796:, which are cholesterol-lowering drugs that are mainly metabolized by CYP3A4. Co-administration of clarithromycin or erythromycin with statins can increase the risk of statin-induced myopathy, a condition that causes muscle pain and damage. Azithromycin, however, does not significantly affect the pharmacokinetics of statins and is considered a safer alternative. Another option is to use fluvastatin, a statin that is metabolized by CYP2C9, an enzyme that is not inhibited by clarithromycin.
41:
781:, on the other hand, has a 15-membered lactone ring, which is less susceptible to demethylation and nitrosoalkene formation. Therefore, azithromycin is a weak inhibitor of CYP3A4, while clarithromycin and erythromycin are strong inhibitors which increase the area under the curve (AUC) value of co-administered drugs more than five-fold. AUC it is a measure of the drug exposure in the body over time. By inhibiting CYP3A4, macrolide antibitiotics, such as
440:
22:
51:
789:, but not azithromycin, can significantly increase the AUC of the drugs that depend on it for clearance, which can lead to higher risk of adverse effects or drug-drug interactions. Azithromycin stands apart from other macrolide antibiotics because it is a weak inhibitor of CYP3A4, and does not significantly increase AUC value of co-administered drugs.
743:, a condition where bile cannot flow from the liver to the duodenum. A study reported in 2019 found an association between erythromycin use during infancy and developing IHPS (Infantile hypertrophic pyloric stenosis) in infants. However, no significant association was found between macrolides use during pregnancy or breastfeeding.
765:
ring and sugar moieties. They can inhibit CYP3A4 by a mechanism called mechanism-based inhibition (MBI), which involves the formation of reactive metabolites that bind covalently and irreversibly to the enzyme, rendering it inactive. MBI is more serious and long-lasting than reversible inhibition,
389:
in airways. The antimicrobial and antibiotic effects of macrolides, however, are not believed to be involved in their beneficial effects toward treating DPB. This is evident, as the treatment dosage is much too low to fight infection, and in DPB cases with the occurrence of the macrolide-resistant
1274:
Hougaard
Christensen MM, Bruun Haastrup M, Øhlenschlaeger T, Esbech P, Arnspang Pedersen S, Bach Dunvald AC, Bjerregaard Stage T, Pilsgaard Henriksen D, Thestrup Pedersen AJ (April 2020). "Interaction potential between clarithromycin and individual statins-A systematic review".
273:
herbivores, such as horses and rabbits. They rapidly produce a reaction causing fatal digestive disturbance. It can be used in horses less than one year old, but care must be taken that other horses (such as a foal's mare) do not come in contact with the macrolide treatment.
1936:
Abdellatif M, Ghozy S, Kamel MG, Elawady SS, Ghorab MM, Attia AW, Le Huyen TT, Duy DT, Hirayama K, Huy NT (March 2019). "Association between exposure to macrolides and the development of infantile hypertrophic pyloric stenosis: a systematic review and meta-analysis".
757:
is an enzyme that metabolizes many drugs in the liver. Macrolides inhibit CYP3A4, which means they reduce its activity and increase the blood levels of the drugs that depend on it for elimination. This can lead to adverse effects or drug-drug interactions.
529:
are a class of antibiotics that are structurally related to the macrolides. They are used to treat respiratory tract infections caused by macrolide-resistant bacteria. Ketolides are especially effective, as they have two ribosomal binding sites.
1862:
Honein MA, Paulozzi LJ, Himelright IM, Lee B, Cragan JD, Patterson L, Correa A, Hall S, Erickson JD (1999). "Infantile hypertrophic pyloric stenosis after pertussis prophylaxis with erythromcyin: a case review and cohort study".
668:
Two other forms of acquired resistance include the production of drug-inactivating enzymes (esterases or kinases), as well as the production of active ATP-dependent efflux proteins that transport the drug outside of the cell.
186:, stemmed from chemically modifying erythromycin; these compounds were designed to be more easily absorbed and have fewer side-effects (erythromycin caused gastrointestinal side-effects in a significant proportion of users).
1006:
1546:
736:
in bile from the liver. This can lead to a buildup of the product in the system, thereby causing nausea. In infants the use of erythromycin has been associated with pyloric stenosis.
2253:
1054:
Tenson T, Lovmar M, Ehrenberg M (July 2003). "The mechanism of action of macrolides, lincosamides and streptogramin B reveals the nascent peptide exit path in the ribosome".
777:
have a 14-membered lactone ring, which is more prone to demethylation by CYP3A4 and subsequent formation of nitrosoalkenes, the reactive metabolites that cause MBI.
2074:"Macrolide - induced clinically relevant drug interactions with cytochrome P-450A (CYP) 3A4: an update focused on clarithromycin, azithromycin and dirithromycin"
2213:
2246:
473:
803:
as it may lead to colchicine toxicity. Symptoms of colchicine toxicity include gastrointestinal upset, fever, myalgia, pancytopenia, and organ failure.
559:
Fluoroketolides are a class of antibiotics that are structurally related to the ketolides. The fluoroketolides have three ribosomal interaction sites.
2239:
1019:
Drainas D, Kalpaxis DL, Coutsogeorgopoulos C (April 1987). "Inhibition of ribosomal peptidyltransferase by chloramphenicol. Kinetic studies".
1827:
SanFilippo A (April 1976). "Infantile hypertrophic pyloric stenosis related to ingestion of erythromycine estolate: A report of five cases".
1980:
Hansen MP, Scott AM, McCullough A, Thorning S, Aronson JK, Beller EM, Glasziou PP, Hoffmann TC, Clark J, Del Mar CB (18 January 2019).
358:
The macrolide antibiotics erythromycin, clarithromycin, and roxithromycin have proven to be an effective long-term treatment for the
1091:"Differential modulation of cytokine production by macrolides: interleukin-6 production is increased by spiramycin and erythromycin"
122:
In general, any macrocyclic lactone having greater than 8-membered rings are candidates for this class. The macrocycle may contain
377:
With macrolide therapy in DPB, great reduction in bronchiolar inflammation and damage is achieved through suppression of not only
220:), and some respiratory tract and soft-tissue infections. The antimicrobial spectrum of macrolides is slightly wider than that of
2231:
178:
in cases where patients were allergic to penicillin or had penicillin-resistant illnesses. Later macrolides developed, including
3049:
2202:
1511:
1191:
López-Boado YS, Rubin BK (June 2008). "Macrolides as immunomodulatory medications for the therapy of chronic lung diseases".
966:
885:
1708:"Mechanisms of Resistance to Macrolides and Lincosamides: Nature of the Resistance Elements and Their Clinical Implications"
1439:"Cruentaren A, a highly cytotoxic benzolactone from Myxobacteria is a novel selective inhibitor of mitochondrial F1-ATPases"
2029:
Zhang L, Xu X, Badawy S, Ihsan A, Liu Z, Xie C, Wang X, Tao Y (2020). "A Review: Effects of
Macrolides on CYP450 Enzymes".
277:
Macrolides can be administered in a variety of ways, including tablets, capsules, suspensions, injections and topically.
1228:"Macrolide activities beyond their antimicrobial effects: macrolides in diffuse panbronchiolitis and cystic fibrosis"
982:
3066:
2220:
746:
A Cochrane review showed gastrointestinal symptoms to be the most frequent adverse event reported in literature.
673:
2141:"Colchicine and macrolides: a cohort study of the risk of adverse outcomes associated with concomitant exposure"
792:
The difference in CYP3A4 inhibition by macrolides has clinical implications, for example, for patients who take
682:) in penicillin-sensitive patients; however, macrolide-resistant strains of GAS occur with moderate frequency.
240:
are usually susceptible to macrolides. Unlike penicillin, macrolides have been shown to be effective against
224:, and, therefore, macrolides are a common substitute for patients with a penicillin allergy. Beta-hemolytic
1594:"A neglected and emerging antimicrobial resistance gene encodes for a serine-dependent macrolide esterase"
2266:
291:
2754:
2658:
2309:
1009:
Pharmamotion. Author: Gary Kaiser. The
Community College of Baltimore County. Retrieved on July 31, 2009
821:
450:
Not approved in the US by FDA but approved in the other countries by respective national authorities:
2998:
629:
A variety of toxic macrolides produced by bacteria have been isolated and characterized, such as the
86:, may be attached. The lactone rings are usually 14-, 15-, or 16-membered. Macrolides belong to the
2517:
642:
363:
200:
158:
family) are excluded. Included are not only 12-16 membered macrocycles but also larger rings as in
2261:
3054:
729:
708:. This is because some macrolides (clarithromycin and erythromycin, not azithromycin) are potent
696:
106:
is also a macrolide and was originally developed as an antifungal, but has since been used as an
1007:
Protein synthesis inhibitors: macrolides mechanism of action animation. Classification of agents
2400:
732:; that is, the drug is absorbed in the gut and sent to the liver, only to be excreted into the
678:
392:
378:
242:
216:
205:
195:
107:
2123:"Life Threatening Colchicine Drug Interactions. Drug Interactions: Insights and Observations"
319:
259:
2707:
1748:
1605:
1450:
1319:
366:(DPB). The successful results of macrolides in DPB stems from controlling symptoms through
303:
210:
8:
3093:
2336:
1982:"Adverse events in people taking macrolide antibiotics versus placebo for any indication"
1503:
769:
The degree of MBI by macrolides depends on the size and structure of their lactone ring.
725:
606:
307:
295:
99:
1609:
1454:
1323:
2165:
2140:
2098:
2073:
2054:
2006:
1981:
1962:
1888:
1809:
1634:
1593:
1592:
Dhindwal P, Thompson C, Kos D, Planedin K, Jain R, Jelinski M, Ruzzini A (2023-02-21).
1522:
1487:
1170:
1032:
846:
2042:
1876:
1414:
1389:
1273:
1115:
1090:
1067:
2978:
2974:
2543:
2198:
2170:
2103:
2089:
2058:
2046:
2011:
1954:
1915:
1880:
1844:
1840:
1801:
1760:
1729:
1688:
1680:
1639:
1621:
1574:
1566:
1527:
1507:
1468:
1419:
1370:
1353:
Nguyen M, Chung EP (August 2005). "Telithromycin: the first ketolide antimicrobial".
1335:
1310:
Rezanka T, Sigler K (February 2008). "Biologically active compounds of semi-metals".
1292:
1249:
1208:
1162:
1145:
Keicho N, Kudoh S (2002). "Diffuse panbronchiolitis: role of macrolides in therapy".
1120:
1071:
1036:
962:
936:
918:
914:
881:
851:
646:
591:
2122:
1966:
1892:
1366:
1331:
3026:
2970:
2598:
2160:
2152:
2093:
2085:
2038:
2001:
1997:
1993:
1946:
1872:
1836:
1813:
1793:
1719:
1670:
1629:
1613:
1558:
1517:
1499:
1458:
1409:
1401:
1362:
1327:
1284:
1239:
1200:
1174:
1154:
1110:
1102:
1063:
1028:
910:
841:
833:
709:
654:
342:
299:
2286:
1463:
1438:
720:. Macrolides, mainly erythromycin and clarithromycin, also have a class effect of
3017:
3012:
2724:
2593:
2588:
1405:
721:
713:
315:
174:, which was first used in 1952. Erythromycin was widely used as a substitute to
64:
2282:
2278:
2274:
2270:
3060:
2877:
2807:
2792:
2553:
2438:
2426:
2304:
2156:
1204:
786:
770:
610:
489:
422:
338:
233:
183:
111:
44:
1950:
1675:
1658:
937:"Macrolide Antibiotics Comparison: Erythromycin, Clarithromycin, Azithromycin"
766:
as it requires the synthesis of new enzyme molecules to restore the activity.
704:(used for lowering cholesterol) is not advisable and can lead to debilitating
569: – the first and so far only fluoroketolide (not yet approved)
3087:
3022:
2966:
2958:
2920:
2910:
2882:
2862:
2852:
2847:
2812:
2797:
2734:
2729:
2653:
2618:
2406:
1684:
1625:
1570:
683:
662:
566:
548:
537:
505:
427:
367:
323:
251:
225:
54:
1617:
837:
3006:
3002:
2930:
2867:
2837:
2802:
2772:
2608:
2583:
2568:
2558:
2548:
2522:
2463:
2411:
2358:
2331:
2321:
2174:
2107:
2050:
2015:
1958:
1884:
1805:
1764:
1733:
1692:
1643:
1578:
1531:
1472:
1374:
1339:
1296:
1253:
1212:
1166:
1106:
1075:
855:
782:
778:
774:
658:
583:
478:
443:
433:
413:
311:
237:
179:
171:
131:
40:
25:
1919:
1848:
1423:
1124:
1040:
922:
396:, macrolide therapy still produces substantial anti-inflammatory results.
2992:
2938:
2915:
2842:
2827:
2822:
2739:
2626:
2603:
2578:
2573:
2563:
2538:
2382:
2353:
1244:
1227:
740:
630:
595:
543:
469:
464:
229:
75:
1547:"Mechanism and diversity of the erythromycin esterase family of enzymes"
822:"apamycin: An InhibiTOR of Aging Emerges From the Soil of Easter Island"
594:
or immunomodulators, are also macrolides. They have similar activity to
2988:
2948:
2943:
2892:
2872:
2857:
2832:
2787:
2782:
2716:
2687:
2667:
2487:
2482:
2473:
2468:
2453:
2448:
2396:
2348:
2262:
1288:
1158:
957:
Giguere S, Prescott JF, Baggot JD, Walker RD, Dowling PM, eds. (2006).
800:
618:
579:
483:
454:
382:
359:
255:
247:
221:
175:
159:
95:
91:
87:
83:
68:
2139:
Tan MS, Gomez-Lumbreras A, Villa-Zapata L, Malone DC (December 2022).
1797:
1659:"Structural Basis for Kinase-Mediated Macrolide Antibiotic Resistance"
1562:
2817:
2777:
2697:
2692:
2682:
2677:
2672:
2503:
2458:
2421:
2416:
2387:
2377:
2367:
587:
515:
459:
439:
386:
155:
103:
79:
2138:
2902:
2372:
2343:
1724:
1707:
1089:
Bailly S, Pocidalo JJ, Fay M, Gougerot-Pocidalo MA (October 1991).
733:
705:
614:
526:
499:
334:
270:
139:
1784:
Sathasivam S, Lecky B (November 2008). "Statin induced myopathy".
1088:
2887:
1018:
901:
Klein JO (April 1997). "History of macrolide use in pediatrics".
762:
701:
653:-mediated or chromosomal, i.e., through mutation, and results in
650:
495:
143:
135:
71:
29:
21:
1657:
Fong DH, Burk DL, Blanchet J, Yan AY, Berghuis AM (2017-05-02).
649:
bacterial ribosomal RNA. This acquired resistance can be either
645:
to macrolides occurs by post-transcriptional methylation of the
50:
2984:
793:
754:
717:
700:
article highlights that the combination of some macrolides and
417:
371:
322:. Another potential mechanism is premature dissociation of the
151:
147:
2120:
1979:
799:
Macrolides, including azithromycin, should not be taken with
486: – approved in the EU, and in other countries
194:
Antibiotic macrolides are used to treat infections caused by
127:
123:
33:
1390:"Chemistry and biology of the polyene macrolide antibiotics"
819:
1935:
1861:
1591:
956:
370:(adjusting the immune response), with the added benefit of
329:
Macrolide antibiotics bind reversibly to the P site on the
2644:
2295:
1544:
330:
2214:"Antibacterial Agents; Structure Activity Relationships"
416: – unique; does not extensively inhibit
2195:
Macrolide antibiotics: chemistry, biology, and practice
1906:
Hautekeete ML (1995). "Hepatotoxicity of antibiotics".
1545:
Morar M, Pengelly K, Koteva K, Wright GD (2012-02-28).
1436:
878:
Macrolide
Antibiotics: Chemistry, Biology, and Practice
540: – the first and only approved ketolide
430: – discontinued but was US FDA approved
345:, and thus are transported into the site of infection.
1749:"Diagnosis and Treatment of Streptococcal Pharyngitis"
1053:
1656:
1437:Kunze B, Sasse F, Wieczorek H, Huss M (July 2007).
146:rings are excluded, in order to differentiate from
2028:
672:Azithromycin has been used to treat strep throat (
3085:
1190:
306:, and they are thought to do this by preventing
90:class of natural products. Some macrolides have
1783:
1705:
1598:Proceedings of the National Academy of Sciences
1387:
1269:
1267:
1265:
1263:
621:is another example of an antifungal macrolide.
1002:
1000:
341:. Macrolides are actively concentrated within
2247:
1309:
2132:
2065:
2022:
1303:
1260:
959:Antimicrobial Therapy in Veterinary Medicine
573:
310:from adding the growing peptide attached to
130:nitrogen (but should be differentiated from
1485:
1352:
1144:
997:
492: – used in Italy and Turkey
353:
2715:
2254:
2240:
1905:
1826:
820:Arriola Apelo SI, Lamming DW (July 2016).
2164:
2097:
2005:
1723:
1674:
1633:
1521:
1462:
1413:
1243:
1232:The Journal of Antimicrobial Chemotherapy
1114:
845:
110:and is being investigated as a potential
2197:(2nd ed.). Boston: Academic Press.
2121:John R. Horn, Philip D. Hansten (2006).
2071:
1186:
1184:
1147:American Journal of Respiratory Medicine
903:The Pediatric Infectious Disease Journal
761:Macrolides have cyclic structure with a
739:Some macrolides are also known to cause
511:Not approved as a drug for medical use:
438:
404:
49:
39:
20:
1986:Cochrane Database of Systematic Reviews
1225:
3086:
1140:
1138:
1136:
1134:
686:is another option for these patients.
280:
2235:
2192:
1931:
1929:
1746:
1488:"Mechanisms of Antibiotic Resistance"
1219:
1181:
1095:Antimicrobial Agents and Chemotherapy
1047:
900:
875:
674:Group A streptococcal (GAS) infection
314:to the next amino acid (similarly to
2211:
1706:Roland Leclercq (15 February 2002).
1504:10.1128/microbiolspec.VMBF-0016-2015
617:etc., are a subgroup of macrolides.
1131:
985:. Food and Drug Administration (US)
624:
601:
348:
170:The first macrolide discovered was
13:
2185:
1926:
1486:Munita JM, Arias CA (April 2016).
1033:10.1111/j.1432-1033.1987.tb10991.x
554:
502: – used in animals
337:. This action is considered to be
14:
3105:
2043:10.2174/1389200221666200817113920
961:(4th ed.). Wiley-Blackwell.
2090:10.1046/j.1365-2125.2000.00261.x
1908:Acta Gastro-Enterologica Belgica
1388:Hamilton-Miller JM (June 1973).
1021:European Journal of Biochemistry
915:10.1097/00006454-199704000-00025
880:(2nd ed.). Academic Press.
285:
2114:
1973:
1899:
1855:
1820:
1777:
1740:
1699:
1650:
1585:
1538:
1479:
1430:
1381:
1367:10.1016/j.clinthera.2005.08.009
1346:
1332:10.1016/j.phytochem.2007.09.018
1193:Current Opinion in Pharmacology
1082:
749:
689:
362:, Asian-prevalent lung disease
320:bacterial ribosomal translation
154:instead of lactones (as in the
2755:transpeptidation/translocation
1998:10.1002/14651858.CD011825.pub2
1939:European Journal of Pediatrics
1012:
975:
950:
929:
894:
869:
813:
665:(an MLS-resistant phenotype).
1:
2219:. p. 143. Archived from
1877:10.1016/S0140-6736(99)10073-4
1464:10.1016/j.febslet.2007.06.069
1068:10.1016/S0022-2836(03)00662-4
826:J Gerontol A Biol Sci Med Sci
806:
636:
117:
2072:Westphal JF (October 2000).
1841:10.1016/0022-3468(76)90283-9
1829:Journal of Pediatric Surgery
1712:Clinical Infectious Diseases
1406:10.1128/br.37.3.166-196.1973
1277:Basic Clin Pharmacol Toxicol
1056:Journal of Molecular Biology
521:
292:protein synthesis inhibitors
28:. The macrolide ring is the
7:
399:
10:
3110:
2157:10.1007/s00296-022-05201-5
1205:10.1016/j.coph.2008.01.010
165:
74:ring to which one or more
3044:
2999:Quinupristin/dalfopristin
2957:
2929:
2901:
2763:
2752:
2706:
2652:
2643:
2617:
2531:
2516:
2496:
2435:
2318:
2303:
2294:
2267:inhibit protein synthesis
1951:10.1007/s00431-018-3287-7
1753:American Family Physician
1676:10.1016/j.str.2017.03.007
574:Non-antibiotic macrolides
562:Fluoroketolides include:
385:activity and obstructive
333:subunit of the bacterial
98:activity and are used as
16:Class of natural products
2518:Tetracycline antibiotics
1226:Schultz MJ (July 2004).
716:system, particularly of
364:diffuse panbronchiolitis
354:Diffuse panbronchiolitis
318:) as well as inhibiting
201:Streptococcus pneumoniae
1618:10.1073/pnas.2219827120
1394:Bacteriological Reviews
730:enterohepatic recycling
697:British Medical Journal
381:proliferation but also
189:
1107:10.1128/AAC.35.10.2016
679:Streptococcus pyogenes
447:
393:Pseudomonas aeruginosa
379:neutrophil granulocyte
243:Legionella pneumophila
217:Haemophilus influenzae
206:Gram-negative bacteria
196:Gram-positive bacteria
108:immunosuppressant drug
63:are a class of mostly
57:
47:
37:
1492:Microbiology Spectrum
1355:Clinical Therapeutics
876:Omura S, ed. (2002).
838:10.1093/gerona/glw090
728:. Macrolides exhibit
641:The primary means of
442:
405:Antibiotic macrolides
112:longevity therapeutic
53:
43:
24:
2708:Peptidyl transferase
724:, which can lead to
643:bacterial resistance
607:Polyene antimycotics
590:, which are used as
304:protein biosynthesis
211:Bordetella pertussis
100:pharmaceutical drugs
2337:Dihydrostreptomycin
2078:Br J Clin Pharmacol
1610:2023PNAS..12019827D
1455:2007FEBSL.581.3523K
1324:2008PChem..69..585R
726:torsades de pointes
533:Ketolides include:
474:midecamycin acetate
326:from the ribosome.
308:peptidyltransferase
296:mechanism of action
281:Mechanism of action
3071:Never to phase III
1604:(8): e2219827120.
1289:10.1111/bcpt.13343
1245:10.1093/jac/dkh309
1159:10.1007/BF03256601
592:immunosuppressants
448:
58:
48:
38:
3081:
3080:
3040:
3039:
3036:
3035:
2748:
2747:
2639:
2638:
2635:
2634:
2544:Chlortetracycline
2512:
2511:
2204:978-0-12-526451-8
2151:(12): 2253–2259.
1798:10.1136/bmj.a2286
1747:Choby BA (2009).
1669:(5): 750–761.e5.
1563:10.1021/bi201790u
1513:978-1-55581-927-9
968:978-0-8138-0656-3
887:978-0-12-526451-8
409:US FDA-approved:
298:of macrolides is
269:to be used on non
3101:
2761:
2760:
2713:
2712:
2650:
2649:
2599:Rolitetracycline
2529:
2528:
2316:
2315:
2301:
2300:
2256:
2249:
2242:
2233:
2232:
2227:
2225:
2218:
2208:
2193:Ōmura S (2002).
2179:
2178:
2168:
2136:
2130:
2129:
2127:
2118:
2112:
2111:
2101:
2069:
2063:
2062:
2026:
2020:
2019:
2009:
1977:
1971:
1970:
1933:
1924:
1923:
1903:
1897:
1896:
1871:(9196): 2101–5.
1859:
1853:
1852:
1824:
1818:
1817:
1781:
1775:
1774:
1772:
1771:
1744:
1738:
1737:
1727:
1703:
1697:
1696:
1678:
1654:
1648:
1647:
1637:
1589:
1583:
1582:
1557:(8): 1740–1751.
1542:
1536:
1535:
1525:
1483:
1477:
1476:
1466:
1434:
1428:
1427:
1417:
1385:
1379:
1378:
1350:
1344:
1343:
1307:
1301:
1300:
1271:
1258:
1257:
1247:
1223:
1217:
1216:
1188:
1179:
1178:
1142:
1129:
1128:
1118:
1086:
1080:
1079:
1051:
1045:
1044:
1016:
1010:
1004:
995:
994:
992:
990:
979:
973:
972:
954:
948:
947:
945:
943:
933:
927:
926:
898:
892:
891:
873:
867:
866:
864:
862:
849:
817:
655:cross-resistance
625:Toxic macrolides
602:Antifungal drugs
368:immunomodulation
349:Immunomodulation
65:natural products
36:) at upper left.
3109:
3108:
3104:
3103:
3102:
3100:
3099:
3098:
3084:
3083:
3082:
3077:
3076:
3061:Clinical trials
3032:
3018:Streptogramin B
3013:Streptogramin A
2953:
2925:
2897:
2744:
2725:Chloramphenicol
2702:
2656:
2631:
2613:
2594:Penimepicycline
2589:Oxytetracycline
2520:
2508:
2492:
2431:
2307:
2305:Aminoglycosides
2290:
2260:
2230:
2223:
2216:
2205:
2188:
2186:Further reading
2183:
2182:
2137:
2133:
2125:
2119:
2115:
2070:
2066:
2037:(12): 928–937.
2031:Curr Drug Metab
2027:
2023:
1992:(1): CD011825.
1978:
1974:
1934:
1927:
1904:
1900:
1860:
1856:
1825:
1821:
1782:
1778:
1769:
1767:
1745:
1741:
1704:
1700:
1655:
1651:
1590:
1586:
1543:
1539:
1514:
1484:
1480:
1435:
1431:
1386:
1382:
1351:
1347:
1308:
1304:
1272:
1261:
1224:
1220:
1189:
1182:
1143:
1132:
1087:
1083:
1052:
1048:
1017:
1013:
1005:
998:
988:
986:
981:
980:
976:
969:
955:
951:
941:
939:
935:
934:
930:
899:
895:
888:
874:
870:
860:
858:
818:
814:
809:
752:
722:QT prolongation
714:cytochrome P450
692:
657:to macrolides,
639:
627:
604:
576:
557:
555:Fluoroketolides
524:
407:
402:
356:
351:
316:chloramphenicol
290:Macrolides are
288:
283:
265:Macrolides are
192:
168:
120:
17:
12:
11:
5:
3107:
3097:
3096:
3079:
3078:
3075:
3074:
3073:
3072:
3069:
3058:
3052:
3046:
3045:
3042:
3041:
3038:
3037:
3034:
3033:
3031:
3030:
3020:
3015:
3010:
2996:
2982:
2963:
2961:
2959:Streptogramins
2955:
2954:
2952:
2951:
2946:
2941:
2935:
2933:
2927:
2926:
2924:
2923:
2918:
2913:
2907:
2905:
2899:
2898:
2896:
2895:
2890:
2885:
2880:
2878:Troleandomycin
2875:
2870:
2865:
2860:
2855:
2850:
2845:
2840:
2835:
2830:
2825:
2820:
2815:
2810:
2808:Flurithromycin
2805:
2800:
2795:
2793:Clarithromycin
2790:
2785:
2780:
2775:
2769:
2767:
2758:
2750:
2749:
2746:
2745:
2743:
2742:
2737:
2732:
2727:
2721:
2719:
2710:
2704:
2703:
2701:
2700:
2695:
2690:
2685:
2680:
2675:
2670:
2664:
2662:
2647:
2641:
2640:
2637:
2636:
2633:
2632:
2630:
2629:
2623:
2621:
2619:Glycylcyclines
2615:
2614:
2612:
2611:
2606:
2601:
2596:
2591:
2586:
2581:
2576:
2571:
2566:
2561:
2556:
2554:Demeclocycline
2551:
2546:
2541:
2535:
2533:
2526:
2514:
2513:
2510:
2509:
2507:
2506:
2500:
2498:
2494:
2493:
2491:
2490:
2485:
2479:
2478:
2477:
2476:
2471:
2466:
2461:
2456:
2445:
2443:
2439:Micromonospora
2433:
2432:
2430:
2429:
2427:Nourseothricin
2424:
2419:
2414:
2409:
2404:
2393:
2392:
2391:
2390:
2385:
2380:
2375:
2364:
2363:
2362:
2361:
2356:
2351:
2340:
2339:
2334:
2328:
2326:
2313:
2298:
2292:
2291:
2263:Antibacterials
2259:
2258:
2251:
2244:
2236:
2229:
2228:
2226:on 2006-03-04.
2209:
2203:
2189:
2187:
2184:
2181:
2180:
2131:
2113:
2064:
2021:
1972:
1945:(3): 301–314.
1925:
1914:(3–4): 290–6.
1898:
1854:
1819:
1776:
1759:(5): 383–390.
1739:
1725:10.1086/324626
1718:(4): 482–492.
1698:
1649:
1584:
1537:
1512:
1498:(2): 481–511.
1478:
1449:(18): 3523–7.
1429:
1380:
1361:(8): 1144–63.
1345:
1318:(3): 585–606.
1312:Phytochemistry
1302:
1283:(4): 307–317.
1259:
1218:
1180:
1130:
1101:(10): 2016–9.
1081:
1062:(5): 1005–14.
1046:
1011:
996:
974:
967:
949:
928:
893:
886:
868:
811:
810:
808:
805:
787:clarithromycin
771:Clarithromycin
751:
748:
691:
688:
663:streptogramins
638:
635:
626:
623:
611:amphotericin B
603:
600:
575:
572:
571:
570:
556:
553:
552:
551:
546:
541:
523:
520:
519:
518:
509:
508:
503:
493:
490:Troleandomycin
487:
481:
476:
467:
462:
457:
437:
436:
431:
425:
423:Clarithromycin
420:
406:
403:
401:
398:
374:requirements.
355:
352:
350:
347:
339:bacteriostatic
287:
284:
282:
279:
204:) and limited
191:
188:
184:clarithromycin
167:
164:
119:
116:
45:Clarithromycin
15:
9:
6:
4:
3:
2:
3106:
3095:
3092:
3091:
3089:
3070:
3068:
3065:
3064:
3062:
3059:
3056:
3053:
3051:
3048:
3047:
3043:
3028:
3024:
3023:Virginiamycin
3021:
3019:
3016:
3014:
3011:
3008:
3004:
3000:
2997:
2994:
2990:
2986:
2983:
2980:
2976:
2972:
2968:
2967:Pristinamycin
2965:
2964:
2962:
2960:
2956:
2950:
2947:
2945:
2942:
2940:
2937:
2936:
2934:
2932:
2928:
2922:
2921:Solithromycin
2919:
2917:
2914:
2912:
2911:Telithromycin
2909:
2908:
2906:
2904:
2900:
2894:
2891:
2889:
2886:
2884:
2883:Tulathromycin
2881:
2879:
2876:
2874:
2871:
2869:
2866:
2864:
2863:Telithromycin
2861:
2859:
2856:
2854:
2853:Solithromycin
2851:
2849:
2848:Roxithromycin
2846:
2844:
2841:
2839:
2836:
2834:
2831:
2829:
2826:
2824:
2821:
2819:
2816:
2814:
2813:Gamithromycin
2811:
2809:
2806:
2804:
2801:
2799:
2798:Dirithromycin
2796:
2794:
2791:
2789:
2786:
2784:
2781:
2779:
2776:
2774:
2771:
2770:
2768:
2766:
2762:
2759:
2756:
2751:
2741:
2738:
2736:
2735:Thiamphenicol
2733:
2731:
2730:Azidamfenicol
2728:
2726:
2723:
2722:
2720:
2718:
2714:
2711:
2709:
2705:
2699:
2696:
2694:
2691:
2689:
2686:
2684:
2681:
2679:
2676:
2674:
2671:
2669:
2666:
2665:
2663:
2660:
2655:
2654:Oxazolidinone
2651:
2648:
2646:
2642:
2628:
2625:
2624:
2622:
2620:
2616:
2610:
2607:
2605:
2602:
2600:
2597:
2595:
2592:
2590:
2587:
2585:
2582:
2580:
2577:
2575:
2572:
2570:
2567:
2565:
2562:
2560:
2557:
2555:
2552:
2550:
2547:
2545:
2542:
2540:
2537:
2536:
2534:
2532:Tetracyclines
2530:
2527:
2524:
2519:
2515:
2505:
2502:
2501:
2499:
2495:
2489:
2486:
2484:
2481:
2480:
2475:
2472:
2470:
2467:
2465:
2462:
2460:
2457:
2455:
2452:
2451:
2450:
2447:
2446:
2444:
2441:
2440:
2434:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2407:Spectinomycin
2405:
2402:
2398:
2395:
2394:
2389:
2386:
2384:
2381:
2379:
2376:
2374:
2371:
2370:
2369:
2366:
2365:
2360:
2357:
2355:
2352:
2350:
2347:
2346:
2345:
2342:
2341:
2338:
2335:
2333:
2330:
2329:
2327:
2324:
2323:
2317:
2314:
2311:
2306:
2302:
2299:
2297:
2293:
2288:
2284:
2280:
2276:
2272:
2268:
2264:
2257:
2252:
2250:
2245:
2243:
2238:
2237:
2234:
2222:
2215:
2210:
2206:
2200:
2196:
2191:
2190:
2176:
2172:
2167:
2162:
2158:
2154:
2150:
2146:
2145:Rheumatol Int
2142:
2135:
2124:
2117:
2109:
2105:
2100:
2095:
2091:
2087:
2084:(4): 285–95.
2083:
2079:
2075:
2068:
2060:
2056:
2052:
2048:
2044:
2040:
2036:
2032:
2025:
2017:
2013:
2008:
2003:
1999:
1995:
1991:
1987:
1983:
1976:
1968:
1964:
1960:
1956:
1952:
1948:
1944:
1940:
1932:
1930:
1921:
1917:
1913:
1909:
1902:
1894:
1890:
1886:
1882:
1878:
1874:
1870:
1866:
1858:
1850:
1846:
1842:
1838:
1835:(2): 177–80.
