342:
572:
749:, and sparked significant public outcry. The most serious error was the falsification and backdating of an ethics approval letter by the lead investigator of the trial, Dr. Abdulhamid Isa Dutse. Dr. Dutse is now the chief medical officer of Aminu Kano Teaching Hospital. The result of the trial was that children treated with oral trovafloxacin had a 5% (5/100) mortality rate compared to a 6% (6/100) mortality rate with intramuscular ceftriaxone.
727:, the drug was administered to approximately 200 infected children. Eleven children died in the trial: five after taking Trovan and six after taking an older antibiotic used for comparison in the clinical trial. Others suffered blindness, deafness and brain damage, common consequences of meningitis that have not been seen in patients treated with trovafloxacin for other infection types. An investigation by the Washington Post concluded that
29:
768:. A US$ 75 million settlement with the State of Kano was reached on July 30, 2009. Additionally two lawsuits also remain pending in New York, United States. According to Wikileaked US embassy cables, Pfizer's country manager admitted that "Pfizer had hired investigators to uncover corruption links to federal attorney general Michael Aondoakaa to expose him and put pressure on him to drop the federal cases."
681:
The U.S. Food and Drug
Administration approved trovafloxacin for therapeutic use in December 1997 for use in patients aged 18 years and older. In June 1999, the agency advised doctors to limit the prescription of trovafloxacin due to adverse events associated with the drug (over 100 cases of acute
689:
recommended suspension of the marketing authorisation for a year. The suspension took effect in August 1999 and was renewed in
September 2000. In October 2000, Pfizer notified the European Commission of its decision to voluntarily withdraw the marketing authorisation which was approved by EMA in
1258:
562:
Trovafloxacin use is significantly restricted due to its high potential for inducing serious and sometimes fatal liver damage. Currently, the drug is not approved for use in the U.S. or the
European Union due to association with cases of acute liver failure and death.
1255:
698:
Trovan sales during its first full year on the market contributed US$ 160 million of Pfizer's total revenue of US$ 12.6 billion. Investors expected it to eventually bring in US$ 1 billion per year.
421:
664:
reaction, this amine is then used to displace the more reactive fluorine at the 7-position in Ethyl 1-(2,4-difluorophenyl)-6,7-difluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (
936:
1647:
463:
InChI=1S/C20H15F3N4O3/c21-8-1-2-15(13(22)3-8)27-7-12(20(29)30)17(28)9-4-14(23)19(25-18(9)27)26-5-10-11(6-26)16(10)24/h1-4,7,10-11,16H,5-6,24H2,(H,29,30)/t10-,11+,16+
1642:
1443:
809:"Activity of the new fluoroquinolone trovafloxacin (CP-99,219) against DNA gyrase and topoisomerase IV mutants of Streptococcus pneumoniae selected in vitro"
85:
609:
results in loss of nitrogen and formation of the cyclopropylpyrrolidine ring. The stereochemistry of the ring simply reflects the thermodynamics, since
479:
1289:
650:
598:
1592:
1149:
Sabatini C, Bosis S, Semino M, Senatore L, Principi N, Esposito S (June 2012). "Clinical presentation of meningococcal disease in childhood".
983:
41:
685:
Trovafloxacin received marketing authorisation in the
European Union in October 1998. In June 1999, in view of reported adverse events, the
2264:
686:
435:
963:
1004:
638:
2185:
1282:
2229:
1396:
753:
707:
486:
1208:
1177:
2279:
1341:
1024:
455:
2202:
1485:
1275:
1234:
908:
1046:
1065:
Williams D, Hopkins S (June 1998). "Safety of trovafloxacin in treatment of lower respiratory tract infections".
139:
115:
2259:
2074:
1891:
1777:
1632:
1843:
1720:
1406:
1048:
Report of the
Investigation Committee on the Clinical Trial of Trovafloxacin (Trovan) by Pfizer, Kano, 1996.
