556:
533:
40:
920:
31:
2686:
2674:
992:(NCI) found that ddA and ddI could inhibit HIV replication in the test tube and conducted initial clinical trials showing that didanosine had activity in patients infected with HIV. On behalf of the NCI, they were awarded patents on these activities. Since the NCI does not market products directly, the
1022:
At the end of its ten-year license, BMS re-formulated Videx as Videx EC and patented that, which reformulation the FDA approved in 2000. The new formulation is a smaller capsule containing coated microspheres instead of using a buffering compound. It is approved by the FDA for once-a-day dosing. Also
1018:
buffering compound to neutralize stomach acid. The chewable tablets were not only large and fragile, they also were foul-tasting and the buffering compound would cause diarrhea. Although the FDA had not approved the original formulation for once-a-day dosing it was possible for some people to take
905:
Oral absorption of didanosine is fairly low (42%) but rapid. Food substantially reduces didanosine bioavailability, and the drug should be administered on an empty stomach. The half-life in plasma is only 1.5 hours, but in the intracellular environment more than 12 hours. An enteric-coated
888:
attached to the sugar ring. Within the cell, ddI is phosphorylated to the active metabolite of dideoxyadenosine triphosphate, ddATP, by cellular enzymes. Like other anti-HIV nucleoside analogs, it acts as a chain terminator by incorporation and inhibits viral
1205:
2071:
1023:
at the end of that ten-year period, the NIH licensed didanosine to Barr
Laboratories under a non-exclusive license, and didanosine became the first generic anti-HIV drug marketed in the United States.
1224:
1357:
Robins MJ, McCarthy JR, Robins RK (January 1966). "Purine nucleosides. XII. The preparation of 2',3'-dideoxyadenosine, 2',5'-dideoxyadenosine, and 2',3',5'-trideoxyadenosine from 2'-deoxyadenosine".
976:
of didanosine, 2′,3′-dideoxyadenosine (ddA), was initially synthesized by Morris J. Robins (professor of
Organic Chemistry at Brigham Young University) and R.K. Robins in 1964. Subsequently,
2045:
1963:
1291:"Measurement of intracellular didanosine and tenofovir phosphorylated metabolites and possible interaction of the two drugs in human immunodeficiency virus-infected patients"
2065:
2706:
2255:
2260:
1014:
Didanosine has weak acid stability and is easily damaged by stomach acid. Therefore, the original formula approved by the FDA used chewable tablets that included an
2206:
1232:
1678:
2645:
142:
1842:
906:
formulation is now marketed as well. Elimination is predominantly renal; the kidneys actively secrete didanosine, the amount being 20% of the oral dose.
625:
2721:
2212:
2270:
2190:
1166:
2275:
1246:
Moyle GJ (August 1996). "Use of viral resistance patterns to antiretroviral drugs in optimising selection of drug combinations and sequences".
809:
plasma levels have been shown to occur when administered simultaneously with didanosine; these drugs should be administered at different times.
2223:
1624:
1003:
Didanosine became the second drug approved for the treatment of HIV infection in many other countries, including in the United States by the
70:
2245:
2229:
639:
2598:
2593:
2240:
2250:
2517:
1167:"VIDEX (didanosine): chewable/dispersible buffered tablets; buffered powder for oral solution; pediatric powder for oral solution"
2161:
1548:
1338:
2616:
2507:
1450:
781:
issued a statement that patients using didanosine (Videx) are at risk for a rare but potentially fatal liver disorder, non-
710:
2265:
1602:
2280:
774:
and alterations of liver functions. The risk of some of these serious adverse events is increased by drinking alcohol.
1026:
One of the patents for ddI expired in the United States on 29 August 2006, but other patents extend beyond that time.
684:
1836:
1617:
1108:
959:
659:
1580:
2726:
2633:
2290:
2174:
2300:
2285:
1948:
1936:
714:
274:
172:
884:. It differs from other nucleoside analogues, because it does not have any of the regular bases, instead it has
2180:
941:
667:
InChI=1S/C10H12N4O3/c15-3-6-1-2-7(17-6)14-5-13-8-9(14)11-4-12-10(8)16/h4-7,15H,1-3H2,(H,11,12,16)/t6-,7+/m0/s1
361:
993:
1610:
1004:
840:
can exacerbate didanosine's toxicity, and avoiding drinking alcohol while taking didanosine is recommended.
778:
551:
412:
2385:
1044:"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"
937:
512:
823:
should be administered at a different time from didanosine due to interactions with the buffering agent.
2664:
481:
1043:
989:
2457:
2367:
2348:
2235:
2196:
528:
501:
2621:
2217:
930:
128:
52:
2295:
894:
461:
231:
2403:
1098:
2716:
2492:
2305:
2185:
2055:
1654:
1542:
1332:
890:
352:
2375:
2201:
2050:
1808:
1514:
1501:
Yarchoan R, Mitsuya H, Thomas RV, Pluda JM, Hartman NR, Perno CF, et al. (July 1989).
1473:
1395:
997:
421:
401:
316:
241:
1632:
1225:"Guidelines for the use of antiretroviral agents in HIV-1-infected adults and adolescents"
720:
Didanosine was first described in 1975 and approved for use in the United States in 1991.
8:
2310:
2169:
2041:
1959:
1758:
1637:
1568:
1556:
1180:
1124:
307:
135:
1518:
1477:
1399:
555:
532:
1407:
1315:
1290:
1271:
102:
341:
2452:
2115:
1530:
1503:"In vivo activity against HIV and favorable toxicity profile of 2',3'-dideoxyinosine"
1489:
1446:
1411:
1374:
1320:
1263:
1259:
1104:
1072:
877:
767:
187:
94:
1306:
1289:
Pruvost A, Negredo E, Benech H, Theodoro F, Puig J, Grau E, et al. (May 2005).
1275:
2711:
2477:
1522:
1481:
1403:
1366:
1310:
1302:
1255:
568:
213:
155:
2651:
80:
39:
2678:
2553:
2512:
1672:
985:
981:
221:
2690:
2627:
1633:
1206:"Serious liver disorder associated with the use of Videx/Videx EC (didanosine)"
771:
741:
2700:
2393:
2143:
1978:
1864:
977:
820:
544:
200:
1526:
1485:
2447:
2437:
2018:
2008:
1826:
1783:
1778:
1773:
1735:
1715:
1645:
1324:
885:
816:
812:
763:
492:
150:
22:
1569:"NIH Oral History of Robert Yarchoan describing development of AIDS drugs"
1534:
1493:
1423:
Männistö PT, Tuominen RK (1996). Koulu M, Tuomisto J, Paasonen MK (eds.).
1415:
1378:
1267:
2573:
2548:
2487:
2472:
2467:
2131:
2098:
2013:
1993:
1788:
1768:
1747:
1694:
1662:
1591:
1007:(FDA) on 9 October 1991. Its FDA approval helped bring down the price of
862:
827:
806:
795:
88:
1557:"NIH Oral History of Samuel Broder describing development of AIDS drugs"
1370:
381:
2578:
2558:
2543:
2538:
2502:
2497:
2411:
2356:
2326:
2138:
2126:
2121:
2093:
2033:
2023:
1998:
1983:
1922:
1917:
1905:
1889:
1879:
1859:
1821:
1731:
1719:
1711:
1008:
944: in this section. Unsourced material may be challenged and removed.
874:
850:
757:
702:
601:
392:
2588:
2568:
2563:
2533:
2462:
2442:
2331:
2088:
2003:
1988:
1911:
1884:
1874:
1869:
1816:
1793:
1706:
881:
831:
802:
782:
327:
254:
74:
1502:
1461:
919:
2583:
1968:
770:
status. Other reported serious adverse events are retinal changes,
749:
737:
729:
706:
441:
372:
1386:
Yarchoan R, Mitsuya H, Broder S (October 1988). "AIDS therapies".
1073:"didanosine, Videx, Videx EC: Drug Facts, Side Effects and Dosing"
849:
Drug resistance to didanosine does develop, though slower than to
624:
2482:
2028:
1798:
1015:
973:
837:
766:
is rarely observed but has caused occasional fatalities, and has
1441:
Watson JD, Hopkins NH, Roberts JW, Steitz JA, Weiner AM (1987).
2432:
2427:
798:, and administration of these drugs together should be avoided.
733:
472:
259:
1231:. U.S. Department of Health and Human Services. Archived from
709:. It is used in combination with other medications as part of
1742:
826:
Administration with drugs with overlapping toxicity, such as
760:
occurred in 21-26% of participants in key didanosine trials.
745:
615:
452:
2685:
1288:
517:
30:
2256:
Elvitegravir/cobicistat/emtricitabine/tenofovir alafenamide
1701:
1689:
1588:
National
Institutes of Health Office of Technology Transfer
753:
432:
2261:
Elvitegravir/cobicistat/emtricitabine/tenofovir disoproxil
1500:
1440:
1726:
1641:
1051:
2207:
Darunavir/cobicistat/emtricitabine/tenofovir alafenamide
1181:"Didanosine Videx - Treatment - National HIV Curriculum"
794:
A significant interaction has also been recorded with
2662:
1459:
1385:
1212:. U.S. Food and Drug Administration. 19 January 2010.
1356:
865:; other mutations observed include K65R and M184V .
1036:
1000:Co. (BMS) to market and sell ddI as Videx tablets.
728:The most common adverse events with didanosine are
360:
2707:Nucleoside analog reverse transcriptase inhibitors
1460:Mitsuya H, Yarchoan R, Broder S (September 1990).
2698:
2213:Dolutegravir/emtricitabine/tenofovir alafenamide
1422:
340:
2271:Emtricitabine/rilpivirine/tenofovir alafenamide
2191:Bictegravir/emtricitabine/tenofovir alafenamide
1169:. U.S. Food and Drug Administration. July 2000.
1125:"Didanosine Side Effects in Detail - Drugs.com"
1096:
315:
2276:Emtricitabine/rilpivirine/tenofovir disoproxil
1762:(Integrase strand transfer inhibitors (INSTI))
1431:
996:(NIH) awarded a ten-year exclusive license to
2224:Dolutegravir/lamivudine/tenofovir alafenamide
1618:
2246:Efavirenz/emtricitabine/tenofovir disoproxil
2230:Dolutegravir/lamivudine/tenofovir disoproxil
1581:"Report on Development and Licensing of ddI"
500:
2241:Doravirine/lamivudine/tenofovir disoproxil
1625:
1611:
1222:
779:United States Food and Drug Administration
554:
531:
400:
290:)-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3
2251:Efavirenz/lamivudine/tenofovir disoproxil
1436:(3rd ed.). Pearson Professional Ltd.
1314:
1161:
1159:
1157:
1155:
1153:
1151:
1149:
1147:
1145:
960:Learn how and when to remove this message
853:(ZDV). The most common mutation observed
420:
2518:Zinc finger protein transcription factor
861:gene, which confers cross-resistance to
2722:Drugs developed by Bristol Myers Squibb
527:
380:
93:
2699:
1142:
1103:. John Wiley & Sons. p. 505.
868:
545:
181:
1606:
1295:Antimicrobial Agents and Chemotherapy
1245:
480:
460:
194:
79:
1462:"Molecular targets for AIDS therapy"
1432:Rang HP, Dale MM, Ritter JM (1995).
1239:
1011:(ZDV), the initial anti-HIV drug.
942:adding citations to reliable sources
913:
788:
711:highly active antiretroviral therapy
154:
2266:Emtricitabine/tenofovir alafenamide
1445:(4th ed.). Benjamin/Cummings.
1216:
900:
440:
331:
13:
2281:Emtricitabine/tenofovir disoproxil
1547:: CS1 maint: overridden setting (
1408:10.1038/scientificamerican1088-110
1349:
1337:: CS1 maint: overridden setting (
723:
14:
2738:
113:
2684:
2672:
2654:. Formerly or rarely used agent.
2291:Lamivudine/nevirapine/zidovudine
2175:Abacavir/dolutegravir/lamivudine
1590:. September 2003. Archived from
1260:10.2165/00003495-199652020-00002
918:
585:
579:
38:
29:
2458:Epigallocatechin gallate (EGCG)
2301:Lamivudine/tenofovir disoproxil
2286:Lamivudine/nevirapine/stavudine
1307:10.1128/AAC.49.5.1907-1914.2005
1282:
1097:Fischer J, Ganellin CR (2006).
929:needs additional citations for
715:reverse-transcriptase inhibitor
672:Key:BXZVVICBKDXVGW-NKWVEPMBSA-N
2181:Abacavir/lamivudine/zidovudine
1198:
1173:
1117:
1090:
1065:
591:
573:
1:
1443:Molecular Biology of the Gene
1210:FDA Drug Safety Communication
1100:Analogue-based Drug Discovery
1029:
994:National Institutes of Health
844:
1425:Farmakologia ja Toksikologia
1005:Food and Drug Administration
697:, sold under the brand name
7:
2056:Tenofovir alafenamide (TAF)
647:O=C3/N=C\Nc1c3ncn12O(CC2)CO
10:
2743:
2051:Tenofovir disoproxil (TDF)
909:
893:by competing with natural
563:Chemical and physical data
2611:
2526:
2420:
2402:
2384:
2366:
2347:
2340:
2319:
2160:
2107:
2081:
2072:Discovery and development
2064:
1947:
1935:
1898:
1852:
1843:Discovery and development
1835:
1807:
1757:
1679:Discovery and development
1671:
1653:
1427:(5th ed.). Medicina.
1223:DHHS Panel (4 May 2006).
990:National Cancer Institute
680:
655:
635:
613:
600:
567:
562:
543:
511:
491:
471:
451:
431:
411:
391:
371:
351:
326:
306:
270:
265:
253:
240:
230:
220:
212:
171:
166:
141:
127:
101:
87:
69:
65:2′,3′-dideoxyinosine, DDI
61:
51:
46:
37:
28:
2368:Transcription inhibitors
2320:Pharmacokinetic boosters
2236:Dolutegravir/rilpivirine
2197:Cabotegravir/rilpivirine
1837:Protease Inhibitors (PI)
2727:Hydroxymethyl compounds
2652:initial regimen options
2218:Dolutegravir/lamivudine
1695:Enfuvirtide (ENF, T-20)
1673:Entry/fusion inhibitors
1527:10.1126/science.2502840
1486:10.1126/science.1699273
2493:Portmanteau inhibitors
2386:Translation inhibitors
2296:Lamivudine/raltegravir
2066:Non-nucleoside (NNRTI)
2024:Islatravir (EFdA, ISL)
873:Didanosine (ddI) is a
777:In February 2010, the
713:(HAART). It is of the
2508:Synergistic enhancers
2306:Lamivudine/zidovudine
2186:Atazanavir/cobicistat
2162:Combined formulations
1999:Zidovudine (AZT, ZDV)
1937:Reverse-transcriptase
1809:Maturation inhibitors
1597:on 30 September 2006.
1573:Office of NIH History
1561:Office of NIH History
891:reverse transcriptase
857:is L74V in the viral
834:, is not recommended.
785:portal hypertension.
2349:Uncoating inhibitors
2202:Darunavir/cobicistat
2042:Nucleotide analogues
1960:Nucleoside analogues
1759:Integrase inhibitors
1638:antiretroviral drugs
998:Bristol-Myers Squibb
938:improve this article
2341:Experimental agents
2311:Lopinavir/ritonavir
2170:Abacavir/lamivudine
2144:Elsulfavirine (ESV)
1979:Emtricitabine (FTC)
1865:Fosamprenavir (FPV)
1519:1989Sci...245..412Y
1478:1990Sci...249.1533M
1400:1988SciAm.259d.110Y
1388:Scientific American
1371:10.1021/bi00865a029
869:Mechanism of action
701:among others, is a
190:(Prescription only)
25:
2638:Never to phase III
1784:Elvitegravir (EVG)
1779:Dolutegravir (DTG)
1774:Cabotegravir (CAB)
1563:. 2 February 1997.
21:
2660:
2659:
2607:
2606:
2453:Diarylpyrimidines
2156:
2155:
2152:
2151:
2132:Rilpivirine (RPV)
2116:diarylpyrimidines
2099:Delavirdine (DLV)
1994:Zalcitabine (ddC)
1951:nucleotide (NRTI)
1931:
1930:
1789:Raltegravir (RAL)
1769:Bictegravir (BIC)
1748:Fostemsavir (FTR)
1663:Lenacapavir (LEN)
1655:Capsid inhibitors
1472:(4976): 1533–44.
1452:978-0-8053-9612-6
970:
969:
962:
789:Drug interactions
768:black box warning
692:
691:
626:Interactive image
513:CompTox Dashboard
198:
185:
117:
16:Chemical compound
2734:
2689:
2688:
2677:
2676:
2675:
2668:
2478:Hydroxycarbamide
2345:
2344:
2139:Doravirine (DOR)
2127:Etravirine (ETR)
2122:Dapivirine (DPV)
2094:Nevirapine (NVP)
2079:
2078:
1984:Lamivudine (3TC)
1974:Didanosine (ddI)
1945:
1944:
1918:Tipranavir (TPV)
1906:Atazanavir (ATV)
1890:Saquinavir (SQV)
1880:Nelfinavir (NFV)
1860:Amprenavir (APV)
1850:
1849:
1732:Ibalizumab (IBA)
1627:
1620:
1613:
1604:
1603:
1598:
1596:
1585:
1576:
1564:
1552:
1546:
1538:
1497:
1456:
1437:
1428:
1419:
1382:
1343:
1342:
1336:
1328:
1318:
1286:
1280:
1279:
1243:
1237:
1236:
1220:
1214:
1213:
1202:
1196:
1195:
1193:
1191:
1177:
1171:
1170:
1163:
1140:
1139:
1137:
1135:
1121:
1115:
1114:
1094:
1088:
1087:
1085:
1083:
1069:
1063:
1062:
1060:
1058:
1048:nctr-crs.fda.gov
1040:
965:
958:
954:
951:
945:
922:
914:
901:Pharmacokinetics
688:
687:
628:
608:
593:
587:
581:
575:
558:
547:
536:
535:
521:
519:
504:
484:
464:
444:
424:
404:
384:
364:
344:
334:
333:
319:
245:
203:
196:
193:
183:
180:
158:
115:
112:
97:
83:
42:
33:
26:
24:
20:
2742:
2741:
2737:
2736:
2735:
2733:
2732:
2731:
2697:
2696:
2695:
2683:
2673:
2671:
2663:
2661:
2656:
2655:
2643:
2628:Clinical trials
2603:
2554:Dexelvucitabine
2522:
2513:Tre recombinase
2416:
2398:
2380:
2376:Tat antagonists
2362:
2336:
2315:
2148:
2103:
2089:Efavirenz (EFV)
2068:
2060:
1989:Stavudine (d4T)
1950:
1938:
1927:
1912:Darunavir (DRV)
1894:
1885:Ritonavir (RTV)
1875:Lopinavir (LPV)
1870:Indinavir (IDV)
1839:
1831:
1803:
1761:
1753:
1707:Maraviroc (MVC)
1675:
1667:
1649:
1634:Antiviral drugs
1631:
1601:
1594:
1583:
1579:
1575:. 3 April 1998.
1567:
1555:
1540:
1539:
1513:(4916): 412–5.
1453:
1352:
1350:Further reading
1347:
1346:
1330:
1329:
1287:
1283:
1244:
1240:
1221:
1217:
1204:
1203:
1199:
1189:
1187:
1179:
1178:
1174:
1165:
1164:
1143:
1133:
1131:
1123:
1122:
1118:
1111:
1095:
1091:
1081:
1079:
1071:
1070:
1066:
1056:
1054:
1042:
1041:
1037:
1032:
986:Robert Yarchoan
982:Hiroaki Mitsuya
966:
955:
949:
946:
935:
923:
912:
903:
871:
847:
791:
726:
724:Adverse effects
683:
681:
676:
673:
668:
663:
662:
651:
648:
643:
642:
631:
606:
596:
590:
584:
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515:
507:
487:
467:
447:
427:
407:
387:
367:
347:
330:
322:
302:
299:
278:
277:
243:
232:Protein binding
222:Bioavailability
214:Pharmacokinetic
208:
201:
162:
130:
123:
104:
57:Videx, Videx EC
17:
12:
11:
5:
2740:
2730:
2729:
2724:
2719:
2714:
2709:
2694:
2693:
2681:
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2657:
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2641:
2640:
2639:
2636:
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2619:
2613:
2612:
2609:
2608:
2605:
2604:
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2601:
2596:
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2586:
2581:
2576:
2571:
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2561:
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2551:
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2541:
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2515:
2510:
2505:
2500:
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2490:
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2465:
2460:
2455:
2450:
2445:
2440:
2435:
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2424:
2422:
2418:
2417:
2415:
2414:
2408:
2406:
2400:
2399:
2397:
2396:
2390:
2388:
2382:
2381:
2379:
2378:
2372:
2370:
2364:
2363:
2361:
2360:
2353:
2351:
2342:
2338:
2337:
2335:
2334:
2329:
2327:Cobicistat (c)
2323:
2321:
2317:
2316:
2314:
2313:
2308:
2303:
2298:
2293:
2288:
2283:
2278:
2273:
2268:
2263:
2258:
2253:
2248:
2243:
2238:
2233:
2227:
2221:
2215:
2210:
2204:
2199:
2194:
2188:
2183:
2178:
2172:
2166:
2164:
2158:
2157:
2154:
2153:
2150:
2149:
2147:
2146:
2141:
2136:
2135:
2134:
2129:
2124:
2111:
2109:
2105:
2104:
2102:
2101:
2096:
2091:
2085:
2083:
2076:
2062:
2061:
2059:
2058:
2053:
2037:
2036:
2031:
2026:
2021:
2016:
2011:
2006:
2001:
1996:
1991:
1986:
1981:
1976:
1971:
1969:Abacavir (ABC)
1955:
1953:
1949:Nucleoside and
1942:
1933:
1932:
1929:
1928:
1926:
1925:
1920:
1915:
1909:
1902:
1900:
1896:
1895:
1893:
1892:
1887:
1882:
1877:
1872:
1867:
1862:
1856:
1854:
1847:
1833:
1832:
1830:
1829:
1824:
1819:
1813:
1811:
1805:
1804:
1802:
1801:
1796:
1791:
1786:
1781:
1776:
1771:
1765:
1763:
1755:
1754:
1752:
1751:
1739:
1723:
1709:
1698:
1685:
1683:
1669:
1668:
1666:
1665:
1659:
1657:
1651:
1650:
1630:
1629:
1622:
1615:
1607:
1600:
1599:
1577:
1565:
1553:
1498:
1457:
1451:
1438:
1429:
1420:
1383:
1353:
1351:
1348:
1345:
1344:
1301:(5): 1907–14.
1281:
1238:
1235:on 6 May 2006.
1215:
1197:
1185:www.hiv.uw.edu
1172:
1141:
1116:
1109:
1089:
1064:
1034:
1033:
1031:
1028:
968:
967:
950:September 2024
926:
924:
917:
911:
908:
902:
899:
870:
867:
846:
843:
842:
841:
835:
824:
810:
799:
790:
787:
772:optic neuritis
742:abdominal pain
725:
722:
705:used to treat
690:
689:
678:
677:
675:
674:
671:
669:
666:
658:
657:
656:
653:
652:
650:
649:
646:
638:
637:
636:
633:
632:
630:
629:
621:
619:
611:
610:
604:
598:
597:
594:
588:
582:
576:
571:
565:
564:
560:
559:
549:
541:
540:
538:
537:
524:
522:
509:
508:
506:
505:
497:
495:
489:
488:
486:
485:
477:
475:
469:
468:
466:
465:
457:
455:
449:
448:
446:
445:
437:
435:
429:
428:
426:
425:
417:
415:
409:
408:
406:
405:
397:
395:
389:
388:
386:
385:
377:
375:
369:
368:
366:
365:
357:
355:
349:
348:
346:
345:
337:
335:
324:
323:
321:
320:
312:
310:
304:
303:
301:
300:
281:
273:
272:
271:
268:
267:
263:
262:
257:
251:
250:
247:
238:
237:
234:
228:
227:
224:
218:
217:
210:
209:
207:
206:
191:
177:
175:
169:
168:
164:
163:
161:
160:
147:
145:
139:
138:
133:
131:administration
125:
124:
122:
121:
119:
109:
107:
99:
98:
91:
85:
84:
77:
67:
66:
63:
59:
58:
55:
49:
48:
44:
43:
35:
34:
15:
9:
6:
4:
3:
2:
2739:
2728:
2725:
2723:
2720:
2718:
2715:
2713:
2710:
2708:
2705:
2704:
2702:
2692:
2687:
2682:
2680:
2670:
2669:
2666:
2653:
2650:
2647:
2637:
2635:
2632:
2631:
2629:
2626:
2623:
2620:
2618:
2615:
2614:
2610:
2600:
2597:
2595:
2592:
2590:
2587:
2585:
2582:
2580:
2577:
2575:
2572:
2570:
2567:
2565:
2562:
2560:
2557:
2555:
2552:
2550:
2547:
2545:
2542:
2540:
2537:
2535:
2532:
2531:
2529:
2527:Failed agents
2525:
2519:
2516:
2514:
2511:
2509:
2506:
2504:
2501:
2499:
2496:
2494:
2491:
2489:
2486:
2484:
2481:
2479:
2476:
2474:
2471:
2469:
2466:
2464:
2461:
2459:
2456:
2454:
2451:
2449:
2446:
2444:
2441:
2439:
2436:
2434:
2431:
2429:
2426:
2425:
2423:
2419:
2413:
2410:
2409:
2407:
2405:
2401:
2395:
2394:Trichosanthin
2392:
2391:
2389:
2387:
2383:
2377:
2374:
2373:
2371:
2369:
2365:
2358:
2355:
2354:
2352:
2350:
2346:
2343:
2339:
2333:
2332:Ritonavir (r)
2330:
2328:
2325:
2324:
2322:
2318:
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:
2231:
2228:
2225:
2222:
2219:
2216:
2214:
2211:
2208:
2205:
2203:
2200:
2198:
2195:
2192:
2189:
2187:
2184:
2182:
2179:
2176:
2173:
2171:
2168:
2167:
2165:
2163:
2159:
2145:
2142:
2140:
2137:
2133:
2130:
2128:
2125:
2123:
2120:
2119:
2118:
2117:
2113:
2112:
2110:
2106:
2100:
2097:
2095:
2092:
2090:
2087:
2086:
2084:
2080:
2077:
2075:
2073:
2067:
2063:
2057:
2054:
2052:
2049:
2047:
2043:
2039:
2038:
2035:
2032:
2030:
2027:
2025:
2022:
2020:
2017:
2015:
2012:
2010:
2007:
2005:
2002:
2000:
1997:
1995:
1992:
1990:
1987:
1985:
1982:
1980:
1977:
1975:
1972:
1970:
1967:
1965:
1961:
1957:
1956:
1954:
1952:
1946:
1943:
1940:
1934:
1924:
1921:
1919:
1916:
1913:
1910:
1907:
1904:
1903:
1901:
1897:
1891:
1888:
1886:
1883:
1881:
1878:
1876:
1873:
1871:
1868:
1866:
1863:
1861:
1858:
1857:
1855:
1851:
1848:
1846:
1844:
1838:
1834:
1828:
1825:
1823:
1820:
1818:
1815:
1814:
1812:
1810:
1806:
1800:
1797:
1795:
1792:
1790:
1787:
1785:
1782:
1780:
1777:
1775:
1772:
1770:
1767:
1766:
1764:
1760:
1756:
1749:
1745:
1744:
1740:
1737:
1733:
1729:
1728:
1724:
1721:
1717:
1713:
1710:
1708:
1704:
1703:
1699:
1696:
1692:
1691:
1687:
1686:
1684:
1682:
1680:
1674:
1670:
1664:
1661:
1660:
1658:
1656:
1652:
1647:
1643:
1640:used against
1639:
1635:
1628:
1623:
1621:
1616:
1614:
1609:
1608:
1605:
1593:
1589:
1582:
1578:
1574:
1570:
1566:
1562:
1558:
1554:
1550:
1544:
1536:
1532:
1528:
1524:
1520:
1516:
1512:
1508:
1504:
1499:
1495:
1491:
1487:
1483:
1479:
1475:
1471:
1467:
1463:
1458:
1454:
1448:
1444:
1439:
1435:
1430:
1426:
1421:
1417:
1413:
1409:
1405:
1401:
1397:
1393:
1389:
1384:
1380:
1376:
1372:
1368:
1365:(1): 224–31.
1364:
1360:
1355:
1354:
1340:
1334:
1326:
1322:
1317:
1312:
1308:
1304:
1300:
1296:
1292:
1285:
1277:
1273:
1269:
1265:
1261:
1257:
1254:(2): 168–85.
1253:
1249:
1242:
1234:
1230:
1226:
1219:
1211:
1207:
1201:
1186:
1182:
1176:
1168:
1162:
1160:
1158:
1156:
1154:
1152:
1150:
1148:
1146:
1130:
1126:
1120:
1112:
1110:9783527607495
1106:
1102:
1101:
1093:
1078:
1074:
1068:
1053:
1049:
1045:
1039:
1035:
1027:
1024:
1020:
1019:it that way.
1017:
1012:
1010:
1006:
1001:
999:
995:
991:
987:
983:
979:
978:Samuel Broder
975:
964:
961:
953:
943:
939:
933:
932:
927:This section
925:
921:
916:
915:
907:
898:
896:
892:
887:
883:
879:
876:
866:
864:
860:
856:
852:
839:
836:
833:
829:
825:
822:
821:ciprofloxacin
818:
814:
811:
808:
804:
801:Reduction in
800:
797:
793:
792:
786:
784:
780:
775:
773:
769:
765:
761:
759:
756:. Peripheral
755:
751:
747:
743:
739:
735:
731:
721:
718:
716:
712:
708:
704:
700:
696:
686:
679:
670:
665:
664:
661:
654:
645:
644:
641:
634:
627:
623:
622:
620:
617:
612:
605:
603:
599:
572:
570:
566:
561:
557:
553:
550:
548:
546:ECHA InfoCard
542:
534:
530:
529:DTXSID6022927
526:
525:
523:
514:
510:
503:
499:
498:
496:
494:
490:
483:
479:
478:
476:
474:
470:
463:
459:
458:
456:
454:
450:
443:
439:
438:
436:
434:
430:
423:
419:
418:
416:
414:
410:
403:
399:
398:
396:
394:
390:
383:
379:
378:
376:
374:
370:
363:
359:
358:
356:
354:
350:
343:
339:
338:
336:
329:
325:
318:
314:
313:
311:
309:
305:
297:
293:
289:
285:
280:
279:
276:
269:
264:
261:
258:
256:
252:
248:
246:
239:
235:
233:
229:
225:
223:
219:
215:
211:
204:
192:
189:
179:
178:
176:
174:
170:
165:
157:
152:
149:
148:
146:
144:
140:
137:
134:
132:
126:
120:
111:
110:
108:
106:
100:
96:
92:
90:
86:
82:
78:
76:
72:
68:
64:
60:
56:
54:
50:
47:Clinical data
45:
41:
36:
32:
27:
19:
2717:Hepatotoxins
2648:
2448:Cyanovirin-N
2438:Calanolide A
2114:
2108:2 generation
2082:1 generation
2069:
2040:
2019:Elvucitabine
2009:Apricitabine
1973:
1958:
1899:2 generation
1853:1 generation
1840:
1827:Fipravirimat
1741:
1736:Semzuvolimab
1725:
1716:Cenicriviroc
1700:
1688:
1676:
1592:the original
1587:
1572:
1560:
1543:cite journal
1510:
1506:
1469:
1465:
1442:
1434:Pharmacology
1433:
1424:
1394:(4): 110–9.
1391:
1387:
1362:
1359:Biochemistry
1358:
1333:cite journal
1298:
1294:
1284:
1251:
1247:
1241:
1233:the original
1228:
1218:
1209:
1200:
1188:. Retrieved
1184:
1175:
1132:. Retrieved
1128:
1119:
1099:
1092:
1080:. Retrieved
1076:
1067:
1055:. Retrieved
1047:
1038:
1025:
1021:
1013:
1002:
972:The related
971:
956:
947:
936:Please help
931:verification
928:
904:
886:hypoxanthine
872:
858:
854:
848:
817:itraconazole
813:Ketoconazole
776:
764:Pancreatitis
762:
727:
719:
698:
694:
693:
682:
493:NIAID ChemDB
462:CHEBI:490877
295:
291:
287:
283:
242:Elimination
236:Less than 5%
173:Legal status
167:Legal status
18:
2649:recommended
2624:from market
2574:Lersivirine
2549:Capravirine
2488:Miltefosine
2473:Griffithsin
2468:Fosdevirine
2014:Censavudine
1644:(primarily
1077:MedicineNet
863:zalcitabine
828:zalcitabine
807:delavirdine
796:allopurinol
609: g·mol
552:100.129.182
266:Identifiers
89:MedlinePlus
62:Other names
53:Trade names
2701:Categories
2579:Lodenosine
2559:Droxinavir
2544:Brecanavir
2539:Atevirdine
2503:Seliciclib
2498:Scytovirin
2412:Elipovimab
2357:TRIM5alpha
2034:Stampidine
1939:inhibitors
1923:TMC-310911
1822:BMS-955176
1720:Leronlimab
1712:Vicriviroc
1057:22 October
1030:References
1009:zidovudine
875:nucleoside
851:zidovudine
845:Resistance
758:neuropathy
703:medication
695:Didanosine
614:3D model (
602:Molar mass
482:ChEMBL1460
422:K3GDH6OH08
393:ChemSpider
353:IUPHAR/BPS
317:69655-05-6
308:CAS Number
294:-purin-6(9
275:IUPAC name
23:Didanosine
2634:Phase III
2622:Withdrawn
2599:Telinavir
2594:Palinavir
2589:Mozenavir
2569:Emivirine
2564:Lasinavir
2534:Aplaviroc
2463:Foscarnet
2443:Ceragenin
2004:Amdoxovir
1817:Bevirimat
1794:BI 224436
1129:Drugs.com
882:adenosine
832:stavudine
803:indinavir
783:cirrhotic
342:135398739
255:Excretion
249:1.5 hours
244:half-life
226:30 to 54%
129:Routes of
103:Pregnancy
81:Monograph
75:Drugs.com
2679:Medicine
2584:Loviride
1325:15855513
1276:27709969
1229:AIDSInfo
1190:8 August
1134:8 August
1082:8 August
974:pro-drug
878:analogue
750:headache
738:vomiting
730:diarrhea
707:HIV/AIDS
685:(verify)
373:DrugBank
143:ATC code
136:By mouth
118: B2
105:category
2712:Purines
2691:Viruses
2665:Portals
2483:KP-1461
2029:Racivir
1799:MK-2048
1535:2502840
1515:Bibcode
1507:Science
1494:1699273
1474:Bibcode
1466:Science
1416:3072667
1396:Bibcode
1379:5938940
1316:1087635
1268:8841736
1016:antacid
988:in the
910:History
855:in vivo
838:Alcohol
717:class.
607:236.231
569:Formula
382:DB00900
328:PubChem
205:Rx-only
202:WARNING
159:)
153: (
151:J05AF02
95:a691006
2617:WHO-EM
2433:BIT225
2428:Abzyme
2359:(gene)
2046:NtRTIs
1941:(RTIs)
1533:
1492:
1449:
1414:
1377:
1323:
1313:
1274:
1266:
1107:
984:, and
752:, and
734:nausea
640:SMILES
502:000004
473:ChEMBL
442:D00296
260:Kidney
199:
186:
2421:Other
2404:BNAbs
1964:NRTIs
1743:gp120
1595:(PDF)
1584:(PDF)
1272:S2CID
1248:Drugs
746:fever
699:Videx
660:InChI
616:JSmol
453:ChEBI
402:45864
298:)-one
282:9-((2
2646:DHHS
1702:CCR5
1690:gp41
1549:link
1531:PMID
1490:PMID
1447:ISBN
1412:PMID
1375:PMID
1339:link
1321:PMID
1264:PMID
1192:2018
1136:2018
1105:ISBN
1084:2018
1059:2023
895:dATP
830:and
805:and
754:rash
433:KEGG
413:UNII
362:4833
216:data
71:AHFS
1727:CD4
1646:J05
1642:HIV
1523:doi
1511:245
1482:doi
1470:249
1404:doi
1392:259
1367:doi
1311:PMC
1303:doi
1256:doi
1052:FDA
940:by
880:of
859:pol
518:EPA
332:CID
188:POM
156:WHO
2703::
2630::
1734:,
1718:,
1714:,
1636::
1586:.
1571:.
1559:.
1545:}}
1541:{{
1529:.
1521:.
1509:.
1505:.
1488:.
1480:.
1468:.
1464:.
1410:.
1402:.
1390:.
1373:.
1361:.
1335:}}
1331:{{
1319:.
1309:.
1299:49
1297:.
1293:.
1270:.
1262:.
1252:52
1250:.
1227:.
1208:.
1183:.
1144:^
1127:.
1075:.
1050:.
1046:.
980:,
897:.
819:,
815:,
748:,
744:,
740:,
736:,
732:,
583:12
577:10
286:,5
195:US
182:UK
114:AU
2667::
2644:°
2232:°
2226:°
2220:°
2209:°
2193:°
2177:°
2074:)
2070:(
2048::
2044:/
1966::
1962:/
1914:°
1908:°
1845:)
1841:(
1750:)
1746:(
1738:)
1730:(
1722:)
1705:(
1697:)
1693:(
1681:)
1677:(
1648:)
1626:e
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