591:
568:
887:(LmbR) of ribose 5-phosphate (C5) with fructose 6-phosphate or sedoheptulose-7-phosphate (providing a C3 unit) forms the octose (C8). Further transformations involving isomerization (LmbN), 1-phosphorylation (LmbP), 8-dephosphorylation (LmbK), guanosine diphosphate attachment at position 1 (LmbO), 4-epimerization (LmbM), 6-oxidation (LmbL), amination (LmbS), imine reduction (LmbZ) and 8-reduction, are performed to construct the amino-octose unit. LmbT protein exchange GDP by
151:
36:
142:
860:
classified as a member of the lincosamide class, which typically features a L-proline amino acid derivative linked through amide group with an eight-carbon aminothio sugar. The two units 4-propyl-L-proline and the amino-octose, are each synthesized separately, and are then condensed by LmbD protein,
828:
The biological half-life after IM or IV administration is 5.4 ± 1.0 h. The serum half-life of lincomycin may be prolonged in patients with severe impairment of renal function, compared to patients with normal renal function. In patients with abnormal hepatic function, serum half-life may be
820:
Intramuscular administration of a single dose of 600 mg of
Lincomycin produces average peak serum levels of 11.6 μg/mL at 60 min, and maintains therapeutic levels for 17 h to 20 h, for most susceptible gram-positive organisms. Urinary excretion after this dose ranges from
824:
A two-hour intravenous infusion of 600 mg of
Lincomycin achieves average peak serum levels of 15.9 μg/mL and yields therapeutic levels for 14 h for most susceptible gram-positive organisms. Urinary excretion ranges from 4.9% to 30.3% (mean: 13.8%).
663:
927:. Lincomycin is used to treat severe bacterial infections in patients who cannot use penicillin antibiotics. Lincomycin shows weak activity against most Gram-negative bacteria. The following represents susceptibility (
1256:
272:
876:
which is transformed to 4-propyl-L-proline by the consecutive action of LmbB1, LmbB2, LmbW, LmbA and LmbX proteins. 4-Propyl-L-proline is activated by LmbC and loaded into LmbN, a bifunctional
997:
883:
The biosynthetic pathway for production of the amino-octose moiety is almost fully elucidated although the order of the steps still needs further research. Condensation through a
705:
InChI=1S/C18H34N2O6S/c1-5-6-10-7-11(20(3)8-10)17(25)19-12(9(2)21)16-14(23)13(22)15(24)18(26-16)27-4/h9-16,18,21-24H,5-8H2,1-4H3,(H,19,25)/t9-,10-,11+,12-,13+,14-,15-,16-,18-/m1/s1
1249:
217:
721:
1242:
907:
moiety is then cleaved by LmbE, and the product is further processed by LmbIH, LmbQ, LmbJ, LmbF and is finally sulphur methylated by LmbG, to afford lincomycin.
173:
844:
is an important route of excretion. Significant levels have been demonstrated in the majority of body tissues. Although lincomycin appears to diffuse in the
677:
891:
and the condensation with 4-propyl-L-proline and catalysed by LmbD can occur. The amide-linked product between the amino acid and the amino-octose bound to
2052:
915:
Lincomycin is a narrow spectrum antibiotic with activity against Gram-positive and cell wall-less bacteria including pathogenic species of
2101:
697:
119:
1216:
1234:
928:
353:
257:
1064:
Birkenmeyer RD, Kagan F (July 1970). "Lincomycin. XI. Synthesis and structure of clindamycin. A potent antibacterial agent".
57:
1025:"Lincomycin: A New Antibiotic Active Against Staphylococci and Other Gram-Positive Cocci: Clinical and Laboratory Studies"
100:
467:
72:
2069:
1269:
547:
53:
804:
However, because of its adverse effects and toxicity, it is rarely used today and reserved for patients allergic to
79:
2001:
753:
1520:
1203:
EP Susceptibility and 0.05 - 0.4 Minimum
Inhibitory >50 Concentration Range (μg/mL) Concentration (MIC) Data
877:
2057:
1142:"Biosynthesis and incorporation of an alkylproline-derivative (APD) precursor into complex natural products"
205:
86:
46:
586:
1403:
969:"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"
2096:
1757:
1661:
1312:
809:
536:
68:
1710:
968:
316:
1339:
845:
834:
778:
563:
382:
183:
1981:
1977:
1546:
1163:
1122:
1081:
1046:
998:"Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017"
163:
1195:
1181:
516:
456:
2029:
1973:
1601:
1153:
1112:
1073:
1036:
762:
603:
298:
476:
2020:
2015:
1727:
1596:
1591:
848:(CSF), levels of lincomycin in the CSF appear inadequate for the treatment of meningitis.
306:
240:
150:
391:
590:
567:
93:
2063:
1880:
1810:
1795:
1556:
1441:
1429:
1307:
1224:
1117:
1100:
1041:
1024:
2090:
2025:
1969:
1961:
1923:
1913:
1885:
1865:
1855:
1850:
1815:
1800:
1737:
1732:
1656:
1621:
1409:
896:
892:
888:
884:
579:
285:
197:
416:
2009:
2005:
1933:
1870:
1840:
1805:
1775:
1611:
1586:
1571:
1561:
1551:
1525:
1466:
1414:
1361:
1334:
1324:
1289:
1285:
1281:
1277:
1273:
830:
786:
749:
235:
230:
225:
1995:
1941:
1918:
1845:
1830:
1825:
1742:
1629:
1606:
1581:
1576:
1566:
1541:
1385:
1356:
758:
742:
191:
35:
1991:
1951:
1895:
1875:
1860:
1835:
1790:
1785:
1719:
1690:
1670:
1490:
1485:
1476:
1471:
1456:
1451:
1399:
1351:
1265:
1182:"Lincocin (Lincomycin HCL): Uses, Dosage, Side Effects, Interactions, Warning"
869:
857:
805:
797:
791:
782:
745:
639:
447:
1820:
1780:
1767:
1700:
1695:
1685:
1680:
1675:
1506:
1461:
1424:
1419:
1390:
1380:
1370:
904:
900:
862:
766:
338:
329:
177:
1167:
1050:
133:
17:
1126:
1085:
1905:
1375:
1346:
873:
427:
1077:
436:
1890:
1158:
1141:
402:
141:
765:
to replace the 7-hydroxy group with a chlorine atom with inversion of
1987:
527:
334:
1140:
Janata J, Kamenik Z, Gazak R, Kadlcik S, Najmanova L (March 2018).
496:
861:
and then further postcondensation reactions involving cleaving of
662:
653:
507:
785:, lincomycin is also effective against other organisms including
841:
487:
1238:
829:
twofold longer than in patients with normal hepatic function.
279:
1647:
1298:
976:
29:
865:, deacetylation, and S-methylation finally yield lincomycin.
552:
266:
1023:
Macleod AJ, Ross HB, Ozere RL, Digout G (November 1964).
837:
are not effective in removing lincomycin from the serum.
728:
769:. It was released for medical use in September 1964.
1960:
1932:
1904:
1766:
1755:
1718:
1709:
1655:
1646:
1620:
1534:
1519:
1499:
1438:
1321:
1306:
1297:
651:
638:
602:
597:
578:
546:
526:
506:
486:
466:
446:
426:
401:
381:
373:-propyl]-1-methyl-4-propylpyrrolidine-2-carboxamide
344:
328:
315:
305:
297:
256:
251:
216:
204:
190:
172:
162:
157:
60:. Unsourced material may be challenged and removed.
895:is then the substrate of LmbV, which substitute
415:
777:Although similar in antibacterial spectrum and
390:
324:5.4 ± 1.0 h after IM or IV administration
1250:
8:
132:
239:
1763:
1715:
1652:
1531:
1318:
1303:
1257:
1243:
1235:
589:
566:
455:
140:
1157:
1116:
1040:
880:, and is ready for condensation by LmbD.
475:
120:Learn how and when to remove this message
960:
702:
685:O=C(N(1O(SC)(O)(O)1O)(O)C)2N(C)C(CCC)C2
682:
562:
435:
358:
196:
1002:Therapeutic Goods Administration (TGA)
931:) data for a few pathogenic bacteria:
761:, is derived from lincomycin by using
580:
131:
1221:The Antimicrobial Index Knowledgebase
1099:Duncan IB, Jeans B (September 1965).
535:
515:
182:
7:
1105:Canadian Medical Association Journal
1029:Canadian Medical Association Journal
229:
58:adding citations to reliable sources
840:Tissue level studies indicate that
495:
406:
950:- 0.04 μg/mL - 0.8 μg/mL
944:- 0.05 μg/mL - 0.4 μg/mL
872:moiety of lincomycin, starts with
25:
1101:"Lincomycin in hospital practice"
808:or where bacteria have developed
938:- 0.2 μg/mL - 32 μg/mL
620:
614:
149:
34:
710:Key:OJMMVQQUTAEWLP-KIDUDLJLSA-N
45:needs additional citations for
1758:transpeptidation/translocation
1066:Journal of Medicinal Chemistry
632:
626:
608:
1:
821:1.8% to 24.8% (mean: 17.3%).
2118:
911:Spectrum of susceptibility
598:Chemical and physical data
2102:Drugs developed by Pfizer
2047:
2002:Quinupristin/dalfopristin
1270:inhibit protein synthesis
1205:. TOKU-E. 6 January 2020.
754:Streptomyces lincolnensis
718:
693:
673:
349:
148:
139:
1521:Tetracycline antibiotics
1223:. TOKU-E. Archived from
942:Streptococcus pneumoniae
878:peptidyl carrier protein
868:The biosynthesis of the
1217:"Lincomycin (Lincocin)"
1146:Natural Product Reports
948:Streptococcus pyogenes
757:. A related compound,
936:Staphylococcus aureus
816:Clinical pharmacology
1711:Peptidyl transferase
789:and some species of
748:that comes from the
54:improve this article
1340:Dihydrostreptomycin
1078:10.1021/jm00298a007
846:cerebrospinal fluid
835:peritoneal dialysis
779:mechanism of action
275:(Prescription only)
136:
2074:Never to phase III
1159:10.1039/c7np00047b
2084:
2083:
2043:
2042:
2039:
2038:
1751:
1750:
1642:
1641:
1638:
1637:
1547:Chlortetracycline
1515:
1514:
1035:(20): 1056–1060.
856:Lincomycin is an
736:
735:
664:Interactive image
548:CompTox Dashboard
283:
270:
168:Biocine, Lincocin
130:
129:
122:
104:
27:Chemical compound
16:(Redirected from
2109:
1764:
1716:
1653:
1602:Rolitetracycline
1532:
1319:
1304:
1259:
1252:
1245:
1236:
1229:
1228:
1227:on 3 March 2016.
1213:
1207:
1206:
1200:
1196:"Lincomycin HCl"
1192:
1186:
1185:
1178:
1172:
1171:
1161:
1137:
1131:
1130:
1120:
1096:
1090:
1089:
1061:
1055:
1054:
1044:
1020:
1014:
1013:
1011:
1009:
994:
988:
987:
985:
983:
973:nctr-crs.fda.gov
965:
763:thionyl chloride
732:
731:
724:
666:
646:
634:
628:
622:
616:
610:
593:
582:
571:
570:
556:
554:
539:
519:
499:
479:
459:
439:
419:
409:
408:
394:
320:
288:
281:
278:
268:
265:
243:
233:
200:
186:
153:
144:
137:
135:
125:
118:
114:
111:
105:
103:
62:
38:
30:
21:
2117:
2116:
2112:
2111:
2110:
2108:
2107:
2106:
2087:
2086:
2085:
2080:
2079:
2064:Clinical trials
2035:
2021:Streptogramin B
2016:Streptogramin A
1956:
1928:
1900:
1747:
1728:Chloramphenicol
1705:
1659:
1634:
1616:
1597:Penimepicycline
1592:Oxytetracycline
1523:
1511:
1495:
1434:
1310:
1308:Aminoglycosides
1293:
1263:
1233:
1232:
1215:
1214:
1210:
1198:
1194:
1193:
1189:
1180:
1179:
1175:
1139:
1138:
1134:
1111:(13): 685–691.
1098:
1097:
1093:
1063:
1062:
1058:
1022:
1021:
1017:
1007:
1005:
996:
995:
991:
981:
979:
967:
966:
962:
957:
921:Staphylococcus,
913:
854:
818:
775:
727:
725:
722:(what is this?)
719:
714:
711:
706:
701:
700:
689:
686:
681:
680:
669:
644:
631:
625:
619:
613:
574:
550:
542:
522:
502:
482:
462:
442:
422:
405:
397:
377:
374:
357:
356:
318:
307:Bioavailability
299:Pharmacokinetic
293:
286:
247:
207:
126:
115:
109:
106:
63:
61:
51:
39:
28:
23:
22:
15:
12:
11:
5:
2115:
2113:
2105:
2104:
2099:
2089:
2088:
2082:
2081:
2078:
2077:
2076:
2075:
2072:
2061:
2055:
2049:
2048:
2045:
2044:
2041:
2040:
2037:
2036:
2034:
2033:
2023:
2018:
2013:
1999:
1985:
1966:
1964:
1962:Streptogramins
1958:
1957:
1955:
1954:
1949:
1944:
1938:
1936:
1930:
1929:
1927:
1926:
1921:
1916:
1910:
1908:
1902:
1901:
1899:
1898:
1893:
1888:
1883:
1881:Troleandomycin
1878:
1873:
1868:
1863:
1858:
1853:
1848:
1843:
1838:
1833:
1828:
1823:
1818:
1813:
1811:Flurithromycin
1808:
1803:
1798:
1796:Clarithromycin
1793:
1788:
1783:
1778:
1772:
1770:
1761:
1753:
1752:
1749:
1748:
1746:
1745:
1740:
1735:
1730:
1724:
1722:
1713:
1707:
1706:
1704:
1703:
1698:
1693:
1688:
1683:
1678:
1673:
1667:
1665:
1650:
1644:
1643:
1640:
1639:
1636:
1635:
1633:
1632:
1626:
1624:
1622:Glycylcyclines
1618:
1617:
1615:
1614:
1609:
1604:
1599:
1594:
1589:
1584:
1579:
1574:
1569:
1564:
1559:
1557:Demeclocycline
1554:
1549:
1544:
1538:
1536:
1529:
1517:
1516:
1513:
1512:
1510:
1509:
1503:
1501:
1497:
1496:
1494:
1493:
1488:
1482:
1481:
1480:
1479:
1474:
1469:
1464:
1459:
1448:
1446:
1442:Micromonospora
1436:
1435:
1433:
1432:
1430:Nourseothricin
1427:
1422:
1417:
1412:
1407:
1396:
1395:
1394:
1393:
1388:
1383:
1378:
1367:
1366:
1365:
1364:
1359:
1354:
1343:
1342:
1337:
1331:
1329:
1316:
1301:
1295:
1294:
1266:Antibacterials
1264:
1262:
1261:
1254:
1247:
1239:
1231:
1230:
1208:
1187:
1173:
1152:(3): 257–289.
1132:
1091:
1072:(4): 616–619.
1056:
1015:
1004:. 21 June 2022
989:
959:
958:
956:
953:
952:
951:
945:
939:
912:
909:
853:
850:
817:
814:
774:
771:
734:
733:
716:
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707:
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600:
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584:
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559:
557:
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543:
541:
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530:
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523:
521:
520:
512:
510:
504:
503:
501:
500:
492:
490:
484:
483:
481:
480:
472:
470:
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463:
461:
460:
452:
450:
444:
443:
441:
440:
432:
430:
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423:
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410:
399:
398:
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395:
387:
385:
379:
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375:
360:
352:
351:
350:
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346:
342:
341:
332:
326:
325:
322:
313:
312:
309:
303:
302:
295:
294:
292:
291:
276:
262:
260:
254:
253:
249:
248:
246:
245:
222:
220:
214:
213:
210:
208:administration
202:
201:
194:
188:
187:
180:
170:
169:
166:
160:
159:
155:
154:
146:
145:
128:
127:
42:
40:
33:
26:
24:
14:
13:
10:
9:
6:
4:
3:
2:
2114:
2103:
2100:
2098:
2095:
2094:
2092:
2073:
2071:
2068:
2067:
2065:
2062:
2059:
2056:
2054:
2051:
2050:
2046:
2031:
2027:
2026:Virginiamycin
2024:
2022:
2019:
2017:
2014:
2011:
2007:
2003:
2000:
1997:
1993:
1989:
1986:
1983:
1979:
1975:
1971:
1970:Pristinamycin
1968:
1967:
1965:
1963:
1959:
1953:
1950:
1948:
1945:
1943:
1940:
1939:
1937:
1935:
1931:
1925:
1924:Solithromycin
1922:
1920:
1917:
1915:
1914:Telithromycin
1912:
1911:
1909:
1907:
1903:
1897:
1894:
1892:
1889:
1887:
1886:Tulathromycin
1884:
1882:
1879:
1877:
1874:
1872:
1869:
1867:
1866:Telithromycin
1864:
1862:
1859:
1857:
1856:Solithromycin
1854:
1852:
1851:Roxithromycin
1849:
1847:
1844:
1842:
1839:
1837:
1834:
1832:
1829:
1827:
1824:
1822:
1819:
1817:
1816:Gamithromycin
1814:
1812:
1809:
1807:
1804:
1802:
1801:Dirithromycin
1799:
1797:
1794:
1792:
1789:
1787:
1784:
1782:
1779:
1777:
1774:
1773:
1771:
1769:
1765:
1762:
1759:
1754:
1744:
1741:
1739:
1738:Thiamphenicol
1736:
1734:
1733:Azidamfenicol
1731:
1729:
1726:
1725:
1723:
1721:
1717:
1714:
1712:
1708:
1702:
1699:
1697:
1694:
1692:
1689:
1687:
1684:
1682:
1679:
1677:
1674:
1672:
1669:
1668:
1666:
1663:
1658:
1657:Oxazolidinone
1654:
1651:
1649:
1645:
1631:
1628:
1627:
1625:
1623:
1619:
1613:
1610:
1608:
1605:
1603:
1600:
1598:
1595:
1593:
1590:
1588:
1585:
1583:
1580:
1578:
1575:
1573:
1570:
1568:
1565:
1563:
1560:
1558:
1555:
1553:
1550:
1548:
1545:
1543:
1540:
1539:
1537:
1535:Tetracyclines
1533:
1530:
1527:
1522:
1518:
1508:
1505:
1504:
1502:
1498:
1492:
1489:
1487:
1484:
1483:
1478:
1475:
1473:
1470:
1468:
1465:
1463:
1460:
1458:
1455:
1454:
1453:
1450:
1449:
1447:
1444:
1443:
1437:
1431:
1428:
1426:
1423:
1421:
1418:
1416:
1413:
1411:
1410:Spectinomycin
1408:
1405:
1401:
1398:
1397:
1392:
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910:
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893:ergothioneine
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787:actinomycetes
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564:DTXSID3023215
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71: –
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65:Find sources:
59:
55:
49:
48:
43:This article
41:
37:
32:
31:
19:
2097:Lincosamides
2010:Quinupristin
2006:Dalfopristin
1946:
1934:Lincosamides
1871:Tildipirosin
1841:Oleandomycin
1806:Erythromycin
1776:Azithromycin
1612:Tetracycline
