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Tenofovir alafenamide

Chemical compound

Tenofovir alafenamide
Summary

Chemical compound

FieldValue
imageTenofovir alafenamide structure.svg
image_classskin-invert-image
width250
pronounce
tradenameVemlidy, Tavin AF
Drugs.com
DailyMedIDTenofovir alafenamide
pregnancy_AUB3
pregnancy_AU_comment
routes_of_administrationBy mouth
ATC_prefixJ05
ATC_suffixAF13
ATC_supplementalCombination codes:
legal_AUS4
legal_AU_comment
legal_BR
legal_CARx-only
legal_CA_comment
legal_DE
legal_NZ
legal_UKPOM
legal_UK_comment
legal_USRx-only
legal_US_comment
legal_EURx-only
legal_EU_comment
legal_UN
legal_statusRx-only
protein_bound~80%
elimination_half-life0.51 hour
excretionFeces (31.7%), urine (
CAS_number379270-37-8
PubChem9574768
DrugBankDB09299
ChemSpiderID7849225
UNIIEL9943AG5J
KEGGD10428
ChEBI90926
ChEMBL2107825
synonymsGS-7340
IUPAC_nameIsopropyl (2S)-2-[[[(1R)-2-(6-aminopurin-9-yl)-1-methyl-ethoxy]methyl-phenoxy-phosphoryl]amino]propanoate
C21H=29N=6O=5P=1
SMILESCC@HOCP@@(NC@@HC(=O)OC(C)C)OC3=CC=CC=C3
StdInChI1S/C21H29N6O5P/c1-14(2)31-21(28)16(4)26-33(29,32-17-8-6-5-7-9-17)13-30-15(3)10-27-12-25-18-19(22)23-11-24-20(18)27/h5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24)/t15-,16+,33+/m1/s1
StdInChIKeyLDEKQSIMHVQZJK-CAQYMETFSA-N

| Drugs.com =

| elimination_half-life = 0.51 hour

Tenofovir alafenamide [[fumarate]], the salt used in drug formulations

Tenofovir alafenamide, sold under the brand name Vemlidy,Tavin AF is an antiviral medication used against hepatitis B and HIV. It is used for the treatment of chronic hepatitis B virus (HBV) infection in adults with compensated liver disease and is given in combination with other medications for the prevention and treatment of HIV. It is taken by mouth.

Tenofovir alafenamide is a nucleotide reverse transcriptase inhibitor and is a prodrug of tenofovir. It was developed by Gilead Sciences based on the protide technology of Chris McGuigan and is applied in the form of tenofovir alafenamide fumarate (TAF). Closely related to the commonly used reverse-transcriptase inhibitor tenofovir disoproxil fumarate (TDF), TAF has greater antiviral activity and better distribution into lymphoid tissues than that agent. It was approved for use in the US for HIV in 2015, and for hepatitis B in 2016. Although the US Food and Drug Administration (FDA) has approved tenofovir alafenamide for manufacture as a generic medication, it is not available.

A generic combination of Emtricitabine/tenofovir alafenamide (Viatris) received marketing authorization in the European Union in July 2025.

Fixed-dose combinations containing tenofovir alafenamide

combinations

  • Elvitegravir/cobicistat/emtricitabine/tenofovir alafenamide (Genvoya) — approved both in the United States and in the European Union in November 2015, (compare elvitegravir/cobicistat/emtricitabine/tenofovir; (Stribild))
  • Emtricitabine/rilpivirine/tenofovir alafenamide (Odefsey) — approved in the United States in March 2016, and in the European Union in June 2016, (compare Emtricitabine/rilpivirine/tenofovir; (Complera))
  • Emtricitabine/tenofovir alafenamide (Descovy) — approved in the European Union and the United States in April 2016 (compare emtricitabine/tenofovir; (Truvada)). In October 2019, Descovy was approved in the United States for HIV-1 pre-exposure prophylaxis (PrEP).
  • Bictegravir/emtricitabine/tenofovir alafenamide (Biktarvy) — approved in the United States in February 2018.
  • Darunavir/cobicistat/emtricitabine/tenofovir alafenamide (Symtuza) — approved in the European Union in September 2017, in the United States in July 2018, and in Australia in November 2019.
  • Dolutegravir/emtricitabine/tenofovir alafenamide.
  • Dolutegravir/lamivudine/tenofovir alafenamide.

Research

Gilead announced a Phase III clinical trial evaluating a single-tablet regimen combining tenofovir alafenamide with cobicistat, emtricitabine and elvitegravir and developed a coformulation of the drug with cobicistat, emtricitabine and the protease inhibitor darunavir. In a 48-week study comparing elvitegravir/cobicistat/emtricitabine/tenofovir disoproxil (Stribild) to elvitegravir/cobicistat/emtricitabine/tenofovir alafenamide (Genvoya), the results showed the newer drug's effects to be non-inferior to the established agent, but at much lower dosages and with lower incidence of adverse side effects such as impaired kidney function. The FDA approved the TAF-based treatment regimen for treatment of HIV-1 in November 2015. Genvoya is the first TAF-based regimen to receive approval.

References

References

  1. (26 December 2018). "Tenofovir alafenamide (Vemlidy) Use During Pregnancy".
  2. (21 June 2022). "Prescription medicines: registration of new chemical entities in Australia, 2016".
  3. (20 August 2020). "Product Monograph: Vemlidy (tenofovir alafenamide) tablets". Government of Canada: The Drug and Health Product Register.
  4. (9 May 2018). "Liver disease".
  5. (8 September 2020). "Vemlidy 25 mg film coated tablets - Summary of Product Characteristics (SmPC)".
  6. (17 September 2018). "Vemlidy EPAR".
  7. (11 February 2020). "Vemlidy- tenofovir alafenamide tablet". U.S. National Library of Medicine.
  8. (October 2018). "Tenofovir Alafenamide for the Treatment of Chronic Hepatitis B Monoinfection". Pharmacotherapy.
  9. (2001). "Metabolism of GS-7340, a novel phenyl monophosphoramidate intracellular prodrug of PMPA, in blood". Nucleosides Nucleotides Nucleic Acids.
  10. (March 2011). "GS-7340 demonstrates greater declines in HIV-1 RNA than tenofovir disoproxil fumarate during 14 days of monotherapy in HIV-1 infected subjects.".
  11. (21 November 2016). "FDA Approves Vemlidy (tenofovir alafenamide) for Chronic Hepatitis B in Adults".
  12. (30 May 2023). "First Generic Drug Approvals 2023".
  13. (12 September 2022). "Gilead settles 5 more Descovy patent feuds, pushing copycats to its PrEP successor out to 2031".
  14. (2025-05-23). "Emtricitabine / Tenofovir alafenamide Viatris {{!}} European Medicines Agency (EMA)".
  15. (11 February 2019). "Genvoya- elvitegravir, cobicistat, emtricitabine, and tenofovir alafenamide tablet". U.S. National Library of Medicine.
  16. (8 December 2015). "Genvoya (elvitegravir, cobicistat, emtricitabine, and tenofovir alafenamide) fixed-dose combination tablet".
  17. (6 August 2012). "Summary Review: Genvoya". US [[Food and Drug Administration]].
  18. (17 September 2018). "Genvoya EPAR".
  19. (4 May 2016). "Health Canada New Drug Authorizations: 2015 Highlights".
  20. (10 October 2012). "Drug Approval Package: Stribild (elvitegravir, cobicistat, emtricitabine, tenofovir disoproxil fumarate) Fixed Dose".
  21. (19 October 2015). "Summary Review: Stribild". US [[Food and Drug Administration]].
  22. (28 January 2019). "Stribild- elvitegravir, cobicistat, emtricitabine, and tenofovir disoproxil fumarate tablet, film coated". U.S. National Library of Medicine.
  23. (17 September 2018). "Stribild EPAR".
  24. (6 December 2019). "Odefsey- emtricitabine, rilpivirine hydrochloride, and tenofovir alafenamide tablet". U.S. National Library of Medicine.
