1178:
1155:
654:
631:
1618:
38:
793:
2578:
4765:
4753:
1433:
Tenofovir disoproxil is generally well tolerated with low discontinuation rates among the HIV and chronic hepatitis B population. There are no contraindications for use of this drug. The most commonly reported side effects due to use of tenofovir disoproxil were dizziness, nausea, and diarrhea. Other
1388:
Tenofovir disoproxil is used for HIV-1 infection and chronic hepatitis B treatment. For HIV-1 infection, tenofovir is indicated in combination with other antiretroviral agents for people 2 years of age and older. For chronic hepatitis B patients, tenofovir is indicated for patients 12 years of age
1726:
The initial form of tenofovir used in these studies had limited potential for widespread use because it poorly penetrated cells and was not absorbed when given by mouth. Gilead developed a pro-drug version of tenofovir, tenofovir disoproxil. This version of tenofovir is often referred to simply as
2698:
1514:
polymerase γ. In vivo tenofovir disoproxil fumarate is converted to tenofovir, an acyclic analog of deoxyadenosine 5'-monophosphate (dAMP). Tenofovir lacks a hydroxyl group in the position corresponding to the 3' carbon of the dAMP, preventing the formation of the 5′ to 3′
1722:
led to the investigation of PMPA's potential as a treatment for HIV infected patients. In 1997 researchers from Gilead and the
University of California, San Francisco demonstrated that tenofovir exhibits anti-HIV effects in humans when dosed by subcutaneous injection.
1457:(GFR). Discontinuation of tenofovir disoproxil can potentially lead to reversal of renal impairment. Nephrotoxicity may be due to proximal tubules accumulation of Tenofovir disoproxil leading to elevated serum concentrations.
2826:
2622:
Houghton SR, Melton J, Fortunak J, Brown Ripin DH, Boddy CN (2010). "Rapid, mild method for phosphonate diester hydrolysis: Development of a one-pot synthesis of tenofovir disoproxil fumarate from tenofovir diethyl ester".
1968:
Martin P, Lau DT, Nguyen MH, Janssen HL, Dieterich DT, Peters MG, et al. (November 2015). "A Treatment
Algorithm for the Management of Chronic Hepatitis B Virus Infection in the United States: 2015 Update".
1481:, by decreasing atazanavir concentrations while increasing tenofovir concentrations. In addition, since tenofovir is excreted by the kidney, medications that impair renal function can also cause problems.
1682:
in the presence of sodium bromide, a further refinement of the original manufacturing route. The synthesis of the alternative ester in tenofovir disoproxil is completed by alkylation with the appropriate
3560:
2714:"Safety, pharmacokinetics, and antiretroviral activity of intravenous 9-[2-(R)-(Phosphonomethoxy)propyl]adenine, a novel anti-human immunodeficiency virus (HIV) therapy, in HIV-infected adults"
2962:
1593:
Tenofovir may be measured in plasma by liquid chromatography. Such testing is useful for monitoring therapy and to prevent drug accumulation and toxicity in people with kidney or liver problems.
2063:
4593:
3534:
2576:, Holy A, Rosenberg I, "9-(phosponylmethoxyalkyl) adenines, the method of preparation and utilization thereof", published 1989-02-28, assigned to Czech Academy of Sciences
1495:
4556:
3452:
2595:
Brown Ripin DH, Teager DS, Fortunak J, Basha SM, Bivins N, Boddy CN, et al. (2010). "Process
Improvements for the Manufacture of Tenofovir Disoproxil Fumarate at Commercial Scale".
2188:
726:
301:
2818:
1840:
1519:
linkage essential for DNA chain elongation. Once incorporated into a growing DNA strand, tenofovir causes premature termination of DNA transcription, preventing viral replication.
768:
InChI=1S/C19H30N5O10P/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22)/t14-/m1/s1
1605:
and this was the chemical starting point for its first published synthesis which was included in patents to the compound. During drug development, attention switched to the
2955:
3554:
4815:
3744:
2485:
Kearney BP, Yale K, Shah J, Zhong L, Flaherty JF (2006). "Pharmacokinetics and dosing recommendations of tenofovir disoproxil fumarate in hepatic or renal impairment".
3749:
3695:
1421:. The results revealed a 48.9% reduced incidence of the virus among the group of subjects who received the drug in comparison to the control group who received a
1334:. It is generally recommended for use with other antiretrovirals. It may be used for prevention of HIV/AIDS among those at high risk before exposure, and after a
2948:
4830:
3167:
3080:
4134:
827:
256:
3331:
1718:
In 1985, De Clercq and Holý described the activity of PMPA against HIV in cell culture. Shortly thereafter, a collaboration with the biotechnology company
2793:
1727:"tenofovir". In this version of the drug, the two negative charges of the tenofovir phosphonic acid group are masked, thus enhancing oral absorption.
2298:"Role of traditional risk factors and antiretroviral drugs in the incidence of chronic kidney disease, ANRS CO3 Aquitaine cohort, France, 2004-2012"
3701:
2071:
3759:
3679:
1773:
1347:
2543:
Holý A, Rosenberg I (1982). "Preparation of 5'-O-phosphonylmethyl analogues of nucleoside-5'-phosphates, 5'-diphosphates and 5'-triphosphates".
1920:
1711:. The patent filed in 1986 makes no mention of the potential use of the compound for the treatment of HIV infection but claims activity against
3764:
2971:
1250:
1764:
Tenofovir disoproxil is also available in pills which combine a number of antiviral drugs into a single dose. Well-known combinations include
3712:
3113:
2180:
154:
3734:
3718:
2762:
1397:
Tenofovir can be used for HIV prevention in people who are at high risk for infection through sexual transmission or injecting drug use. A
1264:
740:
2848:
Mouton JP, Cohen K, Maartens G (November 2016). "Key toxicity issues with the WHO-recommended first-line antiretroviral therapy regimen".
1554:
concentrations are reached after one hour. When taken with fatty food, highest plasma concentrations are reached after two hours, and the
4087:
4082:
2021:
3729:
3042:
3037:
1410:
2410:
3739:
4173:
4006:
4785:
3650:
1555:
2274:
1791:. This allows the active metabolites to accumulate in those cells, leading to lower systemic exposure and potential toxicities.
1612:
derivative, tenofovir disoproxil, which was the subject of extensive process chemistry to provide a viable manufacturing route.
1309:
1292:
InChI=1S/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)/t6-/m1/s1
205:
4707:
4105:
3996:
1373:
2438:"The simultaneous assay of tenofovir and emtricitabine in plasma using LC/MS/MS and isotopically labeled internal standards"
1753:
form of tenofovir phosphonate, which is liberated intracellularly and converted to tenofovir disphophate. It is marketed by
1414:
1353:
Common side effects include nausea, rash, diarrhea, headache, pain, depression, and weakness. Severe side effects include
3754:
3091:
3769:
3052:
1469:
and HIV-1 protease inhibitors. Tenofovir increases didanosine concentrations and can result in adverse effects such as
4233:
3325:
3106:
2669:
2102:
2015:
1765:
1343:
1284:
760:
4724:
4122:
3779:
3663:
3047:
1730:
Tenofovir disoproxil was approved in the U.S. in 2001, for the treatment of HIV, and in 2008, for the treatment of
1704:
2388:
3789:
3774:
3437:
3425:
1417:
to ascertain the effectiveness of providing people who inject drugs illicitly with daily doses of tenofovir as a
1366:
952:
848:
408:
286:
186:
3669:
2801:
4151:
4166:
3099:
2770:
1173:
1054:
649:
510:
2696:, De Clercq E, Holy A, Rosenberg I, "Therapeutical application of phosphonylmethoxyalkyl adenines"
3874:
1812:"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"
1134:
610:
4743:
3057:
1454:
579:
2693:
2573:
1123:
4835:
4805:
4790:
2897:
2035:
1916:
1871:
1811:
164:
2712:
Deeks SG, Barditch-Crovo P, Lietman PS, Hwang F, Cundy KC, Rooney JF, et al. (September 1998).
4795:
4206:
3946:
3856:
3837:
3724:
3685:
1531:
that is quickly absorbed from the gut and cleaved to release tenofovir. Inside cells, tenofovir is
1434:
adverse effects include depression, sleep disturbances, headache, itching, rash, and fever. The US
1402:
1150:
626:
599:
4712:
4159:
4110:
3706:
2940:
1777:
1679:
1406:
1339:
242:
136:
2775:
2296:
Morlat P, Vivot A, Vandenhende MA, Dauchy FA, Asselineau J, Déti E, et al. (12 June 2013).
1656:
4327:
3784:
1636:
1372:
Tenofovir was patented in 1996 and approved for use in the United States in 2001. It is on the
883:
3892:
2005:
1841:"Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017"
1103:
559:
4810:
4800:
4659:
4608:
4464:
3981:
3794:
3674:
3544:
3143:
1784:
1625:
1566:
1499:
1474:
499:
20:
2132:"Antiretroviral pre-exposure prophylaxis (PrEP) for preventing HIV in high-risk individuals"
1783:
Gilead has created a second pro-drug form of the active drug, tenofovir diphosphate, called
1678:
bond. Tenofovir is formed when the diethyl phosphonate group is converted to its acid using
1350:. It does not cure HIV/AIDS or hepatitis B. It is available by mouth as a tablet or powder.
1338:
or other potential exposure. It is sold both by itself and together in combinations such as
1043:
978:
434:
4460:
3864:
3690:
3297:
2309:
1866:
1418:
1063:
919:
519:
3121:
8:
4589:
4552:
4304:
3799:
3658:
3530:
3448:
3247:
3126:
2990:
1746:
1629:
1543:
residue), the active compound that inhibits reverse transcriptase via chain termination.
1516:
969:
425:
249:
4500:
2313:
2156:
2131:
1177:
1154:
653:
630:
4654:
2985:
2921:
2892:
2873:
2675:
2660:
2510:
2462:
2437:
2332:
2297:
2243:
2218:
1684:
1377:
1335:
216:
2738:
2713:
4820:
3941:
3604:
2926:
2877:
2865:
2743:
2665:
2532:(8th ed.). Foster City, California: Biomedical Publications. pp. 1490–1492.
2502:
2498:
2467:
2337:
2266:
2248:
2161:
2064:"Teva Announces Exclusive Launch of a Generic version of Viread in the United States"
2011:
1986:
1942:
1731:
1700:
1668:
1570:
1511:
911:
819:
325:
313:
178:
29:
2679:
459:
4825:
3966:
2916:
2906:
2857:
2733:
2725:
2655:
2632:
2604:
2552:
2514:
2494:
2457:
2449:
2327:
2317:
2238:
2230:
2151:
2147:
2143:
2043:
1978:
1640:
1450:
1409:
combination decreased the risk of contracting HIV for high risk patients. The U.S.
1190:
1003:
875:
666:
383:
360:
269:
55:
4140:
2861:
2453:
4757:
4481:
4243:
4197:
4193:
4042:
4001:
3161:
2322:
1754:
1749:
and is sold under the brand name Viread, among others. Tenofovir disoproxil is a
1719:
1617:
1559:
1547:
1439:
1398:
1354:
898:
893:
378:
368:
37:
4769:
4718:
4270:
4185:
4116:
3122:
3067:
1788:
1712:
1664:
1644:
1507:
1446:
4181:
2893:"Post-exposure prophylaxis for SIV revisited: animal model for HIV prevention"
2636:
2234:
1982:
4779:
4636:
4435:
4215:
3882:
3632:
3467:
3353:
1532:
1435:
1166:
863:
642:
338:
4675:
4446:
4323:
4261:
4189:
3936:
3926:
3507:
3497:
3315:
3272:
3267:
3262:
3224:
3204:
3134:
2930:
2911:
2869:
2506:
2471:
2341:
2252:
2219:"Tenofovir: What We Have Learnt After 7.5 Million Person-Years of Use"
2165:
2040:
World Health
Organization model list of essential medicines: 21st list 2019
1990:
1551:
1470:
1358:
590:
264:
2747:
2729:
2181:"Preventive drug could reduce HIV transmission among injecting drug users"
2113:
1361:. There are no absolute contraindications. It is often recommended during
784:
4684:
4576:
4542:
4528:
4523:
4318:
4279:
4275:
4266:
4062:
4037:
3976:
3961:
3956:
3620:
3587:
3502:
3482:
3277:
3257:
3236:
3183:
3151:
3075:
3006:
2556:
1734:
1606:
1540:
1327:
813:
172:
2048:
1023:
479:
4689:
4646:
4566:
4515:
4505:
4476:
4440:
4424:
4414:
4373:
4358:
4293:
4067:
4047:
4032:
4027:
3991:
3986:
3900:
3845:
3815:
3627:
3615:
3610:
3582:
3522:
3512:
3487:
3472:
3462:
3411:
3406:
3394:
3378:
3368:
3348:
3310:
3220:
3208:
3200:
2396:
1648:
1478:
1466:
1226:
1034:
905:
702:
490:
390:
2608:
4680:
4631:
4581:
4571:
4561:
4472:
4429:
4419:
4394:
4348:
4333:
4257:
4182:
4077:
4057:
4052:
4022:
3951:
3931:
3820:
3577:
3492:
3477:
3400:
3373:
3363:
3358:
3305:
3282:
3195:
3021:
1660:
1652:
1362:
989:
932:
445:
158:
2891:
Emau P, Jiang Y, Agy MB, Tian B, Bekele G, Tsai CC (November 2006).
1787:. It differs from tenofovir disoproxil due to its activation in the
1674:
as base to ensure selective O-alkylation, with the formation of an
792:
16:
Antiviral drug used to treat or prevent HIV and hepatitis infections
4598:
4491:
4368:
4072:
3457:
3016:
1769:
1758:
1750:
1688:
1331:
1083:
1014:
539:
470:
200:
2970:
1776:(tenofovir disoproxil/emtricitabine/elvitegravir/cobicistat), and
1477:. Tenofovir also interacts with HIV-1 protease inhibitors such as
1249:
725:
4342:
4313:
4288:
4252:
3971:
3517:
3287:
2621:
1602:
1528:
1422:
1369:
and works by decreasing the ability of the viruses to replicate.
19:"Tenofovir" redirects here. For the newer tenofovir prodrug, see
4353:
3921:
3916:
2711:
2435:
1708:
1114:
937:
570:
2594:
1703:
at the
Institute of Organic Chemistry and Biochemistry of the
123:
85:
3231:
2763:"FDA letter of approval (regarding treatment of hepatitis B)"
1675:
1609:
1582:
1506:, while showing limited inhibition of human enzymes, such as
1240:
1094:
716:
550:
114:
4764:
2692:
2436:
Delahunty T, Bushman L, Robbins B, Fletcher CV (July 2009).
2295:
1449:
and bone loss. Presentation of nephrotoxicity can appear as
1139:
615:
3745:
Elvitegravir/cobicistat/emtricitabine/tenofovir alafenamide
3190:
3178:
1578:
1574:
1074:
530:
102:
79:
73:
64:
3750:
Elvitegravir/cobicistat/emtricitabine/tenofovir disoproxil
3215:
3130:
2034:
1819:
1503:
1445:
Long term use of tenofovir disoproxil is associated with
96:
3696:
Darunavir/cobicistat/emtricitabine/tenofovir alafenamide
2052:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
1374:
748:
C(Cn1cnc2c1ncnc2N)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C
2364:(in German). Vienna: Österreichischer Apothekerverlag.
1967:
1806:
1804:
1565:
Tenofovir is mainly excreted via the kidneys, both by
4741:
2129:
1919:. The American Society of Health-System Pharmacists.
1413:(CDC) also conducted a study in partnership with the
120:
117:
99:
90:
76:
70:
58:
2650:
Vardanyan R, Hruby V (2016). "34: Antiviral Drugs".
2484:
1667:
is reacted with a phosphonic acid derivative, using
1442:
or liver damage due to use of tenofovir disoproxil.
1401:
examined the use of tenofovir for prevention of HIV
1326:
among others, is a medication used to treat chronic
111:
108:
93:
82:
61:
2847:
2572:
2097:
2095:
2093:
2091:
2089:
1801:
105:
67:
4816:Nucleoside analog reverse transcriptase inhibitors
2545:Collection of Czechoslovak Chemical Communications
1772:(tenofovir disoproxil/emtricitabine/rilpivirine),
1535:to tenofovir diphosphate (which is analogous to a
2216:
1496:nucleotide analog reverse-transcriptase inhibitor
4777:
3702:Dolutegravir/emtricitabine/tenofovir alafenamide
2890:
2130:Okwundu CI, Uthman OA, Okoromah CA (July 2012).
2086:
1768:(tenofovir disoproxil/emtricitabine/efavirenz),
1002:
458:
3760:Emtricitabine/rilpivirine/tenofovir alafenamide
3680:Bictegravir/emtricitabine/tenofovir alafenamide
2530:Disposition of Toxic Drugs and Chemicals in Man
2003:
1539:phosphate, as tenofovir itself already has one
1348:elvitegravir/cobicistat/emtricitabine/tenofovir
977:
433:
3765:Emtricitabine/rilpivirine/tenofovir disoproxil
3251:(Integrase strand transfer inhibitors (INSTI))
2972:Microbicides for sexually transmitted diseases
2800:. Dow Jones & Company, Inc. Archived from
2649:
4831:World Health Organization essential medicines
4167:
3713:Dolutegravir/lamivudine/tenofovir alafenamide
3107:
2956:
2542:
2103:"Tenofovirdisoproxil Prescribing Information"
808:9-(2-Phosphonyl-methoxypropyly)adenine (PMPA)
3735:Efavirenz/emtricitabine/tenofovir disoproxil
3719:Dolutegravir/lamivudine/tenofovir disoproxil
2568:
2566:
2359:
1405:and found that both tenofovir alone and the
1376:. It is available in the United States as a
598:
204:
2383:
2381:
2379:
2377:
2375:
2373:
2371:
2136:The Cochrane Database of Systematic Reviews
1911:
1687:derivative and this may be purified as its
1588:
1558:is increased by 40%. It is an inhibitor of
1502:, a crucial enzyme in retroviruses such as
4174:
4160:
3730:Doravirine/lamivudine/tenofovir disoproxil
3114:
3100:
3043:International Partnership for Microbicides
3038:International Rectal Microbicide Advocates
2963:
2949:
2597:Organic Process Research & Development
1909:
1907:
1905:
1903:
1901:
1899:
1897:
1895:
1893:
1891:
1643:. Under these conditions, the reaction is
1411:Centers for Disease Control and Prevention
1367:nucleotide reverse transcriptase inhibitor
1176:
1153:
1042:
652:
629:
498:
3740:Efavirenz/lamivudine/tenofovir disoproxil
2920:
2910:
2737:
2659:
2563:
2461:
2331:
2321:
2267:"Tenofovir: MedlinePlus Drug Information"
2242:
2155:
2047:
1062:
518:
4007:Zinc finger protein transcription factor
2368:
1971:Clinical Gastroenterology and Hepatology
2819:"Drugs@FDA: FDA Approved Drug Products"
1888:
1699:Tenofovir was initially synthesized by
1498:(NtRTI). It selectively inhibits viral
1149:
1022:
818:
625:
478:
177:
4778:
2850:Expert Review of Clinical Pharmacology
2791:
2590:
2588:
2527:
2217:Ustianowski A, Arends JE (June 2015).
2178:
2028:
2024:from the original on 8 September 2017.
2010:. John Wiley & Sons. p. 505.
1845:Therapeutic Goods Administration (TGA)
1780:(tenofovir disoproxil/emtricitabine).
1489:
1167:
643:
347:
319:
4155:
3095:
2944:
2829:from the original on 10 November 2016
2813:
2811:
2718:Antimicrobial Agents and Chemotherapy
2355:
2353:
2351:
2277:from the original on 10 November 2016
2273:. U.S. National Library of Medicine.
2212:
2210:
2208:
2206:
2042:. Geneva: World Health Organization.
1923:from the original on 30 November 2016
1453:, acute kidney injury, or decline of
1392:
1122:
1102:
857:
578:
558:
332:
195:
163:
2191:from the original on 1 November 2013
416:Bis{methyl} ({oxy}methyl)phosphonate
268:
3755:Emtricitabine/tenofovir alafenamide
2794:"FDA Clears Viread for Hepatitis B"
2585:
2417:. U.S. National Library of Medicine
1949:. U.S. National Library of Medicine
1522:
1082:
993:
538:
449:
13:
3770:Emtricitabine/tenofovir disoproxil
3053:Microbicides Development Programme
2808:
2760:
2661:10.1016/B978-0-12-411492-0.00034-1
2348:
2203:
1745:Tenofovir disoproxil can be taken
1504:human immunodeficiency virus (HIV)
1428:
1415:Thailand Ministry of Public Health
1219:
695:
14:
4847:
1344:efavirenz/emtricitabine/tenofovir
295:
227:
4763:
4751:
4143:. Formerly or rarely used agent.
3780:Lamivudine/nevirapine/zidovudine
3664:Abacavir/dolutegravir/lamivudine
3048:Global Campaign for Microbicides
2499:10.2165/00003088-200645110-00005
2187:. The Conversation Media Group.
1705:Czechoslovak Academy of Sciences
1624:Adenine is first reacted with a
1616:
1365:and appears to be safe. It is a
1207:
1201:
791:
683:
677:
54:
36:
3947:Epigallocatechin gallate (EGCG)
3790:Lamivudine/tenofovir disoproxil
3775:Lamivudine/nevirapine/stavudine
2884:
2841:
2785:
2754:
2705:
2686:
2643:
2615:
2536:
2521:
2478:
2429:
2403:
2289:
2259:
2223:Infectious Diseases and Therapy
2172:
2123:
2112:. November 2012. Archived from
2004:Fischer J, Ganellin CR (2006).
1917:"Tenofovir Disoproxil Fumarate"
1484:
1460:
1383:
1297:Key:SGOIRFVFHAKUTI-ZCFIWIBFSA-N
1272:O=P(O)(O)CO(C)Cn1c2ncnc(c2nc1)N
773:Key:JFVZFKDSXNQEJW-CQSZACIVSA-N
4786:Drugs not assigned an ATC code
3670:Abacavir/lamivudine/zidovudine
2652:Synthesis of Best-Seller Drugs
2148:10.1002/14651858.CD007189.pub3
2056:
1997:
1961:
1935:
1859:
1833:
1213:
1195:
689:
671:
308:
1:
2862:10.1080/17512433.2016.1221760
2454:10.1016/j.jchromb.2009.05.029
2007:Analogue-based Drug Discovery
1794:
1740:
1651:occurring exclusively in the
1601:Tenofovir is a derivative of
1573:using the transport proteins
2771:Food and Drug Administration
2323:10.1371/journal.pone.0066223
1639:, using sodium hydroxide as
1596:
1438:cautions potential onset of
1322:, sold under the brand name
960:({oxy}methyl)phosphonic acid
7:
3545:Tenofovir alafenamide (TAF)
2792:Shwiff K (11 August 2008).
2442:Journal of Chromatography B
10:
4852:
3540:Tenofovir disoproxil (TDF)
3058:Microbicide Trials Network
2360:Haberfeld, H, ed. (2015).
2185:The Conversation Australia
1694:
1663:. In the second step, the
1527:Tenofovir disoproxil is a
1494:Tenofovir disoproxil is a
1455:glomerular filtration rate
1185:Chemical and physical data
661:Chemical and physical data
18:
4702:
4668:
4645:
4624:
4617:
4541:
4514:
4490:
4459:
4407:
4387:
4303:
4242:
4232:
4223:
4214:
4205:
4100:
4015:
3909:
3891:
3873:
3855:
3836:
3829:
3808:
3649:
3596:
3570:
3561:Discovery and development
3553:
3436:
3424:
3387:
3341:
3332:Discovery and development
3324:
3296:
3246:
3168:Discovery and development
3160:
3142:
3066:
3030:
2999:
2978:
2898:AIDS Research and Therapy
2637:10.1016/j.tet.2010.08.037
2487:Clinical Pharmacokinetics
2235:10.1007/s40121-015-0070-1
2179:Bourke E (14 June 2013).
2036:World Health Organization
1983:10.1016/j.cgh.2015.07.007
1872:European Medicines Agency
1465:Tenofovir interacts with
1330:and to prevent and treat
1305:
1280:
1260:
1238:
1225:
1189:
1184:
1165:
1133:
1113:
1093:
1073:
1053:
1033:
1013:
988:
968:
948:
943:
931:
918:
904:
892:
882:
874:
847:
842:
826:
812:
804:
799:
790:
756:
736:
714:
701:
665:
660:
641:
609:
589:
569:
549:
529:
509:
489:
469:
444:
424:
404:
399:
389:
377:
367:
359:
285:
280:
255:
241:
215:
185:
171:
153:
145:
135:
49:
44:
35:
3857:Transcription inhibitors
3809:Pharmacokinetic boosters
3725:Dolutegravir/rilpivirine
3686:Cabotegravir/rilpivirine
3326:Protease Inhibitors (PI)
1589:Detection in body fluids
4625:Nucleic acid inhibitors
4141:initial regimen options
3707:Dolutegravir/lamivudine
3184:Enfuvirtide (ENF, T-20)
3162:Entry/fusion inhibitors
2798:The Wall Street Journal
1680:trimethylsilyl chloride
1407:tenofovir/emtricitabine
1340:emtricitabine/tenofovir
910:Tenofovir diphosphate (
3982:Portmanteau inhibitors
3875:Translation inhibitors
3785:Lamivudine/raltegravir
3555:Non-nucleoside (NNRTI)
3513:Islatravir (EFdA, ISL)
2912:10.1186/1742-6405-3-29
2823:www.accessdata.fda.gov
2411:"Tenofovir disoproxil"
1637:absolute configuration
4660:Peginterferon alfa-2a
4609:Tenofovir alafenamide
3997:Synergistic enhancers
3795:Lamivudine/zidovudine
3675:Atazanavir/cobicistat
3651:Combined formulations
3488:Zidovudine (AZT, ZDV)
3426:Reverse-transcriptase
3298:Maturation inhibitors
2730:10.1128/aac.42.9.2380
2574:US patent 4808716
1785:tenofovir alafenamide
1567:glomerular filtration
1500:reverse transcriptase
21:Tenofovir alafenamide
4604:Tenofovir disoproxil
4590:Nucleotide analogues
4553:Nucleoside analogues
3838:Uncoating inhibitors
3691:Darunavir/cobicistat
3531:Nucleotide analogues
3449:Nucleoside analogues
3248:Integrase inhibitors
3127:antiretroviral drugs
2804:on 8 September 2017.
2781:on 25 February 2009.
2654:. pp. 714–716.
2557:10.1135/cccc19823447
2399:on 8 September 2015.
2110:Gilead Sciences, Inc
1761:, abbreviated TDF).
1556:area under the curve
1550:is 25%, and highest
1546:In fasting persons,
1320:Tenofovir disoproxil
206:Tenofovir disoproxil
30:Tenofovir disoproxil
4305:Pyrimidine analogue
3830:Experimental agents
3800:Lopinavir/ritonavir
3659:Abacavir/lamivudine
3633:Elsulfavirine (ESV)
3468:Emtricitabine (FTC)
3354:Fosamprenavir (FPV)
2991:Vaginal microbicide
2314:2013PLoSO...866223M
2119:on 7 February 2013.
1977:(12): 2071–87.e16.
1630:propylene carbonate
1490:Mechanism of action
787:
328:(Prescription only)
304:(Prescription only)
32:
4729:Never to phase III
4655:Interferon alfa 2b
4127:Never to phase III
3273:Elvitegravir (EVG)
3268:Dolutegravir (DTG)
3263:Cabotegravir (CAB)
2986:Rectal microbicide
2448:(20–21): 1907–14.
2074:on 6 November 2018
1685:chloromethyl ether
1419:prevention measure
1393:HIV risk reduction
1378:generic medication
1355:high blood lactate
1336:needlestick injury
783:
28:
4739:
4738:
4698:
4697:
4537:
4536:
4455:
4454:
4403:
4402:
4383:
4382:
4149:
4148:
4096:
4095:
3942:Diarylpyrimidines
3645:
3644:
3641:
3640:
3621:Rilpivirine (RPV)
3605:diarylpyrimidines
3588:Delavirdine (DLV)
3483:Zalcitabine (ddC)
3440:nucleotide (NRTI)
3420:
3419:
3278:Raltegravir (RAL)
3258:Bictegravir (BIC)
3237:Fostemsavir (FTR)
3152:Lenacapavir (LEN)
3144:Capsid inhibitors
3089:
3088:
2856:(11): 1493–1503.
2631:(41): 8137–8144.
2609:10.1021/op1001337
2551:(12): 3447–3463.
2528:Baselt R (2008).
2068:www.tevapharm.com
1876:. 5 February 2002
1571:tubular secretion
1512:mitochondrial DNA
1317:
1316:
1251:Interactive image
1135:CompTox Dashboard
912:active metabolite
861:
781:
780:
727:Interactive image
611:CompTox Dashboard
351:
336:
323:
311:
299:
231:
198:
4843:
4836:Czech inventions
4806:Isopropyl esters
4791:Carbonate esters
4768:
4767:
4756:
4755:
4754:
4747:
4669:Multiple/unknown
4622:
4621:
4618:Multiple/general
4388:Not TK activated
4240:
4239:
4230:
4229:
4221:
4220:
4212:
4211:
4176:
4169:
4162:
4153:
4152:
3967:Hydroxycarbamide
3834:
3833:
3628:Doravirine (DOR)
3616:Etravirine (ETR)
3611:Dapivirine (DPV)
3583:Nevirapine (NVP)
3568:
3567:
3473:Lamivudine (3TC)
3463:Didanosine (ddI)
3434:
3433:
3407:Tipranavir (TPV)
3395:Atazanavir (ATV)
3379:Saquinavir (SQV)
3369:Nelfinavir (NFV)
3349:Amprenavir (APV)
3339:
3338:
3221:Ibalizumab (IBA)
3116:
3109:
3102:
3093:
3092:
2965:
2958:
2951:
2942:
2941:
2935:
2934:
2924:
2914:
2888:
2882:
2881:
2845:
2839:
2838:
2836:
2834:
2815:
2806:
2805:
2789:
2783:
2782:
2780:
2774:. Archived from
2767:
2758:
2752:
2751:
2741:
2709:
2703:
2702:
2701:
2697:
2690:
2684:
2683:
2663:
2647:
2641:
2640:
2619:
2613:
2612:
2603:(5): 1194–1201.
2592:
2583:
2582:
2581:
2577:
2570:
2561:
2560:
2540:
2534:
2533:
2525:
2519:
2518:
2482:
2476:
2475:
2465:
2433:
2427:
2426:
2424:
2422:
2407:
2401:
2400:
2395:. Archived from
2385:
2366:
2365:
2357:
2346:
2345:
2335:
2325:
2293:
2287:
2286:
2284:
2282:
2263:
2257:
2256:
2246:
2214:
2201:
2200:
2198:
2196:
2176:
2170:
2169:
2159:
2127:
2121:
2120:
2118:
2107:
2099:
2084:
2083:
2081:
2079:
2070:. Archived from
2060:
2054:
2053:
2051:
2032:
2026:
2025:
2001:
1995:
1994:
1965:
1959:
1958:
1956:
1954:
1939:
1933:
1932:
1930:
1928:
1913:
1886:
1885:
1883:
1881:
1863:
1857:
1856:
1854:
1852:
1837:
1831:
1830:
1828:
1826:
1816:nctr-crs.fda.gov
1808:
1655:ring and at the
1620:
1523:Pharmacokinetics
1451:Fanconi syndrome
1313:
1312:
1253:
1233:
1221:
1215:
1209:
1203:
1197:
1180:
1169:
1158:
1157:
1143:
1141:
1126:
1106:
1086:
1066:
1046:
1026:
1006:
996:
995:
981:
923:
866:
859:
856:
822:
795:
788:
786:
782:
729:
709:
697:
691:
685:
679:
673:
656:
645:
634:
633:
619:
617:
602:
582:
562:
542:
522:
502:
482:
462:
452:
451:
437:
384:Ester hydrolysis
349:
346:
341:
334:
331:
321:
318:
310:
307:
297:
294:
272:
229:
226:
208:
197:
194:
181:
167:
130:
129:
126:
125:
122:
119:
116:
113:
110:
107:
104:
101:
98:
95:
92:
88:
87:
84:
81:
78:
75:
72:
69:
66:
63:
60:
40:
33:
31:
27:
4851:
4850:
4846:
4845:
4844:
4842:
4841:
4840:
4796:Gilead Sciences
4776:
4775:
4774:
4762:
4752:
4750:
4742:
4740:
4735:
4734:
4719:Clinical trials
4694:
4664:
4641:
4613:
4533:
4510:
4486:
4482:Podophyllotoxin
4451:
4399:
4379:
4299:
4244:Purine analogue
4225:
4201:
4180:
4150:
4145:
4144:
4132:
4117:Clinical trials
4092:
4043:Dexelvucitabine
4011:
4002:Tre recombinase
3905:
3887:
3869:
3865:Tat antagonists
3851:
3825:
3804:
3637:
3592:
3578:Efavirenz (EFV)
3557:
3549:
3478:Stavudine (d4T)
3439:
3427:
3416:
3401:Darunavir (DRV)
3383:
3374:Ritonavir (RTV)
3364:Lopinavir (LPV)
3359:Indinavir (IDV)
3328:
3320:
3292:
3250:
3242:
3196:Maraviroc (MVC)
3164:
3156:
3138:
3123:Antiviral drugs
3120:
3090:
3085:
3068:Clinical trials
3062:
3026:
2995:
2974:
2969:
2939:
2938:
2889:
2885:
2846:
2842:
2832:
2830:
2817:
2816:
2809:
2790:
2786:
2778:
2765:
2759:
2755:
2710:
2706:
2699:
2691:
2687:
2672:
2648:
2644:
2620:
2616:
2593:
2586:
2579:
2571:
2564:
2541:
2537:
2526:
2522:
2493:(11): 1115–24.
2483:
2479:
2434:
2430:
2420:
2418:
2409:
2408:
2404:
2387:
2386:
2369:
2358:
2349:
2294:
2290:
2280:
2278:
2265:
2264:
2260:
2215:
2204:
2194:
2192:
2177:
2173:
2142:(7): CD007189.
2128:
2124:
2116:
2105:
2101:
2100:
2087:
2077:
2075:
2062:
2061:
2057:
2033:
2029:
2018:
2002:
1998:
1966:
1962:
1952:
1950:
1941:
1940:
1936:
1926:
1924:
1915:
1914:
1889:
1879:
1877:
1865:
1864:
1860:
1850:
1848:
1839:
1838:
1834:
1824:
1822:
1810:
1809:
1802:
1797:
1755:Gilead Sciences
1743:
1720:Gilead Sciences
1697:
1599:
1591:
1560:cytochrome P450
1548:bioavailability
1525:
1508:DNA polymerases
1492:
1487:
1463:
1440:lactic acidosis
1431:
1429:Adverse effects
1403:before exposure
1399:Cochrane review
1395:
1386:
1308:
1306:
1301:
1298:
1293:
1288:
1287:
1276:
1273:
1268:
1267:
1256:
1231:
1218:
1212:
1206:
1200:
1161:
1137:
1129:
1109:
1089:
1069:
1049:
1029:
1009:
992:
984:
964:
961:
956:
955:
921:
899:Phosphorylation
884:Protein binding
876:Pharmacokinetic
870:
864:
838:
777:
774:
769:
764:
763:
752:
749:
744:
743:
732:
707:
694:
688:
682:
676:
637:
613:
605:
585:
565:
545:
525:
505:
485:
465:
448:
440:
420:
417:
412:
411:
369:Bioavailability
361:Pharmacokinetic
355:
339:
276:
244:
237:
218:
211:
89:
57:
53:
24:
17:
12:
11:
5:
4849:
4839:
4838:
4833:
4828:
4823:
4818:
4813:
4808:
4803:
4798:
4793:
4788:
4773:
4772:
4760:
4737:
4736:
4733:
4732:
4731:
4730:
4727:
4716:
4710:
4704:
4703:
4700:
4699:
4696:
4695:
4693:
4692:
4687:
4678:
4672:
4670:
4666:
4665:
4663:
4662:
4657:
4651:
4649:
4643:
4642:
4640:
4639:
4634:
4628:
4626:
4619:
4615:
4614:
4612:
4611:
4606:
4601:
4585:
4584:
4579:
4574:
4569:
4564:
4548:
4546:
4539:
4538:
4535:
4534:
4532:
4531:
4526:
4520:
4518:
4512:
4511:
4509:
4508:
4496:
4494:
4488:
4487:
4485:
4484:
4479:
4469:
4467:
4457:
4456:
4453:
4452:
4450:
4449:
4444:
4432:
4427:
4422:
4417:
4411:
4409:
4405:
4404:
4401:
4400:
4398:
4397:
4391:
4389:
4385:
4384:
4381:
4380:
4378:
4377:
4364:
4363:
4362:
4361:
4356:
4351:
4338:
4337:
4331:
4321:
4309:
4307:
4301:
4300:
4298:
4297:
4284:
4283:
4273:
4271:Valganciclovir
4264:
4248:
4246:
4237:
4227:
4218:
4209:
4203:
4202:
4179:
4178:
4171:
4164:
4156:
4147:
4146:
4131:
4130:
4129:
4128:
4125:
4114:
4108:
4102:
4101:
4098:
4097:
4094:
4093:
4091:
4090:
4085:
4080:
4075:
4070:
4065:
4060:
4055:
4050:
4045:
4040:
4035:
4030:
4025:
4019:
4017:
4013:
4012:
4010:
4009:
4004:
3999:
3994:
3989:
3984:
3979:
3974:
3969:
3964:
3959:
3954:
3949:
3944:
3939:
3934:
3929:
3924:
3919:
3913:
3911:
3907:
3906:
3904:
3903:
3897:
3895:
3889:
3888:
3886:
3885:
3879:
3877:
3871:
3870:
3868:
3867:
3861:
3859:
3853:
3852:
3850:
3849:
3842:
3840:
3831:
3827:
3826:
3824:
3823:
3818:
3816:Cobicistat (c)
3812:
3810:
3806:
3805:
3803:
3802:
3797:
3792:
3787:
3782:
3777:
3772:
3767:
3762:
3757:
3752:
3747:
3742:
3737:
3732:
3727:
3722:
3716:
3710:
3704:
3699:
3693:
3688:
3683:
3677:
3672:
3667:
3661:
3655:
3653:
3647:
3646:
3643:
3642:
3639:
3638:
3636:
3635:
3630:
3625:
3624:
3623:
3618:
3613:
3600:
3598:
3594:
3593:
3591:
3590:
3585:
3580:
3574:
3572:
3565:
3551:
3550:
3548:
3547:
3542:
3526:
3525:
3520:
3515:
3510:
3505:
3500:
3495:
3490:
3485:
3480:
3475:
3470:
3465:
3460:
3458:Abacavir (ABC)
3444:
3442:
3438:Nucleoside and
3431:
3422:
3421:
3418:
3417:
3415:
3414:
3409:
3404:
3398:
3391:
3389:
3385:
3384:
3382:
3381:
3376:
3371:
3366:
3361:
3356:
3351:
3345:
3343:
3336:
3322:
3321:
3319:
3318:
3313:
3308:
3302:
3300:
3294:
3293:
3291:
3290:
3285:
3280:
3275:
3270:
3265:
3260:
3254:
3252:
3244:
3243:
3241:
3240:
3228:
3212:
3198:
3187:
3174:
3172:
3158:
3157:
3155:
3154:
3148:
3146:
3140:
3139:
3119:
3118:
3111:
3104:
3096:
3087:
3086:
3084:
3083:
3078:
3072:
3070:
3064:
3063:
3061:
3060:
3055:
3050:
3045:
3040:
3034:
3032:
3028:
3027:
3025:
3024:
3019:
3014:
3009:
3003:
3001:
2997:
2996:
2994:
2993:
2988:
2982:
2980:
2976:
2975:
2968:
2967:
2960:
2953:
2945:
2937:
2936:
2883:
2840:
2807:
2784:
2753:
2704:
2685:
2670:
2642:
2614:
2584:
2562:
2535:
2520:
2477:
2428:
2402:
2367:
2347:
2288:
2258:
2202:
2171:
2122:
2085:
2055:
2027:
2016:
1996:
1960:
1934:
1887:
1858:
1847:. 21 June 2022
1832:
1799:
1798:
1796:
1793:
1789:lymphoid cells
1742:
1739:
1713:herpes simplex
1696:
1693:
1665:hydroxyl group
1659:carbon of the
1645:regioselective
1622:
1621:
1598:
1595:
1590:
1587:
1533:phosphorylated
1524:
1521:
1517:phosphodiester
1491:
1488:
1486:
1483:
1462:
1459:
1447:nephrotoxicity
1430:
1427:
1394:
1391:
1385:
1382:
1359:enlarged liver
1315:
1314:
1303:
1302:
1300:
1299:
1296:
1294:
1291:
1283:
1282:
1281:
1278:
1277:
1275:
1274:
1271:
1263:
1262:
1261:
1258:
1257:
1255:
1254:
1246:
1244:
1236:
1235:
1229:
1223:
1222:
1216:
1210:
1204:
1198:
1193:
1187:
1186:
1182:
1181:
1171:
1163:
1162:
1160:
1159:
1146:
1144:
1131:
1130:
1128:
1127:
1119:
1117:
1111:
1110:
1108:
1107:
1099:
1097:
1091:
1090:
1088:
1087:
1079:
1077:
1071:
1070:
1068:
1067:
1059:
1057:
1051:
1050:
1048:
1047:
1039:
1037:
1031:
1030:
1028:
1027:
1019:
1017:
1011:
1010:
1008:
1007:
999:
997:
986:
985:
983:
982:
974:
972:
966:
965:
963:
962:
959:
951:
950:
949:
946:
945:
941:
940:
935:
929:
928:
925:
916:
915:
908:
902:
901:
896:
890:
889:
886:
880:
879:
872:
871:
869:
868:
853:
851:
845:
844:
840:
839:
837:
836:
832:
830:
824:
823:
816:
810:
809:
806:
802:
801:
797:
796:
779:
778:
776:
775:
772:
770:
767:
759:
758:
757:
754:
753:
751:
750:
747:
739:
738:
737:
734:
733:
731:
730:
722:
720:
712:
711:
705:
699:
698:
692:
686:
680:
674:
669:
663:
662:
658:
657:
647:
639:
638:
636:
635:
622:
620:
607:
606:
604:
603:
595:
593:
587:
586:
584:
583:
575:
573:
567:
566:
564:
563:
555:
553:
547:
546:
544:
543:
535:
533:
527:
526:
524:
523:
515:
513:
507:
506:
504:
503:
495:
493:
487:
486:
484:
483:
475:
473:
467:
466:
464:
463:
455:
453:
442:
441:
439:
438:
430:
428:
422:
421:
419:
418:
415:
407:
406:
405:
402:
401:
397:
396:
393:
387:
386:
381:
375:
374:
371:
365:
364:
357:
356:
354:
353:
344:
329:
316:
305:
291:
289:
283:
282:
278:
277:
275:
274:
261:
259:
253:
252:
247:
245:administration
239:
238:
236:
235:
233:
223:
221:
213:
212:
210:
209:
191:
189:
183:
182:
175:
169:
168:
161:
151:
150:
147:
143:
142:
141:Viread, others
139:
133:
132:
51:
47:
46:
42:
41:
15:
9:
6:
4:
3:
2:
4848:
4837:
4834:
4832:
4829:
4827:
4824:
4822:
4819:
4817:
4814:
4812:
4809:
4807:
4804:
4802:
4799:
4797:
4794:
4792:
4789:
4787:
4784:
4783:
4781:
4771:
4766:
4761:
4759:
4749:
4748:
4745:
4728:
4726:
4723:
4722:
4720:
4717:
4714:
4711:
4709:
4706:
4705:
4701:
4691:
4688:
4686:
4682:
4679:
4677:
4674:
4673:
4671:
4667:
4661:
4658:
4656:
4653:
4652:
4650:
4648:
4644:
4638:
4637:Brincidofovir
4635:
4633:
4630:
4629:
4627:
4623:
4620:
4616:
4610:
4607:
4605:
4602:
4600:
4597:
4595:
4591:
4587:
4586:
4583:
4580:
4578:
4575:
4573:
4570:
4568:
4565:
4563:
4560:
4558:
4554:
4550:
4549:
4547:
4544:
4540:
4530:
4527:
4525:
4522:
4521:
4519:
4517:
4513:
4507:
4504:
4502:
4498:
4497:
4495:
4493:
4489:
4483:
4480:
4478:
4474:
4471:
4470:
4468:
4466:
4462:
4458:
4448:
4445:
4442:
4438:
4437:
4436:early protein
4433:
4431:
4428:
4426:
4423:
4421:
4418:
4416:
4413:
4412:
4410:
4406:
4396:
4393:
4392:
4390:
4386:
4375:
4371:
4370:
4366:
4365:
4360:
4357:
4355:
4352:
4350:
4347:
4346:
4345:
4344:
4340:
4339:
4335:
4332:
4329:
4325:
4322:
4320:
4316:
4315:
4311:
4310:
4308:
4306:
4302:
4295:
4291:
4290:
4286:
4285:
4281:
4277:
4274:
4272:
4268:
4265:
4263:
4259:
4255:
4254:
4250:
4249:
4247:
4245:
4241:
4238:
4235:
4231:
4228:
4224:DNA-synthesis
4222:
4219:
4217:
4213:
4210:
4208:
4204:
4199:
4195:
4191:
4187:
4184:
4177:
4172:
4170:
4165:
4163:
4158:
4157:
4154:
4142:
4139:
4136:
4126:
4124:
4121:
4120:
4118:
4115:
4112:
4109:
4107:
4104:
4103:
4099:
4089:
4086:
4084:
4081:
4079:
4076:
4074:
4071:
4069:
4066:
4064:
4061:
4059:
4056:
4054:
4051:
4049:
4046:
4044:
4041:
4039:
4036:
4034:
4031:
4029:
4026:
4024:
4021:
4020:
4018:
4016:Failed agents
4014:
4008:
4005:
4003:
4000:
3998:
3995:
3993:
3990:
3988:
3985:
3983:
3980:
3978:
3975:
3973:
3970:
3968:
3965:
3963:
3960:
3958:
3955:
3953:
3950:
3948:
3945:
3943:
3940:
3938:
3935:
3933:
3930:
3928:
3925:
3923:
3920:
3918:
3915:
3914:
3912:
3908:
3902:
3899:
3898:
3896:
3894:
3890:
3884:
3883:Trichosanthin
3881:
3880:
3878:
3876:
3872:
3866:
3863:
3862:
3860:
3858:
3854:
3847:
3844:
3843:
3841:
3839:
3835:
3832:
3828:
3822:
3821:Ritonavir (r)
3819:
3817:
3814:
3813:
3811:
3807:
3801:
3798:
3796:
3793:
3791:
3788:
3786:
3783:
3781:
3778:
3776:
3773:
3771:
3768:
3766:
3763:
3761:
3758:
3756:
3753:
3751:
3748:
3746:
3743:
3741:
3738:
3736:
3733:
3731:
3728:
3726:
3723:
3720:
3717:
3714:
3711:
3708:
3705:
3703:
3700:
3697:
3694:
3692:
3689:
3687:
3684:
3681:
3678:
3676:
3673:
3671:
3668:
3665:
3662:
3660:
3657:
3656:
3654:
3652:
3648:
3634:
3631:
3629:
3626:
3622:
3619:
3617:
3614:
3612:
3609:
3608:
3607:
3606:
3602:
3601:
3599:
3595:
3589:
3586:
3584:
3581:
3579:
3576:
3575:
3573:
3569:
3566:
3564:
3562:
3556:
3552:
3546:
3543:
3541:
3538:
3536:
3532:
3528:
3527:
3524:
3521:
3519:
3516:
3514:
3511:
3509:
3506:
3504:
3501:
3499:
3496:
3494:
3491:
3489:
3486:
3484:
3481:
3479:
3476:
3474:
3471:
3469:
3466:
3464:
3461:
3459:
3456:
3454:
3450:
3446:
3445:
3443:
3441:
3435:
3432:
3429:
3423:
3413:
3410:
3408:
3405:
3402:
3399:
3396:
3393:
3392:
3390:
3386:
3380:
3377:
3375:
3372:
3370:
3367:
3365:
3362:
3360:
3357:
3355:
3352:
3350:
3347:
3346:
3344:
3340:
3337:
3335:
3333:
3327:
3323:
3317:
3314:
3312:
3309:
3307:
3304:
3303:
3301:
3299:
3295:
3289:
3286:
3284:
3281:
3279:
3276:
3274:
3271:
3269:
3266:
3264:
3261:
3259:
3256:
3255:
3253:
3249:
3245:
3238:
3234:
3233:
3229:
3226:
3222:
3218:
3217:
3213:
3210:
3206:
3202:
3199:
3197:
3193:
3192:
3188:
3185:
3181:
3180:
3176:
3175:
3173:
3171:
3169:
3163:
3159:
3153:
3150:
3149:
3147:
3145:
3141:
3136:
3132:
3129:used against
3128:
3124:
3117:
3112:
3110:
3105:
3103:
3098:
3097:
3094:
3082:
3079:
3077:
3074:
3073:
3071:
3069:
3065:
3059:
3056:
3054:
3051:
3049:
3046:
3044:
3041:
3039:
3036:
3035:
3033:
3031:Organizations
3029:
3023:
3020:
3018:
3015:
3013:
3010:
3008:
3005:
3004:
3002:
2998:
2992:
2989:
2987:
2984:
2983:
2981:
2977:
2973:
2966:
2961:
2959:
2954:
2952:
2947:
2946:
2943:
2932:
2928:
2923:
2918:
2913:
2908:
2904:
2900:
2899:
2894:
2887:
2879:
2875:
2871:
2867:
2863:
2859:
2855:
2851:
2844:
2828:
2824:
2820:
2814:
2812:
2803:
2799:
2795:
2788:
2777:
2773:
2772:
2764:
2757:
2749:
2745:
2740:
2735:
2731:
2727:
2724:(9): 2380–4.
2723:
2719:
2715:
2708:
2695:
2689:
2681:
2677:
2673:
2671:9780124114920
2667:
2662:
2657:
2653:
2646:
2638:
2634:
2630:
2626:
2618:
2610:
2606:
2602:
2598:
2591:
2589:
2575:
2569:
2567:
2558:
2554:
2550:
2546:
2539:
2531:
2524:
2516:
2512:
2508:
2504:
2500:
2496:
2492:
2488:
2481:
2473:
2469:
2464:
2459:
2455:
2451:
2447:
2443:
2439:
2432:
2416:
2412:
2406:
2398:
2394:
2390:
2384:
2382:
2380:
2378:
2376:
2374:
2372:
2363:
2362:Austria-Codex
2356:
2354:
2352:
2343:
2339:
2334:
2329:
2324:
2319:
2315:
2311:
2308:(6): e66223.
2307:
2303:
2299:
2292:
2276:
2272:
2268:
2262:
2254:
2250:
2245:
2240:
2236:
2232:
2229:(2): 145–57.
2228:
2224:
2220:
2213:
2211:
2209:
2207:
2190:
2186:
2182:
2175:
2167:
2163:
2158:
2153:
2149:
2145:
2141:
2137:
2133:
2126:
2115:
2111:
2104:
2098:
2096:
2094:
2092:
2090:
2073:
2069:
2065:
2059:
2050:
2045:
2041:
2037:
2031:
2023:
2019:
2017:9783527607495
2013:
2009:
2008:
2000:
1992:
1988:
1984:
1980:
1976:
1972:
1964:
1948:
1944:
1938:
1922:
1918:
1912:
1910:
1908:
1906:
1904:
1902:
1900:
1898:
1896:
1894:
1892:
1875:
1873:
1868:
1867:"Viread EPAR"
1862:
1846:
1842:
1836:
1821:
1817:
1813:
1807:
1805:
1800:
1792:
1790:
1786:
1781:
1779:
1775:
1771:
1767:
1762:
1760:
1756:
1752:
1748:
1738:
1736:
1733:
1728:
1724:
1721:
1716:
1714:
1710:
1706:
1702:
1692:
1690:
1686:
1681:
1677:
1673:
1672:-butyllithium
1671:
1666:
1662:
1658:
1657:less-hindered
1654:
1650:
1646:
1642:
1638:
1635:
1631:
1627:
1619:
1615:
1614:
1613:
1611:
1608:
1604:
1594:
1586:
1584:
1580:
1576:
1572:
1568:
1563:
1561:
1557:
1553:
1549:
1544:
1542:
1538:
1534:
1530:
1520:
1518:
1513:
1509:
1505:
1501:
1497:
1482:
1480:
1476:
1472:
1468:
1458:
1456:
1452:
1448:
1443:
1441:
1437:
1436:boxed warning
1426:
1424:
1420:
1416:
1412:
1408:
1404:
1400:
1390:
1381:
1379:
1375:
1370:
1368:
1364:
1360:
1356:
1351:
1349:
1345:
1341:
1337:
1333:
1329:
1325:
1321:
1311:
1304:
1295:
1290:
1289:
1286:
1279:
1270:
1269:
1266:
1259:
1252:
1248:
1247:
1245:
1242:
1237:
1230:
1228:
1224:
1194:
1192:
1188:
1183:
1179:
1175:
1172:
1170:
1168:ECHA InfoCard
1164:
1156:
1152:
1151:DTXSID9040132
1148:
1147:
1145:
1136:
1132:
1125:
1121:
1120:
1118:
1116:
1112:
1105:
1101:
1100:
1098:
1096:
1092:
1085:
1081:
1080:
1078:
1076:
1072:
1065:
1061:
1060:
1058:
1056:
1052:
1045:
1041:
1040:
1038:
1036:
1032:
1025:
1021:
1020:
1018:
1016:
1012:
1005:
1001:
1000:
998:
991:
987:
980:
976:
975:
973:
971:
967:
958:
957:
954:
947:
942:
939:
936:
934:
930:
926:
924:
917:
913:
909:
907:
903:
900:
897:
895:
891:
887:
885:
881:
877:
873:
867:
855:
854:
852:
850:
846:
841:
834:
833:
831:
829:
825:
821:
817:
815:
811:
807:
803:
800:Clinical data
798:
794:
789:
771:
766:
765:
762:
755:
746:
745:
742:
735:
728:
724:
723:
721:
718:
713:
706:
704:
700:
670:
668:
664:
659:
655:
651:
648:
646:
644:ECHA InfoCard
640:
632:
628:
627:DTXSID9040132
624:
623:
621:
612:
608:
601:
597:
596:
594:
592:
588:
581:
577:
576:
574:
572:
568:
561:
557:
556:
554:
552:
548:
541:
537:
536:
534:
532:
528:
521:
517:
516:
514:
512:
508:
501:
497:
496:
494:
492:
488:
481:
477:
476:
474:
472:
468:
461:
457:
456:
454:
447:
443:
436:
432:
431:
429:
427:
423:
414:
413:
410:
403:
398:
394:
392:
388:
385:
382:
380:
376:
372:
370:
366:
362:
358:
352: Rx-only
345:
342:
330:
327:
317:
315:
306:
303:
293:
292:
290:
288:
284:
279:
271:
266:
263:
262:
260:
258:
254:
251:
248:
246:
240:
234:
225:
224:
222:
220:
214:
207:
202:
193:
192:
190:
188:
184:
180:
176:
174:
170:
166:
162:
160:
156:
152:
148:
144:
140:
138:
134:
128:
52:
50:Pronunciation
48:
45:Clinical data
43:
39:
34:
26:
22:
4811:Microbicides
4801:Hepatotoxins
4676:Filociclovir
4603:
4588:
4551:
4499:
4447:Tromantadine
4434:
4367:
4341:
4324:Trifluridine
4312:
4287:
4262:Valaciclovir
4251:
4137:
3937:Cyanovirin-N
3927:Calanolide A
3603:
3597:2 generation
3571:1 generation
3558:
3539:
3529:
3508:Elvucitabine
3498:Apricitabine
3447:
3388:2 generation
3342:1 generation
3329:
3316:Fipravirimat
3230:
3225:Semzuvolimab
3214:
3205:Cenicriviroc
3189:
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2886:
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2769:
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2645:
2628:
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2291:
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2270:
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2222:
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2184:
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2114:the original
2109:
2076:. Retrieved
2072:the original
2067:
2058:
2049:10665/325771
2039:
2030:
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1999:
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1970:
1963:
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1946:
1937:
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1870:
1861:
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1844:
1835:
1823:. Retrieved
1815:
1782:
1763:
1744:
1729:
1725:
1717:
1701:Antonín Holý
1698:
1669:
1633:
1623:
1600:
1592:
1564:
1552:blood plasma
1545:
1536:
1526:
1493:
1485:Pharmacology
1471:pancreatitis
1464:
1461:Interactions
1444:
1432:
1396:
1387:
1384:Medical uses
1380:as of 2017.
1371:
1352:
1323:
1319:
1318:
1307:
920:Elimination
849:Legal status
843:Legal status
591:NIAID ChemDB
287:Legal status
281:Legal status
187:License data
149:Bis(POC)PMPA
25:
4715:from market
4685:Taribavirin
4577:Telbivudine
4543:Hepatitis B
4529:Tecovirimat
4524:Methisazone
4319:Idoxuridine
4280:Famciclovir
4276:Penciclovir
4267:Ganciclovir
4216:Herpesvirus
4207:Baltimore I
4188:(primarily
4138:recommended
4113:from market
4063:Lersivirine
4038:Capravirine
3977:Miltefosine
3962:Griffithsin
3957:Fosdevirine
3503:Censavudine
3133:(primarily
3076:CAPRISA 004
3007:Nonoxynol-9
2625:Tetrahedron
2389:"Tenofovir"
1927:29 November
1735:hepatitis B
1628:version of
1607:phosphonate
1541:phosphonate
1389:and older.
1328:hepatitis B
1234: g·mol
1174:100.129.993
1104:CHEBI:63625
979:147127-20-6
944:Identifiers
906:Metabolites
814:MedlinePlus
805:Other names
710: g·mol
650:100.129.993
560:CHEBI:63717
435:201341-05-1
400:Identifiers
391:Metabolites
173:MedlinePlus
146:Other names
137:Trade names
4780:Categories
4690:Moroxydine
4647:Interferon
4567:Lamivudine
4516:Poxviridae
4506:Rifampicin
4477:Resiquimod
4441:Fomivirsen
4425:Letermovir
4415:Amenamevir
4374:Cytarabine
4359:Sorivudine
4328:+tipiracil
4294:Vidarabine
4186:antivirals
4068:Lodenosine
4048:Droxinavir
4033:Brecanavir
4028:Atevirdine
3992:Seliciclib
3987:Scytovirin
3901:Elipovimab
3846:TRIM5alpha
3523:Stampidine
3428:inhibitors
3412:TMC-310911
3311:BMS-955176
3209:Leronlimab
3201:Vicriviroc
2833:9 November
2761:Shwiff K.
2694:US 4724233
2281:9 November
2078:6 November
1953:6 February
1943:"Stribild"
1825:22 October
1795:References
1741:Drug forms
1649:alkylation
1510:α, β, and
1479:atazanavir
1475:neuropathy
1467:didanosine
1239:3D model (
1227:Molar mass
1064:99YXE507IL
1035:ChemSpider
970:CAS Number
953:IUPAC name
894:Metabolism
715:3D model (
703:Molar mass
580:ChEMBL1538
520:F4YU4LON7I
491:ChemSpider
426:CAS Number
409:IUPAC name
379:Metabolism
4725:Phase III
4713:Withdrawn
4681:Ribavirin
4632:Cidofovir
4582:Clevudine
4572:Lobucavir
4562:Entecavir
4473:Imiquimod
4430:Maribavir
4420:Docosanol
4395:Foscarnet
4349:Brivudine
4334:Edoxudine
4258:Aciclovir
4236:activated
4226:inhibitor
4183:DNA virus
4123:Phase III
4111:Withdrawn
4088:Telinavir
4083:Palinavir
4078:Mozenavir
4058:Emivirine
4053:Lasinavir
4023:Aplaviroc
3952:Foscarnet
3932:Ceragenin
3493:Amdoxovir
3306:Bevirimat
3283:BI 224436
3022:BufferGel
3012:Tenofovir
2878:205930751
1661:dioxolane
1653:imidazole
1597:Chemistry
1363:pregnancy
1124:ChEMBL483
933:Excretion
922:half-life
785:Tenofovir
395:Tenofovir
243:Routes of
217:Pregnancy
165:Monograph
159:Drugs.com
4821:Prodrugs
4758:Medicine
4599:Adefovir
4501:assembly
4492:Vaccinia
4369:cytosine
4073:Loviride
3017:PRO 2000
3000:Products
2931:17132170
2870:27498720
2827:Archived
2680:75449475
2507:17048975
2472:19493710
2421:17 April
2393:DrugBank
2342:23776637
2302:PLOS ONE
2275:Archived
2271:MedlineP
2253:26032649
2189:Archived
2166:22786505
2157:11324012
2038:(2019).
2022:Archived
1991:26188135
1921:Archived
1851:30 March
1774:Stribild
1770:Complera
1759:fumarate
1757:(as the
1751:pro-drug
1747:by mouth
1689:fumarate
1332:HIV/AIDS
1310:(verify)
1015:DrugBank
927:17 hours
828:ATC code
471:DrugBank
257:ATC code
250:By mouth
232: B3
219:category
201:DailyMed
4826:Purines
4770:Viruses
4744:Portals
4343:thymine
4314:uridine
4289:adenine
4253:guanine
4192:, also
3972:KP-1461
3518:Racivir
3288:MK-2048
2922:1687192
2748:9736567
2515:6322957
2463:2714254
2415:Pubchem
2333:3680439
2310:Bibcode
2244:4471058
2195:17 June
1947:PubChem
1778:Truvada
1766:Atripla
1732:chronic
1715:virus.
1695:History
1647:, with
1603:adenine
1569:and by
1529:prodrug
1423:placebo
1357:and an
1232:287.216
1191:Formula
1024:DB14126
990:PubChem
888:< 1%
865:WARNING
820:a602018
708:519.448
667:Formula
500:4587262
480:DB00300
460:5481350
446:PubChem
343:Rx-only
340:WARNING
312::
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267: (
265:J05AF07
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179:a602018
4708:WHO-EM
4594:NtRTIs
4557:NARTIs
4354:FV-100
4106:WHO-EM
3922:BIT225
3917:Abzyme
3848:(gene)
3535:NtRTIs
3430:(RTIs)
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1709:Prague
1691:salt.
1626:chiral
1346:, and
1324:Viread
1265:SMILES
1115:ChEMBL
1084:D06074
1044:408154
1004:464205
938:Kidney
862:
741:SMILES
600:080741
571:ChEMBL
540:C13480
337:
324:
314:℞-only
300:
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4545:(VII)
4408:Other
4198:D06BB
4194:S01AD
3910:Other
3893:BNAbs
3453:NRTIs
3232:gp120
3081:VOICE
2979:Types
2874:S2CID
2779:(PDF)
2766:(PDF)
2676:S2CID
2511:S2CID
2117:(PDF)
2106:(PDF)
1874:(EMA)
1676:ether
1632:with
1610:ester
1583:ABCC4
1562:1A2.
1285:InChI
1241:JSmol
1095:ChEBI
761:InChI
717:JSmol
551:ChEBI
4196:and
4135:DHHS
3191:CCR5
3179:gp41
2927:PMID
2866:PMID
2835:2016
2744:PMID
2666:ISBN
2503:PMID
2468:PMID
2423:2018
2338:PMID
2283:2016
2249:PMID
2197:2013
2162:PMID
2080:2018
2012:ISBN
1987:PMID
1955:2022
1929:2016
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1055:UNII
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531:KEGG
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155:AHFS
4461:HPV
4190:J05
3216:CD4
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3131:HIV
2917:PMC
2907:doi
2858:doi
2734:PMC
2726:doi
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2458:PMC
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2318:doi
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2144:doi
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1979:doi
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