300:
175:
36:
717:
751:
732:
27:
432:
1173:
Valentin, Sencio; Cyril, Robil; François, Trottein; David, Péricat; Emmanuelle, Näser; Céline, Cougoule; Etienne, Meunier; Anne-Laure, Bègue; Hélène, Salmon; Nicolas, Manel; Alain, Puisieux; Sarah, Watson; Mark A., Dawson; Nicolas, Servant; Guido, Kroemer; Djillali, Annane; Raphaël, Rodriguez (2023).
1172:
Solier, Stéphanie; Müller, Sebastian; Tatiana, Cañeque; Antoine, Versini; Arnaud, Mansart; Fabien, Sindikubwabo; Leeroy, Baron; Laila, Emam; Pierre, Gestraud; G. Dan, Pantoș; Vincent, Gandon; Christine, Gaillet; Ting-Di, Wu; Florent, Dingli; Damarys, Loew; Sylvain, Baulande; Sylvère, Durand;
870:. Kidney function should be assessed before starting metformin. Phenformin and buformin are more prone to cause acidosis than metformin; therefore they have been practically replaced by it. However, when metformin is combined with other drugs (combination therapy),
846:
in the liver, and, as a result, reduce the level of glucose in the blood. Biguanides also tend to make the cells of the body more willing to absorb glucose already present in the bloodstream, and there again reducing the level of glucose in the plasma.
640:
838:
Mainly used in Type II diabetes, metformin is considered to increase insulin sensitivity in vivo, resulting in reduced plasma glucose concentrations, increased glucose uptake, and decreased gluconeogenesis.
1285:
808:
resulted in its withdrawal from most pharmacopeias (in the U.S. in 1978). Metformin has a much better safety profile, and it is the principal biguanide drug used in pharmacotherapy worldwide.
2458:
850:
Biguanides have been shown to interact with copper, specifically in mitochondria, where they interfere with cell metabolism by chelating Copper in its 2+ oxidation state (Cu(II)).
445:
1278:
3177:
969:
1271:
339:
2451:
547:
842:
However, in hyperinsulinemia, biguanides can lower fasting levels of insulin in plasma. Their therapeutic uses derive from their tendency to reduce
1861:
1263:
716:
2444:
3123:
2398:
1488:
993:
35:
2255:
2766:
1156:
1082:
895:
314:
1958:
1713:
1438:
2436:
2995:
1026:
835:. Therefore, they are effective in Type 2 diabetics; and in Type 1 diabetes when used in conjunction with insulin therapy.
2559:
1400:
731:
513:. It is a colorless solid that dissolves in water to give a highly basic solution. These solutions slowly hydrolyse to
452:
1442:
750:
257:
3140:
2415:
2091:
1505:
278:
2053:
1919:
1452:
977:
403:
2839:
2360:
2260:
2250:
937:
182:
788:
extracts. Animal studies showed that these compounds lowered blood glucose levels. Some less toxic derivatives,
2365:
2335:
2280:
2240:
1704:
1540:
692:
2345:
2325:
2270:
2320:
2315:
669:
The term "biguanidine" often refers specifically to a class of drugs that function as oral antihyperglycemic
3128:
2990:
2967:
2734:
2403:
2375:
2350:
2330:
2295:
2275:
2265:
2245:
2235:
2158:
1493:
898:
100:
26:
2310:
2305:
170:
2978:
2854:
2810:
2380:
2340:
2300:
2163:
867:
658:
2984:
2370:
2355:
2290:
2285:
2904:
2230:
891:
883:
48:
3172:
3167:
2471:
1295:
817:
295:
66:
1982:
1752:
862:
and dyspepsia, occurring in up to 30% of patients. The most important and serious side effect is
2884:
2666:
2002:
1416:
824:
776:
112:
2535:
1220:"Structural requirements of guanide, biguanide, and bisbiguanide agents for antiplaque activity"
2615:
2526:
1931:
1577:
1464:
1350:
1249:
1200:
1152:
1129:
1078:
1022:
989:
887:
674:
820:
of biguanides is not fully understood, and many mechanisms have been proposed for metformin.
2673:
2652:
2218:
1434:
1396:
1239:
1231:
1190:
1182:
1119:
1111:
1055:
1014:
981:
949:
470:
362:
266:
1391:
1373:
863:
843:
805:
646:
538:
201:
152:
1195:
299:
174:
76:
3134:
3105:
2793:
2644:
2475:
2409:
2153:
1818:
1747:
1499:
1448:
1355:
1345:
1325:
1303:
915:
423:
132:
1244:
1219:
1124:
1099:
3161:
3109:
3077:
2774:
2577:
2569:
2467:
2199:
2178:
2173:
2168:
2148:
2143:
2138:
2133:
2128:
2022:
1778:
1737:
1625:
1620:
1610:
1605:
1411:
1174:
933:
530:
163:
3095:
3081:
2930:
2910:
2743:
2729:
2606:
2582:
2551:
2540:
2516:
2479:
2032:
2027:
2007:
1909:
1899:
1894:
1783:
1757:
1725:
1685:
1663:
1658:
1653:
1640:
1630:
1615:
1595:
1581:
1307:
941:
927:
871:
828:
1018:
974:
Nomenclature of
Organic Chemistry: IUPAC Recommendations and Preferred Names 2013
246:
3049:
2959:
2935:
2920:
2915:
2869:
2818:
2779:
2687:
2661:
2656:
2587:
2510:
2499:
2017:
2012:
1997:
1992:
1987:
1943:
1937:
1904:
1889:
1879:
1874:
1869:
1847:
1842:
1837:
1828:
1813:
1798:
1788:
1767:
1742:
1690:
1648:
1600:
1590:
1406:
909:
890:. Much later it was demonstrated that they are prodrugs metabolised into active
832:
792:
A and synthalin B, were used for diabetes treatment, but after the discovery of
678:
635:{\displaystyle \mathrm {C_{2}H_{4}N_{4}+NH_{3}\longrightarrow C_{2}H_{7}N_{5}} }
1186:
3041:
2972:
2900:
2879:
2864:
2757:
2703:
2677:
2592:
2194:
2081:
2071:
2066:
2061:
1977:
1972:
1967:
1808:
1793:
1762:
1567:
1059:
801:
756:
697:
390:
143:
2925:
2874:
2823:
2798:
2713:
2682:
2488:
2204:
2119:
2109:
2076:
1927:
1884:
1803:
1562:
945:
905:
789:
781:
770:
722:
688:
1204:
1133:
780:(French lilac) was used in diabetes treatment for centuries. In the 1920s,
985:
2633:
2104:
2099:
1557:
1253:
1235:
859:
797:
737:
703:
3067:
2708:
1321:
1299:
1009:
Güthner T, Mertschenk B, Schulz B (2006). "Guanidine and
Derivatives".
793:
534:
514:
233:
183:
1673:
1115:
1043:
422:
Except where otherwise noted, data are given for materials in their
221:
1677:
886:
discovered (see details there) that some biguanides are useful as
741:
700:- withdrawn from the market in most countries due to toxic effects
123:
99:
89:
1175:"A druggable copper-signalling pathway that drives inflammation"
670:
518:
212:
2440:
1528:
1319:
1267:
1077:(5th ed.). Edinburgh: Churchill Livingstone. p. 388.
796:, their use declined. Biguanides were reintroduced into Type 2
823:
Biguanides do not affect the output of insulin, unlike other
894:
derivatives which, until recently, were believed to work by
283:
494:
476:
488:
482:
1151:. Oxford : Oxford University Press. pp. 53–54, 59.
725:, could be referred to as asymmetric dimethylbiguanidine
804:
was widely used, but its potential for sometimes fatal
440:
866:, therefore metformin is contraindicated in advanced
550:
505:) is the organic compound with the formula HN(C(NH)NH
491:
485:
497:
473:
3094:
3066:
3040:
3004:
2957:
2948:
2893:
2853:
2832:
2809:
2765:
2756:
2722:
2696:
2643:
2632:
2623:
2614:
2605:
2568:
2550:
2525:
2509:
2498:
2487:
2217:
2187:
2118:
2090:
2052:
2045:
1957:
1918:
1860:
1827:
1724:
1712:
1703:
1672:
1639:
1576:
1548:
1539:
1462:
1425:
1382:
1364:
1336:
479:
634:
970:International Union of Pure and Applied Chemistry
706:- withdrawn from the market due to toxic effects
245:
661:of biguanide are used as pharmaceutical drugs.
529:Biguanide can be obtained from the reaction of
75:
1218:Tanzer JM, Slee AM, Kamay BA (December 1977).
1149:Clinical trials: design, conduct, and analysis
1073:Rang HP, Dale MM, Ritter KM, Moore PK (2003).
1048:Berichte der Deutschen Chemischen Gesellschaft
1011:Ullmann's Encyclopedia of Industrial Chemistry
323:InChI=1S/C2H7N5/c3-1(4)7-2(5)6/h(H7,3,4,5,6,7)
2452:
1279:
8:
2954:
2762:
2640:
2629:
2620:
2611:
2522:
2506:
2495:
2459:
2445:
2437:
2223:
2049:
1915:
1721:
1709:
1545:
1536:
1525:
1333:
1316:
1286:
1272:
1264:
298:
173:
151:
18:
3178:Substances discovered in the 19th century
1243:
1194:
1123:
625:
615:
605:
592:
576:
566:
556:
551:
549:
265:
961:
800:treatment in the late 1950s. Initially
709:
344:
319:
294:
164:
1224:Antimicrobial Agents and Chemotherapy
874:and other side effects are possible.
326:Key: XNCOSPRUTUOJCJ-UHFFFAOYSA-N
131:
7:
1306:, and other drugs used in diabetes (
2276:Glibenclamide (glyburide)/metformin
2256:Dapagliflozin/saxagliptin/metformin
645:Biguanide was first synthesized by
236:
220:
1100:"The blooming of the French lilac"
882:During WWII a British team led by
622:
612:
602:
589:
585:
573:
563:
553:
14:
749:
730:
715:
469:
430:
380:
374:
34:
25:
1147:Tonascia S, Meinert CL (1986).