  25. (29 November 2016). "Odefsey (emtricitabine, rilpivirine, and tenofovir alafenamide) Tablets".
  26. (17 September 2018). "Odefsey EPAR".
  27. (9 May 2018). "Immune system health".
  28. (6 September 2012). "Drug Approval Package: (emtricitabine/rilpivirine/tenofovir disoproxil fumarate) NDA #202123".
  29. (19 July 2011). "Summary Review: Complera". US [[Food and Drug Administration]].
  30. (9 December 2019). "Complera- emtricitabine, rilpivirine hydrochloride, and tenofovir disoproxil fumarate tablet, film coated". U.S. National Library of Medicine.
  31. (13 January 2020). "Descovy- emtricitabine and tenofovir alafenamide tablet". U.S. National Library of Medicine.
  32. (28 May 2018). "Descovy EPAR".
  33. (3 October 2019). "FDA approves second drug to prevent HIV infection as part of ongoing efforts to end the HIV epidemic".
  34. (4 October 2019). "F.D.A. Approves New H.I.V.-Prevention Drug, but Not for Everyone".
  35. (8 August 2019). "Biktarvy- bictegravir sodium, emtricitabine, and tenofovir alafenamide fumarate tablet". U.S. National Library of Medicine.
  36. (6 March 2020). "Symtuza- darunavir, cobicistat, emtricitabine, and tenofovir alafenamide tablet, film coated". U.S. National Library of Medicine.
  37. (11 December 2018). "Drug Approval Package: Symtuza (darunavir, cobicistat, emtricitabine, and tenofovir alafenamide)".
  38. (17 September 2018). "Symtuza EPAR".
  39. "TGA eBS - Product and Consumer Medicine Information Licence".
  40. (15 July 2021). "Symtuza 800/150/200/10 Tablets".
  41. (14 October 2020). "Drug and medical device highlights 2018: Helping you maintain and improve your health".
  42. "Drugs@FDA: FDA-Approved Drugs".
  43. "Drugs@FDA: FDA-Approved Drugs".
  44. (30 March 2022). "Tentative Approval: Dolutegravir, Lamivudine, and Tenofovir Alafenamide Tablets". US [[Food and Drug Administration]].
  45. (24 January 2013). "Gilead Initiates Phase 3 Clinical Program for Tenofovir Alafenamide, a Novel Low-Dose Prodrug for the Treatment of HIV". Gilead.
  46. (15 November 2011). "Gilead Sciences Finalizes Agreement with Tibotec Pharmaceuticals to Develop and Commercialize a Single-Tablet Regimen of Prezista with Emtriva, GS 7340 and Cobicistat".
  47. (15 March 2012). "GS-7340 Packs Greater HIV Punch, Potentially Better Safety, Versus Viread". AIDSmeds.com.
  48. (April 2012). "Pharmacokinetics of a Novel EVG/COBI/FTC/GS-7340 Single Tablet Regimen". 13th International Workshop on Clinical Pharmacology of HIV Therapy..
  49. (1 November 2012). "Once-Daily Tenofovir Prodrug Combo Pill as Effective as Stribild".
  50. Highleyman, Liz. (6 March 2013). "CROI 2013: New Pro-drug Tenofovir Alafenamide Appears Equally Effective but Better Tolerated".
  51. (13 June 2013). "Tenefovir Alafenamide Fumarate (TAF) Sign-On Letter to Gilead". Treatment Action Group.
  52. (5 November 2015). "U.S. Food and Drug Administration Approves Gilead's Single Tablet Regimen Genvoya (Elvitegravir, Cobicistat, Emtricitabine and Tenofovir Alafenamide) for Treatment of HIV-1 Infection". Gilead.
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carboxylate-esters fixed-dose-combination-(antiretroviral) gilead-sciences isopropyl-esters nucleoside-analog-reverse-transcriptase-inhibitors organophosphates phenol-esters pre-exposure-prophylaxis
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