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379270-37-8

379270-37-8 structure
379270-37-8 structure
  • Name: Tenofovir alafenamide
  • Chemical Name: propan-2-yl (2S)-2-[[[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-phenoxyphosphoryl]amino]propanoate
  • CAS Number: 379270-37-8
  • Molecular Formula: C21H29N6O5P
  • Molecular Weight: 476.466
  • Catalog: API Inhibitor
  • Create Date: 2018-02-06 08:00:00
  • Modify Date: 2024-01-02 11:19:21
  • Tenofovir alafenamide (GS-7340) is an investigational oral prodrug of Tenofovir. Tenofovir is a HIV-1 nucleotide reverse transcriptase inhibitor.

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

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)
Hazard Codes Xi

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379270-37-8 structure

379270-37-8

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

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379270-37-8 structure

379270-37-8

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

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379270-37-8 structure

379270-37-8

Literature: Colby, Denise A.; Martins, Andrew Anthony; Roberts, Benjamin James; Scott, Robert William; Solomon, Nicole S. Patent: US2013/90473 A1, 2013 ;

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379270-37-8 structure

379270-37-8

Literature: Colby, Denise A.; Martins, Andrew Anthony; Roberts, Benjamin James; Scott, Robert William; Solomon, Nicole S. Patent: US2013/90473 A1, 2013 ;

~%

379270-37-8 structure

379270-37-8

Literature: Colby, Denise A.; Martins, Andrew Anthony; Roberts, Benjamin James; Scott, Robert William; Solomon, Nicole S. Patent: US2013/90473 A1, 2013 ;

~%

379270-37-8 structure

379270-37-8

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