retrieved
2476:
2472:
2416:
2412:
2375:February 22,
2373:. Retrieved
2329:
2319:
2295:February 22,
2293:. Retrieved
2273:
2236:
2232:
2222:
2187:
2183:
2173:
2141:(1): 23–30.
2138:
2134:
2124:
2081:
2077:
2067:
2026:
2022:
2010:
1975:
1971:
1961:
1928:
1924:
1918:
1877:
1873:
1867:
1842:
1790:
1786:
1748:
1744:
1740:
1736:
1730:
1705:
1701:
1695:
1683:. Retrieved
1630:
1626:
1616:
1573:
1554:February 27,
1552:. Retrieved
1511:
1507:
1497:
1464:
1458:
1452:
1435:. Adelaide:
1432:
1387:
1383:
1373:
1361:. Retrieved
1344:
1288:
1284:
1278:
1270:
1238:(1): 87–95.
1235:
1231:
1225:
1221:
1213:
1180:
1176:
1170:
1158:. Retrieved
1142:
1136:
1124:. Retrieved
1120:the original
1107:
1103:
1093:
1028:
1020:
1013:
960:
957:Biosynthesis
948:
944:
919:carbacephems
839:thiazolidine
825:
819:
815:
811:
807:
803:
799:
795:
791:
787:
761:Nomenclature
752:
744:
737:
723:
719:
711:
687:
629:
616:
606:
602:
595:binding site
582:
574:
572:
546:
534:
510:chloroplasts
506:glaucophytes
463:
432:bactericidal
429:
422:spheroplasts
362:
351:
331:
322:parenterally
319:
300:
281:
256:
237:
213:
208:
202:
190:carbacephems
147:
146:
142:
141:
129:Legal status
67:ring in red.
40:
29:
4055:from market
4034:Teixobactin
4012:Tyrothricin
3981:bactoprenol
3975:Cycloserine
3781:Vaborbactam
3771:Durlobactam
3699:Monobactams
3657:Cefiderocol
3649:Siderophore
3634:Ceftolozane
3548:Cefpimizole
3518:Cefpodoxime
3513:Cefpiramide
3508:Cefmenoxime
3503:Ceftizoxime
3498:Cefdaloxime
3477:Ceftazidime
3466:Ceftriaxone
3438:Carbacephem
3432:Cefmetazole
3388:Cefamandole
3350:Cefatrizine
3330:Cefacetrile
3315:Cefroxadine
3259:Cephamycins
3185:Carbapenems
3141:Mezlocillin
3098:Ticarcillin
3039:Amoxicillin
3005:Methicillin
2980:Cloxacillin
2950:Azidocillin
2940:Propicillin
2885:Penicillins
2689:October 28,
2239:(9): 5229.
1279:Penicillium
1126:November 8,
988:oxidatively
939:monobactams
892:carbapenems
861:oxazolidine
854:carbapenams
850:pyrrolidine
743:-resistant
741:methicillin
698:amoxicillin
683:Amoxicillin
635:β-lactamase
587:carboxylate
369:spirochetal
346:Anaphylaxis
301:Infrequent
296:candidiasis
294:(including
234:Medical use
220:β-lactamase
186:carbapenems
182:monobactams
174:cephamycins
154:antibiotics
135:In Wikidata
57:penicillins
4086:Categories
4022:Tyrocidine
4017:Gramicidin
3985:Bacitracin
3961:Fosfomycin
3932:Ramoplanin
3910:Daptomycin
3776:Relebactam
3749:Tazobactam
3680:Cefquinome
3667:Veterinary
3611:Cefquinome
3601:Cefozopran
3563:Ceftiolene
3553:Cefsulodin
3543:Cefodizime
3528:Cefditoren
3523:Ceftibuten
3471:Cefotaxime
3442:Loracarbef
3408:Cephamycin
3398:Ceforanide
3378:Cefuroxime
3335:Cefalonium
3305:Cefazaflur
3300:Cefazedone
3290:Cefadroxil
3157:Mecillinam
3136:Azlocillin
3112:Temocillin
3053:Hetacillin
3044:Ampicillin
1648:10059/2129
1460:Pediatrics
1345:StatPearls
1232:IMA Fungus
1085:References
1079:Nitrocefin
982:-cysteine-
972:tripeptide
930:oxacephems
814:A cephem.
