807:, 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.
52:
792:, 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
451:
33:
62:
800:, 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.
754:, 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.
776:
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,
400:
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
1285:
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".
284:
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.
1947:
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".
768:
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.
540:
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.
1873:
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".
679:
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.
197:, 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).
1017:
1557:
747:
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.
2264:
1065:
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".
788:
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.
2085:"Macrolide - induced clinically relevant drug interactions with cytochrome P-450A (CYP) 3A4: an update focused on clarithromycin, azithromycin and dirithromycin"
2224:
2257:
484:
814:
as it may lead to colchicine toxicity. Symptoms of colchicine toxicity include gastrointestinal upset, fever, myalgia, pancytopenia, and organ failure.
570:
Fluoroketolides are a class of antibiotics that are structurally related to the ketolides. The fluoroketolides have three ribosomal interaction sites.
2250:
1030:
Drainas D, Kalpaxis DL, Coutsogeorgopoulos C (April 1987). "Inhibition of ribosomal peptidyltransferase by chloramphenicol. Kinetic studies".
1838:
SanFilippo A (April 1976). "Infantile hypertrophic pyloric stenosis related to ingestion of erythromycine estolate: A report of five cases".
1991:
Hansen MP, Scott AM, McCullough A, Thorning S, Aronson JK, Beller EM, Glasziou PP, Hoffmann TC, Clark J, Del Mar CB (18 January 2019).
369:
The macrolide antibiotics erythromycin, clarithromycin, and roxithromycin have proven to be an effective long-term treatment for the
1102:"Differential modulation of cytokine production by macrolides: interleukin-6 production is increased by spiramycin and erythromycin"
133:
In general, any macrocyclic lactone having greater than 8-membered rings are candidates for this class. The macrocycle may contain
388:
With macrolide therapy in DPB, great reduction in bronchiolar inflammation and damage is achieved through suppression of not only
231:), and some respiratory tract and soft-tissue infections. The antimicrobial spectrum of macrolides is slightly wider than that of
2242:
189:
in cases where patients were allergic to penicillin or had penicillin-resistant illnesses. Later macrolides developed, including
3060:
2213:
1522:
1202:
López-Boado YS, Rubin BK (June 2008). "Macrolides as immunomodulatory medications for the therapy of chronic lung diseases".
977:
896:
1719:"Mechanisms of Resistance to Macrolides and Lincosamides: Nature of the Resistance Elements and Their Clinical Implications"
1450:"Cruentaren A, a highly cytotoxic benzolactone from Myxobacteria is a novel selective inhibitor of mitochondrial F1-ATPases"
2040:
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".
288:
Macrolides can be administered in a variety of ways, including tablets, capsules, suspensions, injections and topically.
1239:"Macrolide activities beyond their antimicrobial effects: macrolides in diffuse panbronchiolitis and cystic fibrosis"
993:
3077:
2231:
757:
A Cochrane review showed gastrointestinal symptoms to be the most frequent adverse event reported in literature.
684:
2152:"Colchicine and macrolides: a cohort study of the risk of adverse outcomes associated with concomitant exposure"
803:
The difference in CYP3A4 inhibition by macrolides has clinical implications, for example, for patients who take
693:) in penicillin-sensitive patients; however, macrolide-resistant strains of GAS occur with moderate frequency.
251:
are usually susceptible to macrolides. Unlike penicillin, macrolides have been shown to be effective against
235:, and, therefore, macrolides are a common substitute for patients with a penicillin allergy. Beta-hemolytic
1605:"A neglected and emerging antimicrobial resistance gene encodes for a serine-dependent macrolide esterase"
2277:
302:
2765:
2669:
2320:
1020:
Pharmamotion. Author: Gary Kaiser. The
Community College of Baltimore County. Retrieved on July 31, 2009
17:
832:
461:
Not approved in the US by FDA but approved in the other countries by respective national authorities:
3009:
640:
A variety of toxic macrolides produced by bacteria have been isolated and characterized, such as the
97:, may be attached. The lactone rings are usually 14-, 15-, or 16-membered. Macrolides belong to the
2528:
653:
374:
211:
169:
family) are excluded. Included are not only 12-16 membered macrocycles but also larger rings as in
2272:
3065:
740:
719:. This is because some macrolides (clarithromycin and erythromycin, not azithromycin) are potent
707:
117:
is also a macrolide and was originally developed as an antifungal, but has since been used as an
1018:
Protein synthesis inhibitors: macrolides mechanism of action animation. Classification of agents
2411:
743:; that is, the drug is absorbed in the gut and sent to the liver, only to be excreted into the
689:
403:
389:
253:
227:
216:
206:
118:
2134:"Life Threatening Colchicine Drug Interactions. Drug Interactions: Insights and Observations"
330:
270:
2718:
1759:
1616:
1461:
1330:
377:(DPB). The successful results of macrolides in DPB stems from controlling symptoms through
314:
221:
8:
3104:
2347:
1993:"Adverse events in people taking macrolide antibiotics versus placebo for any indication"
1514:
780:
The degree of MBI by macrolides depends on the size and structure of their lactone ring.
736:
617:
318:
306:
110:
1620:
1465:
1334:
2176:
2151:
2109:
2084:
2065:
2017:
1992:
1973:
1899:
1820:
1645:
1604:
1603:
Dhindwal P, Thompson C, Kos D, Planedin K, Jain R, Jelinski M, Ruzzini A (2023-02-21).
