Tenofovir alafenamide

Names

[ Name ]:
Tenofovir alafenamide

[Synonym ]:
Isopropyl N-[(S)-({[(2R)-1-(6-amino-9H-purin-9-yl)-2-propanyl]oxy}methyl)(phenoxy)phosphoryl]-L-alaninate
GS7340
Sp-Tenofovir-phosphonamidate,phenyl,L-alanine isopropyl ester
L-Alanine, N-[(S)-[(1S)-[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]phenoxyphosphinyl]-, 1-methylethyl ester
Tenofovir alafenamide
GS-7340

Biological Activity

[Description]:

Tenofovir alafenamide (GS-7340) is an investigational oral prodrug of Tenofovir. Tenofovir is a HIV-1 nucleotide reverse transcriptase inhibitor.

[Related Catalog]:

Signaling Pathways >> Anti-infection >> HIV

Signaling Pathways >> Anti-infection >> Reverse Transcriptase

Research Areas >> Infection

[Target]

HIV-1, NRTIs[1]

[In Vitro]

Tenofovir alafenamide antiviral activities are similar across all cell types, ranging from 5 to 7 nM, while the CC50 varies from 4.7 to 42 μM for MT-4 and MT-2 cells, respectively. The antiviral activity of TAF is evaluated against a panel of HIV-1 and HIV-2 isolates, including HIV-1 group M subtypes A to G, as well as group N and O isolates. Overall, for the 29 primary HIV-1 isolates tested in PBMCs, TAF EC50s range from 0.1 to 12 nM, with a mean EC50 of 3.5 nM compared to a mean EC50 of 11.8 nM for AZT, which is used as an internal control. For the HIV-2 isolates, the mean EC50s are 1.8 nM for TAF and 6.4 nM for AZT[2].

[In Vivo]

Tenofovir alafenamide hemifumarate is an amidate prodrug of Tenofovir with good oral bioavailability and increases plasma stability compared to Tenofovir disoproxil fumarate (TDF)[1].

[References]

[1]. Babusis D, et al. Mechanism for effective lymphoid cell and tissue loading following oral administration of nucleotide prodrug GS-7340. Mol Pharm. 2013 Feb 4;10(2):459-66.

[2]. Ruane PJ, et al. Antiviral activity, safety, and pharmacokinetics/pharmacodynamics of tenofovir alafenamide as 10-day monotherapy in HIV-1-positive adults. J Acquir Immune Defic Syndr. 2013 Aug 1;63(4):449-55.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.39±0.1 g/cm3

[ Boiling Point ]:
640.4±65.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₁H₂₉N₆O₅P

[ Molecular Weight ]:
476.466

[ Flash Point ]:
341.1±34.3 °C

[ Exact Mass ]:
476.193695

[ PSA ]:
153.29000

[ LogP ]:
2.20

[ Vapour Pressure ]:
0.0±1.9 mmHg at 25°C

[ Index of Refraction ]:
1.630

[ Water Solubility ]:
Practically insoluble (0.04 g/L) (25 ºC)

Safety Information

[ Hazard Codes ]:
Xi

Tenofovir alafenamide

Names

Biological Activity

Chemical & Physical Properties

Safety Information

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds