Tenofovir alafenamide

Modify Date: 2024-01-02 11:19:21

Tenofovir alafenamide Structure
Tenofovir alafenamide structure
 Common Name Tenofovir alafenamide
CAS Number 379270-37-8 Molecular Weight 476.466
Density 1.39±0.1 g/cm3 Boiling Point 640.4±65.0 °C at 760 mmHg
Molecular Formula C21H29N6O5P Melting Point N/A
MSDS N/A Flash Point 341.1±34.3 °C

 Use of Tenofovir alafenamide


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

 Names

Name propan-2-yl (2S)-2-[[[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-phenoxyphosphoryl]amino]propanoate
Synonym More Synonyms

 Tenofovir alafenamide 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
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.

 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

 Synthetic Route

H-Ala-OiPr structure

H-Ala-OiPr

CAS#:39825-33-7
[[(1R)-2-(6-aMino-9H-purin-9-yl)-1-Methylethoxy]Methyl]-, Monophenylester structure

[[(1R)-2-(6-aMi...

CAS#:379270-35-6

~%

Tenofovir alafenamide Structure

Tenofovir alafe...

CAS#:379270-37-8

Tenofovir alafenamide structure

Tenofovir alafe...

CAS#:383365-04-6
Literature: Chapman; Kernan; Prisbe; Rohloff; Sparacino; Terhorst; Yu Nucleosides, Nucleotides and Nucleic Acids, 2001 , vol. 20, # 4-7 p. 621 - 628
Tenofovir structure

Tenofovir

CAS#:147127-20-6

~%

Tenofovir alafenamide Structure

Tenofovir alafe...

CAS#:379270-37-8
Literature: Chapman; Kernan; Prisbe; Rohloff; Sparacino; Terhorst; Yu Nucleosides, Nucleotides and Nucleic Acids, 2001 , vol. 20, # 4-7 p. 621 - 628
D-Alanine isopropyl ester hydrochloride structure

D-Alanine isopr...

CAS#:39613-92-8

~%

Tenofovir alafenamide Structure

Tenofovir alafe...

CAS#:379270-37-8
Literature: Colby, Denise A.; Martins, Andrew Anthony; Roberts, Benjamin James; Scott, Robert William; Solomon, Nicole S. Patent: US2013/90473 A1, 2013 ;
[[(1R)-2-(6-aMino-9H-purin-9-yl)-1-Methylethoxy]Methyl]-, Monophenylester structure

[[(1R)-2-(6-aMi...

CAS#:379270-35-6

~%

Tenofovir alafenamide Structure

Tenofovir alafe...

CAS#:379270-37-8
Literature: Colby, Denise A.; Martins, Andrew Anthony; Roberts, Benjamin James; Scott, Robert William; Solomon, Nicole S. Patent: US2013/90473 A1, 2013 ;
Triphenyl phosphite structure

Triphenyl phosphite

CAS#:101-02-0

~%

Tenofovir alafenamide Structure

Tenofovir alafe...

CAS#:379270-37-8
Literature: Colby, Denise A.; Martins, Andrew Anthony; Roberts, Benjamin James; Scott, Robert William; Solomon, Nicole S. Patent: US2013/90473 A1, 2013 ;
Phenol structure

Phenol

CAS#:108-95-2

~%

Tenofovir alafenamide Structure

Tenofovir alafe...

CAS#:379270-37-8
Literature: Chapman; Kernan; Prisbe; Rohloff; Sparacino; Terhorst; Yu Nucleosides, Nucleotides and Nucleic Acids, 2001 , vol. 20, # 4-7 p. 621 - 628

 Synonyms

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
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  • Product Name: GS-7340
  • Price: $200.0/100mg $400.0/250mg $800.0/1g
  • Purity: 98.0%
  • Stocking Period: 3 Day
  • Contact: Tony Cao

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Related Compounds: More...
Tenofovir alafenamide
383365-04-6
TENOFOVIR ALAFENAMIDE
377091-31-1
Tenofovir alafenamide fumarate
1392275-56-7
Tenofovir alafenamide fumarate
379270-38-9
Tenofovir Alafenamide PMPA Impurity
1607007-18-0
Tenofovir Related Compound 14
1244022-52-3
Tenofovir disoproxil
201341-05-1
Tenofovir disoproxil aspartate
1571075-19-8
Tenofovir dimethyl ester
1340601-82-2
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