1533:
1498:
1181:
1043:
857:
2053:
1887:
1425:
1400:
1284:
1126:
1101:
1078:
2989:
2985:
2554:
2209:
2181:
2114:
2100:
2069:
2057:
2022:
1965:
1926:
1891:
1855:
1851:
1812:
1771:
1740:
1699:
1691:
1650:
1632:
1585:
1577:
1538:
1518:
1479:
1430:
1381:
1364:
Nguyen M, Chung EP (August 2005). "Telithromycin: the first ketolide antimicrobial".
1346:
1321:
Rezanka T, Sigler K (February 2008). "Biologically active compounds of semi-metals".
1303:
1260:
1219:
1173:
1156:
Keicho N, Kudoh S (2002). "Diffuse panbronchiolitis: role of macrolides in therapy".
1131:
1082:
1047:
973:
947:
929:
925:
892:
862:
657:
602:
2133:
1977:
1903:
1377:
1342:
3037:
2981:
2609:
2171:
2163:
2104:
2096:
2049:
2012:
2008:
2004:
1957:
1883:
1847:
1824:
1804:
1730:
1681:
1640:
1624:
1569:
1528:
1510:
1469:
1420:
1412:
1373:
1338:
1295:
1250:
1211:
1185:
1165:
1121:
1113:
1074:
1039:
921:
852:
844:
720:
665:
353:
310:
2297:
1474:
1449:
731:. Macrolides, mainly erythromycin and clarithromycin, also have a class effect of
3028:
3023:
2735:
2604:
2599:
1416:
732:
724:
326:
185:, which was first used in 1952. Erythromycin was widely used as a substitute to
75:
2293:
2289:
2285:
2281:
3071:
2888:
2818:
2803:
2564:
2449:
2437:
2315:
2167:
1215:
797:
781:
621:
500:
433:
349:
244:
194:
122:
55:
1961:
1686:
1669:
948:"Macrolide Antibiotics Comparison: Erythromycin, Clarithromycin, Azithromycin"
777:
as it requires the synthesis of new enzyme molecules to restore the activity.
715:(used for lowering cholesterol) is not advisable and can lead to debilitating
580: – the first and so far only fluoroketolide (not yet approved)
3098:
3033:
2977:
2969:
2931:
2921:
2893:
2873:
2863:
2858:
2823:
2808:
2745:
2740:
2664:
2629:
2417:
1695:
1636:
1581:
694:
673:
577:
559:
548:
516:
438:
378:
334:
262:
236:
65:
1628:
848:
3017:
3013:
2941:
2878:
2848:
2813:
2783:
2619:
2594:
2579:
2569:
2559:
2533:
2474:
2422:
2369:
2342:
2332:
2185:
2118:
2061:
2026:
1969:
1895:
1816:
1775:
1744:
1703:
1654:
1589:
1542:
1483:
1385:
1350:
1307:
1264:
1223:
1177:
1117:
1086:
866:
793:
789:
785:
669:
594:
489:
454:
444:
424:
322:
248:
190:
182:
142:
51:
36:
1930:
1859:
1434:
1135:
1051:
933:
407:, macrolide therapy still produces substantial anti-inflammatory results.
3003:
2949:
2926:
2853:
2838:
2833:
2750:
2637:
2614:
2589:
2584:
2574:
2549:
2393:
2364:
1255:
1238:
751:
641:
606:
554:
480:
475:
240:
86:
1558:"Mechanism and diversity of the erythromycin esterase family of enzymes"
833:"apamycin: An InhibiTOR of Aging Emerges From the Soil of Easter Island"
605:
or immunomodulators, are also macrolides. They have similar activity to
2999:
2959:
2954:
2903:
2883:
2868:
2843:
2798:
2793:
2727:
2698:
2678:
2498:
2493:
2484:
2479:
2464:
2459:
2407:
2359:
2273:
1299:
1169:
968:
Giguere S, Prescott JF, Baggot JD, Walker RD, Dowling PM, eds. (2006).
811:
629:
590:
494:
465:
393:
370:
266:
258:
232:
186:
170:
106:
102:
98:
94:
79:
2150:
Tan MS, Gomez-Lumbreras A, Villa-Zapata L, Malone DC (December 2022).
1808:
1670:"Structural Basis for Kinase-Mediated Macrolide Antibiotic Resistance"
1573:
2828:
2788:
2708:
2703:
2693:
2688:
2683:
2514:
2469:
2432:
2427:
2398:
2388:
2378:
598:
526:
470:
450:
397:
166:
114:
90:
2149:
2913:
2383:
2354:
1735:
1718:
1100:
Bailly S, Pocidalo JJ, Fay M, Gougerot-Pocidalo MA (October 1991).
744:
716:
625:
537:
510:
345:
281:
150:
1795:
Sathasivam S, Lecky B (November 2008). "Statin induced myopathy".
1099:
2898:
1029:
912:
Klein JO (April 1997). "History of macrolide use in pediatrics".
773:
712:
664:-mediated or chromosomal, i.e., through mutation, and results in
661:
506:
154:
146:
82:
40:
32:
1668:
Fong DH, Burk DL, Blanchet J, Yan AY, Berghuis AM (2017-05-02).
660:
bacterial ribosomal RNA. This acquired resistance can be either
656:
to macrolides occurs by post-transcriptional methylation of the
61:
2995:
804:
765:
728:
711:
article highlights that the combination of some macrolides and
428:
382:
333:. Another potential mechanism is premature dissociation of the
162:
158:
2131:
1990:
810:
Macrolides, including azithromycin, should not be taken with
497: – approved in the EU, and in other countries
205:
Antibiotic macrolides are used to treat infections caused by
138:
134:
44:
1401:"Chemistry and biology of the polyene macrolide antibiotics"
830:
1946:
1872:
1602:
967:
381:(adjusting the immune response), with the added benefit of
340:
Macrolide antibiotics bind reversibly to the P site on the
2655:
2306:
1555:
341:
2225:"Antibacterial Agents; Structure Activity Relationships"
427: – unique; does not extensively inhibit
2206:
Macrolide antibiotics: chemistry, biology, and practice
1917:
Hautekeete ML (1995). "Hepatotoxicity of antibiotics".
1556:
Morar M, Pengelly K, Koteva K, Wright GD (2012-02-28).
1447:
889:
Macrolide
Antibiotics: Chemistry, Biology, and Practice
551: – the first and only approved ketolide
441: – discontinued but was US FDA approved
356:, and thus are transported into the site of infection.
1760:"Diagnosis and Treatment of Streptococcal Pharyngitis"
1064:
1667:
1448:Kunze B, Sasse F, Wieczorek H, Huss M (July 2007).
157:rings are excluded, in order to differentiate from
2039:
683:Azithromycin has been used to treat strep throat (
3096:
1201:
317:, and they are thought to do this by preventing
101:class of natural products. Some macrolides have
1794:
1716:
1609:Proceedings of the National Academy of Sciences
1398:
1280:
1278:
1276:
1274:
632:is another example of an antifungal macrolide.
1013:
1011:
352:. Macrolides are actively concentrated within
2258:
1320:
2143:
2076:
2033:
1314:
1271:
970:Antimicrobial Therapy in Veterinary Medicine
584:
321:from adding the growing peptide attached to
141:nitrogen (but should be differentiated from
1496:
1363:
1155:
1008:
503: – used in Italy and Turkey
364:
2726:
2265:
2251:
1916:
1837:
831:Arriola Apelo SI, Lamming DW (July 2016).
2175:
2108:
2016:
1734:
1685:
1644:
1532:
1473:
1424:
1254:
1243:The Journal of Antimicrobial Chemotherapy
1125:
856:
121:and is being investigated as a potential
2208:(2nd ed.). Boston: Academic Press.
2132:John R. Horn, Philip D. Hansten (2006).
2082:
1197:
1195:
1158:American Journal of Respiratory Medicine
914:The Pediatric Infectious Disease Journal
772:Macrolides have cyclic structure with a
750:Some macrolides are also known to cause
522:Not approved as a drug for medical use:
449:
415:
60:
50:
31:
1997:Cochrane Database of Systematic Reviews
1236:
14:
3097:
1151:
1149:
1147:
1145:
697:is another option for these patients.
291:
2246:
2203:
1942:
1940:
1757:
1499:"Mechanisms of Antibiotic Resistance"
1230:
1192:
1106:Antimicrobial Agents and Chemotherapy
1058:
911:
886:
685:Group A streptococcal (GAS) infection
325:to the next amino acid (similarly to
2222:
1717:Roland Leclercq (15 February 2002).
1515:10.1128/microbiolspec.VMBF-0016-2015
628:etc., are a subgroup of macrolides.
1142:
996:. Food and Drug Administration (US)
635:
612:
359:
181:The first macrolide discovered was
24:
2196:
1937:
1497:Munita JM, Arias CA (April 2016).
1044:10.1111/j.1432-1033.1987.tb10991.x
565:
513: – used in animals
348:. This action is considered to be
25:
3116:
2054:10.2174/1389200221666200817113920
972:(4th ed.). Wiley-Blackwell.
2101:10.1046/j.1365-2125.2000.00261.x
1919:Acta Gastro-Enterologica Belgica
1399:Hamilton-Miller JM (June 1973).
1032:European Journal of Biochemistry
926:10.1097/00006454-199704000-00025
891:(2nd ed.). Academic Press.
296:
2125:
1984:
1910:
1866:
1831:
1788:
1751:
1710:
1661:
1596:
1549:
1490:
1441:
1392:
1378:10.1016/j.clinthera.2005.08.009
1357:
1343:10.1016/j.phytochem.2007.09.018
1204:Current Opinion in Pharmacology
1093:
760:
700:
373:, Asian-prevalent lung disease
331:bacterial ribosomal translation
165:instead of lactones (as in the
2766:transpeptidation/translocation
2009:10.1002/14651858.CD011825.pub2
1950:European Journal of Pediatrics
1023:
986:
961:
940:
905:
880:
824:
676:(an MLS-resistant phenotype).
13:
1:
2230:. p. 143. Archived from
1888:10.1016/S0140-6736(99)10073-4
1475:10.1016/j.febslet.2007.06.069
1079:10.1016/S0022-2836(03)00662-4
837:J Gerontol A Biol Sci Med Sci
817:
647:
128:
2083:Westphal JF (October 2000).