2121:
1513:
916:
756:
in the United States. However, in
January 2009, the United States Court of Appeals for the Second Circuit
241:
1963:
743:
from the children's parents. The case came to light in
December 2000 as the result of an investigation by
937:"Public statement on Trovan / Trovan IV / Turvel / Turvel IV: Withdrawal of the marketing authorisations"
321:
1267:
682:
liver injury reported to FDA). In May 2000, the FDA withdrew marketing authorisation for trovafloxacin.
147:
7-(6-Amino-3-azabicyclohex-3-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo- naphthyridine-3-carboxylic acid
310:
2254:
2249:
944:
617:
configuration of the ester group. The ester is then saponified to the corresponding carboxylic acid (
586:
2239:
1637:
626:
337:
856:
Pannu HK, Gottlieb L, Fishman EK (2001). "Acute liver failure due to trovafloxacin: CT findings".
807:
Gootz TD, Zaniewski R, Haskell S, Schmieder B, Tankovic J, Girard D, et al. (December 1996).
2244:
2190:
1698:
646:
73:
2269:
1546:
1391:
1302:
230:
2234:
1469:
1465:
1349:
736:
622:
512:
290:
165:
1768:
1692:
787:
250:
8:
1818:
1182:
745:
156:
341:
2069:
1541:
1090:
988:
968:
873:
765:
590:
833:
808:
1325:
1158:
1131:
1082:
1020:
838:
65:
877:
1814:
1521:
1493:
1121:
1094:
1074:
1012:
865:
828:
820:
653:
551:
358:
98:
190:
2274:
1710:
1536:
1262:
760:
that the
Nigerian victims and their families were entitled to bring suit against
1310:
1306:
51:
2196:
2083:
1953:
1753:
1748:
1738:
1602:
1597:
1561:
1419:
1016:
777:
732:
539:
757:
577:
20:
2223:
2051:
2001:
1991:
1939:
1929:
1861:
1785:
1743:
1663:
1587:
1556:
1475:
1461:
1449:
1439:
1433:
1429:
1424:
1414:
1369:
1235:"WikiLeaks cables: Pfizer 'used dirty tricks to avoid clinical trial payout'"
547:
543:
535:
2006:
1996:
1981:
1971:
1944:
1924:
1919:
1914:
1909:
1904:
1899:
1881:
1876:
1871:
1866:
1856:
1851:
1810:
1805:
1607:
1498:
1379:
1162:
1135:
824:
520:
93:
1086:
842:
571:
2167:
2159:
2139:
2092:
2026:
1986:
1934:
1823:
1673:
1612:
1566:
1526:
1503:
1374:
1354:
1298:
1297:
752:
Between 2002 and 2005 the victims of the Trovan tests in
Nigeria filed a
720:
594:
59:
1209:"Pfizer to Pay $ 75 Million to Settle Nigerian Trovan Drug-Testing Suit"
210:
2129:
2055:
2042:
2031:
1976:
1833:
1828:
1800:
1733:
1703:
1551:
1364:
1319:
1078:
869:
713:
531:
516:
397:
221:
1110:"Fluoroquinolone toxicity profiles: a review focusing on newer agents"
2149:
2144:
2134:
2116:
1790:
1758:
1728:
1678:
1531:
1454:
661:
606:
176:
45:
1795:
1582:
1359:
1126:
1109:
1067:
European
Journal of Clinical Microbiology & Infectious Diseases
716:
527:
270:
201:
420:
1668:
781:
740:
724:
28:
761:
728:
634:
504:
301:
806:
613:
ring fusion is by far the most stable arrangement, as is the
411:
281:
326:
1148:
261:
1256:
Abdullahi v Pfizer. US Court of Appeals 2d Cir 30 Jan 2009
2106:
2082:
909:"Trovafloxacin – Approval Letter & Printed Labelling"
523:
538:
IV. It was withdrawn from the market due to the risk of
1178:"Panel Faults Pfizer in '96 Clinical Trial In Nigeria"
701:
637:
from the reaction medium to afford the product as its
855:
443:
O=C(O)C2=CN(c1nc(c(F)cc1C2=O)N3C4(N)4C3)c5ccc(F)cc5F
585:The key reaction in building the ring consists of
1202:
1200:
1009:The SAGE Encyclopedia of Pharmacology and Society
2221:
964:"Unforeseen Side Effects Ruined One Blockbuster"
731:had administered the drug as part of an illegal
189:
1064:
784:of trovafloxacin for intravenous administration
164:
1197:
1011:. SAGE Publications, Inc. pp. 1444–1447.
984:"Suspension of Trovan Drug in Europe Is Urged"
1283:
687:Committee for Proprietary Medicinal Products
1107:
629:(DPPA) to afford the transient isocyanate (
1290:
1276:
1151:Journal of Preventive Medicine and Hygiene
340:
229:
1125:
832:
249:
1206:
1175:
961:
575:Trovafloxacin synthesis: K. E. Brighty,
570:
52:Micromedex Detailed Consumer Information
1232:
892:The organic chemistry of Drug Synthesis
621:). The acid undergoes a version of the
336:
209:
64:
2222:
1002:
957:
955:
671:
639:tert-Butyloxycarbonyl protecting group
1271:
1108:Lipsky BA, Baker CA (February 1999).
1054:, Federal Ministry of Health, Nigeria
813:Antimicrobial Agents and Chemotherapy
309:
289:
50:
1005:"Trovafloxacin (Trovan) Controversy"
931:
929:
927:
557:
97:
2265:Heterocyclic compounds with 2 rings
976:
952:
708:Kano Trovafloxacin trial litigation
702:Nigerian clinical trial controversy
269:
180:
13:
1169:
14:
2291:
1249:
924:
566:
381:
375:
369:
27:
1226:
1142:
1101:
1058:
764:in the United States under the
754:series of unsuccessful lawsuits
735:without authorization from the
676:
656:to afford the secondary amine (
519:that inhibits the uncoiling of
468:Key:WVPSKSLAZQPAKQ-CDMJZVDBSA-N
1039:
996:
962:Petersen M (August 27, 2000).
901:
884:
849:
800:
633:). The reactive function adds
387:
363:
1:
1633:Trimethoprim/sulfamethoxazole
1233:Boseley S (9 December 2010).
992:. June 12, 1999. p. C.3.
793:
1207:Stephens J (July 31, 2009).
1114:Clinical Infectious Diseases
917:Food and Drug Administration
693:
546:bacterial coverage but less
530:by blocking the activity of
7:
2230:Fluoroquinolone antibiotics
1638:Ormetoprim/sulfadimethoxine
771:
550:coverage than the previous
10:
2296:
1176:Stephens J (May 7, 2006).
1017:10.4135/9781483349985.n409
705:
353:Chemical and physical data
2280:Fluorobenzene derivatives
2180:
2158:
2115:
2105:
2068:
2040:
2019:
1962:
1890:
1842:
1776:
1767:
1719:
1691:
1656:
1648:Pyrimethamine/sulfadoxine
1625:
1575:
1512:
1484:
1405:
1390:
1340:
1318:
945:European Medicines Agency
587:1,3-Dipolar cycloaddition
476:
451:
431:
409:
396:
357:
352:
320:
300:
280:
260:
240:
220:
200:
175:
155:
135:
130:
114:
109:
84:
72:
58:
40:
35:
26:
627:diphenylphosphoryl azide
647:Catalytic hydrogenation
1547:Sulfamethoxypyridazine
825:10.1128/AAC.40.12.2691
582:
515:) is a broad spectrum
2260:Nitrogen heterocycles
2020:Newer non-fluorinated
1657:Other DHPS inhibitors
1643:Pyrimethamine/dapsone
1470:Succinylsulfathiazole
1466:Phthalylsulfathiazole
1350:2,4-Diaminopyrimidine
623:Curtius rearrangement
578:U.S. patent 5,164,402
574:
513:Laboratorios Almirall
123:Withdrawn from market
1444:Acetyl sulfisoxazole
1303:inhibit nucleic acid
1261:13 June 2011 at the
1819:Alalevonadifloxacin
1486:Intermediate-acting
1213:The Washington Post
1183:The Washington Post
858:Emergency Radiology
746:The Washington Post
737:Nigerian government
672:Society and culture
23:
2207:Never to phase III
1708:thereby inhibiting
1696:(inhibit bacterial
1542:Sulfametoxydiazine
1330:thereby inhibiting
1323:(inhibit bacterial
1079:10.1007/bf01691582
989:The New York Times
969:The New York Times
870:10.1007/PL00011876
766:Alien Tort Statute
712:In 1996, during a
625:when treated with
591:ethyl diazoacetate
583:
19:
2217:
2216:
2176:
2175:
2101:
2100:
2064:
2063:
2015:
2014:
1687:
1686:
1621:
1620:
1326:purine metabolism
1003:Oldani M (2016).
819:(12): 2691–2697.
660:). In a standard
649:then removes the
581:(1992 to Pfizer).
558:Adverse reactions
494:
493:
422:Interactive image
322:CompTox Dashboard
80:Oral, intravenous
2287:
2255:Aromatic ketones
2250:Alpha-keto acids
2113:
2112:
2080:
2079:
1815:Levonadifloxacin
1774:
1773:
1769:Fluoroquinolones
1717:
1716:
1522:Sulfadimethoxine
1494:Sulfamethoxazole
1415:Sulfaisodimidine
1403:
1402:
1338:
1337:
1292:
1285:
1278:
1269:
1268:
1243:
1242:
1230:
1224:
1223:
1221:
1219:
1204:
1195:
1194:
1192:
1191:
1173:
1167:
1166:
1146:
1140:
1139:
1129:
1105:
1099:
1098:
1062:
1056:
1055:
1053:
1043:
1037:
1036:
1034:
1033:
1000:
994:
993:
980:
974:
973:
959:
950:
949:
941:
933:
922:
921:
913:
905:
899:
888:
882:
881:
853:
847:
846:
836:
804:
654:protecting group
580:
552:fluoroquinolones
542:. It had better
490:
489:
482:
424:
404:
389:
383:
377:
371:
365:
345:
344:
330:
328:
313:
293:
273:
253:
233:
213:
193:
183:
182:
168:
101:
68:
54:
31:
24:
22:
18:
2295:
2294:
2290:
2289:
2288:
2286:
2285:
2284:
2240:Withdrawn drugs
2220:
2219:
2218:
2213:
2212:
2197:Clinical trials
2172:
2154:
2120:
2097:
2073:
2060:
2036:
2011:
1958:
1886:
1838:
1763:
1711:DNA replication
1709:
1707:
1701:
1697:
1695:
1683:
1652:
1617:
1576:Other/ungrouped
1571:
1537:Sulfametomidine
1508:
1480:
1394:
1386:
1333:
1331:
1329:
1324:
1322:
1314:
1296:
1263:Wayback Machine
1252:
1247:
1246:
1231:
1227:
1217:
1215:
1205:
1198:
1189:
1187:
1174:
1170:
1147:
1143:
1106:
1102:
1063:
1059:
1051:
1045:
1044:
1040:
1031:
1029:
1027:
1001:
997:
982:
981:
977:
972:. p. 3.11.
960:
953:
939:
935:
934:
925:
911:
907:
906:
902:
898:, p 123 (1995).
889:
885:
854:
850:
805:
801:
796:
774:
710:
704:
696:
679:
674:
576:
569:
560:
485:
483:
480:(what is this?)
