1154:
47:
667:
644:
38:
1197:
3180:
1181:(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.
1294:"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"
2048:
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".
1145:
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.
292:
2099:
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".
3235:
3225:
3215:
237:
1842:
1613:
1583:
2238:
1138:
and can affect folate metabolism, there has been growing evidence of the risk of structural birth defects associated with trimethoprim, especially during the first
123:
1153:
750:
1643:
2185:
Brumfitt W, Hamilton-Miller JM (December 1993). "Reassessment of the rationale for the combinations of sulphonamides with diaminopyrimidines".
1193:
are commonly used in combination due to possible synergistic effects, and reduced development of resistance. This benefit has been questioned.
3134:
2231:
1484:
1454:
886:
2345:
1349:
1553:
1936:
1885:
1086:
2290:
770:
2224:
1834:
1605:
1575:
1212:
Trimethoprim was first used in 1962. In 1972, it was used as a prophylactic treatment for urinary tract infections in
Finland.
413:
277:
155:
1270:
736:
46:
1738:"Effects of moderate-dose versus high-dose trimethoprim on serum creatinine and creatinine clearance and adverse reactions"
2581:
1190:
916:
854:
Common side effects include nausea, changes in taste, and rash. Rarely it may result in blood problems such as not enough
829:
1787:"Toxin gene expression by shiga toxin-producing Escherichia coli: the role of antibiotics and the bacterial SOS response"
3070:
979:
515:
174:
1550:"Three-day courses of antibiotics for uncomplicated urinary tract infection | Guidance and guidelines | NICE"
3151:
923:
623:
3240:
3170:
1417:
1060:
778:
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)
3210:
3205:
2596:
1635:
1186:
987:
898:
3139:
2647:
1991:
Andersen JT, Petersen M, Jimenez-Solem E, Broedbaek K, Andersen EW, Andersen NL, et al. (August 2013).
1170:
871:
817:
211:
20:
2591:
1993:"Trimethoprim use in early pregnancy and the risk of miscarriage: a register-based nationwide cohort study"
662:
3220:
3023:
2495:
2462:
2434:
2392:
2355:
2340:
2251:
994:
907:
837:
825:
357:
2418:
2414:
2298:
2216:
956:
1866:"Disulfiram-like reaction associated with intravenous trimethoprim-sulfamethoxazole and metronidazole"
3230:
3200:
2912:
2840:
2792:
2726:
2717:
2669:
2641:
1695:
Choi MJ, Fernandez PC, Patnaik A, Coupaye-Gerard B, D'Andrea D, Szerlip H, et al. (March 1993).
1178:
1111:
1053:
929:
Resistance to trimethoprim is increasing, but it is still a first line antibiotic in many countries.
584:
379:
937:
Cultures and susceptibility tests should be done to make sure bacteria are treated by trimethoprim.
2767:
848:
639:
430:
2541:
922:(the leading cause of antibiotic-induced diarrhea). Trimethoprim has been used in trials to treat
3018:
2490:
2159:
2124:
2074:
2030:
1928:
912:
821:
185:
1549:
1341:
1082:
for secretion into the renal tubule. This can cause an artificial rise in the serum creatinine.
605:
2274:
2202:
2167:
2116:
2066:
2022:
1973:
1920:
1877:
1816:
1767:
1718:
1531:
1480:
1450:
1399:
1323:
1174:
949:
859:
595:
564:
329:
316:
304:
230:
113:
2763:
2586:
2470:
2442:
2194:
2151:
2108:
2058:
2012:
2004:
1963:
1912:
1806:
1798:
1757:
1749:
1708:
1521:
1513:
1425:
1389:
1313:
1305:
1200:
1182:
1123:
1104:
1041:
942:
902:
679:
339:
64:
2155:
1900:
1865:
524:
3184:
2659:
2485:
504:
367:
347:
260:
2142:
Burchall JJ (November 1973). "Mechanism of action of trimethoprim-sulfamethoxazole. II".
1684:. Vol. 1 (22nd ed.). Greenwood Village, CO.: Thomson Health Care. p. 2849.
439:
666:
643:
3145:
3032:
2902:
2702:
2697:
2687:
2551:
2546:
2510:
2368:
2017:
1992:
1968:
1951:
1916:
1811:
1786:
1526:
1501:
1318:
1293:
1122:
when alcohol is consumed after it is used, in particular when used in combination with
974:
1762:
1737:
3194:
3000:
2950:
2940:
2898:
2888:
2878:
2810:
2734:
2692:
2612:
2536:
2505:
2424:
2410:
2398:
2388:
2382:
2378:
2373:
2363:
2318:
2112:
1064:
655:
147:
2128:
2034:
1932:
1266:
133:
2955:
2945:
2930:
2920:
2893:
2873:
2868:
2863:
2858:
2853:
2848:
2830:
2825:
2820:
2815:
2805:
2800:
2759:
2754:
2556:
2447:
2259:
2255:
2198:
2078:
1517:
1196:
1072:
963:
255:
250:
245:
464:
3116:
3108:
3088:
3041:
2975:
2935:
2883:
2772:
2622:
2561:
2515:
2475:
2452:
2323:
2303:
2247:
1713:
1696:
1090:
141:
3078:
3004:
2991:
2980:
2925:
2782:
2777:
2749:
2682:
2652:
2500:
2313:
2268:
2008:
1224:
1119:
1079:
1049:
863:
813:
712:
495:
225:
1422:
World Health
Organization model list of essential medicines: 22nd list (2021)
29:
3098:
3093:
3083:
3065:
2739:
2707:
2677:
2627:
2480:
2403:
1162:
1139:
1068:
1045:
970:
855:
392:
127:
2070:
2026:
1977:
1820:
1802:
1753:
1535:
1403:
1327:
2206:
2171:
2120:
1924:
1881:
1771:
1722:
37:
2744:
2531:
2308:
1479:(2013 ed.). Adelaide: The Australian Medicines Handbook Unit Trust.
1309:
1135:
862:. Trimethoprim may cause sun sensitivity. There is evidence of potential
844:
475:
218:
169:
2163:
1697:"Brief report: trimethoprim-induced hyperkalemia in a patient with AIDS"
1430:
1292:
Masur H, Brooks JT, Benson CA, Holmes KK, Pau AK, Kaplan JE (May 2014).
484:
2617:
2062:
833:
450:
867:
575:
397:
1950:
Sivojelezova A, Einarson A, Shuhaiber S, Koren G (September 2003).
1394:
1377:
544:
1502:"Antibiotics versus no treatment for toxoplasma retinochoroiditis"
1195:
1152:
735:
726:
611:
555:
372:
1952:"Trimethoprim-sulfonamide combination therapy in early pregnancy"
911:
pneumonia. It is generally not recommended for the treatment of
535:
310:
2220:
323:
164:
3055:
879:
875:
1134:
Based on the studies that show that trimethoprim crosses the
628:
85:
1636:"PROLOPRIM® (trimethoprim)100-mg and 200-mg Scored Tablets"
1189:, an enzyme involved further upstream in the same pathway.
286:
196:
88:
82:
73:
1667:
American
Hospital Formulary Service- Drug Information 2002
1500:
Pradhan E, Bhandari S, Gilbert RE, Stanford M (May 2016).
1447:
1071:. This can cause increased potassium levels in the body (
97:
299:
887:
795:
1160:
DHFR in complex with NADPH and trimethoprim PDB entry
3168:
1269:. The American Society of Health-System Pharmacists.
866:
in some animals but not humans. It works by blocking
1736:
Naderer O, Nafziger AN, Bertino JS (November 1997).
1665:
Ellenhorn MJ, Schonwald S, Ordog G, Wasserberger J.
1089:
infections may lead to an increase in expression of
94:
91:
70:
67:
3107:
3064:
3054:
3031:
3017:
2989:
2968:
2911:
2839:
2791:
2725:
2716:
2668:
2640:
2605:
2574:
2524:
2461:
2433:
2354:
2339:
2289:
2267:
1669:. Baltimore, MD: Williams and Wilkins. p. 236.
874:in some bacteria, preventing creation of bacterial
724:
711:
678:
673:
654:
622:
594:
574:
554:
534:
514:
494:
474:
449:
429:
404:
391:
378:
366:
356:
346:
338:
276:
271:
236:
224:
210:
184:
154:
140:
122:
112:
100:
79:
76:
58:
53:
1864:Edwards DL, Fink PC, Van Dyke PO (December 1986).
901:, although it may be used against any susceptible
885:Trimethoprim was first used in 1962. It is on the
1682:Drug Information for the Health Care Professional
463:
421:5-(3,4,5-Trimethoxybenzyl)pyrimidine-2,4-diamine
438:
1835:"PRIMSOL- trimethoprim hydrochloride solution"
1680:MICROMEDEX Thomson Health Care. USPDI (2002).
1606:"PRIMSOL- trimethoprim hydrochloride solution"
1449:. Jones & Bartlett Learning. p. 113.
3236:World Health Organization essential medicines
2232:
1378:"Resistance to trimethoprim-sulfamethoxazole"
1342:"Prescribing medicines in pregnancy database"
8:
3226:Protozoal dihydrofolate reductase inhibitors
3216:Bacterial dihydrofolate reductase inhibitors
1118:It may be involved in a reaction similar to
173:
28:
1506:The Cochrane Database of Systematic Reviews
905:. It may also be used to treat and prevent
889:. It is available as a generic medication.
259:
3061:
3028:
2722:
2665:
2351:
2286:
2239:
2225:
2217:
2094:
2092:
2090:
2088:
1261:
1259:
1257:
1255:
1253:
1251:
1249:
1247:
665:
642:
503:
2016:
1967:
1810:
1785:Kimmitt PT, Harwood CR, Barer MR (2000).
1761:
1712:
1525:
1429:
1393:
1371:
1369:
1367:
1317:
897:It is primarily used in the treatment of
523:
3175:
1243:
775:
755:
638:
483:
418:
146:
1586:from the original on 30 September 2015
1273:from the original on 24 September 2015
656:
27:
1939:from the original on 24 January 2009.
1888:from the original on 24 January 2009.
1845:from the original on 17 November 2015
1841:. U.S. National Library of Medicine.
1742:Antimicrobial Agents and Chemotherapy
1646:from the original on 17 November 2015
1642:. U.S. National Library of Medicine.
1616:from the original on 17 November 2015
1612:. U.S. National Library of Medicine.
1582:. U.S. National Library of Medicine.
1470:
1468:
1466:
1424:. Geneva: World Health Organization.
882:and leading to bacterial cell death.
604:
583:
563:
132:
7:
2156:10.1093/infdis/128.Supplement_3.S437
1556:from the original on 8 December 2015
610:
249:
118:Proloprim, Monotrim, Triprim, others
1901:"Disulfiram-cotrimoxazole reaction"
1701:The New England Journal of Medicine
1576:"TRIMETHOPRIM- trimethoprim tablet"
543:
454:
2144:The Journal of Infectious Diseases
1917:10.1002/j.1875-9114.1998.tb03913.x
14:
1352:from the original on 8 April 2014
1191:Trimethoprim and sulfamethoxazole
3178:
2113:10.2165/00003495-198223060-00001
816:used mainly in the treatment of
696:
690:
63:
45:
36:
783:Key:IEDVJHCEMCRBQM-UHFFFAOYSA-N
758:Nc1nc(N)ncc1Cc(cc2OC)cc(OC)c2OC
2199:10.1080/1120009X.1993.11741097
1518:10.1002/14651858.CD002218.pub2
1173:and inhibits the reduction of
702:
684:
1:
2582:Trimethoprim/sulfamethoxazole
1477:Australian Medicines Handbook
1059:Trimethoprim antagonizes the
1791:Emerging Infectious Diseases
1382:Clinical Infectious Diseases
1298:Clinical Infectious Diseases
1052:levels; this may also cause
2587:Ormetoprim/sulfadimethoxine
1899:Heelon MW, White M (1998).
1714:10.1056/NEJM199303113281006
3257:
1997:Epidemiology and Infection
1434:. WHO/MHP/HPS/EML/2021.02.
933:Spectrum of susceptibility
674:Chemical and physical data
18:
3129:
2597:Pyrimethamine/sulfadoxine
2150:: Suppl: 437-Suppl: 441.
2009:10.1017/S0950268812002178
1956:Canadian Family Physician
1418:World Health Organization
1215:Its name is derived from
1061:epithelial sodium channel
903:aerobic bacterial species
820:. Other uses include for
791:
766:
746:
409:
44:
35:
1376:Huovinen P (June 2001).
1187:dihydropteroate synthase
1114:due to folate deficiency
988:Streptococcus pneumoniae
899:urinary tract infections
19:Not to be confused with
2187:Journal of Chemotherapy
1171:dihydrofolate reductase
872:dihydrofolate reductase
21:Thymidine monophosphate
2496:Sulfamethoxypyridazine
1803:10.3201/eid0605.000503
1754:10.1128/AAC.41.11.2466
1204:
1169:Trimethoprim binds to
1166:
995:Haemophilus influenzae
908:Pneumocystis jirovecii
851:(swallowed by mouth).
2969:Newer non-fluorinated
2606:Other DHPS inhibitors
2592:Pyrimethamine/dapsone
2419:Succinylsulfathiazole
2415:Phthalylsulfathiazole
2299:2,4-Diaminopyrimidine
1475:Rossi S, ed. (2013).
1346:Australian Government
1199:
1158:Staphylococcus aureus
1156:
957:Klebsiella pneumoniae
918:Clostridium difficile
864:harm during pregnancy
822:middle ear infections
400:(50–60%), faeces (4%)
2393:Acetyl sulfisoxazole
2252:inhibit nucleic acid
1179:tetrahydrofolic acid
1112:megaloblastic anemia
1054:megaloblastic anemia
913:anaerobic infections
2768:Alalevonadifloxacin
2435:Intermediate-acting
1552:. 15 January 2015.
1445:Hamilton R (2015).
1149:Mechanism of action
1067:, thus acting like
978:species, including
836:it may be used for
826:travelers' diarrhea
319:(Prescription only)
295:(Prescription only)
32:
3156:Never to phase III
2657:thereby inhibiting
2645:(inhibit bacterial
2491:Sulfametoxydiazine
2279:thereby inhibiting
2272:(inhibit bacterial
2063:10.1002/prot.22383
1310:10.1093/cid/ciu094
1205:
1167:
971:Coagulase-negative
818:bladder infections
231:Diaminopyrimidines
3241:CYP2C8 inhibitors
3166:
3165:
3125:
3124:
3050:
3049:
3013:
3012:
2964:
2963:
2636:
2635:
2570:
2569:
2275:purine metabolism
1870:Clinical Pharmacy
1748:(11): 2466–2470.
1486:978-0-9805790-9-3
1456:978-1-284-05756-0
1388:(11): 1608–1614.
1203:synthesis pathway
1175:dihydrofolic acid
1098:Contraindications
1078:Can compete with
950:Proteus mirabilis
860:white blood cells
803:
802:
737:Interactive image
624:CompTox Dashboard
327:
314:
302:
290:
200:
167:
3248:
3183:
3182:
3181:
3174:
3062:
3029:
2764:Levonadifloxacin
2723:
2718:Fluoroquinolones
2666:
2471:Sulfadimethoxine
2443:Sulfamethoxazole
2364:Sulfaisodimidine
2352:
2287:
2241:
2234:
2227:
2218:
2211:
2210:
2182:
2176:
2175:
2139:
2133:
2132:
2096:
2083:
2082:
2045:
2039:
2038:
2020:
2003:(8): 1749–1755.
1988:
1982:
1981:
1971:
1947:
1941:
1940:
1896:
1890:
1889:
1876:(12): 999–1000.
1861:
1855:
1854:
1852:
1850:
1831:
1825:
1824:
1814:
1782:
1776:
1775:
1765:
1733:
1727:
1726:
1716:
1692:
1686:
1685:
1677:
1671:
1670:
1662:
1656:
1655:
1653:
1651:
1632:
1626:
1625:
1623:
1621:
1602:
1596:
1595:
1593:
1591:
1572:
1566:
1565:
1563:
1561:
1546:
1540:
1539:
1529:
1497:
1491:
1490:
1472:
1461:
1460:
1442:
1436:
1435:
1433:
1414:
1408:
1407:
1397:
1373:
1362:
1361:
1359:
1357:
1348:. 3 March 2014.
1338:
1332:
1331:
1321:
1304:(9): 1308–1311.
1289:
1283:
1282:
1280:
1278:
1263:
1201:Tetrahydrofolate
1183:Sulfamethoxazole
1165:
1124:sulfamethoxazole
1105:hypersensitivity
1042:thrombocytopenia
981:S. saprophyticus
943:Escherichia coli
830:sulfamethoxazole
799:
798:
739:
719:
704:
698:
692:
686:
669:
658:
647:
646:
632:
630:
614:
608:
587:
567:
547:
527:
507:
487:
467:
457:
456:
442:
383:
325:
322:
312:
309:
301:
298:
288:
285:
263:
253:
198:
195:
177:
166:
163:
150:
136:
107:
106:
103:
102:
99:
96:
93:
90:
87:
84:
81:
78:
75:
72:
69:
49:
40:
33:
31:
3256:
3255:
3251:
3250:
3249:
3247:
3246:
3245:
3211:Aromatic amines
3206:Antimetabolites
3191:
3190:
3189:
3179:
3177:
3169:
3167:
3162:
3161:
3146:Clinical trials
3121:
3103:
3069:
3046:
3022:
3009:
2985:
2960:
2907:
2835:
2787:
2712:
2660:DNA replication
2658:
2656:
2650:
2646:
2644:
2632:
2601:
2566:
2525:Other/ungrouped
2520:
2486:Sulfametomidine
2457:
2429:
2343:
2335:
2282:
2280:
2278:
2273:
2271:
2263:
2245:
2215:
2214:
2184:
2183:
2179:
2141:
2140:
2136:
2098:
2097:
2086:
2047:
2046:
2042:
1990:
1989:
1985:
1949:
1948:
1944:
1905:Pharmacotherapy
1898:
1897:
1893:
1863:
1862:
1858:
1848:
1846:
1833:
1832:
1828:
1784:
1783:
1779:
1735:
1734:
1730:
1707:(10): 703–706.
1694:
1693:
1689:
1679:
1678:
1674:
1664:
1663:
1659:
1649:
1647:
1634:
1633:
1629:
1619:
1617:
1604:
1603:
1599:
1589:
1587:
1574:
1573:
1569:
1559:
1557:
1548:
1547:
1543:
1512:(5): CD002218.
1499:
1498:
1494:
1487:
1474:
1473:
1464:
1457:
1444:
1443:
1439:
1416:
1415:
1411:
1375:
1374:
1365:
1355:
1353:
1340:
1339:
1335:
1291:
1290:
1286:
1276:
1274:
1265:
1264:
1245:
1240:
1210:
1161:
1151:
1132:
1107:to trimethoprim
1100:
1044:(low levels of
1037:
1027:Sun sensitivity
1015:Change in taste
1009:
1004:
935:
895:
870:metabolism via
843:in people with
794:
792:
787:
784:
779:
774:
773:
762:
759:
754:
753:
742:
717:
707:
701:
695:
689:
650:
626:
618:
590:
570:
550:
530:
510:
490:
470:
453:
445:
425:
422:
417:
416:
381:
358:Protein binding
348:Bioavailability
340:Pharmacokinetic
334:
267:
213:
206:
187:
180:
66:
62:
24:
17:
12:
11:
5:
3254:
3252:
3244:
3243:
3238:
3233:
3228:
3223:
3218:
3213:
3208:
3203:
3193:
3192:
3188:
3187:
3164:
3163:
3160:
3159:
3158:
3157:
3154:
3143:
3137:
3131:
3130:
3127:
3126:
3123:
3122:
3120:
3119:
3113:
3111:
3105:
3104:
3102:
3101:
3096:
3091:
3086:
3081:
3075:
3073:
3071:RNA polymerase
3059:
3052:
3051:
3048:
3047:
3045:
3044:
3038:
3036:
3033:Nitroimidazole
3026:
3015:
3014:
3011:
3010:
3008:
3007:
3001:Aminocoumarins
2997:
2995:
2987:
2986:
2984:
2983:
2978:
2972:
2970:
2966:
2965:
2962:
2961:
2959:
2958:
2953:
2948:
2943:
2938:
2933:
2928:
2923:
2917:
2915:
2909:
2908:
2906:
2905:
2903:Alatrofloxacin
2896:
2891:
2886:
2881:
2876:
2871:
2866:
2861:
2856:
2851:
2845:
2843:
2841:4th generation
2837:
2836:
2834:
2833:
2828:
2823:
2818:
2813:
2808:
2803:
2797:
2795:
2793:3rd generation
2789:
2788:
2786:
2785:
2780:
2775:
2770:
2757:
2752:
2747:
2742:
2737:
2731:
2729:
2727:2nd generation
2720:
2714:
2713:
2711:
2710:
2705:
2703:Piromidic acid
2700:
2698:Pipemidic acid
2695:
2690:
2688:Nalidixic acid
2685:
2680:
2674:
2672:
2670:1st generation
2663:
2638:
2637:
2634:
2633:
2631:
2630:
2625:
2620:
2615:
2609:
2607:
2603:
2602:
2600:
2599:
2594:
2589:
2584:
2578:
2576:
2572:
2571:
2568:
2567:
2565:
2564:
2559:
2554:
2552:Sulfaguanidine
2549:
2547:Sulfadicramide
2544:
2539:
2534:
2528:
2526:
2522:
2521:
2519:
2518:
2513:
2511:Sulfaphenazole
2508:
2503:
2498:
2493:
2488:
2483:
2478:
2473:
2467:
2465:
2459:
2458:
2456:
2455:
2450:
2445:
2439:
2437:
2431:
2430:
2428:
2427:
2422:
2408:
2407:
2406:
2396:
2386:
2376:
2371:
2369:Sulfamethizole
2366:
2360:
2358:
2349:
2346:DHPS inhibitor
2337:
2336:
2334:
2333:
2332:
2331:
2326:
2321:
2316:
2311:
2306:
2295:
2293:
2291:DHFR inhibitor
2284:
2265:
2264:
2248:Antibacterials
2246:
2244:
2243:
2236:
2229:
2221:
2213:
2212:
2193:(6): 465–469.
2177:
2134:
2107:(6): 405–430.
2084:
2057:(3): 706–717.
2040:
1983:
1942:
1911:(4): 869–870.
1891:
1856:
1826:
1797:(5): 458–465.
1777:
1728:
1687:
1672:
1657:
1627:
1597:
1567:
1541:
1492:
1485:
1462:
1455:
1437:
1409:
1395:10.1086/320532
1363:
1333:
1284:
1267:"Trimethoprim"
1242:
1241:
1239:
1236:
1209:
1206:
1150:
1147:
1142:of pregnancy.
1131:
1128:
1116:
1115:
1108:
1099:
1096:
1095:
1094:
1083:
1076:
1057:
1048:) by lowering
1036:
1033:
1032:
1031:
1028:
1025:
1022:
1019:
1016:
1013:
1008:
1005:
1003:
1000:
999:
998:
991:
984:
975:Staphylococcus
968:
960:
953:
946:
934:
931:
894:
891:
847:. It is taken
801:
800:
789:
788:
786:
785:
782:
780:
777:
769:
768:
767:
764:
763:
761:
760:
757:
749:
748:
747:
744:
743:
741:
740:
732:
730:
722:
721:
715:
709:
708:
705:
699:
693:
687:
682:
676:
675:
671:
670:
660:
652:
651:
649:
648:
635:
633:
620:
619:
617:
616:
600:
598:
592:
591:
589:
588:
580:
578:
572:
571:
569:
568:
560:
558:
552:
551:
549:
548:
540:
538:
532:
531:
529:
528:
520:
518:
512:
511:
509:
508:
500:
498:
492:
491:
489:
488:
480:
478:
472:
471:
469:
468:
460:
458:
447:
446:
444:
443:
435:
433:
427:
426:
424:
423:
420:
412:
411:
410:
407:
406:
402:
401:
395:
389:
388:
385:
376:
375:
370:
364:
363:
360:
354:
353:
350:
344:
343:
336:
335:
333:
332:
320:
307:
296:
282:
280:
274:
273:
269:
268:
266:
265:
242:
240:
234:
233:
228:
222:
221:
216:
214:administration
208:
207:
205:
204:
202:
192:
190:
182:
181:
179:
178:
160:
158:
152:
151:
144:
138:
137:
130:
120:
119:
116:
110:
109:
60:
56:
55:
51:
50:
42:
41:
15:
13:
10:
9:
6:
4:
3:
2:
3253:
3242:
3239:
3237:
3234:
3232:
3229:
3227:
3224:
3222:
3221:Phenol ethers
3219:
3217:
3214:
3212:
3209:
3207:
3204:
3202:
3199:
3198:
3196:
3186:
3176:
3172:
3155:
3153:
3150:
3149:
3147:
3144:
3141:
3138:
3136:
3133:
3132:
3128:
3118:
3115:
3114:
3112:
3110:
3106:
3100:
3097:
3095:
3092:
3090:
3087:
3085:
3082:
3080:
3077:
3076:
3074:
3072:
3067:
3063:
3060:
3057:
3053:
3043:
3040:
3039:
3037:
3034:
3030:
3027:
3025:
3020:
3016:
3006:
3002:
2999:
2998:
2996:
2993:
2988:
2982:
2979:
2977:
2974:
2973:
2971:
2967:
2957:
2954:
2952:
2951:Pradofloxacin
2949:
2947:
2944:
2942:
2941:Marbofloxacin
2939:
2937:
2934:
2932:
2929:
2927:
2924:
2922:
2919:
2918:
2916:
2914:
2910:
2904:
2900:
2899:Trovafloxacin
2897:
2895:
2892:
2890:
2889:Prulifloxacin
2887:
2885:
2882:
2880:
2879:Clinafloxacin
2877:
2875:
2872:
2870:
2867:
2865:
2862:
2860:
2857:
2855:
2852:
2850:
2847:
2846:
2844:
2842:
2838:
2832:
2829:
2827:
2824:
2822:
2819:
2817:
2814:
2812:
2811:Grepafloxacin
2809:
2807:
2804:
2802:
2799:
2798:
2796:
2794:
2790:
2784:
2781:
2779:
2776:
2774:
2771:
2769:
2765:
2761:
2758:
2756:
2753:
2751:
2748:
2746:
2743:
2741:
2738:
2736:
2735:Ciprofloxacin
2733:
2732:
2730:
2728:
2724:
2721:
2719:
2715:
2709:
2706:
2704:
2701:
2699:
2696:
2694:
2693:Oxolinic acid
2691:
2689:
2686:
2684:
2681:
2679:
2676:
2675:
2673:
2671:
2667:
2664:
2661:
2654:
2649:
2648:topoisomerase
2643:
2639:
2629:
2626:
2624:
2621:
2619:
2616:
2614:
2613:Acediasulfone
2611:
2610:
2608:
2604:
2598:
2595:
2593:
2590:
2588:
2585:
2583:
2580:
2579:
2577:
2573:
2563:
2560:
2558:
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2537:Sulfacetamide
2535:
2533:
2530:
2529:
2527:
2523:
2517:
2514:
2512:
2509:
2507:
2506:Sulfamerazine
2504:
2502:
2499:
2497:
2494:
2492:
2489:
2487:
2484:
2482:
2479:
2477:
2474:
2472:
2469:
2468:
2466:
2464:
2460:
2454:
2451:
2449:
2446:
2444:
2441:
2440:
2438:
2436:
2432:
2426:
2425:Sulfathiourea
2423:
2420:
2416:
2412:
2411:Sulfathiazole
2409:
2405:
2402:
2401:
2400:
2399:Sulfanilamide
2397:
2394:
2390:
2389:Sulfafurazole
2387:
2384:
2383:Sulfasalazine
2380:
2379:Sulfapyridine
2377:
2375:
2374:Sulfadimidine
2372:
2370:
2367:
2365:
2362:
2361:
2359:
2357:
2353:
2350:
2347:
2342:
2338:
2330:
2327:
2325:
2322:
2320:
2319:Pyrimethamine
2317:
2315:
2312:
2310:
2307:
2305:
2302:
2301:
2300:
2297:
2296:
2294:
2292:
2288:
2285:
2276:
2270:
2266:
2261:
2257:
2253:
2249:
2242:
2237:
2235:
2230:
2228:
2223:
2222:
2219:
2208:
2204:
2200:
2196:
2192:
2188:
2181:
2178:
2173:
2169:
2165:
2161:
2157:
2153:
2149:
2145:
2138:
2135:
2130:
2126:
2122:
2118:
2114:
2110:
2106:
2102:
2095:
2093:
2091:
2089:
2085:
2080:
2076:
2072:
2068:
2064:
2060:
2056:
2052:
2044:
2041:
2036:
2032:
2028:
2024:
2019:
2014:
2010:
2006:
2002:
1998:
1994:
1987:
1984:
1979:
1975:
1970:
1965:
1962:: 1085–1086.
1961:
1957:
1953:
1946:
1943:
1938:
1934:
1930:
1926:
1922:
1918:
1914:
1910:
1906:
1902:
1895:
1892:
1887:
1883:
1879:
1875:
1871:
1867:
1860:
1857:
1844:
1840:
1836:
1830:
1827:
1822:
1818:
1813:
1808:
1804:
1800:
1796:
1792:
1788:
1781:
1778:
1773:
1769:
1764:
1759:
1755:
1751:
1747:
1743:
1739:
1732:
1729:
1724:
1720:
1715:
1710:
1706:
1702:
1698:
1691:
1688:
1683:
1676:
1673:
1668:
1661:
1658:
1645:
1641:
1637:
1631:
1628:
1615:
1611:
1607:
1601:
1598:
1585:
1581:
1577:
1571:
1568:
1555:
1551:
1545:
1542:
1537:
1533:
1528:
1523:
1519:
1515:
1511:
1507:
1503:
1496:
1493:
1488:
1482:
1478:
1471:
1469:
1467:
1463:
1458:
1452:
1448:
1441:
1438:
1432:
1427:
1423:
1419:
1413:
1410:
1405:
1401:
1396:
1391:
1387:
1383:
1379:
1372:
1370:
1368:
1364:
1351:
1347:
1343:
1337:
1334:
1329:
1325:
1320:
1315:
1311:
1307:
1303:
1299:
1295:
1288:
1285:
1272:
1268:
1262:
1260:
1258:
1256:
1254:
1252:
1250:
1248:
1244:
1237:
1235:
1233:
1231:
1227:
1222:
1218:
1213:
1207:
1202:
1198:
1194:
1192:
1188:
1184:
1180:
1176:
1172:
1164:
1159:
1155:
1148:
1146:
1143:
1141:
1137:
1129:
1127:
1125:
1121:
1113:
1109:
1106:
1102:
1101:
1097:
1092:
1088:
1084:
1081:
1077:
1074:
1070:
1066:
1065:distal tubule
1062:
1058:
1055:
1051:
1047:
1043:
1039:
1038:
1034:
1029:
1026:
1023:
1020:
1017:
1014:
1011:
1010:
1006:
1001:
997:
996:
992:
990:
989:
985:
983:
982:
977:
976:
972:
969:
966:
965:
961:
959:
958:
954:
952:
951:
947:
945:
944:
940:
939:
938:
932:
930:
927:
925:
921:
919:
914:
910:
909:
904:
900:
892:
890:
888:
883:
881:
877:
873:
869:
865:
861:
857:
852:
850:
846:
842:
840:
835:
831:
827:
823:
819:
815:
811:
807:
797:
790:
781:
776:
772:
765:
756:
752:
745:
738:
734:
733:
731:
728:
723:
716:
714:
710:
683:
681:
677:
672:
668:
664:
661:
659:
657:ECHA InfoCard
653:
645:
641:
640:DTXSID3023712
637:
636:
634:
625:
621:
613:
612:RCSB PDB
607:
602:
601:
599:
597:
593:
586:
582:
581:
579:
577:
573:
566:
562:
561:
559:
557:
553:
546:
542:
541:
539:
537:
533:
526:
522:
521:
519:
517:
513:
506:
502:
501:
499:
497:
493:
486:
482:
481:
479:
477:
473:
466:
462:
461:
459:
452:
448:
441:
437:
436:
434:
432:
428:
419:
415:
408:
403:
399:
396:
394:
390:
386:
384:
377:
374:
371:
369:
365:
361:
359:
355:
351:
349:
345:
341:
337:
331:
321:
318:
308:
306:
297:
294:
284:
283:
281:
279:
275:
270:
262:
257:
252:
247:
244:
243:
241:
239:
235:
232:
229:
227:
223:
220:
217:
215:
209:
203:
194:
193:
191:
189:
183:
176:
171:
162:
161:
159:
157:
153:
149:
145:
143:
139:
135:
131:
129:
125:
121:
117:
115:
111:
105:
61:
59:Pronunciation
57:
54:Clinical data
52:
48:
43:
39:
34:
26:
22:
3109:Lipiarmycins
2956:Sarafloxacin
2946:Orbifloxacin
2931:Enrofloxacin
2921:Danofloxacin
2894:Sitafloxacin
2874:Moxifloxacin
2869:Gemifloxacin
2864:Finafloxacin
2859:Gatifloxacin
2854:Delafloxacin
2849:Besifloxacin
2831:Tosufloxacin
2826:Temafloxacin
2821:Sparfloxacin
2816:Pazufloxacin
2806:Balofloxacin
2801:Levofloxacin
2760:Nadifloxacin
2755:Lomefloxacin
2575:Combinations
2557:Sulfametrole
2542:Sulfaclozine
2448:Sulfadiazine
2356:Short-acting
2341:Sulfonamides
2329:Trimethoprim
2328:
2190:
2186:
2180:
2147:
2143:
2137:
2104:
2100:
2054:
2050:
2043:
2000:
1996:
1986:
1959:
1955:
1945:
1908:
1904:
1894:
1873:
1869:
1859:
1847:. Retrieved
1838:
1829:
1794:
1790:
1780:
1745:
1741:
1731:
1704:
1700:
1690:
1681:
1675:
1666:
1660:
1648:. Retrieved
1639:
1630:
1618:. Retrieved
1609:
1600:
1588:. Retrieved
1579:
1570:
1558:. Retrieved
1544:
1509:
1505:
1495:
1476:
1446:
1440:
1431:10665/345533
1421:
1412:
1385:
1381:
1354:. Retrieved
1345:
1336:
1301:
1297:
1287:
1275:. Retrieved
1229:
1225:
1220:
1216:
1214:
1211:
1168:
1157:
1144:
1133:
1117:
1073:hyperkalemia
1002:Side effects
993:
986:
980:
973:
964:Enterobacter
962:
955:
948:
941:
936:
928:
917:
906:
896:
893:Medical uses
884:
853:
839:Pneumocystis
838:
809:
806:Trimethoprim
805:
804:
793:
380:Elimination
278:Legal status
272:Legal status
175:Trimethoprim
156:License data
30:Trimethoprim
25:
3231:Pyrimidines
3201:Antibiotics
3142:from market
3117:Fidaxomicin
3089:Rifapentine
3042:Secnidazole
3035:derivatives
2976:Nemonoxacin
2936:Ibafloxacin
2884:Garenoxacin
2773:Norfloxacin
2623:Solasulfone
2562:Sulfanitran
2516:Sulfamazone
2476:Sulfadoxine
2463:Long-acting
2453:Sulfamoxole
2324:Tetroxoprim
2304:Brodimoprim
2281:DNA and RNA
2269:Antifolates
1560:30 December
1110:History of
1091:Shiga toxin
720: g·mol
663:100.010.915
565:CHEBI:45924
405:Identifiers
142:MedlinePlus
114:Trade names
3195:Categories
3079:Rifampicin
3066:Rifamycins
3024:inhibitors
3005:Novobiocin
2981:Ozenoxacin
2926:Difloxacin
2913:Veterinary
2783:Rufloxacin
2778:Pefloxacin
2750:Fleroxacin
2683:Flumequine
2653:DNA gyrase
2642:Quinolones
2501:Sulfaperin
2314:Ormetoprim
2283:synthesis)
1849:4 November
1650:4 November
1620:4 November
1590:4 November
1238:References
1120:disulfiram
1080:creatinine
1050:folic acid
1040:Can cause
814:antibiotic
725:3D model (
713:Molar mass
596:PDB ligand
525:AN164J8Y0X
496:ChemSpider
431:CAS Number
414:IUPAC name
387:8–12 hours
368:Metabolism
226:Drug class
16:Antibiotic
3152:Phase III
3140:Withdrawn
3099:Rifalazil
3094:Rifaximin
3084:Rifabutin
3058:synthesis
3019:Anaerobic
2990:Related (
2740:Ofloxacin
2708:Rosoxacin
2678:Cinoxacin
2628:Sulfoxone
2481:Sulfalene
2404:Prontosil
1185:inhibits
1177:(DHF) to
1140:trimester
1130:Pregnancy
1069:amiloride
1046:platelets
1030:Itchiness
924:retinitis
856:platelets
841:pneumonia
393:Excretion
382:half-life
212:Routes of
186:Pregnancy
134:Monograph
128:Drugs.com
3185:Medicine
2745:Enoxacin
2532:Mafenide
2309:Iclaprim
2164:30105875
2129:21806926
2071:19280600
2051:Proteins
2035:19917493
2027:23010291
1978:14526858
1937:Archived
1933:23968977
1886:Archived
1843:Archived
1839:DailyMed
1821:10998375
1644:Archived
1640:DailyMed
1614:Archived
1610:DailyMed
1584:Archived
1580:DailyMed
1554:Archived
1536:27198629
1420:(2021).
1404:11340533
1356:22 April
1350:Archived
1328:24585567
1277:1 August
1271:Archived
1136:placenta
1021:Diarrhea
1018:Vomiting
915:such as
845:HIV/AIDS
812:) is an
796:(verify)
585:ChEMBL22
476:DrugBank
440:738-70-5
256:QJ51EA01
238:ATC code
219:By mouth
201: B3
188:category
170:DailyMed
2651:and/or
2618:Dapsone
2207:8195839
2172:4585969
2121:7049657
2079:1373618
2018:9151599
1969:2214286
1925:9692665
1882:3492326
1812:2627954
1772:9371351
1723:8433730
1527:7100541
1319:3982842
1217:trimeth
1208:History
1085:Use in
1063:in the
1012:Nauseas
967:species
920:colitis
834:dapsone
828:. With
718:290.323
680:Formula
485:DB00440
451:PubChem
352:90–100%
303::
258: (
254:)
248: (
246:J01EA01
172::
148:a684025
3171:Portal
3135:WHO-EM
2205:
2170:
2162:
2127:
2119:
2077:
2069:
2033:
2025:
2015:
1976:
1966:
1931:
1923:
1880:
1819:
1809:
1770:
1763:164146
1760:
1721:
1534:
1524:
1483:
1453:
1402:
1326:
1316:
1103:Known
1024:Rashes
1007:Common
868:folate
849:orally
751:SMILES
576:ChEMBL
545:D00145
398:Kidney
330:℞-only
328:
315:
305:℞-only
291:
168:
108:
2250:that
2160:JSTOR
2125:S2CID
2101:Drugs
2075:S2CID
2031:S2CID
1929:S2CID
1232:idine
771:InChI
727:JSmol
603:TOP (
556:ChEBI
373:Liver
2260:J01M
2256:J01E
2203:PMID
2168:PMID
2117:PMID
2067:PMID
2023:PMID
1974:PMID
1921:PMID
1878:PMID
1851:2015
1817:PMID
1768:PMID
1719:PMID
1652:2015
1622:2015
1592:2015
1562:2015
1532:PMID
1510:2016
1481:ISBN
1451:ISBN
1400:PMID
1358:2014
1324:PMID
1279:2015
1163:2W9G
1087:EHEC
1035:Rare
878:and
824:and
606:PDBe
536:KEGG
516:UNII
505:5376
465:5578
342:data
124:AHFS
3056:RNA
3021:DNA
2195:doi
2152:doi
2148:128
2109:doi
2059:doi
2013:PMC
2005:doi
2001:141
1964:PMC
1913:doi
1807:PMC
1799:doi
1758:PMC
1750:doi
1709:doi
1705:328
1522:PMC
1514:doi
1426:hdl
1390:doi
1314:PMC
1306:doi
1230:rim
1223:xy-
880:RNA
876:DNA
858:or
832:or
810:TMP
629:EPA
455:CID
362:44%
317:POM
261:WHO
251:WHO
3197::
3148::
3003::
2992:DG
2417:,
2258:,
2201:.
2189:.
2166:.
2158:.
2146:.
2123:.
2115:.
2105:23
2103:.
2087:^
2073:.
2065:.
2055:76
2053:.
2029:.
2021:.
2011:.
1999:.
1995:.
1972:.
1960:49
1958:.
1954:.
1935:.
1927:.
1919:.
1909:18
1907:.
1903:.
1884:.
1872:.
1868:.
1837:.
1815:.
1805:.
1793:.
1789:.
1766:.
1756:.
1746:41
1744:.
1740:.
1717:.
1703:.
1699:.
1638:.
1608:.
1578:.
1530:.
1520:.
1508:.
1504:.
1465:^
1398:.
1386:32
1384:.
1380:.
1366:^
1344:.
1322:.
1312:.
1302:58
1300:.
1296:.
1246:^
1234:.
1219:yl
1126:.
1075:).
926:.
694:18
688:14
609:,
324:US
311:UK
300:CA
293:S4
287:AU
197:AU
165:US
74:aɪ
3173::
3068:/
2994:)
2901:/
2766:/
2762:/
2662:)
2655:,
2421:)
2413:(
2395:)
2391:(
2385:)
2381:(
2348:)
2344:(
2277:,
2262:)
2254:(
2240:e
2233:t
2226:v
2209:.
2197::
2191:5
2174:.
2154::
2131:.
2111::
2081:.
2061::
2037:.
2007::
1980:.
1915::
1874:5
1853:.
1823:.
1801::
1795:6
1774:.
1752::
1725:.
1711::
1654:.
1624:.
1594:.
1564:.
1538:.
1516::
1489:.
1459:.
1428::
1406:.
1392::
1360:.
1330:.
1308::
1281:.
1228:y
1226:p
1221:o
1093:.
1056:.
808:(
729:)
706:3
703:O
700:4
697:N
691:H
685:C
631:)
627:(
615:)
326::
313::
289::
264:)
199::
126:/
104:/
101:m
98:ɪ
95:r
92:p
89:ə
86:θ
83:ɛ
80:m
77:ˈ
71:r
68:t
65:/
23:.
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
