tenofovir   Click here for help

GtoPdb Ligand ID: 10948

Abbreviated name: TDF
Synonyms: (R)-PMPA | PMPA | tenofovir (anhydrous)
Approved drug PDB Ligand
tenofovir is an approved drug
Compound class: Synthetic organic
Comment: Tenofovir is a nucleotide reverse transcriptase inhibitor (NtRTI) antiretroviral compound. The R-enantiomer, as shown here, is more effective at inhibiting retroviruses than the S-enantiomer [1]. Tenofovir has poor oral bioavailability and is delivered as either the prodrug tenofovir disoproxil fumarate (Viread®) or tenofovir alafenamide fumerate (Vemlidy®).
2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 8
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 146.19
Molecular weight 287.08
XLogP -1.65
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES C[C@H](Cn1cnc2c1ncnc2N)OCP(=O)(O)O
Isomeric SMILES C[C@H](Cn1cnc2c1ncnc2N)OCP(=O)(O)O
InChI InChI=1S/C9H14N5O4P/c1-6(18-5-19(15,16)17)2-14-4-13-7-8(10)11-3-12-9(7)14/h3-4,6H,2,5H2,1H3,(H2,10,11,12)(H2,15,16,17)/t6-/m1/s1
InChI Key SGOIRFVFHAKUTI-ZCFIWIBFSA-N
Bioactivity Comments
OAT1 and OAT3 in the basal membrane actively transport 20-30% of tenofovir into proximal tubule cells [3]. ABCC2 (MRP2) and ABCC4 (MRP4) at the apical surface secrete tenofovir into the tubular lumen [5].
Transporters Moving this Compound Across a Lipid Membrane
Transporter EC number Reaction Reference
ABCC2 5
ABCC4 5
Organic anion transporter 1 3
Organic anion transporter 3 3
Targets where the ligand is described in the comment field
Target Comment