Tenofovir alafenamide

Tenofovir alafenamide
Clinical data
Pronunciation	/ˌtəˈnoʊfəvɪər ˌæləˈfɛnəmaɪd/
Trade names	Vemlidy
Other names	GS-7340
AHFS/Drugs.com	Monograph
License data	US DailyMed: Tenofovir alafenamide;
Pregnancy; category	AU: B3;
Routes of; administration	By mouth
ATC code	J05AF13 (WHO) Combination codes: J05AR17 (WHO) J05AR18 (WHO) J05AR19 (WHO) J05AR20 (WHO) J05AR22 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only; UK: POM (Prescription only); US: ℞-only; EU: Rx-only; In general: ℞ (Prescription only);
Pharmacokinetic data
Protein binding	~80%
Elimination half-life	0.51 hour
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;
CAS Number	379270-37-8;
PubChem CID	9574768;
DrugBank	DB09299;
ChemSpider	7849225;
UNII	EL9943AG5J;
KEGG	D10428;
ChEBI	CHEBI:90926;
ChEMBL	ChEMBL2107825;
CompTox Dashboard (EPA)	DTXSID50958941 ;
Chemical and physical data
Formula	C21H29N6O5P
Molar mass	476.474 g·mol−1
3D model (JSmol)	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, 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 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.