765:See also:
727:amide bond
706:antagonist
657:transfer (
651:chromosome
567:See also:
537:hydrolases
514:bryophytes
502:organelles
474:amino acid
444:cell walls
336:-mediated
311:angioedema
240:prevention
216:resistance
207:(named as
199:penicillin
162:penicillin
59:(top) and
42:Drug class
4065:Phase III
4053:Withdrawn
4029:Isoniazid
3915:Surfactin
3766:Avibactam
3744:Sulbactam
3717:Carumonam
3712:Tigemonam
3707:Aztreonam
3685:Cefovecin
3675:Ceftiofur
3606:Cefpirome
3577:Latamoxef
3568:Oxacephem
3538:Cefetamet
3493:Cefcapene
3417:Cefotetan
3412:Cefoxitin
3403:Cefuzonam
3393:Cefonicid
3373:Cefprozil
3345:Cefalotin
3320:Ceftezole
3310:Cefradine
3295:Cefapirin
3285:Cefalexin
3280:Cefazolin
3240:Ritipenem
3235:Faropenem
3228:Panipenem
3217:Meropenem
3207:Doripenem
3198:Ertapenem
3079:Epicillin
3000:Nafcillin
2995:Oxacillin
2843:β-lactams
2822:cell wall
2569:S. aureus
2098:0001-4842
2043:1478-7210
1945:0022-2623
1902:0962-8436
1859:1364-5471
1608:210814189
1528:1473-6322
1226:P. rubens
1147:Cited in
1064:Cell wall
832:saturated
802:A penem.
790:A penam.
694:Augmentin
643:hydrolyse
579:angstroms
530:evolution
488:) the Ser
354:urticaria
288:urticaria
194:cell wall
4005:lysozyme
3951:Inhibit
3596:Cefepime
3572:Flomoxef
3558:Cefteram
3533:Cefotiam
3488:Cefdinir
3461:Cefixime
3422:Cefminox
3368:Cefaclor
3233:Penems (
3223:Biapenem
3212:Imipenem
3021:spectrum
3019:Extended
2901:spectrum
2871:-alanine
2867:-alanyl-
2826:envelope
2683:Archived
2679:18163649
2640:16413506
2507:Archived
2503:31205331
2451:23163348
2385:cite web
2369:Archived
2305:cite web
2286:Archived
2265:35563620
2214:36788654
2165:22477821
2116:23902256
2059:68837323
2051:17547502
2002:20065329
1825:22517853
1722:15700950
1679:Archived
1667:27392605
1658:11108400
1600:31939154
1548:Archived
1544:13925217
1536:28742538
1489:21246804
1481:15805383
1414:20930076
1357:Archived
1353:31424895
1323:32973216
1262:22679592
1205:43996071
1197:12679848
1154:Archived
1116:10950216
1059:Bacteria
1038:See also
992:bicyclic
966:(NRPS),
915:pyridine
904:thiazine
877:thiazole
597:and the
591:carbonyl
518:plastids
486:acylates
480:-alanyl-
468:-alanyl-
373:syphilis
338:allergic
307:erythema
226:such as
158:β-lactam
87:ATC code
65:β-lactam
3251:Cephems
2750:9689037
2718:Bibcode
2605:2708325
2563:of the
2494:6535930
2442:3970115
2421:Bibcode
2256:9100253
2205:9970833
2156:3136230
2107:4018812
1993:2806661
1953:6827544
1910:6109320
1882:Bibcode
1816:3357493
1795:Bibcode
1787:Science
1753:Bibcode
1675:2065821
1405:2952976
1314:7515868
1293:Bibcode
1253:3317369
1160:May 27,
926:oxazine
908:cephems
888:pyrrole
865:clavams
655:plasmid
563:Potency
549:guanine
504:of the
282:Common
178:cephems
122:D047090
4048:WHO-EM
3755:Clavam
3189:Penems
2899:Narrow
2889:Penams
2748:
2738:
2677:
2638:
2603:
2596:209980
2593:
2501:
2491:
2449:
2439:
2344:
2263:
2253:
2212:
2202:
2163:
2153:
2114:
2104:
2096:
2057:
2049:
2041:
2000:
1990:
1951:
1943:
1908:
1900:
1857:
1823:
1813:
1720:
1685:May 5,
1673:
1665:
1655:
1606:
1598:
1588:
1542:
1534:
1526:
1487:
1479:
1443:
1412:
1402:
1363:May 5,
1351:
1321:
1311:
1260:
1250:
1203:
1195:
1114:
881:penems
843:penams
712:Other
632:enzyme
434:, and
166:penams
152:) are
3995:Other
3967:DADAL
3924:Other
3740:Penam
3150:Other
2741:21295
2289:(PDF)
2282:(PDF)
2055:S2CID
1671:S2CID
1604:S2CID
1540:S2CID
1485:S2CID
1201:S2CID
951:IUPAC
2859:PBPs
2834:J01D
2830:J01C
2824:and
2746:PMID
2691:2017
2675:PMID
2636:PMID
2601:PMID
2565:mecA
2515:2024
2499:PMID
2447:PMID
2417:1277
2391:link
2377:2024
2342:ISBN
2311:link
2297:2024
2261:PMID
2210:PMID
2161:PMID
2112:PMID
2094:ISSN
2047:PMID
2039:ISSN
1998:PMID
1949:PMID
1941:ISSN
1906:PMID
1898:ISSN
1855:ISSN
1821:PMID
1743:)".