1834:
1830:
1823:
1815:
1811:
1807:
1803:
1799:
1795:
1791:
1787:
1780:
1766:
1762:
1758:
1754:
1750:
1743:
1735:
1731:
1726:
1721:
1717:
1713:
1709:
1702:
1694:
1690:
1686:
1682:
1677:
1672:
1668:
1664:
1660:
1653:
1645:
1641:
1636:
1631:
1627:
1623:
1619:
1615:
1611:
1607:
1603:
1599:
1595:
1588:
1580:
1576:
1572:
1568:
1564:
1560:
1556:
1552:
1548:
1541:
1533:
1529:
1524:
1519:
1515:
1509:
1505:
1501:
1497:
1493:
1489:
1482:
1474:
1470:
1465:
1460:
1456:
1452:
1448:
1444:
1440:
1433:
1425:
1421:
1416:
1411:
1407:
1403:
1400:(2): 166–96.
1399:
1395:
1391:
1384:
1376:
1372:
1368:
1364:
1360:
1356:
1349:
1341:
1337:
1333:
1329:
1325:
1321:
1317:
1313:
1306:
1298:
1294:
1290:
1286:
1282:
1278:
1270:
1268:
1266:
1264:
1255:
1251:
1246:
1241:
1237:
1233:
1229:
1222:
1214:
1210:
1206:
1202:
1199:(3): 286–91.
1198:
1194:
1187:
1185:
1176:
1172:
1168:
1164:
1160:
1156:
1153:(2): 119–31.
1152:
1148:
1141:
1139:
1137:
1135:
1126:
1122:
1117:
1112:
1108:
1104:
1100:
1096:
1092:
1085:
1077:
1073:
1069:
1065:
1061:
1057:
1050:
1042:
1038:
1034:
1030:
1026:
1022:
1015:
1008:
1003:
1001:
984:
978:
970:
964:
960:
953:
938:
932:
924:
920:
916:
912:
909:(4): 427–31.
908:
904:
897:
889:
883:
879:
872:
857:
853:
848:
843:
839:
835:
831:
827:
823:
816:
812:
804:
802:
797:
795:
790:
788:
784:
780:
776:
772:
767:
764:
759:
756:
747:
744:
742:
737:
735:
731:
727:
723:
719:
715:
711:
707:
703:
699:
698:
687:
685:
684:Cephalosporin
681:
680:
675:
670:
666:
664:
660:
656:
652:
648:
644:
634:
632:
622:
620:
616:
612:
608:
599:
597:
593:
589:
585:
581:
568:
567:Solithromycin
565:
564:
563:
560:
550:
549:Solithromycin
547:
545:
542:
539:
538:Telithromycin
536:
535:
534:
531:
528:
517:
514:
513:
512:
507:
506:Roxithromycin
504:
501:
497:
494:
491:
488:
485:
482:
480:
477:
475:
471:
468:
466:
463:
461:
458:
456:
453:
452:
451:
445:
441:
435:
432:
429:
428:Dirithromycin
426:
424:
421:
419:
415:
412:
411:
410:
397:
395:
394:
388:
384:
380:
375:
373:
369:
365:
361:
346:
344:
340:
336:
332:
327:
325:
324:peptidyl-tRNA
321:
317:
313:
309:
305:
302:of bacterial
301:
297:
293:
286:Antibacterial
278:
275:
272:
268:
263:
261:
257:
253:
252:Mycobacterium
249:
245:
244:
239:
235:
234:staphylococci
231:
227:
223:
219:
218:
213:
212:
207:
203:
202:
197:
187:
185:
181:
177:
173:
163:
161:
157:
153:
149:
145:
141:
137:
133:
132:cyclopeptides
129:
125:
115:
113:
109:
105:
101:
97:
93:
89:
85:
81:
77:
73:
70:
67:with a large
66:
62:
56:
55:Roxithromycin
52:
46:
42:
35:
31:
27:
23:
19:
3007:Quinupristin
3003:Dalfopristin
2931:Lincosamides
2868:Tildipirosin
2838:Oleandomycin
2803:Erythromycin
2773:Azithromycin
2764:
2609:Tetracycline
2584:Omadacycline
2569:Meclocycline
2559:Eravacycline
2549:Clomocycline
2464:Micronomicin
2437:
2412:Hygromycin B
2401:+loteprednol
2359:Ribostamycin
2332:Streptomycin
2322:Streptomyces
2320:
2221:the original
2212:Bryskier A.
2194:
2148:
2144:
2134:
2116:
2081:
2077:
2067:
2034:
2030:
2024:
1989:
1985:
1975:
1942:
1938:
1911:
1907:
1901:
1868:
1864:
1857:
1832:
1828:
1822:
1789:
1785:
1779:
1768:. Retrieved
1756:
1752:
1742:
1715:
1711:
1701:
1666:
1662:
1652:
1601:
1597:
1587:
1554:
1551:Biochemistry
1550:
1540:
1495:
1491:
1481:
1446:
1443:FEBS Letters
1442:
1432:
1397:
1393:
1383:
1358:
1354:
1348:
1315:
1311:
1305:
1280:
1276:
1235:
1231:
1221:
1196:
1192:
1150:
1146:
1098:
1094:
1084:
1059:
1055:
1049:
1024:
1020:
1014:
987:. Retrieved
977:
958:
952:
940:. Retrieved
931:
906:
902:
896:
877:
871:
859:. Retrieved
832:(7): 841–9.
