Genvoya

Tenofovir alafenamide

Clinical data
Trade names	Vemlidy Genvoya (with elvitegravir, cobicistat and emtricitabine) Odefsey (with emtricitabine and rilpivirine) Descovy (with emtricitabine)
Routes of administration	Oral (tablets)
ATC code	J05AF13 (WHO) Combination codes: J05AR17 (WHO) J05AR18 (WHO) J05AR19 (WHO)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Protein binding	~80%
Biological half-life	0.51 hours
Excretion	Feces (31.7%), urine (<1%)
Identifiers
IUPAC name Isopropyl (2S)-2-[[[(1R)-2-(6-aminopurin-9-yl)-1-methyl-ethoxy]methyl-phenoxy-phosphoryl]amino]propanoate
Synonyms	GS-7340
CAS Number	379270-37-8
PubChem CID	9574768
DrugBank	DB09299
ChemSpider	7849225
UNII	EL9943AG5J
KEGG	D10428
ChEBI	CHEBI:90926 Y
ChEMBL	CHEMBL2107825
Chemical and physical data
Formula	C21H29N6O5P
Molar mass	476.466 g/mol
3D model (Jmol)	Interactive image
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
InChI InChI=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 Key:LDEKQSIMHVQZJK-CAQYMETFSA-N

Tenofovir alafenamide (INN/USAN; trade name Vemlidy) is a nucleotide reverse transcriptase inhibitor and a prodrug of tenofovir. It was developed by Gilead Sciences for use in the treatment of HIV infection and chronic hepatitis B, 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. Gilead was awarded FDA approval in November 2016 for the drug Vemlidy.

Gilead announced a phase 3 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 (trade name Stribild) to elvitegravir/cobicistat/emtricitabine/tenofovir alafenamide (trade name Genvoya), the results showed the newer drug to be noninferior 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.