477:
472:
469:
464:
459:
458:
447:
444:
439:
438:
427:
402:
392:
386:
380:
374:
368:
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324:
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276:
256:
236:
216:
196:
179:
171:
151:
148:
143:
142:
126:
105:
75:
17:
12:
11:
5:
2293:
2283:
2282:
2277:
2272:
2267:
2262:
2257:
2252:
2247:
2245:Naphthyridines
2242:
2237:
2232:
2215:
2214:
2211:
2210:
2209:
2208:
2205:
2194:
2188:
2182:
2181:
2178:
2177:
2174:
2173:
2171:
2170:
2164:
2162:
2156:
2155:
2153:
2152:
2147:
2142:
2137:
2132:
2126:
2124:
2122:RNA polymerase
2110:
2103:
2102:
2099:
2098:
2096:
2095:
2089:
2087:
2084:Nitroimidazole
2077:
2066:
2065:
2062:
2061:
2059:
2058:
2052:Aminocoumarins
2048:
2046:
2038:
2037:
2035:
2034:
2029:
2023:
2021:
2017:
2016:
2013:
2012:
2010:
2009:
2004:
1999:
1994:
1989:
1984:
1979:
1974:
1968:
1966:
1960:
1959:
1957:
1956:
1954:Alatrofloxacin
1947:
1942:
1937:
1932:
1927:
1922:
1917:
1912:
1907:
1902:
1896:
1894:
1892:4th generation
1888:
1887:
1885:
1884:
1879:
1874:
1869:
1864:
1859:
1854:
1848:
1846:
1844:3rd generation
1840:
1839:
1837:
1836:
1831:
1826:
1821:
1808:
1803:
1798:
1793:
1788:
1782:
1780:
1778:2nd generation
1771:
1765:
1764:
1762:
1761:
1756:
1754:Piromidic acid
1751:
1749:Pipemidic acid
1746:
1741:
1739:Nalidixic acid
1736:
1731:
1725:
1723:
1721:1st generation
1714:
1689:
1688:
1685:
1684:
1682:
1681:
1676:
1671:
1666:
1660:
1658:
1654:
1653:
1651:
1650:
1645:
1640:
1635:
1629:
1627:
1623:
1622:
1619:
1618:
1616:
1615:
1610:
1605:
1603:Sulfaguanidine
1600:
1598:Sulfadicramide
1595:
1590:
1585:
1579:
1577:
1573:
1572:
1570:
1569:
1564:
1562:Sulfaphenazole
1559:
1554:
1549:
1544:
1539:
1534:
1529:
1524:
1518:
1516:
1510:
1509:
1507:
1506:
1501:
1496:
1490:
1488:
1482:
1481:
1479:
1478:
1473:
1459:
1458:
1457:
1447:
1437:
1427:
1422:
1420:Sulfamethizole
1417:
1411:
1409:
1400:
1397:DHPS inhibitor
1388:
1387:
1385:
1384:
1383:
1382:
1377:
1372:
1367:
1362:
1357:
1346:
1344:
1342:DHFR inhibitor
1335:
1316:
1315:
1299:Antibacterials
1295:
1294:
1287:
1280:
1272:
1266:
1265:
1251:
1250:External links
1248:
1245:
1244:
1225:
1196:
1168:
1157:(2): 116–119.
1141:
1127:10.1086/515104
1120:(2): 352–364.
1100:
1073:(6): 454–458.
1057:
1038:
1025:
995:
975:
951:
923:
900:
883:
864:(2): 108–110.
848:
798:
797:
795:
792:
791:
790:
785:
778:Alatrofloxacin
773:
770:
733:clinical trial
706:Main article:
703:
700:
695:
692:
678:
675:
673:
670:
651:carbobenzyloxy
597:to afford the
568:
565:
559:
556:
540:hepatotoxicity
492:
491:
474:
473:
471:
470:
467:
465:
462:
454:
453:
452:
449:
448:
446:
445:
442:
434:
433:
432:
429:
428:
426:
425:
417:
415:
407:
406:
400:
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384:
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372:
366:
361:
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354:
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333:
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306:
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138:
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125:
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120:
118:
112:
111:
107:
106:
104:
103:
90:
88:
82:
81:
78:
76:administration
70:
69:
62:
56:
55:
48:
38:
37:
33:
32:
15:
9:
6:
4:
3:
2:
2292:
2281:
2278:
2276:
2273:
2271:
2270:Cyclopropanes
2268:
2266:
2263:
2261:
2258:
2256:
2253:
2251:
2248:
2246:
2243:
2241:
2238:
2236:
2233:
2231:
2228:
2227:
2225:
2206:
2204:
2201:
2200:
2198:
2195:
2192:
2189:
2187:
2184:
2183:
2179:
2169:
2166:
2165:
2163:
2161:
2157:
2151:
2148:
2146:
2143:
2141:
2138:
2136:
2133:
2131:
2128:
2127:
2125:
2123:
2118:
2114:
2111:
2108:
2104:
2094:
2091:
2090:
2088:
2085:
2081:
2078:
2076:
2071:
2067:
2057:
2053:
2050:
2049:
2047:
2044:
2039:
2033:
2030:
2028:
2025:
2024:
2022:
2018:
2008:
2005:
2003:
2002:Pradofloxacin
2000:
1998:
1995:
1993:
1992:Marbofloxacin
1990:
1988:
1985:
1983:
1980:
1978:
1975:
1973:
1970:
1969:
1967:
1965:
1961:
1955:
1951:
1950:Trovafloxacin
1948:
1946:
1943:
1941:
1940:Prulifloxacin
1938:
1936:
1933:
1931:
1930:Clinafloxacin
1928:
1926:
1923:
1921:
1918:
1916:
1913:
1911:
1908:
1906:
1903:
1901:
1898:
1897:
1895:
1893:
1889:
1883:
1880:
1878:
1875:
1873:
1870:
1868:
1865:
1863:
1862:Grepafloxacin
1860:
1858:
1855:
1853:
1850:
1849:
1847:
1845:
1841:
1835:
1832:
1830:
1827:
1825:
1822:
1820:
1816:
1812:
1809:
1807:
1804:
1802:
1799:
1797:
1794:
1792:
1789:
1787:
1786:Ciprofloxacin
1784:
1783:
1781:
1779:
1775:
1772:
1770:
1766:
1760:
1757:
1755:
1752:
1750:
1747:
1745:
1744:Oxolinic acid
1742:
1740:
1737:
1735:
1732:
1730:
1727:
1726:
1724:
1722:
1718:
1715:
1712:
1705:
1700:
1699:topoisomerase
1694:
1690:
1680:
1677:
1675:
1672:
1670:
1667:
1665:
1664:Acediasulfone
1662:
1661:
1659:
1655:
1649:
1646:
1644:
1641:
1639:
1636:
1634:
1631:
1630:
1628:
1624:
1614:
1611:
1609:
1606:
1604:
1601:
1599:
1596:
1594:
1591:
1589:
1588:Sulfacetamide
1586:
1584:
1581:
1580:
1578:
1574:
1568:
1565:
1563:
1560:
1558:
1557:Sulfamerazine
1555:
1553:
1550:
1548:
1545:
1543:
1540:
1538:
1535:
1533:
1530:
1528:
1525:
1523:
1520:
1519:
1517:
1515:
1511:
1505:
1502:
1500:
1497:
1495:
1492:
1491:
1489:
1487:
1483:
1477:
1476:Sulfathiourea
1474:
1471:
1467:
1463:
1462:Sulfathiazole
1460:
1456:
1453:
1452:
1451:
1450:Sulfanilamide
1448:
1445:
1441:
1440:Sulfafurazole
1438:
1435:
1434:Sulfasalazine
1431:
1430:Sulfapyridine
1428:
1426:
1425:Sulfadimidine
1423:
1421:
1418:
1416:
1413:
1412:
1410:
1408:
1404:
1401:
1398:
1393:
1389:
1381:
1378:
1376:
1373:
1371:
1370:Pyrimethamine
1368:
1366:
1363:
1361:
1358:
1356:
1353:
1352:
1351:
1348:
1347:
1345:
1343:
1339:
1336:
1327:
1321:
1317:
1312:
1308:
1304:
1300:
1293:
1288:
1286:
1281:
1279:
1274:
1273:
1270:
1264:
1260:
1257:
1254:
1253:
1240:
1236:
1229:
1214:
1210:
1203:
1201:
1186:. p. A01
1185:
1184:
1179:
1172:
1164:
1160:
1156:
1152:
1145:
1137:
1133:
1128:
1123:
1119:
1115:
1111:
1104:
1096:
1092:
1088:
1084:
1080:
1076:
1072:
1068:
1061:
1050:
1049:
1042:
1028:
1026:9781483350004
1022:
1018:
1014:
1010:
1006:
999:
991:
990:
985:
979:
971:
970:
965:
958:
956:
947:
946:
938:
932:
930:
928:
919:
918:
910:
904:
897:
893:
890:D. Lednicer,
887:
879:
875:
871:
867:
863:
859:
852:
844:
840:
835:
830:
826:
822:
818:
814:
810:
803:
799:
789:
786:
783:
779:
776:
775:
769:
767:
763:
759:
755:
750:
748:
747:
742:
738:
734:
730:
726:
722:
718:
715:
709:
699:
691:
688:
683:
669:
667:
663:
659:
655:
652:
648:
644:
640:
636:
632:
628:
624:
620:
616:
612:
608:
604:
600:
599:pyrrazolidine
596:
592:
588:
579:
573:
567:Manufacturing
564:
555:
553:
549:
548:Gram-negative
545:
544:Gram-positive
541:
537:
536:topoisomerase
533:
529:
525:
522:
518:
514:
510:
506:
502:
498:
497:Trovafloxacin
488:
481:
475:
466:
461:
460:
457:
450:
441:
440:
437:
430:
423:
419:
418:
416:
413:
408:
401:
399:
395:
362:
360:
356:
351:
343:
339:
338:DTXSID0041145
335:
334:
332:
323:
319:
312:
308:
307:
305:
303:
299:
292:
288:
287:
285:
283:
279:
272:
268:
267:
265:
263:
259:
252:
248:
247:
245:
243:
239:
232:
228:
227:
225:
223:
219:
212:
208:
207:
205:
203:
199:
192:
188:
187:
185:
178:
174:
167:
163:
162:
160:
158:
154:
145:
144:
141:
134:
129:
122:
121:
119:
117:
113:
108:
100:
95:
92:
91:
89:
87:
83:
79:
77:
71:
67:
63:
61:
57:
53:
49:
47:
43:
39:
36:Clinical data
34:
30:
25:
21:Trovafloxacin
2235:Hepatotoxins
2160:Lipiarmycins
2007:Sarafloxacin
1997:Orbifloxacin
1982:Enrofloxacin
1972:Danofloxacin
1949:
1945:Sitafloxacin
1925:Moxifloxacin
1920:Gemifloxacin
1915:Finafloxacin
1910:Gatifloxacin
1905:Delafloxacin
1900:Besifloxacin
1882:Tosufloxacin
1877:Temafloxacin
1872:Sparfloxacin
1867:Pazufloxacin
1857:Balofloxacin
1852:Levofloxacin
1811:Nadifloxacin
1806:Lomefloxacin
1626:Combinations
1608:Sulfametrole
1593:Sulfaclozine
1499:Sulfadiazine
1407:Short-acting
1392:Sulfonamides
1380:Trimethoprim
1239:The Guardian
1238:
1228:
1216:. Retrieved
1212:
1188:. Retrieved
1181:
1171:
1154:
1150:
1144:
1117:
1113:
1103:
1070:
1066:
1060:
1047:
1041:
1030:. Retrieved
1008:
998:
987:
978:
967:
943:
915:
903:
895:
891:
886:
861:
857:
851:
816:
812:
802:
751:
744:
711:
697:
690:March 2001.