1852:10.1016/0022-3468(76)90283-9
1840:Journal of Pediatric Surgery
1723:Clinical Infectious Diseases
1417:10.1128/br.37.3.166-196.1973
1288:Basic Clin Pharmacol Toxicol
1067:Journal of Molecular Biology
532:
303:protein synthesis inhibitors
39:. The macrolide ring is the
7:
410:
10:
3121:
2168:10.1007/s00296-022-05201-5
1216:10.1016/j.coph.2008.01.010
176:
85:ring to which one or more
3055:
3010:Quinupristin/dalfopristin
2968:
2940:
2912:
2774:
2763:
2717:
2663:
2654:
2628:
2542:
2527:
2507:
2446:
2329:
2314:
2305:
2278:inhibit protein synthesis
1962:10.1007/s00431-018-3287-7
1764:American Family Physician
1687:10.1016/j.str.2017.03.007
585:Non-antibiotic macrolides
573:Fluoroketolides include:
396:activity and obstructive
344:subunit of the bacterial
109:activity and are used as
27:Class of natural products
2529:Tetracycline antibiotics
1237:Schultz MJ (July 2004).
727:system, particularly of
375:diffuse panbronchiolitis
365:Diffuse panbronchiolitis
329:) as well as inhibiting
212:Streptococcus pneumoniae
1629:10.1073/pnas.2219827120
1405:Bacteriological Reviews
741:enterohepatic recycling
708:British Medical Journal
392:proliferation but also
200:
1118:10.1128/AAC.35.10.2016
690:Streptococcus pyogenes
458:
404:Pseudomonas aeruginosa
390:neutrophil granulocyte
254:Legionella pneumophila
228:Haemophilus influenzae
217:Gram-negative bacteria
207:Gram-positive bacteria
119:immunosuppressant drug
74:are a class of mostly
68:
58:
48:
1503:Microbiology Spectrum
1366:Clinical Therapeutics
887:Omura S, ed. (2002).
849:10.1093/gerona/glw090
739:. Macrolides exhibit
652:The primary means of
453:
416:Antibiotic macrolides
123:longevity therapeutic
64:
54:
35:
2719:Peptidyl transferase
735:, which can lead to
654:bacterial resistance
618:Polyene antimycotics
601:, which are used as
315:protein biosynthesis
222:Bordetella pertussis
111:pharmaceutical drugs
2348:Dihydrostreptomycin
2089:Br J Clin Pharmacol
1621:2023PNAS..12019827D
1466:2007FEBSL.581.3523K
1335:2008PChem..69..585R
737:torsades de pointes
544:Ketolides include:
485:midecamycin acetate
337:from the ribosome.
319:peptidyltransferase
307:mechanism of action
292:Mechanism of action
3082:Never to phase III
1615:(8): e2219827120.
1300:10.1111/bcpt.13343
1256:10.1093/jac/dkh309
1170:10.1007/BF03256601
603:immunosuppressants
459:
69:
59:
49:
3092:
3091:
3051:
3050:
3047:
3046:
2759:
2758:
2650:
2649:
2646:
2645:
2555:Chlortetracycline
2523:
2522:
2215:978-0-12-526451-8
2162:(12): 2253–2259.
1809:10.1136/bmj.a2286
1758:Choby BA (2009).
1680:(5): 750–761.e5.
1574:10.1021/bi201790u
1524:978-1-55581-927-9
979:978-0-8138-0656-3
898:978-0-12-526451-8
420:US FDA-approved:
309:of macrolides is
280:to be used on non
16:(Redirected from
3112:
2772:
2771:
2724:
2723:
2661:
2660:
2610:Rolitetracycline
2540:
2539:
2327:
2326:
2312:
2311:
2267:
2260:
2253:
2244:
2243:
2238:
2236:
2229:
2219:
2204:Ōmura S (2002).
2190:
2189:
2179:
2147:
2141:
2140:
2138:
2129:
2123:
2122:
2112:
2080:
2074:
2073:
2037:
2031:
2030:
2020:
1988:
1982:
1981:
1944:
1935:
1934:
1914:
1908:
1907:
1882:(9196): 2101–5.
1870:
1864:
1863:
1835:
1829:
1828:
1792:
1786:
1785:
1783:
1782:
1755:
1749:
1748:
1738:
1714:
1708:
1707:
1689:
1665:
1659:
1658:
1648:
1600:
1594:
1593:
1568:(8): 1740–1751.
1553:
1547:
1546:
1536:
1494:
1488:
1487:
1477:
1445:
1439:
1438:
1428:
1396:
1390:
1389:
1361:
1355:
1354:
1318:
1312:
1311:
1282:
1269:
1268:
1258:
1234:
1228:
1227:
1199:
1190:
1189:
1153:
1140:
1139:
1129:
1097:
1091:
1090:
1062:
1056:
1055:
1027:
1021:
1015:
1006:
1005:
1003:
1001:
990:
984:
983:
965:
959:
958:
956:
954:
944:
938:
937:
909:
903:
902:
884:
878:
877:
875:
873:
860:
828:
666:cross-resistance
636:Toxic macrolides
613:Antifungal drugs
379:immunomodulation
360:Immunomodulation
76:natural products
47:) at upper left.
21:
3120:
3119:
3115:
3114:
3113:
3111:
3110:
3109:
3095:
3094:
3093:
3088:
3087:
3072:Clinical trials
3043:
3029:Streptogramin B
3024:Streptogramin A
2964:
2936:
2908:
2755:
2736:Chloramphenicol
2713:
2667:
2642:
2624:
2605:Penimepicycline
2600:Oxytetracycline
2531:
2519:
2503:
2442:
2318:
2316:Aminoglycosides
2301:
2271:
2241:
2234:
2227:
2216:
2199:
2197:Further reading
2194:
2193:
2148:
2144:
2136:
2130:
2126:
2081:
2077:
2048:(12): 928–937.
2042:Curr Drug Metab
2038:
2034:
2003:(1): CD011825.
1989:
1985:
1945:
1938:
1915:
1911:
1871:
1867:
1836:
1832:
1793:
1789:
1780:
1778:
1756:
1752:
1715:
1711:
1666:
1662:
1601:
1597:
1554:
1550:
1525:
1495:
1491:
1446:
1442:
1397:
1393:
1362:
1358:
1319:
1315:
1283:
1272:
1235:
1231:
1200:
1193:
1154:
1143:
1098:
1094:
1063:
1059:
1028:
1024:
1016:
1009:
999:
997:
992:
991:
987:
980:
966:
962:
952:
950:
946:
945:
941:
910:
906:
899:
885:
881:
871:
869:
829:
825:
820:
763:
733:QT prolongation
725:cytochrome P450
703:
668:to macrolides,
650:
638:
615:
587:
568:
566:Fluoroketolides
535:
418:
413:
367:
362:
327:chloramphenicol
301:Macrolides are
299:
294:
276:Macrolides are
203:
179:
131:
28:
23:
22:
15:
12:
11:
5:
3118:
3108:
3107:
3090:
3089:
3086:
3085:
3084:
3083:
3080:
3069:
3063:
3057:
3056:
3053:
3052:
3049:
3048:
3045:
3044:
3042:
3041:
3031:
3026:
3021:
3007:
2993:
2974:
2972:
2970:Streptogramins
2966:
2965:
2963:
2962:
2957:
2952:
2946:
2944:
2938:
2937:
2935:
2934:
2929:
2924:
2918:
2916:
2910:
2909:
2907:
2906:
2901:
2896:
2891:
2889:Troleandomycin
2886:
2881:
2876:
2871:
2866:
2861:
2856:
2851:
2846:
2841:
2836:
2831:
2826:
2821:
2819:Flurithromycin
2816:
2811:
2806:
2804:Clarithromycin
2801:
2796:
2791:
2786:
2780:
2778:
2769:
2761:
2760:
2757:
2756:
2754:
2753:
2748:
2743:
2738:
2732:
2730:
2721:
2715:
2714:
2712:
2711:
2706:
2701:
2696:
2691:
2686:
2681:
2675:
2673:
2658:
2652:
2651:
2648:
2647:
2644:
2643:
2641:
2640:
2634:
2632:
2630:Glycylcyclines
2626:
2625:
2623:
2622:
2617:
2612:
2607:
2602:
2597:
2592:
2587:
2582:
2577:
2572:
2567:
2565:Demeclocycline
2562:
2557:
2552:
2546:
2544:
2537:
2525:
2524:
2521:
2520:
2518:
2517:
2511:
2509:
2505:
2504:
2502:
2501:
2496:
2490:
2489:
2488:
2487:
2482:
2477:
2472:
2467:
2456:
2454:
2450:Micromonospora
2444:
2443:
2441:
2440:
2438:Nourseothricin
2435:
2430:
2425:
2420:
2415:
2404:
2403:
2402:
2401:
2396:
2391:
2386:
2375:
2374:
2373:
2372:
2367:
2362:
2351:
2350:
2345:
2339:
2337:
2324:
2309:
2303:
2302:
2274:Antibacterials
2270:
2269:
2262:
2255:
2247:
2240:
2239:
2237:on 2006-03-04.
2220:
2214:
2200:
2198:
2195:
2192:
2191:
2142:
2124:
2075:
2032:
1983:
1956:(3): 301–314.
1936:
1925:(3–4): 290–6.
1909:
1865:
1830:
1787:
1770:(5): 383–390.
1750:
1736:10.1086/324626
1729:(4): 482–492.
1709:
1660:
1595:
1548:
1523:
1509:(2): 481–511.
1489:
1460:(18): 3523–7.
1440:
1391:
1372:(8): 1144–63.
1356:
1329:(3): 585–606.
1323:Phytochemistry
1313:
1294:(4): 307–317.
1270:
1229:
1191:
1141:
1112:(10): 2016–9.
1092:
1073:(5): 1005–14.
1057:
1022:
1007:
985:
978:
960:
939:
904:
897:
879:
822:
821:
819:
816:
798:clarithromycin
782:Clarithromycin
762:
759:
702:
699:
674:streptogramins
649:
646:
637:
634:
622:amphotericin B
614:
611:
586:
583:
582:
581:
567:
564:
563:
562:
557:
552:
534:
531:
530:
529:
520:
519:
514:
504:
501:Troleandomycin
498:
492:
487:
478:
473:
468:
448:
447:
442:
436:
434:Clarithromycin
431:
417:
414:
412:
409:
385:requirements.