1587:Omadacycline
1572:Meclocycline
1562:Eravacycline
1552:Clomocycline
1467:Micronomicin
1440:
1415:Hygromycin B
1404:+loteprednol
1362:Ribostamycin
1335:Streptomycin
1325:Streptomyces
1323:
1225:the original
1220:
1211:
1202:
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1006:. Retrieved
1001:
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980:. Retrieved
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852:Biosynthesis
839:
831:Hemodialysis
827:
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819:
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796:
790:
776:
752:
750:actinomycete
738:
737:
726:
720:
370:
366:
362:
317:Elimination
258:Legal status
252:Legal status
116:
107:
97:
90:
83:
76:
69:"Lincomycin"
64:
52:Please help
47:verification
44:
2060:from market
1996:Linopristin
1942:Clindamycin
1919:Cethromycin
1846:Rokitamycin
1831:Midecamycin
1826:Kitasamycin
1743:Florfenicol
1720:Amphenicols
1664:inhibitors)
1630:Tigecycline
1607:Sarecycline
1582:Minocycline
1577:Metacycline
1567:Lymecycline
1542:Doxycycline
1386:Bekanamycin
1357:Paromomycin
1315:inhibitors)
759:clindamycin
743:lincosamide
647: g·mol
587:100.005.296
345:Identifiers
192:MedlinePlus
164:Trade names
18:Lincosamine
2091:Categories
1992:Flopristin
1952:Pirlimycin
1947:Lincomycin
1896:Tylvalosin
1876:Tilmicosin
1861:Spiramycin
1836:Miocamycin
1791:Carrimycin
1786:Carbomycin
1768:Macrolides
1691:Ranbezolid
1671:Eperezolid
1662:initiation
1491:Astromicin
1486:Verdamicin
1477:Isepamicin
1472:Plazomicin
1457:Netilmicin
1452:Gentamicin
1400:Tobramycin
1352:Framycetin
1313:initiation
955:References
925:Mycoplasma
870:amino acid
858:antibiotic
810:resistance
806:penicillin
798:Plasmodium
792:Mycoplasma
783:macrolides
746:antibiotic
739:Lincomycin
652:3D model (
640:Molar mass
537:ChEMBL1447
517:CHEBI:6472
477:BOD072YW0F
448:ChemSpider
383:CAS Number
354:IUPAC name
134:Lincomycin
80:newspapers
2070:Phase III
2058:Withdrawn
1906:Ketolides
1821:Josamycin
1781:Boromycin
1701:Tedizolid
1696:Sutezolid
1686:Radezolid
1681:Posizolid
1676:Linezolid
1507:Butirosin
1462:Sisomicin
1425:Apramycin
1420:Totomycin
1391:Dibekacin
1381:Arbekacin
1371:Kanamycin
905:mycothiol
901:mycothiol
863:mycothiol
767:chirality
339:bile duct
330:Excretion
319:half-life
206:Routes of
184:Monograph
178:Drugs.com
110:July 2008
1528:binding)
1439:-micin (
1376:Amikacin
1347:Neomycin
1322:-mycin (
1168:29517100
1051:14217764
1008:30 March
874:tyrosine
729:(verify)
428:DrugBank
392:154-21-2
236:QJ51FF02
218:ATC code
1891:Tylosin
1127:5828940
1118:1928825
1086:4916317
1042:1928283
604:Formula
457:2272112
437:DB01627
417:3000540
403:PubChem
290:Rx-only
287:WARNING
238: (
234:)
228: (
226:J01FF02
198:a609005
94:scholar
2053:WHO-EM
1988:NXL103
1290:QJ01XQ
1166:
1125:
1115:
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1049:
1039:
982:22 Oct
903:. The
678:SMILES
645:406.54
528:ChEMBL
497:D00223
335:Kidney
284:
271:
96:
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82:
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1756:MLS (
1500:other
1268:that
1199:(PDF)
741:is a
698:InChI
654:JSmol
508:ChEBI
212:IM/IV
101:JSTOR
87:books
1526:tRNA
1286:J01G
1282:J01F
1278:J01B
1274:J01A
1164:PMID
1123:PMID
1082:PMID
1047:PMID
1010:2024
984:2023
923:and
842:bile
833:and
795:and
773:Uses
488:KEGG
468:UNII
337:and
301:data
174:AHFS
73:news
1982:IIB
1978:IIA
1648:50S
1299:30S
1154:doi
1113:PMC
1074:doi
1037:PMC
977:FDA
929:MIC
899:by
781:to
553:EPA
407:CID
311:N/A
241:WHO
231:WHO
56:by
2093::
2066::
2030:S1
2008:,
1994:,
1980:,
1976:,
1974:IA
1288:,
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1219:.
1201:.
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267:AU
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