829:
825:
815:
798:
791:
783:erythromycin
779:Azithromycin
775:erythromycin
768:
760:
753:
750:Interactions
745:
738:
695:
693:
690:Side-effects
677:
671:
667:
659:lincosamides
640:
631:mycolactones
628:
605:
584:pimecrolimus
577:
561:
558:
532:
525:
510:
479:Oleandomycin
455:Carbomycin A
449:
444:Azithromycin
434:Erythromycin
414:Azithromycin
408:
391:
376:
357:
328:
289:
276:
266:
264:
241:
226:streptococci
215:
209:
199:
193:
180:azithromycin
172:erythromycin
169:
121:
76:deoxy sugars
60:
59:
26:Erythromycin
18:
3057:from market
2993:Linopristin
2939:Clindamycin
2916:Cethromycin
2843:Rokitamycin
2828:Midecamycin
2823:Kitasamycin
2740:Florfenicol
2717:Amphenicols
2661:inhibitors)
2627:Tigecycline
2604:Sarecycline
2579:Minocycline
2574:Metacycline
2564:Lymecycline
2539:Doxycycline
2383:Bekanamycin
2354:Paromomycin
2312:inhibitors)
1238:(1): 21–8.
1027:(1): 53–8.
741:cholestasis
596:ciclosporin
544:Cethromycin
470:Midecamycin
465:Kitasamycin
238:enterococci
230:pneumococci
138:ring, or a
69:macrocyclic
3094:Macrolides
2989:Flopristin
2949:Pirlimycin
2944:Lincomycin
2893:Tylvalosin
2873:Tilmicosin
2858:Spiramycin
2833:Miocamycin
2788:Carrimycin
2783:Carbomycin
2765:Macrolides
2688:Ranbezolid
2668:Eperezolid
2659:initiation
2488:Astromicin
2483:Verdamicin
2474:Isepamicin
2469:Plazomicin
2454:Netilmicin
2449:Gentamicin
2397:Tobramycin
2349:Framycetin
2310:initiation
1770:2024-01-25
983:"DailyMed"
807:References
801:colchicine
710:inhibitors
676:caused by
637:Resistance
619:Cruentaren
609:, such as
580:tacrolimus
578:The drugs
484:Spiramycin
390:bacterium
387:secretions
383:lymphocyte
360:idiopathic
343:leukocytes
300:inhibition
256:Rickettsia
248:Mycoplasma
222:penicillin
176:penicillin
160:tacrolimus
126:nitrogen,
118:Definition
96:antifungal
92:antibiotic
88:polyketide
84:desosamine
78:, usually
61:Macrolides
3067:Phase III
3055:Withdrawn
2903:Ketolides
2818:Josamycin
2778:Boromycin
2698:Tedizolid
2693:Sutezolid
2683:Radezolid
2678:Posizolid
2673:Linezolid
2504:Butirosin
2459:Sisomicin
2422:Apramycin
2417:Totomycin
2388:Dibekacin
2378:Arbekacin
2368:Kanamycin
2059:221162650
1792:: a2286.
1685:1878-4186
1663:Structure
1626:0027-8424
1571:1520-4995
588:sirolimus
527:Ketolides
522:Ketolides
516:Boromycin
460:Josamycin
260:Chlamydia
156:ansamycin
104:Rapamycin
80:cladinose
3088:Category
2525:binding)
2436:-micin (
2373:Amikacin
2344:Neomycin
2319:-mycin (
2175:36104598
2108:11012550
2051:32807049
2016:30656650
1967:53711818
1959:30470884
1893:24160212
1885:10609814
1806:18988647
1765:19275067
1734:11797175
1693:28416110
1644:36791107
1579:22303981
1532:27227291
1473:17624334
1375:16199242
1340:17991498
1297:31628882
1254:15190022
1213:18339582
1167:14720066
1076:12860123
989:22 March
942:22 March
856:27208895
734:duodenum
706:myopathy
615:nystatin
500:tylocine
446:capsules
400:Examples
372:low-dose
335:ribosome
271:ruminant
140:thiazole
32:(cyclic
2888:Tylosin
2166:9473467
2099:2015000
2007:6353052
1920:7491842
1849:1263054
1814:3239804
1635:9974460
1606:Bibcode
1523:4888801
1451:Bibcode
1424:4578757
1320:Bibcode
1175:7634677
1125:1759822
1041:3549307
923:9109154
861:17 July
847:4906330
794:statins
763:lactone
712:of the
702:statins
694:A 2008
651:plasmid
496:Tylosin
254:, some
208:(e.g.,
198:(e.g.,
166:History
152:lactams
150:. Also
148:tannins
144:Benzene
136:oxazole
72:lactone
30:lactone
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2985:NXL103
2287:QJ01XQ
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2163:
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718:CYP3A4
661:, and
586:, and
418:CYP3A4
294:. The
258:, and
236:, and
142:ring.
134:), an
2753:MLS (
2497:other
2265:that
2224:(PDF)
2217:(PDF)
2126:(PDF)
2055:S2CID
1963:S2CID
1889:S2CID
1810:S2CID
1171:S2CID
128:amide
124:amino
34:ester
2523:tRNA
2283:J01G
2279:J01F
2275:J01B
2271:J01A
2199:ISBN
2171:PMID
2104:PMID
2047:PMID
2012:PMID
1955:PMID
1916:PMID
1881:PMID
1845:PMID
1802:PMID
1761:PMID
1730:PMID
1689:PMID
1681:ISSN
1640:PMID
1622:ISSN
1575:PMID
1567:ISSN
1528:PMID
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1420:PMID
1371:PMID
1336:PMID
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1250:PMID
1209:PMID
1163:PMID
1121:PMID
1072:PMID
1037:PMID
991:2017
963:ISBN
944:2017
919:PMID
882:ISBN
863:2022
852:PMID
785:and
773:and
312:tRNA
190:Uses
182:and
82:and
2979:IIB
2975:IIA
2645:50S
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2161:PMC
2153:doi
2094:PMC
2086:doi
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2002:PMC
1994:doi
1947:doi
1943:178
1873:doi
1869:354
1837:doi
1794:doi
1790:337
1786:BMJ
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1671:doi
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1614:doi
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