366:
363:
361:
358:
350:bacteriostatic
298:
295:
293:
290:
215:) and limited
202:
199:
195:clarithromycin
178:
175:
130:
127:
56:Clarithromycin
26:
9:
6:
4:
3:
2:
3117:
3106:
3103:
3102:
3100:
3081:
3079:
3076:
3075:
3073:
3070:
3067:
3064:
3062:
3059:
3058:
3054:
3039:
3035:
3034:Virginiamycin
3032:
3030:
3027:
3025:
3022:
3019:
3015:
3011:
3008:
3005:
3001:
2997:
2994:
2991:
2987:
2983:
2979:
2978:Pristinamycin
2976:
2975:
2973:
2971:
2967:
2961:
2958:
2956:
2953:
2951:
2948:
2947:
2945:
2943:
2939:
2933:
2932:Solithromycin
2930:
2928:
2925:
2923:
2922:Telithromycin
2920:
2919:
2917:
2915:
2911:
2905:
2902:
2900:
2897:
2895:
2894:Tulathromycin
2892:
2890:
2887:
2885:
2882:
2880:
2877:
2875:
2874:Telithromycin
2872:
2870:
2867:
2865:
2864:Solithromycin
2862:
2860:
2859:Roxithromycin
2857:
2855:
2852:
2850:
2847:
2845:
2842:
2840:
2837:
2835:
2832:
2830:
2827:
2825:
2824:Gamithromycin
2822:
2820:
2817:
2815:
2812:
2810:
2809:Dirithromycin
2807:
2805:
2802:
2800:
2797:
2795:
2792:
2790:
2787:
2785:
2782:
2781:
2779:
2777:
2773:
2770:
2767:
2762:
2752:
2749:
2747:
2746:Thiamphenicol
2744:
2742:
2741:Azidamfenicol
2739:
2737:
2734:
2733:
2731:
2729:
2725:
2722:
2720:
2716:
2710:
2707:
2705:
2702:
2700:
2697:
2695:
2692:
2690:
2687:
2685:
2682:
2680:
2677:
2676:
2674:
2671:
2666:
2665:Oxazolidinone
2662:
2659:
2657:
2653:
2639:
2636:
2635:
2633:
2631:
2627:
2621:
2618:
2616:
2613:
2611:
2608:
2606:
2603:
2601:
2598:
2596:
2593:
2591:
2588:
2586:
2583:
2581:
2578:
2576:
2573:
2571:
2568:
2566:
2563:
2561:
2558:
2556:
2553:
2551:
2548:
2547:
2545:
2543:Tetracyclines
2541:
2538:
2535:
2530:
2526:
2516:
2513:
2512:
2510:
2506:
2500:
2497:
2495:
2492:
2491:
2486:
2483:
2481:
2478:
2476:
2473:
2471:
2468:
2466:
2463:
2462:
2461:
2458:
2457:
2455:
2452:
2451:
2445:
2439:
2436:
2434:
2431:
2429:
2426:
2424:
2421:
2419:
2418:Spectinomycin
2416:
2413:
2409:
2406:
2405:
2400:
2397:
2395:
2392:
2390:
2387:
2385:
2382:
2381:
2380:
2377:
2376:
2371:
2368:
2366:
2363:
2361:
2358:
2357:
2356:
2353:
2352:
2349:
2346:
2344:
2341:
2340:
2338:
2335:
2334:
2328:
2325:
2322:
2317:
2313:
2310:
2308:
2304:
2299:
2295:
2291:
2287:
2283:
2279:
2275:
2268:
2263:
2261:
2256:
2254:
2249:
2248:
2245:
2233:
2226:
2221:
2217:
2211:
2207:
2202:
2201:
2187:
2183:
2178:
2173:
2169:
2165:
2161:
2157:
2156:Rheumatol Int
2153:
2146:
2135:
2128:
2120:
2116:
2111:
2106:
2102:
2098:
2095:(4): 285–95.
2094:
2090:
2086:
2079:
2071:
2067:
2063:
2059:
2055:
2051:
2047:
2043:
2036:
2028:
2024:
2019:
2014:
2010:
2006:
2002:
1998:
1994:
1987:
1979:
1975:
1971:
1967:
1963:
1959:
1955:
1951:
1943:
1941:
1932:
1928:
1924:
1920:
1913:
1905:
1901:
1897:
1893:
1889:
1885:
1881:
1877:
1869:
1861:
1857:
1853:
1849:
1846:(2): 177–80.
1845:
1841:
1834:
1826:
1822:
1818:
1814:
1810:
1806:
1802:
1798:
1791:
1777:
1773:
1769:
1765:
1761:
1754:
1746:
1742:
1737:
1732:
1728:
1724:
1720:
1713:
1705:
1701:
1697:
1693:
1688:
1683:
1679:
1675:
1671:
1664:
1656:
1652:
1647:
1642:
1638:
1634:
1630:
1626:
1622:
1618:
1614:
1610:
1606:
1599:
1591:
1587:
1583:
1579:
1575:
1571:
1567:
1563:
1559:
1552:
1544:
1540:
1535:
1530:
1526:
1520:
1516:
1512:
1508:
1504:
1500:
1493:
1485:
1481:
1476:
1471:
1467:
1463:
1459:
1455:
1451:
1444:
1436:
1432:
1427:
1422:
1418:
1414:
1411:(2): 166–96.
1410:
1406:
1402:
1395:
1387:
1383:
1379:
1375:
1371:
1367:
1360:
1352:
1348:
1344:
1340:
1336:
1332:
1328:
1324:
1317:
1309:
1305:
1301:
1297:
1293:
1289:
1281:
1279:
1277:
1275:
1266:
1262:
1257:
1252:
1248:
1244:
1240:
1233:
1225:
1221:
1217:
1213:
1210:(3): 286–91.
1209:
1205:
1198:
1196:
1187:
1183:
1179:
1175:
1171:
1167:
1164:(2): 119–31.
1163:
1159:
1152:
1150:
1148:
1146:
1137:
1133:
1128:
1123:
1119:
1115:
1111:
1107:
1103:
1096:
1088:
1084:
1080:
1076:
1072:
1068:
1061:
1053:
1049:
1045:
1041:
1037:
1033:
1026:
1019:
1014:
1012:
995:
989:
981:
975:
971:
964:
949:
943:
935:
931:
927:
923:
920:(4): 427–31.
919:
915:
908:
900:
894:
890:
883:
868:
864:
859:
854:
850:
846:
842:
838:
834:
827:
823:
815:
813:
808:
806:
801:
799:
795:
791:
787:
783:
778:
775:
770:
767:
758:
755:
753:
748:
746:
742:
738:
734:
730:
726:
722:
718:
714:
710:
709:
698:
696:
695:Cephalosporin
692:
691:
686:
681:
677:
675:
671:
667:
663:
659:
655:
645:
643:
633:
631:
627:
623:
619:
610:
608:
604:
600:
596:
592:
579:
578:Solithromycin
576:
575:
574:
571:
561:
560:Solithromycin
558:
556:
553:
550:
549:Telithromycin
547:
546:
545:
542:
539:
528:
525:
524:
523:
518:
517:Roxithromycin
515:
512:
508:
505:
502:
499:
496:
493:
491:
488:
486:
482:
479:
477:
474:
472:
469:
467:
464:
463:
462:
456:
452:
446:
443:
440:
439:Dirithromycin
437:
435:
432:
430:
426:
423:
422:
421:
408:
406:
405:
399:
395:
391:
386:
384:
380:
376:
372:
357:
355:
351:
347:
343:
338:
336:
335:peptidyl-tRNA
332:
328:
324:
320:
316:
313:of bacterial
312:
308:
304:
297:Antibacterial
289:
286:
283:
279:
274:
272:
268:
264:
263:Mycobacterium
260:
256:
255:
250:
246:
245:staphylococci
242:
238:
234:
230:
229:
224:
223:
218:
214:
213:
208:
198:
196:
192:
188:
184:
174:
172:
168:
164:
160:
156:
152:
148:
144:
143:cyclopeptides
140:
136:
126:
124:
120:
116:
112:
108:
104:
100:
96:
92:
88:
84:
81:
78:with a large
77:
73:
67:
66:Roxithromycin
63:
57:
53:
46:
42:
38:
34:
30:
19:
3018:Quinupristin
3014:Dalfopristin
2942:Lincosamides
2879:Tildipirosin
2849:Oleandomycin
2814:Erythromycin
2784:Azithromycin
2775:
2620:Tetracycline
2595:Omadacycline
2580:Meclocycline
2570:Eravacycline
2560:Clomocycline
2475:Micronomicin
2448:
2423:Hygromycin B
2412:+loteprednol
2370:Ribostamycin
2343:Streptomycin
2333:Streptomyces
2331:
2232:the original
2223:Bryskier A.
2205:
2159:
2155:
2145:
2127:
2092:
2088:
2078:
2045:
2041:
2035:
2000:
1996:
1986:
1953:
1949:
1922:
1918:
1912:
1879:
1875:
1868:
1843:
1839:
1833:
1800:
1796:
1790:
1779:. Retrieved
1767:
1763:
1753:
1726:
1722:
1712:
1677:
1673:
1663:
1612:
1608:
1598:
1565:
1562:Biochemistry
1561:
1551:
1506:
1502:
1492:
1457:
1454:FEBS Letters
1453:
1443:
1408:
1404:
1394:
1369:
1365:
1359:
1326:
1322:
1316:
1291:
1287:
1246:
1242:
1232:
1207:
1203:
1161:
1157:
1109:
1105:
1095:
1070:
1066:
1060:
1035:
1031:
1025:
998:. Retrieved
988:
969:
963:
951:. Retrieved
942:
917:
913:
907:
888:
882:
870:. Retrieved
843:(7): 841–9.
840:
836:
826:
809:
802:
794:erythromycin
790:Azithromycin
786:erythromycin
779:
771:
764:
761:Interactions
756:
749:
706:
704:
701:Side-effects
688:
682:
678:
670:lincosamides
651:
642:mycolactones
639:
616:
595:pimecrolimus
588:
572:
569:
543:
536:
521:
490:Oleandomycin
466:Carbomycin A
460:
455:Azithromycin
445:Erythromycin
425:Azithromycin
419:
402:
387:
368:
339:
300:
287:
277:
275:
252:
237:streptococci
226:
220:
210:
204:
191:azithromycin
183:erythromycin
180:
132:
87:deoxy sugars
71:
70:
37:Erythromycin
29:
3068:from market
3004:Linopristin
2950:Clindamycin
2927:Cethromycin
2854:Rokitamycin
2839:Midecamycin
2834:Kitasamycin
2751:Florfenicol
2728:Amphenicols
2672:inhibitors)
2638:Tigecycline
2615:Sarecycline
2590:Minocycline
2585:Metacycline
2575:Lymecycline
2550:Doxycycline
2394:Bekanamycin
2365:Paromomycin
2323:inhibitors)
1249:(1): 21–8.
1038:(1): 53–8.
752:cholestasis
607:ciclosporin
555:Cethromycin
481:Midecamycin
476:Kitasamycin
249:enterococci
241:pneumococci
149:ring, or a
80:macrocyclic
3105:Macrolides
3000:Flopristin
2960:Pirlimycin
2955:Lincomycin
2904:Tylvalosin
2884:Tilmicosin
2869:Spiramycin
2844:Miocamycin
2799:Carrimycin
2794:Carbomycin
2776:Macrolides
2699:Ranbezolid
2679:Eperezolid
2670:initiation
2499:Astromicin
2494:Verdamicin
2485:Isepamicin
2480:Plazomicin
2465:Netilmicin
2460:Gentamicin
2408:Tobramycin
2360:Framycetin
2321:initiation
1781:2024-01-25
994:"DailyMed"
818:References
812:colchicine
721:inhibitors
687:caused by
648:Resistance
630:Cruentaren
620:, such as
591:tacrolimus
589:The drugs
495:Spiramycin
401:bacterium
398:secretions
394:lymphocyte
371:idiopathic
354:leukocytes
311:inhibition
267:Rickettsia
259:Mycoplasma
233:penicillin
187:penicillin
171:tacrolimus
137:nitrogen,
129:Definition
107:antifungal
103:antibiotic
99:polyketide
95:desosamine
89:, usually
72:Macrolides
18:Macrolides
3078:Phase III
3066:Withdrawn
2914:Ketolides
2829:Josamycin
2789:Boromycin
2709:Tedizolid
2704:Sutezolid
2694:Radezolid
2689:Posizolid
2684:Linezolid
2515:Butirosin
2470:Sisomicin
2433:Apramycin
2428:Totomycin
2399:Dibekacin
2389:Arbekacin
2379:Kanamycin
2070:221162650
1803:: a2286.
1696:1878-4186
1674:Structure
1637:0027-8424
1582:1520-4995
599:sirolimus
538:Ketolides
533:Ketolides
527:Boromycin
471:Josamycin
271:Chlamydia
167:ansamycin
115:Rapamycin
91:cladinose
3099:Category
2536:binding)
2447:-micin (
2384:Amikacin
2355:Neomycin
2330:-mycin (
2186:36104598
2119:11012550
2062:32807049
2027:30656650
1978:53711818
1970:30470884
1904:24160212
1896:10609814
1817:18988647
1776:19275067
1745:11797175
1704:28416110
1655:36791107
1590:22303981
1543:27227291
1484:17624334
1386:16199242
1351:17991498
1308:31628882
1265:15190022
1224:18339582
1178:14720066
1087:12860123
1000:22 March
953:22 March
867:27208895
745:duodenum
717:myopathy
626:nystatin
511:tylocine
457:capsules
411:Examples
383:low-dose
346:ribosome
282:ruminant
151:thiazole
43:(cyclic
2899:Tylosin
2177:9473467
2110:2015000
2018:6353052
1931:7491842
1860:1263054
1825:3239804
1646:9974460
1617:Bibcode
1534:4888801
1462:Bibcode
1435:4578757
1331:Bibcode
1186:7634677
1136:1759822
1052:3549307
934:9109154
872:17 July
858:4906330
805:statins
774:lactone
723:of the
713:statins
705:A 2008
662:plasmid
507:Tylosin
265:, some
219:(e.g.,
209:(e.g.,
177:History
163:lactams
161:. Also
159:tannins
155:Benzene
147:oxazole
83:lactone
41:lactone
3061:WHO-EM
2996:NXL103
2298:QJ01XQ
2212:
2184:
2174:
2117:
2107:
2068:
2060:
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1976:
1968:
1929:
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1876:Lancet
1858:
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1643:
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766:CYP3A4
729:CYP3A4
672:, and
597:, and
429:CYP3A4
305:. The
269:, and
247:, and
153:ring.
145:), an
2764:MLS (
2508:other
2276:that
2235:(PDF)
2228:(PDF)
2137:(PDF)
2066:S2CID
1974:S2CID
1900:S2CID
1821:S2CID
1182:S2CID
139:amide
135:amino
45:ester
2534:tRNA
2294:J01G
2290:J01F
2286:J01B
2282:J01A
2210:ISBN
2182:PMID
2115:PMID
2058:PMID
2023:PMID
1966:PMID
1927:PMID
1892:PMID
1856:PMID
1813:PMID
1772:PMID
1741:PMID
1700:PMID
1692:ISSN
1651:PMID
1633:ISSN
1586:PMID
1578:ISSN
1539:PMID
1519:ISBN
1480:PMID
1431:PMID
1382:PMID
1347:PMID
1304:PMID
1261:PMID
1220:PMID
1174:PMID
1132:PMID
1083:PMID
1048:PMID
1002:2017
974:ISBN
955:2017
930:PMID
893:ISBN
874:2022
863:PMID
796:and
784:and
323:tRNA
201:Uses
193:and
93:and
2990:IIB
2986:IIA
2656:50S
2307:30S
2172:PMC
2164:doi
2105:PMC
2097:doi
2050:doi
2013:PMC
2005:doi
1958:doi
1954:178
1884:doi
1880:354
1848:doi
1805:doi
1801:337
1797:BMJ
1731:doi
1682:doi
1641:PMC
1625:doi
1613:120
1570:doi
1529:PMC
1511:doi
1470:doi
1458:581
1421:PMC
1413:doi
1374:doi
1339:doi
1296:doi
1292:126
1251:doi
1212:doi
1166:doi
1122:PMC
1114:doi
1075:doi
1071:330
1040:doi
1036:164
922:doi
853:PMC
845:doi
658:23S
342:50S
278:not
105:or
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