684:
680:
677:Legal status
665:
657:
642:
641:derivative (
630:
618:
614:
610:
602:
584:
561:
508:
500:
496:
495:
484:
478:
116:Legal status
110:Legal status
2193:from market
2168:Fidaxomicin
2140:Rifapentine
2093:Secnidazole
2086:derivatives
2027:Nemonoxacin
1987:Ibafloxacin
1935:Garenoxacin
1824:Norfloxacin
1674:Solasulfone
1613:Sulfanitran
1567:Sulfamazone
1527:Sulfadoxine
1514:Long-acting
1504:Sulfamoxole
1375:Tetroxoprim
1355:Brodimoprim
1332:DNA and RNA
1320:Antifolates
595:3-pyrroline
526:in various
521:supercoiled
405: g·mol
166:147059-72-1
131:Identifiers
60:MedlinePlus
2224:Categories
2130:Rifampicin
2117:Rifamycins
2075:inhibitors
2056:Novobiocin
2032:Ozenoxacin
1977:Difloxacin
1964:Veterinary
1834:Rufloxacin
1829:Pefloxacin
1801:Fleroxacin
1734:Flumequine
1704:DNA gyrase
1693:Quinolones
1552:Sulfaperin
1365:Ormetoprim
1334:synthesis)
1190:2006-08-28
1032:2019-01-21
794:References
714:meningitis
532:DNA gyrase
517:antibiotic
410:3D model (
398:Molar mass
291:CHEBI:9763
251:9F388J00UK
222:ChemSpider
157:CAS Number
140:IUPAC name
16:Antibiotic
2203:Phase III
2191:Withdrawn
2150:Rifalazil
2145:Rifaximin
2135:Rifabutin
2109:synthesis
2070:Anaerobic
2041:Related (
1791:Ofloxacin
1759:Rosoxacin
1729:Cinoxacin
1679:Sulfoxone
1532:Sulfalene
1455:Prontosil
788:Quinolone
694:Economics
662:quinoline
607:Pyrolysis
593:to N-Cbz-
499:(sold as
311:ChEMBL428
74:Routes of
46:Drugs.com
1796:Enoxacin
1583:Mafenide
1360:Iclaprim
1259:Archived
1163:23240173
1136:10064255
878:43307678
772:See also
717:epidemic
528:bacteria
487:(verify)
231:16736478
202:DrugBank
86:ATC code
1702:and/or
1669:Dapsone
1218:May 26,
1095:1325773
1087:9758292
843:9124824
782:prodrug
741:consent
725:Nigeria
403:416.360
359:Formula
211:DB00685
177:PubChem
102:)
96: (
94:J01MA13
66:a605016
2275:Amines
2186:WHO-EM
1161:
1134:
1093:
1085:
1023:
896:Vol. 5
876:
841:
834:163605
831:
762:Pfizer
729:Pfizer
635:t-BuOH
509:Turvel
505:Pfizer
501:Trovan
436:SMILES
302:ChEMBL
271:D08654
1301:that
1091:S2CID
1052:(PDF)
940:(PDF)
912:(PDF)
874:S2CID
758:ruled
456:InChI
412:JSmol
282:ChEBI
191:62959
1311:J01M
1307:J01E
1220:2010
1159:PMID
1132:PMID
1083:PMID
1021:ISBN
839:PMID
780:, a
721:Kano
534:and
507:and
262:KEGG
242:UNII
42:AHFS
2107:RNA
2072:DNA
1122:doi
1075:doi
1013:doi
866:doi
829:PMC
821:doi
739:or
719:in
668:).
645:).
615:cis
611:cis
605:).
589:of
524:DNA
511:by
503:by
327:EPA
181:CID
99:WHO
2226::
2199::
2054::
2043:DG
1468:,
1309:,
1237:.
1211:.
1199:^
1180:.
1155:53
1153:.
1130:.
1118:28
1116:.
1112:.
1089:.
1081:.
1071:17
1069:.
1019:.
1007:.
986:.
966:.
954:^
942:.
926:^
914:.
894:,
872:.
860:.
837:.
827:.
817:40
815:.
811:.
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2119:/
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1952:/
1817:/
1813:/
1713:)
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1222:.
1193:.
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1138:.
1124::
1097:.
1077::
1035:.
1015::
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920:.
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823::
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391:3
388:O
385:4
382:N
379:3
376:F
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325:(
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