858:The most common side effect is
426:(at 25 °C , 100 kPa).
2996:piperaquine/dihydroartemisinin
978:The Royal Society of Chemistry
759:. A phenethylated biguanidine.
691:- widely used in treatment of
598:
368:
1:
2560:trimethoprim/sulfamethoxazole
1019:10.1002/14356007.a12_545.pub2
784:compounds were discovered in
2958:Fixed-dose (co-formulated)
2092:Alpha-glucosidase inhibitors
2054:Aldose reductase inhibitors
1042:Rathke, B. (January 1879).
53:Imidodicarbonimidic diamide
3194:
1920:GLP1 poly-agonist peptides
1187:10.1038/s41586-023-06017-4
925:
768:
744:derivative of biguanidine.
3118:
2840:sulfadoxine/pyrimethamine
2366:Sitagliptin/ertugliflozin
2361:Sitagliptin/dapagliflozin
2281:Glimepiride/rosiglitazone
2261:Empagliflozin/linagliptin
2251:Dapagliflozin/saxagliptin
2226:
1779:Glibenclamide (glyburide)
1535:
1524:
1332:
1315:
1060:10.1002/cber.187901201219
938:polyaminopropyl biguanide
854:Side effects and toxicity
420:
355:
335:
310:
59:
47:
42:
33:
24:
2346:Pioglitazone/sitagliptin
2336:Pioglitazone/glimepiride
2326:Phenformin/sulfonylureas
2271:Gemigliptin/rosuvastatin
2241:Cagrilintide/semaglutide
771:metformin § History
693:diabetes mellitus type 2
665:Antihyperglycemic agents
2991:artesunate/pyronaridine
2968:artemether/lumefantrine
2376:Sitagliptin/simvastatin
2351:Rosiglitazone/metformin
2331:Pioglitazone/alogliptin
2321:Metformin/teneligliptin
2316:Metformin/sulfonylureas
2296:Metformin/ertugliflozin
2266:Empagliflozin/metformin
2246:Dapagliflozin/metformin
2236:Canagliflozin/metformin
1862:GLP-1 receptor agonists
1013:. Weinheim: Wiley-VCH.
899:dihydrofolate reductase
2979:artesunate/amodiaquine
2381:Vildagliptin/metformin
2341:Pioglitazone/metformin
868:chronic kidney disease
711:bioactive biguanidines
636:
3013:artesunate/mefloquine
2985:artesunate/mefloquine
2371:Sitagliptin/metformin
2356:Saxagliptin/metformin
2311:Metformin/repaglinide
2306:Metformin/gemigliptin
2286:Linagliptin/metformin
986:10.1039/9781849733069
769:Further information:
637:
3025:quinine/tetracycline
2697:4-Methanolquinolines
2472:antiprotozoal agents
2301:Metformin/evogliptin
2231:Alogliptin/metformin
1236:10.1128/aac.12.6.721
901:. Examples include:
548:
49:Preferred IUPAC name
3022:quinine/doxycycline
3019:quinine/clindamycin
3007:(not co-formulated)
1541:Insulin sensitizers
1296:diabetes medication
825:hypoglycemic agents
818:mechanism of action
812:Mechanism of action
398: g·mol
113:Beilstein Reference
21:
3145:Never to phase III
3005:Other combinations
2885:dihydroartemisinin
2667:hydroxychloroquine
2420:Never to phase III
2291:Metformin/acarbose
1641:Dual PPAR agonists
1510:Never to phase III
1417:Ultralente insulin
1098:Witters L (2001).
948:feature biguanide
932:The disinfectants
888:antimalarial drugs
777:Galega officinalis
684:Examples include:
632:
453:Infobox references
19:
3155:
3154:
3090:
3089:
3062:
3061:
3058:
3057:
3036:
3035:
3032:
3031:
2944:
2943:
2849:
2848:
2752:
2751:
2601:
2600:
2527:Cryptosporidiosis
2434:
2433:
2430:
2429:
2393:
2392:
2389:
2388:
2213:
2212:
2041:
2040:
1953:
1952:
1856:
1855:
1699:
1698:
1520:
1519:
1483:
1482:
1427:ultra-long-acting
1351:Insulin glulisine
995:978-0-85404-182-4
950:functional groups
675:diabetes mellitus
653:Biguanidine drugs
461:Chemical compound
459:
458:
279:CompTox Dashboard
101:Interactive image
16:Chemical compound
3185:
2955:
2763:
2641:
2630:
2621:
2612:
2523:
2507:
2496:
2478:antiparasitics (
2461:
2454:
2447:
2438:
2224:
2120:SGLT2 inhibitors
2050:
1959:DPP-4 inhibitors
1940:(GLP-1/GIP/GCGR)
1916:
1722:
1710:
1546:
1537:
1526:
1435:Insulin degludec
1397:Insulin glargine
1334:
1317:
1288:
1281:
1274:
1265:
1258:
1257:
1247:
1215:
1209:
1208:
1198:
1169:
1163:
1162:
1144:
1138:
1137:
1127:
1116:10.1172/JCI14178
1095:
1089:
1088:
1070:
1064:
1063:
1044:"Ueber Biguanid"
1039:
1033:
1032:
1006:
1000:
999:
966:
753:
734:
719:
641:
639:
638:
633:
631:
630:
629:
620:
619:
610:
609:
597:
596:
581:
580:
571:
570:
561:
560:
504:
503:
500:
499:
496:
493:
490:
487:
484:
481:
478:
475:
443:
437:
434:
433:
397:
382:
376:
370:
363:Chemical formula
303:
302:
287:
285:
269:
249:
238:
224:
202:Gmelin Reference
185:
177:
166:
155:
135:
103:
79:
38:
29:
22:
3193:
3192:
3188:
3187:
3186:
3184:
3183:
3182:
3158:
3157:
3156:
3151:
3150:
3135:Clinical trials
3114:
3097:
3086:
3069:
3054:
3028:
3006:
3000:
2950:
2940:
2889:
2856:
2845:
2828:
2805:
2767:DHFR inhibitors
2748:
2718:
2692:
2645:Aminoquinolines
2635:
2625:
2597:
2564:
2546:
2514:
2501:
2490:
2483:
2465:
2435:
2426:
2425:
2410:Clinical trials
2385:
2209:
2183:
2114:
2086:
2037:
1949:
1914:
1852:
1823:
1717:
1695:
1668:
1635:
1580:/"glitazones" (
1572:
1531:
1516:
1515:
1500:Clinical trials
1479:
1458:
1439:+insulin aspart
1421:
1392:Insulin detemir
1378:
1374:Regular insulin
1360:
1328:
1326:insulin analogs
1311:
1304:insulin analogs
1292:
1262:
1261:
1217:
1216:
1212:
1171:
1170:
1166:
1159:
1146:
1145:
1141:
1097:
1096:
1092:
1085:
1072:
1071:
1067:
1041:
1040:
1036:
1029:
1008:
1007:
1003:
996:
980:. p. 885.
968:
967:
963:
958:
930:
924:
892:dihydrotriazine
880:
864:lactic acidosis
856:
844:gluconeogenesis
814:
806:lactic acidosis
773:
767:
760:
754:
745:
735:
726:
720:
667:
655:
647:Bernhard Rathke
621:
611:
601:
588:
572:
562:
552:
546:
545:
541:-type process.
527:
512:
508:
472:
468:
462:
455:
450:
449:
448: ?)
439:
435:
431:
427:
412:
395:
385:
379:
373:
365:
351:
348:
343:
342:
331:
328:
327:
324:
318:
317:
306:
288:
281:
272:
252:
239:
227:
204:
195:
158:
138:
115:
106:
93:
82:
69:
55:
54:
17:
12:
11:
5:
3191:
3189:
3181:
3180:
3175:
3170:
3160:
3159:
3153:
3152:
3149:
3148:
3147:
3146:
3143:
3132:
3126:
3120:
3119:
3116:
3115:
3113:
3112:
3106:Blastocystosis
3102:
3100:
3092:
3091:
3088:
3087:
3085:
3084:
3074:
3072:
3064:
3063:
3060:
3059:
3056:
3055:
3053:
3052:
3046:
3044:
3038:
3037:
3034:
3033:
3030:
3029:
3027:
3026:
3023:
3020:
3017:
3014:
3010:
3008:
3002:
3001:
2999:
2998:
2993:
2988:
2982:
2976:
2970:
2964:
2962:
2952:
2946:
2945:
2942:
2941:
2939:
2938:
2933:
2928:
2923:
2918:
2913:
2908:
2897:
2895:
2891:
2890:
2888:
2887:
2882:
2877:
2872:
2867:
2861:
2859:
2851:
2850:
2847:
2846:
2844:
2843:
2836:
2834:
2833:Co-formulation
2830:
2829:
2827:
2826:
2821:
2815:
2813:
2807:
2806:
2804:
2803:
2802:
2801:
2796:
2794:chlorproguanil
2783:
2782:
2777:
2771:
2769:
2760:
2754:
2753:
2750:
2749:
2747:
2746:
2740:
2739:
2738:
2737:
2726:
2724:
2720:
2719:
2717:
2716:
2711:
2706:
2700:
2698:
2694:
2693:
2691:
2690:
2685:
2680:
2670:
2669:
2664:
2659:
2649:
2647:
2638:
2627:
2618:
2609:
2603:
2602:
2599:
2598:
2596:
2595:
2590:
2585:
2580:
2574:
2572:
2566:
2565:
2563:
2562:
2556:
2554:
2548:
2547:
2545:
2544:
2531:
2529:
2520:
2504:
2493:
2485:
2484:
2476:Chromalveolata
2468:Antiparasitics
2466:
2464:
2463:
2456:
2449:
2441:
2432:
2431:
2428:
2427:
2424:
2423:
2422:
2421:
2418:
2407:
2401:
2395:
2394:
2391:
2390:
2387:
2386:
2384:
2383:
2378:
2373:
2368:
2363:
2358:
2353:
2348:
2343:
2338:
2333:
2328:
2323:
2318:
2313:
2308:
2303:
2298:
2293:
2288:
2283:
2278:
2273:
2268:
2263:
2258:
2253:
2248:
2243:
2238:
2233:
2227:
2221:
2215:
2214:
2211:
2210:
2208:
2207:
2202:
2197:
2191:
2189:
2185:
2184:
2182:
2181:
2176:
2171:
2166:
2161:
2156:
2154:Luseogliflozin
2151:
2146:
2141:
2136:
2131:
2125:
2123:
2116:
2115:
2113:
2112:
2107:
2102:
2096:
2094:
2088:
2087:
2085:
2084:
2079:
2074:
2069:
2064:
2058:
2056:
2047:
2043:
2042:
2039:
2038:
2036:
2035:
2030:
2025:
2020:
2015:
2010:
2005:
2000:
1995:
1990:
1985:
1980:
1975:
1970:
1964:
1962:
1955:
1954:
1951:
1950:
1948:
1947:
1941:
1935:
1924:
1922:
1913:
1912:
1907:
1902:
1897:
1892:
1887:
1882:
1877:
1872:
1866:
1864:
1858:
1857:
1854:
1853:
1851:
1850:
1845:
1840:
1834:
1832:
1825:
1824:
1822:
1821:
1819:Glyclopyramide
1816:
1811:
1806:
1801:
1796:
1791:
1786:
1781:
1775:2nd generation
1771:
1770:
1765:
1760:
1755:
1750:
1748:Chlorpropamide
1745:
1740:
1734:1st generation
1730:
1728:
1719:
1715:
1707:
1701:
1700:
1697:
1696:
1694:
1693:
1688:
1682:
1680:
1670:
1669:
1667:
1666:
1661:
1656:
1651:
1645:
1643:
1637:
1636:
1634:
1633:
1628:
1623:
1618:
1613:
1608:
1603:
1598:
1593:
1587:
1585:
1574:
1573:
1571:
1570:
1565:
1560:
1554:
1552:
1543:
1533:
1532:
1529:
1522:
1521:
1518:
1517:
1514:
1513:
1512:
1511:
1508:
1497:
1491:
1485:
1484:
1481:
1480:
1478:
1477:
1474:
1470:
1468:
1460:
1459:
1457:
1456:
1449:Insulin icodec
1446:
1431:
1429:
1423:
1422:
1420:
1419:
1414:
1409:
1404:
1394:
1388:
1386:
1380:
1379:
1377:
1376:
1370:
1368:
1362:
1361:
1359:
1358:
1356:Insulin lispro
1353:
1348:
1346:Insulin aspart
1342:
1340:
1330:
1329:
1320:
1313:
1312:
1293:
1291:
1290:
1283:
1276:
1268:
1260:
1259:
1210:
1164:
1157:
1139:
1090:
1083:
1065:
1054:(1): 776–784.
1034:
1027:
1001:
994:
960:
959:
957:
954:
923:
920:
919:
918:
916:Chlorproguanil
913:
879:
876:
855:
852:
813:
810:
766:
763:
762:
761:
755:
748:
746:
736:
729:
727:
721:
714:
712:
708:
707:
701:
695:
666:
663:
654:
651:
643:
642:
628:
624:
618:
614:
608:
604:
600:
595:
591:
587:
584:
579:
575:
569:
565:
559:
555:
526:
523:
510:
506:
460:
457:
456:
451:
429:
428:
424:standard state
421:
418:
417:
414:
410:
400:
399:
393:
387:
386:
383:
377:
371:
366:
361:
358:
357:
353:
352:
350:
349:
346:
338:
337:
336:
333:
332:
330:
329:
325:
322:
321:
313:
312:
311:
308:
307:
305:
304:
291:
289:
277:
274:
273:
271:
270:
262:
260:
254:
253:
251:
250:
242:
240:
232:
229:
228:
226:
225:
217:
215:
209:
208:
205:
200:
197:
196:
194:
193:
189:
187:
179:
178:
168:
160:
159:
157:
156:
148:
146:
140:
139:
137:
136:
128:
126:
120:
119:
116:
111:
108:
107:
105:
104:
96:
94:
87:
84:
83:
81:
80:
72:
70:
65:
62:
61:
57:
56:
52:
51:
45:
44:
40:
39:
31:
30:
15:
13:
10:
9:
6:
4:
3:
2:
3190:
3179:
3176:
3174:
3171:
3169:
3166:
3165:
3163:
3144:
3142:
3139:
3138:
3136:
3133:
3130:
3127:
3125:
3122:
3121:
3117:
3111:
3110:metronidazole
3107:
3104:
3103:
3101:
3099:
3093:
3083:
3079:
3078:Balantidiasis
3076:
3075:
3073:
3071:
3065:
3051:
3048:
3047:
3045:
3043:
3039:
3024:
3021:
3018:
3016:artesunate/SP
3015:
3012:
3011:
3009:
3003:
2997:
2994:
2992:
2989:
2986:
2983:
2980:
2977:
2974:
2971:
2969:
2966:
2965:
2963:
2961:
2956:
2953:
2947:
2937:
2934:
2932:
2929:
2927:
2924:
2922:
2919:
2917:
2914:
2912:
2909:
2906:
2902:
2899:
2898:
2896:
2892:
2886:
2883:
2881:
2878:
2876:
2873:
2871:
2868:
2866:
2863:
2862:
2860:
2858:
2855:Sesquiterpene
2852:
2841:
2838:
2837:
2835:
2831:
2825:
2822:
2820:
2817:
2816:
2814:
2812:
2808:
2800:
2797:
2795:
2792:
2791:
2790:
2789:
2785:
2784:
2781:
2778:
2776:
2775:pyrimethamine
2773:
2772:
2770:
2768:
2764:
2761:
2759:
2755:
2745:
2742:
2741:
2736:
2733:
2732:
2731:
2728:
2727:
2725:
2721:
2715:
2712:
2710:
2707:
2705:
2702:
2701:
2699:
2695:
2689:
2686:
2684:
2681:
2679:
2675:
2672:
2671:
2668:
2665:
2663:
2660:
2658:
2654:
2651:
2650:
2648:
2646:
2642:
2639:
2637:
2631:
2628:
2622:
2619:
2617:
2613:
2610:
2608:
2604:
2594:
2591:
2589:
2586:
2584:
2581:
2579:
2578:pyrimethamine
2576:
2575:
2573:
2571:
2570:Toxoplasmosis
2567:
2561:
2558:
2557:
2555:
2553:
2549:
2542:
2538:
2537:
2533:
2532:
2530:
2528:
2524:
2521:
2518:
2517:Coccidiostats
2512:
2508:
2505:
2503:
2497:
2494:
2492:
2486:
2481:
2477:
2473:
2469:
2462:
2457:
2455:
2450:
2448:
2443:
2442:
2439:
2419:
2417:
2414:
2413:
2411:
2408:
2405:
2402:
2400:
2397:
2396:
2382:
2379:
2377:
2374:
2372:
2369:
2367:
2364:
2362:
2359:
2357:
2354:
2352:
2349:
2347:
2344:
2342:
2339:
2337:
2334:
2332:
2329:
2327:
2324:
2322:
2319:
2317:
2314:
2312:
2309:
2307:
2304:
2302:
2299:
2297:
2294:
2292:
2289:
2287:
2284:
2282:
2279:
2277:
2274:
2272:
2269:
2267:
2264:
2262:
2259:
2257:
2254:
2252:
2249:
2247:
2244:
2242:
2239:
2237:
2234:
2232:
2229:
2228:
2225:
2222:
2220:
2216:
2206:
2203:
2201:
2200:Bromocriptine
2198:
2196:
2193:
2192:
2190:
2186:
2180:
2179:Velagliflozin
2177:
2175:
2174:Tofogliflozin
2172:
2170:
2169:Sotagliflozin
2167:
2165:
2162:
2160:
2159:Remogliflozin
2157:
2155:
2152:
2150:
2149:Ipragliflozin
2147:
2145:
2144:Ertugliflozin
2142:
2140:
2139:Empagliflozin
2137:
2135:
2134:Dapagliflozin
2132:
2130:
2129:Canagliflozin
2127:
2126:
2124:
2122:/"gliflozins"
2121:
2117:
2111:
2108:
2106:
2103:
2101:
2098:
2097:
2095:
2093:
2089:
2083:
2080:
2078:
2075:
2073:
2070:
2068:
2065:
2063:
2060:
2059:
2057:
2055:
2051:
2048:
2044:
2034:
2031:
2029:
2026:
2024:
2023:Teneligliptin
2021:
2019:
2016:
2014:
2011:
2009:
2006:
2004:
2001:
1999:
1996:
1994:
1991:
1989:
1986:
1984:
1981:
1979:
1976:
1974:
1971:
1969:
1966:
1965:
1963:
1960:
1956:
1945:
1942:
1939:
1936:
1933:
1929:
1926:
1925:
1923:
1921:
1917:
1911:
1908:
1906:
1903:
1901:
1898:
1896:
1893:
1891:
1888:
1886:
1883:
1881:
1878:
1876:
1873:
1871:
1868:
1867:
1865:
1863:
1859:
1849:
1846:
1844:
1841:
1839:
1836:
1835:
1833:
1830:
1826:
1820:
1817:
1815:
1812:
1810:
1807:
1805:
1802:
1800:
1797:
1795:
1792:
1790:
1787:
1785:
1782:
1780:
1776:
1773:
1772:
1769:
1766:
1764:
1761:
1759:
1756:
1754:
1751:
1749:
1746:
1744:
1741:
1739:
1738:Acetohexamide
1735:
1732:
1731:
1729:
1727:
1726:Sulfonylureas
1723:
1720:
1718:
1711:
1708:
1706:
1705:Secretagogues
1702:
1692:
1689:
1687:
1684:
1683:
1681:
1679:
1675:
1671:
1665:
1662:
1660:
1657:
1655:
1652:
1650:
1647:
1646:
1644:
1642:
1638:
1632:
1629:
1627:
1626:Rosiglitazone
1624:
1622:
1621:Rivoglitazone
1619:
1617:
1614:
1612:
1611:Netoglitazone
1609:
1607:
1606:Lobeglitazone
1604:
1602:
1599:
1597:
1594:
1592:
1589:
1588:
1586:
1583:
1579:
1575:
1569:
1566:
1564:
1561:
1559:
1556:
1555:
1553:
1551:
1547:
1544:
1542:
1538:
1534:
1527:
1523:
1509:
1507:
1504:
1503:
1501:
1498:
1495:
1492:
1490:
1487:
1486:
1475:
1472:
1471:
1469:
1467:
1466:
1461:
1454:
1450:
1447:
1444:
1440:
1436:
1433:
1432:
1430:
1428:
1424:
1418:
1415:
1413:
1412:Lente insulin
1410:
1408:
1405:
1402:
1401:+lixisenatide
1398:
1395:
1393:
1390:
1389:
1387:
1385:
1381:
1375:
1372:
1371:
1369:
1367:
1363:
1357:
1354:
1352:
1349:
1347:
1344:
1343:
1341:
1339:
1335:
1331:
1327:
1323:
1318:
1314:
1309:
1305:
1301:
1297:
1289:
1284:
1282:
1277:
1275:
1270:
1269:
1266:
1255:
1251:
1246:
1241:
1237:
1233:
1229:
1225:
1221:
1214:
1211:
1206:
1202:
1197:
1192:
1188:
1184:
1180:
1176:
1168:
1165:
1160:
1158:0-19-503568-2
1154:
1150:
1143:
1140:
1135:
1131:
1126:
1121:
1117:
1113:
1110:(8): 1105–7.
1109:
1105:
1104:J Clin Invest
1101:
1094:
1091:
1086:
1084:0-443-07145-4
1080:
1076:
1069:
1066:
1061:
1057:
1053:
1049:
1045:
1038:
1035:
1030:
1024:
1020:
1016:
1012:
1005:
1002:
997:
991:
987:
983:
979:
975:
971:
965:
962:
955:
953:
951:
947:
943:
939:
935:
934:chlorhexidine
929:
922:Disinfectants
921:
917:
914:
911:
907:
904:
903:
902:
900:
897:
893:
889:
885:
877:
875:
873:
869:
865:
861:
853:
851:
848:
845:
840:
836:
834:
830:
829:sulfonylureas
826:
821:
819:
811:
809:
807:
803:
799:
795:
791:
787:
783:
779:
778:
772:
764:
758:
752:
747:
743:
739:
733:
728:
724:
718:
713:
710:
705:
702:
699:
696:
694:
690:
687:
686:
685:
682:
680:
676:
672:
664:
662:
660:
657:A variety of
652:
650:
648:
626:
616:
606:
593:
582:
577:
567:
557:
544:
543:
542:
540:
536:
532:
531:dicyandiamide
524:
522:
520:
516:
502:
466:
454:
447:
442:
425:
419:
415:
409:
405:
402:
401:
394:
392:
389:
388:
367:
364:
360:
359:
354:
347:N=C(N)NC(=N)N
345:
341:
334:
320:
316:
309:
301:
297:
296:DTXSID7074664
293:
292:
290:
280:
276:
275:
268:
264:
263:
261:
259:
256:
255:
248:
244:
243:
241:
235:
231:
230:
223:
219:
218:
216:
214:
211:
210:
206:
203:
199:
198:
191:
190:
188:
186:
181:
180:
176:
172:
169:
167:
165:ECHA InfoCard
162:
161:
154:
150:
149:
147:
145:
142:
141:
134:
130:
129:
127:
125:
122:
121:
117:
114:
110:
109:
102:
98:
97:
95:
91:
86:
85:
78:
74:
73:
71:
68:
64:
63:
58:
50:
46:
41:
37:
32:
28:
23:
3082:tetracycline
2975:/piperaquine
2931:pyronaridine
2911:tetracycline
2811:Sulfonamides
2787:
2786:
2744:halofantrine
2735:+ artemether
2730:lumefantrine
2607:Aconoidasida
2583:sulfadiazine
2552:Isosporiasis
2541:nitazoxanide
2534:
2219:Combinations
2164:Sergliflozin
2033:Vildagliptin
2028:Trelagliptin
2008:Omarigliptin
1983:Garvagliptin
1910:Taspoglutide
1900:Orforglipron
1895:Lixisenatide
1829:Meglitinides
1784:Glibornuride
1774:
1758:Metahexamide
1753:Glycyclamide
1733:
1686:Cagrilintide
1676:analogs and
1664:Tesaglitazar
1659:Saroglitazar
1654:Muraglitazar
1631:Troglitazone
1616:Pioglitazone
1596:Darglitazone
1549:
1530:Non-insulins
1463:
1453:+semaglutide
1443:+liraglutide
1426:
1383:
1366:short-acting
1365:
1337:
1230:(6): 721–9.
1227:
1223:
1213:
1178:
1167:
1148:
1142:
1107:
1103:
1093:
1075:Pharmacology
1074:
1068:
1051:
1047:
1037:
1010:
1004:
973:
964:
942:polihexanide
931:
928:Bisbiguanide
881:
878:Antimalarial
872:hypoglycemia
857:
849:
841:
837:
833:meglitinides
822:
815:
785:
775:
774:
683:
668:
656:
644:
528:
464:
463:
416:3.07, 13.25
407:
60:Identifiers
3131:from market
3050:clindamycin
2936:piperaquine
2921:clindamycin
2916:doxycycline
2905:+ proguanil
2870:artemisinin
2819:sulfadoxine
2780:cycloguanil
2758:Antifolates
2688:tafenoquine
2662:chloroquine
2657:amodiaquine
2624:Individual
2588:clindamycin
2536:thiazolides
2511:Conoidasida
2406:from market
2018:Sitagliptin
2013:Saxagliptin
2003:Melogliptin
1998:Linagliptin
1993:Gosogliptin
1988:Gemigliptin
1961:/"gliptins"
1946:(GLP-1/GIP)
1944:Tirzepatide
1938:Retatrutide
1905:Semaglutide
1890:Liraglutide
1880:Dulaglutide
1875:Danuglipron
1870:Albiglutide
1848:Repaglinide
1843:Nateglinide
1838:Mitiglinide
1831:/"glinides"
1814:Glisoxepide
1799:Glimepiride
1789:Glicaramide
1768:Tolbutamide
1743:Carbutamide
1691:Pramlintide
1649:Aleglitazar
1601:Englitazone
1591:Ciglitazone
1496:from market
1407:NPH insulin
1384:long-acting
1338:fast-acting
910:cycloguanil
681:treatment.
679:prediabetes
659:derivatives
356:Properties
171:100.000.229
3173:Guanidines
3168:Biguanides
3162:Categories
3042:Babesiosis
2973:arterolane
2901:atovaquone
2880:artesunate
2865:artemether
2788:biguanides
2704:mefloquine
2678:primaquine
2636:inhibitors
2593:atovaquone
2195:Benfluorex
2082:Zenarestat
2072:Ranirestat
2067:Fidarestat
2062:Epalrestat
1978:Evogliptin
1973:Anagliptin
1968:Alogliptin
1809:Gliquidone
1794:Gliclazide
1763:Tolazamide
1568:Phenformin
1550:Biguanides
1028:3527306730
956:References
926:See also:
896:inhibiting
884:Frank Rose
802:phenformin
757:Phenformin
698:Phenformin
391:Molar mass
267:FB4Q52I9K2
144:ChemSpider
133:CHEBI:3095
88:3D model (
67:CAS Number
20:Biguanide
3141:Phase III
3129:Withdrawn
2926:mepacrine
2875:artemotil
2824:sulfalene
2799:proguanil
2714:quinidine
2683:pamaquine
2416:Phase III
2404:Withdrawn
2205:Imeglimin
2110:Voglibose
2077:Tolrestat
1928:Mazdutide
1885:Exenatide
1804:Glipizide
1563:Metformin
1506:Phase III
1494:Withdrawn
1465:inhalable
946:alexidine
906:Proguanil
790:synthalin
782:guanidine
723:Metformin
689:Metformin
673:used for
649:in 1879.
599:⟶
525:Synthesis
465:Biguanide
192:200-251-8
184:EC Number
3096:Stramen-
2857:lactones
2634:Hemozoin
2105:Miglitol
2100:Acarbose
1558:Buformin
1322:Insulins
1300:insulins
1205:37100912
1196:10131557
1134:11602616
972:(2014).
940:(PAPB),
860:diarrhea
827:such as
798:diabetes
738:Buformin
704:Buformin
537:, via a
2951:nations
2709:quinine
2616:Malaria
2500:Apicom-
1930:(GLP-1/
1476:Afrezza
1473:Exubera
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794:insulin
765:History
535:ammonia
515:ammonia
446:what is
444: (
404:Acidity
396:101.113
234:PubChem
207:240093
118:507183
77:56-03-1
3124:WHO-EM
3068:Cilio-
2987:(ASMQ)
2981:(ASAQ)
2949:Combi-
2626:agents
2489:Alveo-
2399:WHO-EM
1678:DACRAs
1674:Amylin
1489:WHO-EM
1254:931371
1252:
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1179:Nature
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1125:209536
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944:, and
786:Galega
539:Pinner
441:verify
438:
340:SMILES
222:C07672
43:Names
3098:opile
3070:phora
2894:Other
2723:Other
2502:plexa
2188:Other
2046:Other
1294:Oral
908:(>
742:butyl
671:drugs
533:with
315:InChI
124:ChEBI
90:JSmol
2960:ACTs
2842:(SP)
2674:(8-)
2653:(4-)
2491:late
1932:GCGR
1582:PPAR
1578:TZDs
1302:and
1250:PMID
1201:PMID
1153:ISBN
1130:PMID
1079:ISBN
1023:ISBN
990:ISBN
831:and
816:The
740:. A
519:urea
517:and
258:UNII
247:5939
213:KEGG
153:5726
2480:P01
1716:ATP
1308:A10
1240:PMC
1232:doi
1191:PMC
1183:doi
1120:PMC
1112:doi
1108:108
1056:doi
1015:doi
982:doi
677:or
284:EPA
237:CID
3164::
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2470:–
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483:ɡ
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378:7
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372:2
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282:(
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