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
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
ChemSpider
58828414
ChEBI
90923
ChEMBL
CHEMBL2364637
Wikipedia
Tenofovir_alafenamide
Predicted Properties
PropertyValueSource
Water Solubility0.236 mg/mLALOGPS
logP1.49ALOGPS
logP1.88ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)11.36ChemAxon
pKa (Strongest Basic)3.74ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area143.48 Å2ChemAxon
Rotatable Bond Count26ChemAxon
Refractivity122.74 m3·mol-1ChemAxon
Polarizability47.24 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon