1165:
58:
678:
655:
49:
1208:
3191:
1192:(THF). THF is an essential precursor in the thymidine synthesis pathway and interference with this pathway inhibits bacterial DNA synthesis. Trimethoprim's inhibitory activity for bacterial dihydrofolate reductase is sixty thousand times greater than for human dihydrofolate reductase.
1305:"Prevention and treatment of opportunistic infections in HIV-infected adults and adolescents: Updated Guidelines from the Centers for Disease Control and Prevention, National Institutes of Health, and HIV Medicine Association of the Infectious Diseases Society of America"
2059:
Heaslet H, Harris M, Fahnoe K, Sarver R, Putz H, Chang J, et al. (August 2009). "Structural comparison of chromosomal and exogenous dihydrofolate reductase from
Staphylococcus aureus in complex with the potent inhibitor trimethoprim".
1156:
The trophoblasts in the early fetus are sensitive to changes in the folate cycle. A 2013 study found a doubling in the risk of miscarriage in women exposed to trimethoprim in the early pregnancy.
2110:
Brogden RN, Carmine AA, Heel RC, Speight TM, Avery GS (June 1982). "Trimethoprim: a review of its antibacterial activity, pharmacokinetics and therapeutic use in urinary tract infections".
303:
1853:
1624:
1594:
2607:
1149:
and can affect folate metabolism, there has been growing evidence of the risk of structural birth defects associated with trimethoprim, especially during the first
2602:
3246:
2403:
3236:
3226:
248:
1654:
2249:
2552:
2196:
Brumfitt W, Hamilton-Miller JM (December 1993). "Reassessment of the rationale for the combinations of sulphonamides with diaminopyrimidines".
1204:
are commonly used in combination due to possible synergistic effects, and reduced development of resistance. This benefit has been questioned.
134:
1360:
761:
1564:
1947:
1896:
1845:
1616:
1586:
1223:
Trimethoprim was first used in 1962. In 1972, it was used as a prophylactic treatment for urinary tract infections in
Finland.
1281:
1164:
747:
3145:
2242:
1495:
1465:
897:
2356:
1749:"Effects of moderate-dose versus high-dose trimethoprim on serum creatinine and creatinine clearance and adverse reactions"
865:
Common side effects include nausea, changes in taste, and rash. Rarely it may result in blood problems such as not enough
1798:"Toxin gene expression by shiga toxin-producing Escherichia coli: the role of antibiotics and the bacterial SOS response"
806:
185:
1561:"Three-day courses of antibiotics for uncomplicated urinary tract infection | Guidance and guidelines | NICE"
1097:
2301:
781:
3162:
2445:
2235:
424:
288:
166:
789:
InChI=1S/C14H18N4O3/c1-19-10-5-8(6-11(20-2)12(10)21-3)4-9-7-17-14(16)18-13(9)15/h5-7H,4H2,1-3H3,(H4,15,16,17,18)
1646:
3034:
2851:
2737:
2592:
1201:
927:
840:
2803:
2680:
2366:
2002:
Andersen JT, Petersen M, Jimenez-Solem E, Broedbaek K, Andersen EW, Andersen NL, et al. (August 2013).
3081:
2473:
2004:"Trimethoprim use in early pregnancy and the risk of miscarriage: a register-based nationwide cohort study"
990:
673:
526:
2923:
934:
634:
2227:
3251:
3181:
1877:"Disulfiram-like reaction associated with intravenous trimethoprim-sulfamethoxazole and metronidazole"
1706:
Choi MJ, Fernandez PC, Patnaik A, Coupaye-Gerard B, D'Andrea D, Szerlip H, et al. (March 1993).
1428:
1071:
940:
Resistance to trimethoprim is increasing, but it is still a first line antibiotic in many countries.
595:
57:
948:
Cultures and susceptibility tests should be done to make sure bacteria are treated by trimethoprim.
3221:
3216:
2597:
1197:
998:
909:
650:
933:(the leading cause of antibiotic-induced diarrhea). Trimethoprim has been used in trials to treat
3150:
2658:
1181:
882:
828:
222:
124:
31:
17:
1560:
1352:
1093:
for secretion into the renal tubule. This can cause an artificial rise in the serum creatinine.
3231:
2506:
2351:
2262:
1005:
918:
848:
836:
616:
368:
575:
2429:
2425:
2309:
967:
3241:
3211:
2728:
2652:
2166:
1911:
1876:
1189:
1122:
1064:
535:
390:
515:
271:
8:
2778:
2153:
Burchall JJ (November 1973). "Mechanism of action of trimethoprim-sulfamethoxazole. II".
1695:. Vol. 1 (22nd ed.). Greenwood Village, CO.: Thomson Health Care. p. 2849.
859:
450:
441:
677:
654:
3029:
2501:
2170:
2135:
2085:
2041:
2028:
2003:
1979:
1962:
1939:
1927:
1822:
1797:
1537:
1512:
1329:
1304:
1133:
when alcohol is consumed after it is used, in particular when used in combination with
923:
832:
196:
1773:
1748:
2285:
2213:
2178:
2127:
2123:
2077:
2033:
1984:
1931:
1888:
1827:
1778:
1729:
1542:
1491:
1461:
1410:
1334:
1185:
960:
870:
606:
340:
327:
315:
241:
158:
2139:
2045:
1943:
1277:
144:
2774:
2481:
2453:
2209:
2205:
2162:
2119:
2089:
2069:
2023:
2015:
1974:
1923:
1817:
1809:
1768:
1760:
1719:
1532:
1528:
1524:
1436:
1400:
1324:
1316:
1211:
1193:
1134:
1115:
1052:
953:
913:
690:
350:
261:
75:
3195:
2670:
2496:
475:
378:
358:
2270:
2266:
1724:
1707:
3156:
3043:
2913:
2713:
2708:
2698:
2562:
2557:
2521:
2379:
985:
2019:
3205:
3011:
2961:
2951:
2909:
2899:
2889:
2821:
2745:
2703:
2623:
2547:
2516:
2435:
2421:
2409:
2399:
2393:
2389:
2384:
2374:
2329:
1433:
World Health
Organization model list of essential medicines: 22nd list (2021)
1075:
666:
40:
1173:
2966:
2956:
2941:
2931:
2904:
2884:
2879:
2874:
2869:
2864:
2859:
2841:
2836:
2831:
2826:
2816:
2811:
2770:
2765:
2567:
2458:
2081:
2037:
1988:
1831:
1813:
1764:
1546:
1414:
1338:
1083:
974:
266:
256:
2217:
2182:
2131:
1935:
1892:
1782:
1733:
3127:
3119:
3099:
3052:
2986:
2946:
2894:
2783:
2633:
2572:
2526:
2486:
2463:
2334:
2314:
2258:
2257:
1490:(2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust.
1320:
1101:
873:. Trimethoprim may cause sun sensitivity. There is evidence of potential
152:
2174:
1708:"Brief report: trimethoprim-induced hyperkalemia in a patient with AIDS"
1441:
1303:
Masur H, Brooks JT, Benson CA, Holmes KK, Pau AK, Kaplan JE (May 2014).
495:
3089:
3015:
3002:
2991:
2936:
2793:
2788:
2760:
2693:
2663:
2511:
2324:
2279:
2073:
1235:
1130:
1090:
1060:
874:
824:
723:
506:
236:
2001:
1207:
3109:
3104:
3094:
3076:
2750:
2718:
2688:
2638:
2491:
2414:
1690:
1150:
1079:
1056:
981:
866:
461:
403:
138:
2755:
2542:
2319:
1961:
Sivojelezova A, Einarson A, Shuhaiber S, Koren G (September 2003).
1405:
1388:
1146:
855:
555:
486:
229:
180:
1960:
1705:
1513:"Antibiotics versus no treatment for toxoplasma retinochoroiditis"
746:
622:
2628:
1963:"Trimethoprim-sulfonamide combination therapy in early pregnancy"
844:
922:
pneumonia. It is generally not recommended for the treatment of
1675:
878:
586:
408:
48:
1510:
1145:
Based on the studies that show that trimethoprim crosses the
737:
566:
383:
639:
96:
1647:"PROLOPRIM® (trimethoprim)100-mg and 200-mg Scored Tablets"
1200:, an enzyme involved further upstream in the same pathway.
546:
99:
93:
84:
1678:
American
Hospital Formulary Service- Drug Information 2002
1511:
Pradhan E, Bhandari S, Gilbert RE, Stanford M (May 2016).
1458:
1082:. This can cause increased potassium levels in the body (
3066:
3042:
2109:
2058:
1427:
890:
886:
108:
2195:
1302:
898:
1954:
1746:
1171:
DHFR in complex with NADPH and trimethoprim PDB entry
3179:
1280:. The American Society of Health-System Pharmacists.
877:
in some animals but not humans. It works by blocking
1747:
Naderer O, Nafziger AN, Bertino JS (November 1997).
1676:
Ellenhorn MJ, Schonwald S, Ordog G, Wasserberger J.
1579:
1100:
infections may lead to an increase in expression of
105:
102:
81:
78:
1874:
1795:
1680:. Baltimore, MD: Williams and Wilkins. p. 236.
885:in some bacteria, preventing creation of bacterial
111:
90:
87:
1875:Edwards DL, Fink PC, Van Dyke PO (December 1986).
912:, although it may be used against any susceptible
896:Trimethoprim was first used in 1962. It is on the
1693:Drug Information for the Health Care Professional
3203:
474:
432:5-(3,4,5-Trimethoxybenzyl)pyrimidine-2,4-diamine
449:
1846:"PRIMSOL- trimethoprim hydrochloride solution"
1691:MICROMEDEX Thomson Health Care. USPDI (2002).
1617:"PRIMSOL- trimethoprim hydrochloride solution"
1460:. Jones & Bartlett Learning. p. 113.
3247:World Health Organization essential medicines
2243:
1389:"Resistance to trimethoprim-sulfamethoxazole"
1353:"Prescribing medicines in pregnancy database"
943:
3237:Protozoal dihydrofolate reductase inhibitors
3227:Bacterial dihydrofolate reductase inhibitors
2189:
1129:It may be involved in a reaction similar to
184:
1909:
1517:The Cochrane Database of Systematic Reviews
916:. It may also be used to treat and prevent
900:. It is available as a generic medication.
270:
2250:
2236:
2105:
2103:
2101:
2099:
1272:
1270:
1268:
1266:
1264:
1262:
1260:
1258:
676:
653:
514:
2027:
1978:
1821:
1796:Kimmitt PT, Harwood CR, Barer MR (2000).
1772:
1723:
1536:
1440:
1404:
1382:
1380:
1378:
1328:
908:It is primarily used in the treatment of
534:
1455:
1386:
1206:
1163:
2096:
1255:
649:
494:
157:
14:
3204:
1597:from the original on 30 September 2015
1504:
1449:
1421:
1375:
1345:
1284:from the original on 24 September 2015
1159:
667:
321:
2231:
1950:from the original on 24 January 2009.
1899:from the original on 24 January 2009.
1856:from the original on 17 November 2015
1852:. U.S. National Library of Medicine.
1753:Antimicrobial Agents and Chemotherapy
1657:from the original on 17 November 2015
1653:. U.S. National Library of Medicine.
1627:from the original on 17 November 2015
1623:. U.S. National Library of Medicine.
1593:. U.S. National Library of Medicine.
1485:
1481:
1479:
1477:
1435:. Geneva: World Health Organization.
893:and leading to bacterial cell death.
615:
594:
574:
334:
175:
143:
2167:10.1093/infdis/128.Supplement_3.S437
1567:from the original on 8 December 2015
1108:
621:
260:
129:Proloprim, Monotrim, Triprim, others
1912:"Disulfiram-cotrimoxazole reaction"
1712:The New England Journal of Medicine
1587:"TRIMETHOPRIM- trimethoprim tablet"
554:
465:
24:
2155:The Journal of Infectious Diseases
1928:10.1002/j.1875-9114.1998.tb03913.x
1838:
1684:
1639:
1474:
25:
3263:
1363:from the original on 8 April 2014
1202:Trimethoprim and sulfamethoxazole
297:
207:
3189:
2124:10.2165/00003495-198223060-00001
827:used mainly in the treatment of
707:
701:
74:
56:
47:
2146:
2052:
1995:
1903:
1868:
1789:
1740:
1699:
1669:
1609:
1012:
903:
794:Key:IEDVJHCEMCRBQM-UHFFFAOYSA-N
769:Nc1nc(N)ncc1Cc(cc2OC)cc(OC)c2OC
2210:10.1080/1120009X.1993.11741097
1553:
1529:10.1002/14651858.CD002218.pub2
1296:
1184:and inhibits the reduction of
713:
695:
310:
13:
1:
2593:Trimethoprim/sulfamethoxazole
1488:Australian Medicines Handbook
1248:
1070:Trimethoprim antagonizes the
1802:Emerging Infectious Diseases
1393:Clinical Infectious Diseases
1309:Clinical Infectious Diseases
1140:
1063:levels; this may also cause
7:
2598:Ormetoprim/sulfadimethoxine
1910:Heelon MW, White M (1998).
1725:10.1056/NEJM199303113281006
10:
3268:
2008:Epidemiology and Infection
1445:. WHO/MHP/HPS/EML/2021.02.
1218:
944:Spectrum of susceptibility
685:Chemical and physical data
29:
3140:
3118:
3075:
3065:
3028:
3000:
2979:
2922:
2850:
2802:
2736:
2727:
2679:
2651:
2616:
2608:Pyrimethamine/sulfadoxine
2585:
2535:
2472:
2444:
2365:
2350:
2300:
2278:
2161:: Suppl: 437-Suppl: 441.
2152:
2020:10.1017/S0950268812002178
1967:Canadian Family Physician
1429:World Health Organization
1226:Its name is derived from
1072:epithelial sodium channel
1017:
914:aerobic bacterial species
831:. Other uses include for
802:
777:
757:
735:
722:
689:
684:
665:
633:
605:
585:
565:
545:
525:
505:
485:
460:
440:
420:
415:
402:
389:
377:
367:
357:
349:
287:
282:
247:
235:
221:
195:
165:
151:
133:
123:
69:
64:
55:
46:
1387:Huovinen P (June 2001).
1198:dihydropteroate synthase
1125:due to folate deficiency
999:Streptococcus pneumoniae
910:urinary tract infections
30:Not to be confused with
2198:Journal of Chemotherapy
1182:dihydrofolate reductase
1045:
883:dihydrofolate reductase
32:Thymidine monophosphate
2507:Sulfamethoxypyridazine
1814:10.3201/eid0605.000503
1765:10.1128/AAC.41.11.2466
1215:
1180:Trimethoprim binds to
1177:
1006:Haemophilus influenzae
919:Pneumocystis jirovecii
862:(swallowed by mouth).
2980:Newer non-fluorinated
2617:Other DHPS inhibitors
2603:Pyrimethamine/dapsone
2430:Succinylsulfathiazole
2426:Phthalylsulfathiazole
2310:2,4-Diaminopyrimidine
1486:Rossi S, ed. (2013).
1357:Australian Government
1210:
1169:Staphylococcus aureus
1167:
968:Klebsiella pneumoniae
929:Clostridium difficile
875:harm during pregnancy
833:middle ear infections
411:(50–60%), faeces (4%)
2404:Acetyl sulfisoxazole
2263:inhibit nucleic acid
1190:tetrahydrofolic acid
1123:megaloblastic anemia
1065:megaloblastic anemia
924:anaerobic infections
2779:Alalevonadifloxacin
2446:Intermediate-acting
1563:. 15 January 2015.
1456:Hamilton R (2015).
1160:Mechanism of action
1078:, thus acting like
989:species, including
847:it may be used for
837:travelers' diarrhea
330:(Prescription only)
306:(Prescription only)
43:
3167:Never to phase III
2668:thereby inhibiting
2656:(inhibit bacterial
2502:Sulfametoxydiazine
2290:thereby inhibiting
2283:(inhibit bacterial
2074:10.1002/prot.22383
1321:10.1093/cid/ciu094
1216:
1178:
982:Coagulase-negative
829:bladder infections
242:Diaminopyrimidines
39:
3252:CYP2C8 inhibitors
3177:
3176:
3136:
3135:
3061:
3060:
3024:
3023:
2975:
2974:
2647:
2646:
2581:
2580:
2286:purine metabolism
1881:Clinical Pharmacy
1759:(11): 2466–2470.
1497:978-0-9805790-9-3
1467:978-1-284-05756-0
1399:(11): 1608–1614.
1214:synthesis pathway
1186:dihydrofolic acid
1109:Contraindications
1089:Can compete with
961:Proteus mirabilis
871:white blood cells
814:
813:
748:Interactive image
635:CompTox Dashboard
338:
325:
313:
301:
211:
178:
16:(Redirected from
3259:
3194:
3193:
3192:
3185:
3073:
3072:
3040:
3039:
2775:Levonadifloxacin
2734:
2733:
2729:Fluoroquinolones
2677:
2676:
2482:Sulfadimethoxine
2454:Sulfamethoxazole
2375:Sulfaisodimidine
2363:
2362:
2298:
2297:
2252:
2245:
2238:
2229:
2228:
2222:
2221:
2193:
2187:
2186:
2150:
2144:
2143:
2107:
2094:
2093:
2056:
2050:
2049:
2031:
2014:(8): 1749–1755.
1999:
1993:
1992:
1982:
1958:
1952:
1951:
1907:
1901:
1900:
1887:(12): 999–1000.
1872:
1866:
1865:
1863:
1861:
1842:
1836:
1835:
1825:
1793:
1787:
1786:
1776:
1744:
1738:
1737:
1727:
1703:
1697:
1696:
1688:
1682:
1681:
1673:
1667:
1666:
1664:
1662:
1643:
1637:
1636:
1634:
1632:
1613:
1607:
1606:
1604:
1602:
1583:
1577:
1576:
1574:
1572:
1557:
1551:
1550:
1540:
1508:
1502:
1501:
1483:
1472:
1471:
1453:
1447:
1446:
1444:
1425:
1419:
1418:
1408:
1384:
1373:
1372:
1370:
1368:
1359:. 3 March 2014.
1349:
1343:
1342:
1332:
1315:(9): 1308–1311.
1300:
1294:
1293:
1291:
1289:
1274:
1212:Tetrahydrofolate
1194:Sulfamethoxazole
1176:
1135:sulfamethoxazole
1116:hypersensitivity
1053:thrombocytopenia
992:S. saprophyticus
954:Escherichia coli
841:sulfamethoxazole
810:
809:
750:
730:
715:
709:
703:
697:
680:
669:
658:
657:
643:
641:
625:
619:
598:
578:
558:
538:
518:
498:
478:
468:
467:
453:
394:
336:
333:
323:
320:
312:
309:
299:
296:
274:
264:
209:
206:
188:
177:
174:
161:
147:
118:
117:
114:
113:
110:
107:
104:
101:
98:
95:
92:
89:
86:
83:
80:
60:
51:
44:
42:
38:
21:
3267:
3266:
3262:
3261:
3260:
3258:
3257:
3256:
3222:Aromatic amines
3217:Antimetabolites
3202:
3201:
3200:
3190:
3188:
3180:
3178:
3173:
3172:
3157:Clinical trials
3132:
3114:
3080:
3057:
3033:
3020:
2996:
2971:
2918:
2846:
2798:
2723:
2671:DNA replication
2669:
2667:
2661:
2657:
2655:
2643:
2612:
2577:
2536:Other/ungrouped
2531:
2497:Sulfametomidine
2468:
2440:
2354:
2346:
2293:
2291:
2289:
2284:
2282:
2274:
2256:
2226:
2225:
2194:
2190:
2151:
2147:
2108:
2097:
2057:
2053:
2000:
1996:
1959:
1955:
1916:Pharmacotherapy
1908:
1904:
1873:
1869:
1859:
1857:
1844:
1843:
1839:
1794:
1790:
1745:
1741:
1718:(10): 703–706.
1704:
1700:
1689:
1685:
1674:
1670:
1660:
1658:
1645:
1644:
1640:
1630:
1628:
1615:
1614:
1610:
1600:
1598:
1585:
1584:
1580:
1570:
1568:
1559:
1558:
1554:
1523:(5): CD002218.
1509:
1505:
1498:
1484:
1475:
1468:
1454:
1450:
1426:
1422:
1385:
1376:
1366:
1364:
1351:
1350:
1346:
1301:
1297:
1287:
1285:
1276:
1275:
1256:
1251:
1221:
1172:
1162:
1143:
1118:to trimethoprim
1111:
1055:(low levels of
1048:
1038:Sun sensitivity
1026:Change in taste
1020:
1015:
946:
906:
881:metabolism via
854:in people with
805:
803:
798:
795:
790:
785:
784:
773:
770:
765:
764:
753:
728:
718:
712:
706:
700:
661:
637:
629:
601:
581:
561:
541:
521:
501:
481:
464:
456:
436:
433:
428:
427:
392:
369:Protein binding
359:Bioavailability
351:Pharmacokinetic
345:
278:
224:
217:
198:
191:
77:
73:
35:
28:
23:
22:
15:
12:
11:
5:
3265:
3255:
3254:
3249:
3244:
3239:
3234:
3229:
3224:
3219:
3214:
3199:
3198:
3175:
3174:
3171:
3170:
3169:
3168:
3165:
3154:
3148:
3142:
3141:
3138:
3137:
3134:
3133:
3131:
3130:
3124:
3122:
3116:
3115:
3113:
3112:
3107:
3102:
3097:
3092:
3086:
3084:
3082:RNA polymerase
3070:
3063:
3062:
3059:
3058:
3056:
3055:
3049:
3047:
3044:Nitroimidazole
3037:
3026:
3025:
3022:
3021:
3019:
3018:
3012:Aminocoumarins
3008:
3006:
2998:
2997:
2995:
2994:
2989:
2983:
2981:
2977:
2976:
2973:
2972:
2970:
2969:
2964:
2959:
2954:
2949:
2944:
2939:
2934:
2928:
2926:
2920:
2919:
2917:
2916:
2914:Alatrofloxacin
2907:
2902:
2897:
2892:
2887:
2882:
2877:
2872:
2867:
2862:
2856:
2854:
2852:4th generation
2848:
2847:
2845:
2844:
2839:
2834:
2829:
2824:
2819:
2814:
2808:
2806:
2804:3rd generation
2800:
2799:
2797:
2796:
2791:
2786:
2781:
2768:
2763:
2758:
2753:
2748:
2742:
2740:
2738:2nd generation
2731:
2725:
2724:
2722:
2721:
2716:
2714:Piromidic acid
2711:
2709:Pipemidic acid
2706:
2701:
2699:Nalidixic acid
2696:
2691:
2685:
2683:
2681:1st generation
2674:
2649:
2648:
2645:
2644:
2642:
2641:
2636:
2631:
2626:
2620:
2618:
2614:
2613:
2611:
2610:
2605:
2600:
2595:
2589:
2587:
2583:
2582:
2579:
2578:
2576:
2575:
2570:
2565:
2563:Sulfaguanidine
2560:
2558:Sulfadicramide
2555:
2550:
2545:
2539:
2537:
2533:
2532:
2530:
2529:
2524:
2522:Sulfaphenazole
2519:
2514:
2509:
2504:
2499:
2494:
2489:
2484:
2478:
2476:
2470:
2469:
2467:
2466:
2461:
2456:
2450:
2448:
2442:
2441:
2439:
2438:
2433:
2419:
2418:
2417:
2407:
2397:
2387:
2382:
2380:Sulfamethizole
2377:
2371:
2369:
2360:
2357:DHPS inhibitor
2348:
2347:
2345:
2344:
2343:
2342:
2337:
2332:
2327:
2322:
2317:
2306:
2304:
2302:DHFR inhibitor
2295:
2276:
2275:
2259:Antibacterials
2255:
2254:
2247:
2240:
2232:
2224:
2223:
2204:(6): 465–469.
2188:
2145:
2118:(6): 405–430.
2095:
2068:(3): 706–717.
2051:
1994:
1953:
1922:(4): 869–870.
1902:
1867:
1837:
1808:(5): 458–465.
1788:
1739:
1698:
1683:
1668:
1638:
1608:
1578:
1552:
1503:
1496:
1473:
1466:
1448:
1420:
1406:10.1086/320532
1374:
1344:
1295:
1278:"Trimethoprim"
1253:
1252:
1250:
1247:
1220:
1217:
1161:
1158:
1153:of pregnancy.
1142:
1139:
1127:
1126:
1119:
1110:
1107:
1106:
1105:
1094:
1087:
1068:
1059:) by lowering
1047:
1044:
1043:
1042:
1039:
1036:
1033:
1030:
1027:
1024:
1019:
1016:
1014:
1011:
1010:
1009:
1002:
995:
986:Staphylococcus
979:
971:
964:
957:
945:
942:
905:
902:
858:. It is taken
812:
811:
800:
799:
797:
796:
793:
791:
788:
780:
779:
778:
775:
774:
772:
771:
768:
760:
759:
758:
755:
754:
752:
751:
743:
741:
733:
732:
726:
720:
719:
716:
710:
704:
698:
693:
687:
686:
682:
681:
671:
663:
662:
660:
659:
646:
644:
631:
630:
628:
627:
611:
609:
603:
602:
600:
599:
591:
589:
583:
582:
580:
579:
571:
569:
563:
562:
560:
559:
551:
549:
543:
542:
540:
539:
531:
529:
523:
522:
520:
519:
511:
509:
503:
502:
500:
499:
491:
489:
483:
482:
480:
479:
471:
469:
458:
457:
455:
454:
446:
444:
438:
437:
435:
434:
431:
423:
422:
421:
418:
417:
413:
412:
406:
400:
399:
396:
387:
386:
381:
375:
374:
371:
365:
364:
361:
355:
354:
347:
346:
344:
343:
331:
318:
307:
293:
291:
285:
284:
280:
279:
277:
276:
253:
251:
245:
244:
239:
233:
232:
227:
225:administration
219:
218:
216:
215:
213:
203:
201:
193:
192:
190:
189:
171:
169:
163:
162:
155:
149:
148:
141:
131:
130:
127:
121:
120:
71:
67:
66:
62:
61:
53:
52:
26:
9:
6:
4:
3:
2:
3264:
3253:
3250:
3248:
3245:
3243:
3240:
3238:
3235:
3233:
3232:Phenol ethers
3230:
3228:
3225:
3223:
3220:
3218:
3215:
3213:
3210:
3209:
3207:
3197:
3187:
3186:
3183:
3166:
3164:
3161:
3160:
3158:
3155:
3152:
3149:
3147:
3144:
3143:
3139:
3129:
3126:
3125:
3123:
3121:
3117:
3111:
3108:
3106:
3103:
3101:
3098:
3096:
3093:
3091:
3088:
3087:
3085:
3083:
3078:
3074:
3071:
3068:
3064:
3054:
3051:
3050:
3048:
3045:
3041:
3038:
3036:
3031:
3027:
3017:
3013:
3010:
3009:
3007:
3004:
2999:
2993:
2990:
2988:
2985:
2984:
2982:
2978:
2968:
2965:
2963:
2962:Pradofloxacin
2960:
2958:
2955:
2953:
2952:Marbofloxacin
2950:
2948:
2945:
2943:
2940:
2938:
2935:
2933:
2930:
2929:
2927:
2925:
2921:
2915:
2911:
2910:Trovafloxacin
2908:
2906:
2903:
2901:
2900:Prulifloxacin
2898:
2896:
2893:
2891:
2890:Clinafloxacin
2888:
2886:
2883:
2881:
2878:
2876:
2873:
2871:
2868:
2866:
2863:
2861:
2858:
2857:
2855:
2853:
2849:
2843:
2840:
2838:
2835:
2833:
2830:
2828:
2825:
2823:
2822:Grepafloxacin
2820:
2818:
2815:
2813:
2810:
2809:
2807:
2805:
2801:
2795:
2792:
2790:
2787:
2785:
2782:
2780:
2776:
2772:
2769:
2767:
2764:
2762:
2759:
2757:
2754:
2752:
2749:
2747:
2746:Ciprofloxacin
2744:
2743:
2741:
2739:
2735:
2732:
2730:
2726:
2720:
2717:
2715:
2712:
2710:
2707:
2705:
2704:Oxolinic acid
2702:
2700:
2697:
2695:
2692:
2690:
2687:
2686:
2684:
2682:
2678:
2675:
2672:
2665:
2660:
2659:topoisomerase
2654:
2650:
2640:
2637:
2635:
2632:
2630:
2627:
2625:
2624:Acediasulfone
2622:
2621:
2619:
2615:
2609:
2606:
2604:
2601:
2599:
2596:
2594:
2591:
2590:
2588:
2584:
2574:
2571:
2569:
2566:
2564:
2561:
2559:
2556:
2554:
2551:
2549:
2548:Sulfacetamide
2546:
2544:
2541:
2540:
2538:
2534:
2528:
2525:
2523:
2520:
2518:
2517:Sulfamerazine
2515:
2513:
2510:
2508:
2505:
2503:
2500:
2498:
2495:
2493:
2490:
2488:
2485:
2483:
2480:
2479:
2477:
2475:
2471:
2465:
2462:
2460:
2457:
2455:
2452:
2451:
2449:
2447:
2443:
2437:
2436:Sulfathiourea
2434:
2431:
2427:
2423:
2422:Sulfathiazole
2420:
2416:
2413:
2412:
2411:
2410:Sulfanilamide
2408:
2405:
2401:
2400:Sulfafurazole
2398:
2395:
2394:Sulfasalazine
2391:
2390:Sulfapyridine
2388:
2386:
2385:Sulfadimidine
2383:
2381:
2378:
2376:
2373:
2372:
2370:
2368:
2364:
2361:
2358:
2353:
2349:
2341:
2338:
2336:
2333:
2331:
2330:Pyrimethamine
2328:
2326:
2323:
2321:
2318:
2316:
2313:
2312:
2311:
2308:
2307:
2305:
2303:
2299:
2296:
2287:
2281:
2277:
2272:
2268:
2264:
2260:
2253:
2248:
2246:
2241:
2239:
2234:
2233:
2230:
2219:
2215:
2211:
2207:
2203:
2199:
2192:
2184:
2180:
2176:
2172:
2168:
2164:
2160:
2156:
2149:
2141:
2137:
2133:
2129:
2125:
2121:
2117:
2113:
2106:
2104:
2102:
2100:
2091:
2087:
2083:
2079:
2075:
2071:
2067:
2063:
2055:
2047:
2043:
2039:
2035:
2030:
2025:
2021:
2017:
2013:
2009:
2005:
1998:
1990:
1986:
1981:
1976:
1973:: 1085–1086.
1972:
1968:
1964:
1957:
1949:
1945:
1941:
1937:
1933:
1929:
1925:
1921:
1917:
1913:
1906:
1898:
1894:
1890:
1886:
1882:
1878:
1871:
1855:
1851:
1847:
1841:
1833:
1829:
1824:
1819:
1815:
1811:
1807:
1803:
1799:
1792:
1784:
1780:
1775:
1770:
1766:
1762:
1758:
1754:
1750:
1743:
1735:
1731:
1726:
1721:
1717:
1713:
1709:
1702:
1694:
1687:
1679:
1672:
1656:
1652:
1648:
1642:
1626:
1622:
1618:
1612:
1596:
1592:
1588:
1582:
1566:
1562:
1556:
1548:
1544:
1539:
1534:
1530:
1526:
1522:
1518:
1514:
1507:
1499:
1493:
1489:
1482:
1480:
1478:
1469:
1463:
1459:
1452:
1443:
1438:
1434:
1430:
1424:
1416:
1412:
1407:
1402:
1398:
1394:
1390:
1383:
1381:
1379:
1362:
1358:
1354:
1348:
1340:
1336:
1331:
1326:
1322:
1318:
1314:
1310:
1306:
1299:
1283:
1279:
1273:
1271:
1269:
1267:
1265:
1263:
1261:
1259:
1254:
1246:
1244:
1242:
1238:
1233:
1229:
1224:
1213:
1209:
1205:
1203:
1199:
1195:
1191:
1187:
1183:
1175:
1170:
1166:
1157:
1154:
1152:
1148:
1138:
1136:
1132:
1124:
1120:
1117:
1113:
1112:
1103:
1099:
1095:
1092:
1088:
1085:
1081:
1077:
1076:distal tubule
1073:
1069:
1066:
1062:
1058:
1054:
1050:
1049:
1040:
1037:
1034:
1031:
1028:
1025:
1022:
1021:
1008:
1007:
1003:
1001:
1000:
996:
994:
993:
988:
987:
983:
980:
977:
976:
972:
970:
969:
965:
963:
962:
958:
956:
955:
951:
950:
949:
941:
938:
936:
932:
930:
925:
921:
920:
915:
911:
901:
899:
894:
892:
888:
884:
880:
876:
872:
868:
863:
861:
857:
853:
851:
846:
842:
838:
834:
830:
826:
822:
818:
808:
801:
792:
787:
786:
783:
776:
767:
766:
763:
756:
749:
745:
744:
742:
739:
734:
727:
725:
721:
694:
692:
688:
683:
679:
675:
672:
670:
668:ECHA InfoCard
664:
656:
652:
651:DTXSID3023712
648:
647:
645:
636:
632:
624:
623:RCSB PDB
618:
613:
612:
610:
608:
604:
597:
593:
592:
590:
588:
584:
577:
573:
572:
570:
568:
564:
557:
553:
552:
550:
548:
544:
537:
533:
532:
530:
528:
524:
517:
513:
512:
510:
508:
504:
497:
493:
492:
490:
488:
484:
477:
473:
472:
470:
463:
459:
452:
448:
447:
445:
443:
439:
430:
429:
426:
419:
414:
410:
407:
405:
401:
397:
395:
388:
385:
382:
380:
376:
372:
370:
366:
362:
360:
356:
352:
348:
342:
332:
329:
319:
317:
308:
305:
295:
294:
292:
290:
286:
281:
273:
268:
263:
258:
255:
254:
252:
250:
246:
243:
240:
238:
234:
231:
228:
226:
220:
214:
205:
204:
202:
200:
194:
187:
182:
173:
172:
170:
168:
164:
160:
156:
154:
150:
146:
142:
140:
136:
132:
128:
126:
122:
116:
72:
70:Pronunciation
68:
65:Clinical data
63:
59:
54:
50:
45:
37:
33:
19:
3120:Lipiarmycins
2967:Sarafloxacin
2957:Orbifloxacin
2942:Enrofloxacin
2932:Danofloxacin
2905:Sitafloxacin
2885:Moxifloxacin
2880:Gemifloxacin
2875:Finafloxacin
2870:Gatifloxacin
2865:Delafloxacin
2860:Besifloxacin
2842:Tosufloxacin
2837:Temafloxacin
2832:Sparfloxacin
2827:Pazufloxacin
2817:Balofloxacin
2812:Levofloxacin
2771:Nadifloxacin
2766:Lomefloxacin
2586:Combinations
2568:Sulfametrole
2553:Sulfaclozine
2459:Sulfadiazine
2367:Short-acting
2352:Sulfonamides
2340:Trimethoprim
2339:
2201:
2197:
2191:
2158:
2154:
2148:
2115:
2111:
2065:
2061:
2054:
2011:
2007:
1997:
1970:
1966:
1956:
1919:
1915:
1905:
1884:
1880:
1870:
1858:. Retrieved
1849:
1840:
1805:
1801:
1791:
1756:
1752:
1742:
1715:
1711:
1701:
1692:
1686:
1677:
1671:
1659:. Retrieved
1650:
1641:
1629:. Retrieved
1620:
1611:
1599:. Retrieved
1590:
1581:
1569:. Retrieved
1555:
1520:
1516:
1506:
1487:
1457:
1451:
1442:10665/345533
1432:
1423:
1396:
1392:
1365:. Retrieved
1356:
1347:
1312:
1308:
1298:
1286:. Retrieved
1240:
1236:
1231:
1227:
1225:
1222:
1179:
1168:
1155:
1144:
1128:
1084:hyperkalemia
1013:Side effects
1004:
997:
991:
984:
975:Enterobacter
973:
966:
959:
952:
947:
939:
928:
917:
907:
904:Medical uses
895:
864:
850:Pneumocystis
849:
820:
817:Trimethoprim
816:
815:
804:
391:Elimination
289:Legal status
283:Legal status
186:Trimethoprim
167:License data
41:Trimethoprim
36:
3242:Pyrimidines
3212:Antibiotics
3153:from market
3128:Fidaxomicin
3100:Rifapentine
3053:Secnidazole
3046:derivatives
2987:Nemonoxacin
2947:Ibafloxacin
2895:Garenoxacin
2784:Norfloxacin
2634:Solasulfone
2573:Sulfanitran
2527:Sulfamazone
2487:Sulfadoxine
2474:Long-acting
2464:Sulfamoxole
2335:Tetroxoprim
2315:Brodimoprim
2292:DNA and RNA
2280:Antifolates
1571:30 December
1121:History of
1102:Shiga toxin
731: g·mol
674:100.010.915
576:CHEBI:45924
416:Identifiers
153:MedlinePlus
125:Trade names
3206:Categories
3090:Rifampicin
3077:Rifamycins
3035:inhibitors
3016:Novobiocin
2992:Ozenoxacin
2937:Difloxacin
2924:Veterinary
2794:Rufloxacin
2789:Pefloxacin
2761:Fleroxacin
2694:Flumequine
2664:DNA gyrase
2653:Quinolones
2512:Sulfaperin
2325:Ormetoprim
2294:synthesis)
1860:4 November
1661:4 November
1631:4 November
1601:4 November
1249:References
1131:disulfiram
1091:creatinine
1061:folic acid
1051:Can cause
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2689:Cinoxacin
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1196:inhibits
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2082:19280600
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2038:23010291
1989:14526858
1948:Archived
1944:23968977
1897:Archived
1854:Archived
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1832:10998375
1655:Archived
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1625:Archived
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1431:(2021).
1415:11340533
1367:22 April
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1288:1 August
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