1718:PMID
1687:2020
1663:PMID
1596:PMID
1586:ISBN
1556:2021
1532:PMID
1524:ISSN
1477:PMID
1441:ISBN
1410:PMID
1365:2020
1349:PMID
1319:PMID
1258:PMID
1224:but
1193:PMID
1162:2019
1128:2008
1112:PMID
749:MRSA
261:/AUC
188:and
172:and
148:beta
116:MeSH
92:J01C
3957:NAM
2773:doi
2769:105
2736:PMC
2726:doi
2667:doi
2628:doi
2591:PMC
2583:doi
2579:171
2489:PMC
2481:doi
2437:PMC
2429:doi
2334:doi
2251:PMC
2241:doi
2200:PMC
2192:doi
2151:PMC
2143:doi
2102:PMC
2086:doi
2031:doi
1988:PMC
1980:doi
1933:doi
1890:doi
1878:289
1847:doi
1811:PMC
1803:doi
1791:336
1761:doi
1749:150
1710:doi
1706:105
1653:PMC
1643:hdl
1635:doi
1578:doi
1516:doi
1469:doi
1465:115
1400:PMC
1392:doi
1309:PMC
1301:doi
1248:PMC
1240:doi
1185:doi
1024:ATP
974:δ-(
820:(I)
816:(H)
812:(G)
808:(F)
804:(E)
800:(D)
796:(C)
792:(B)
788:(A)
553:DNA
512:of
490:403
436:act
344:).
334:IgE
298:).
259:CSF
180:),
168:),
78:Use
4088::
4061::
3971:AR
3953:PG
3187:/
3105:/
2767:.
2744:.
2734:.
2724:.
2714:95
2712:.
2708:.
2681:.
2673:.
2663:47
2661:.
2657:.
2634:.
2624:71
2622:.
2599:.
2589:.
2577:.
2573:.
2505:.
2497:.
2487:.
2477:54
2475:.
2471:.
2459:^
2445:.
2435:.
2427:.
2415:.
2411:.
2399:^
2387:}}
2383:{{
2367:.
2356:^
2340:.
2328:.
2307:}}
2303:{{
2284:.
2259:.
2249:.
2237:23
2235:.
2231:.
2208:.
2198:.
2188:31
2186:.
2182:.
2159:.
2149:.
2139:16
2137:.
2133:.
2110:.
2100:.
2092:.
2082:46
2080:.
2076:.
2053:.
2045:.
2037:.
2025:.
2021:.
1996:.
1986:.
1976:23
1974:.
1970:.
1947:.
1939:.
1929:26
1927:.
1904:.
1896:.
1888:.
1876:.
1853:.
1833:^
1819:.
1809:.
1801:.
1789:.
1785:.
1773:^
1759:.
1747:.
1716:.
1704:.
1677:.
1669:.
1661:.
1651:.
1641:.
1631:73
1629:.
1625:.
1602:.
1594:.
1584:.
1564:^
1546:.
1538:.
1530:.
1522:.
1512:17
1510:.
1506:.
1483:.
1475:.
1463:.
1439:.
1422:^
1408:.
1398:.
1388:23
1386:.
1382:.
1355:.
1347:.
1343:.
1331:^
1317:.
1307:.
1299:.
1289:10
1287:.
1283:.
1256:.
1246:.
1234:.
1230:.
1199:.
1191:.
1181:61
1179:.
1108:62
1106:.
1102:.
453:DD
363:A
317:.
313:,
290:,
230:.
184:,
3987:)
3977:)
3969:/
3963:)
3814:)
3810:(
3783:)
3761:)
3757:(
3751:)
3742:(
3579:)
3570:(
3484:)
3444:)
3440:(
3434:)
3410:(
3242:)
3230:)
3219:)
3205:(
3163:)
3159:(
3075:)
3046:(
2991:)
2982:(
2891:)
2887:(
2875:)
2869:D
2865:D
2836:)
2832:-
2828:(
2810:e
2803:t
2796:v
2779:.
2775::
2752:.
2728::
2720::
2693:.
2669::
2642:.
2630::
2607:.
2585::
2517:.
2483::
2453:.
2431::
2423::
2393:)
2379:.
2350:.
2336::
2313:)
2299:.
2267:.
2243::
2216:.
2194::
2167:.
2145::
2118:.
2088::
2061:.
2033::
2027:5
2004:.
1982::
1955:.
1935::
1912:.
1892::
1884::
1861:.
1849::
1827:.
1805::
1797::
1767:.
1763::
1755::
1724:.
1712::
1689:.
1645::
1637::
1610:.
1580::
1558:.
1518::
1491:.
1471::
1447:.
1416:.
1394::
1367:.
1325:.
1303::
1295::
1264:.
1242::
1236:2
1228:"
1207:.
1187::
1130:.
984:D
980:L
976:L
941:.
932:.
921:.
910:.
894:.
883:.
867:.
856:.
845:.
747:(
607:c
603:h
583:c
575:h
482:d
478:d
470:d
466:d
424:.
263:S
176:(
145:(
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
