Tenofovir alafenamide explained

Width:250
Tradename:Vemlidy
Dailymedid:Tenofovir alafenamide
Pregnancy Au:B3
Pregnancy Au Comment:[1]
Routes Of Administration:By mouth
Atc Prefix:J05
Atc Suffix:AF13
Atc Supplemental:Combination codes:
Legal Au:S4
Legal Au Comment:[2]
Legal Ca:Rx-only
Legal Ca Comment:[3] [4]
Legal Uk:POM
Legal Uk Comment:[5]
Legal Us:Rx-only
Legal Eu:Rx-only
Legal Eu Comment:[6]
Legal Status:Rx-only
Protein Bound:~80%[7]
Elimination Half-Life:0.51 hour
Excretion:Feces (31.7%), urine (<1%)
Cas Number:379270-37-8
Pubchem:9574768
Drugbank:DB09299
Chemspiderid:7849225
Unii:EL9943AG5J
Kegg:D10428
Chebi:90926
Chembl:2107825
Synonyms:GS-7340
Iupac Name:Isopropyl (2S)-2-(1R)-2-(6-aminopurin-9-yl)-1-methyl-ethoxymethyl-phenoxy-phosphoryl]amino]propanoate| C=21 | H=29 | N=6 | O=5 | P=1| SMILES = C[C@H](CN1C=NC2=C(N=CN=C21)N)OC[P@@](=O)(N[C@@H](C)C(=O)OC(C)C)OC3=CC=CC=C3| StdInChI=1S/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| StdInChI_comment = | StdInChIKey = LDEKQSIMHVQZJK-CAQYMETFSA-N| density = | density_notes = | melting_point = | melting_high = | melting_notes = | boiling_point = | boiling_notes = | solubility = | sol_units = | specific_rotation = }}

Tenofovir alafenamide, sold under the brand name Vemlidy, 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[8] 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.[9] [10] It was approved for use in the US for HIV in 2015, and for hepatitis B in 2016.[11] Although the US Food and Drug Administration (FDA) has approved tenofovir alafenamide for manufacture as a generic medication,[12] it is not available.[13]

Fixed-dose combinations containing tenofovir alafenamide

Research

Gilead announced a Phase III clinical trial evaluating a single-tablet regimen combining tenofovir alafenamide with cobicistat, emtricitabine and elvitegravir[43] and developed a coformulation of the drug with cobicistat, emtricitabine and the protease inhibitor darunavir.[44] [45] [46] 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.[47] [48] [49] The FDA approved the TAF-based treatment regimen for treatment of HIV-1 in November 2015.[50] Genvoya is the first TAF-based regimen to receive approval.

References

Notes and References

  1. Web site: Tenofovir alafenamide (Vemlidy) Use During Pregnancy . Drugs.com . 26 December 2018 . 18 April 2020 . 9 July 2021 . https://web.archive.org/web/20210709181854/https://www.drugs.com/pregnancy/tenofovir-alafenamide.html . live .
  2. Web site: Prescription medicines: registration of new chemical entities in Australia, 2016 . Therapeutic Goods Administration (TGA) . 21 June 2022 . 10 April 2023.
  3. Web site: Product Monograph: Vemlidy (tenofovir alafenamide) tablets. 20 August 2020. Government of Canada: The Drug and Health Product Register. 7 June 2022. 10 June 2022. https://web.archive.org/web/20220610030032/https://pdf.hres.ca/dpd_pm/00058101.PDF. live.
  4. Web site: Liver disease . . 9 May 2018 . 13 April 2024.
  5. Web site: Vemlidy 25 mg film coated tablets - Summary of Product Characteristics (SmPC) . (emc) . 8 September 2020 . 12 November 2020 . 11 July 2021 . https://web.archive.org/web/20210711140434/https://www.medicines.org.uk/emc/product/2314 . live .
  6. Web site: Vemlidy EPAR . European Medicines Agency (EMA) . 17 September 2018 . 12 November 2020 . 13 July 2021 . https://web.archive.org/web/20210713062603/https://www.ema.europa.eu/en/medicines/human/EPAR/vemlidy . live .
  7. Web site: Vemlidy- tenofovir alafenamide tablet . DailyMed . U.S. National Library of Medicine. 11 February 2020 . 18 April 2020 . 9 July 2021 . https://web.archive.org/web/20210709181655/https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=72e6b33c-0351-4070-9172-eeaa186c01d2 . live .
  8. Childs-Kean LM, Egelund EF, Jourjy J . Tenofovir Alafenamide for the Treatment of Chronic Hepatitis B Monoinfection . Pharmacotherapy . 38 . 10 . 1051–1057 . October 2018 . 30120841 . 10.1002/phar.2174 . 52033420 .
  9. Eisenberg EJ, He GX, Lee WA . Metabolism of GS-7340, a novel phenyl monophosphoramidate intracellular prodrug of PMPA, in blood . Nucleosides Nucleotides Nucleic Acids . 20 . 4–7 . 1091–8 . 2001 . 11562963 . 10.1081/NCN-100002496 . 24652157 .
  10. Markowitz M, Zolopa A, Ruane P, Squires K, Zhong L, Kearney BP, Lee W . GS-7340 demonstrates greater declines in HIV-1 RNA than tenofovir disoproxil fumarate during 14 days of monotherapy in HIV-1 infected subjects. . 18th Conference on Retroviruses and Opportunistic Infections . March 2011. https://web.archive.org/web/20120425231312/http://hivandhepatitis.com/2011_conference/croi2011/posters/diamond.pdf . 25 April 2012 .
  11. Web site: FDA Approves Vemlidy (tenofovir alafenamide) for Chronic Hepatitis B in Adults . . 21 November 2016 . https://web.archive.org/web/20191011163514/https://www.hhs.gov/hepatitis/blog/2016/11/21/fda-approves-vemlidy-tenofovir-alafenamide-for-chronic-hepatitis-b-in-adults.html . 11 October 2019 . live . 11 October 2019.
  12. Web site: First Generic Drug Approvals 2023 . U.S. Food and Drug Administration (FDA) . 30 May 2023 . https://web.archive.org/web/20230630003621/https://www.fda.gov/drugs/drug-and-biologic-approval-and-ind-activity-reports/first-generic-drug-approvals . 30 June 2023 . live . 30 June 2023.
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  15. Web site: Genvoya (elvitegravir, cobicistat, emtricitabine, and tenofovir alafenamide) fixed-dose combination tablet . U.S. Food and Drug Administration (FDA) . 8 December 2015 . 28 July 2020 . 29 July 2020 . https://web.archive.org/web/20200729061124/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/207561Orig1s000TOC.cfm . live .
  16. Web site: Summary Review: Genvoya. US Food and Drug Administration. 6 August 2012. 29 July 2020. 29 July 2020. https://web.archive.org/web/20200729060109/https://www.accessdata.fda.gov/drugsatfda_docs/nda/2015/207561Orig1s000SumR.pdf. live.
  17. Web site: Genvoya EPAR . European Medicines Agency (EMA) . 17 September 2018 . 28 July 2020 . 8 August 2020 . https://web.archive.org/web/20200808060505/https://www.ema.europa.eu/en/medicines/human/EPAR/genvoya . live .
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  49. Web site: Horn T . Tenefovir Alafenamide Fumarate (TAF) Sign-On Letter to Gilead . https://web.archive.org/web/20191119064020/http://www.treatmentactiongroup.org/hiv/taf-letter . 19 November 2019 . 13 June 2013 . Treatment Action Group .
  50. 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. 5 November 2015. Gilead. https://web.archive.org/web/20151108232941/http://www.gilead.com/news/press-releases/2015/11/us-food-and-drug-administration-approves-gileads-single-tablet-regimen-genvoya-elvitegravir-cobicistat-emtricitabine-and-tenofovir-alafenamide-for-treatment-of-hiv1-infection. 8 November 2015. dead.

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