Tenofovir alafenamide fumarateProduct ingredient for Tenofovir alafenamide
- Name
- Tenofovir alafenamide fumarate
- Drug Entry
- Tenofovir alafenamide
Tenofovir alafenamide is a novel tenofovir prodrug developed in order to improve renal safety when compared to the counterpart tenofovir disoproxil.1 Both of these prodrugs were first created to cover the polar phosphonic acid group on tenofovir by using a novel oxycarbonyloxymethyl linkers to improve the oral bioavailability and intestinal diffusion.8 Tenofovir alafenamide is an alanine ester form characterized for presenting low systemic levels but high intracellular concentration.2 It has been reported to produce a large antiviral efficacy at doses ten times lower than tenofovir disoproxil.6 Tenofovir alafenamide is indicated to treat chronic hepatitis B,9 treat HIV-1,11,12,13,14 and prevent HIV-1 infections.11,17
Tenofovir alafenamide was developed by Gilead Sciences Inc and granted FDA approval on 5 November 2015.10
- Accession Number
- DBSALT002533
- Structure
Structure for Tenofovir alafenamide fumarate (DBSALT002533)
- Synonyms
- TAF / Tenofovir Alafenamide fumarate / Tenofovir alafenamide fumarate (2:1) / Tenofovir alafenamide hemifumarate
- External IDs
- GS-7340 hemifumarate
- UNII
- FWF6Q91TZO
- CAS Number
- 1392275-56-7
- Weight
- Average: 1069.02
Monoisotopic: 1068.39836872 - Chemical Formula
- C46H62N12O14P2
- InChI Key
- SVUJNSGGPUCLQZ-LVWWUONPSA-N
- InChI
- InChI=1S/2C21H29N6O5P.C4H4O4/c2*1-14(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;5-3(6)1-2-4(7)8/h2*5-9,11-12,14-16H,10,13H2,1-4H3,(H,26,29)(H2,22,23,24);1-2H,(H,5,6)(H,7,8)/b;;2-1+/t2*15-,16+,33-;/m11./s1
- IUPAC Name
- (2E)-but-2-enedioic acid; bis(propan-2-yl (2S)-2-{[(R)-({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)(phenoxy)phosphoryl]amino}propanoate)
- SMILES
- OC(=O)\C=C\C(O)=O.CC(C)OC(=O)[C@H](C)N[P@@](=O)(CO[C@H](C)CN1C=NC2=C(N)N=CN=C12)OC1=CC=CC=C1.CC(C)OC(=O)[C@H](C)N[P@@](=O)(CO[C@H](C)CN1C=NC2=C(N)N=CN=C12)OC1=CC=CC=C1
- External Links
- ChemSpider
- 58828414
- ChEBI
- 90923
- ChEMBL
- CHEMBL2364637
- Wikipedia
- Tenofovir_alafenamide
- Predicted Properties
Property Value Source Water Solubility 0.236 mg/mL ALOGPS logP 1.49 ALOGPS logP 1.88 Chemaxon logS -3.3 ALOGPS pKa (Strongest Acidic) 11.36 Chemaxon pKa (Strongest Basic) 3.74 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 7 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 143.48 Å2 Chemaxon Rotatable Bond Count 26 Chemaxon Refractivity 122.74 m3·mol-1 Chemaxon Polarizability 47.24 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon