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Tenofovir Alafenamide

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Category Human immunodeficiency Virus (HIV)
CAS 379270-37-8
Description Tenofovir Alafenamide is a prodrug of Tenofovir, which is a reverse transcriptase inhibitor used to treat HIV and Hepatitis B. Antiviral.
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Product Information

Synonyms (S)-isopropyl 2-(((S)-((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)(phenoxy)phosphoryl)amino)propanoate; GS7340; GS-7340; GS 7340; Tenofovir alafenamide
IUPAC Name propan-2-yl (2S)-2-[[[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-phenoxyphosphoryl]amino]propanoate
Molecular Weight 476.47
Molecular Formula C21H29N6O5P
Canonical SMILES C[C@H](N[P@@](OC1=CC=CC=C1)(CO[C@H](C)CN2C=NC3=C(N)N=CN=C23)=O)C(OC(C)C)=O
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
InChIKey LDEKQSIMHVQZJK-AZFZMOAFSA-N
Boiling Point 640.4±65.0 °C at 760 mmHg
Melting Point 104-107 °C
Flash Point 341.1±34.3 °C
Purity >98%
Density 1.4±0.1 g/cm3
Solubility In vitro:
10 mM in DMSO
Appearance White to off-white solid powder
Storage Powder:
-20°C: 3 years
4°C: 2 years
In solvent:
-80°C: 6 months
-20°C: 1 month
Complexity 680
Exact Mass 476.19370504
Index Of Refraction 1.630
In Vitro Tenofovir alafenamide (GS-7340) 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.
In Vivo Tenofovir alafenamide (GS-7340) hemifumarate is an amidate prodrug of Tenofovir with good oral bioavailability and increases plasma stability compared to Tenofovir disoproxil fumarate (TDF).
PSA 153.29000
Target HIV; Reverse Transcriptase
Vapor Pressure 0.0±1.9 mmHg at 25°C
XLogP3-AA 1.9

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