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®).
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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
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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
1. Balzarini J, Holy A, Jindrich J, Naesens L, Snoeck R, Schols D, De Clercq E. (1993)
Differential antiherpesvirus and antiretrovirus effects of the (S) and (R) enantiomers of acyclic nucleoside phosphonates: potent and selective in vitro and in vivo antiretrovirus activities of (R)-9-(2-phosphonomethoxypropyl)-2,6-diaminopurine.
Antimicrob Agents Chemother, 37 (2): 332-8. [PMID:8452366]
2. Cooper RD, Wiebe N, Smith N, Keiser P, Naicker S, Tonelli M. (2010)
Systematic review and meta-analysis: renal safety of tenofovir disoproxil fumarate in HIV-infected patients.
Clin Infect Dis, 51 (5): 496-505. [PMID:20673002]
3. Fernandez-Fernandez B, Montoya-Ferrer A, Sanz AB, Sanchez-Niño MD, Izquierdo MC, Poveda J, Sainz-Prestel V, Ortiz-Martin N, Parra-Rodriguez A, Selgas R et al.. (2011)
Tenofovir nephrotoxicity: 2011 update.
AIDS Res Treat, 2011: 354908. [PMID:21716719]
4. Gordon CJ, Tchesnokov EP, Woolner E, Perry JK, Feng JY, Porter DP, Götte M. (2020)
Remdesivir is a direct-acting antiviral that inhibits RNA-dependent RNA polymerase from severe acute respiratory syndrome coronavirus 2 with high potency.
J Biol Chem, 295 (20): 6785-6797. [PMID:32284326]
5. Kalyesubula R, Perazella MA. (2011)
Nephrotoxicity of HAART.
AIDS Res Treat, 2011: 562790. [PMID:21860787]
6. Wang Y, Anirudhan V, Du R, Cui Q, Rong L. (2020)
RNA-dependent RNA polymerase of SARS-CoV-2 as a therapeutic target.
J Med Virol, [Epub ahead of print]. DOI: 10.1002/jmv.26264 [PMID:32633831]
7. Zaidan M, Lescure FX, Brochériou I, Dettwiler S, Guiard-Schmid JB, Pacanowski J, Rondeau E, Pialoux G, Girard PM, Ronco P et al.. (2013)
Tubulointerstitial nephropathies in HIV-infected patients over the past 15 years: a clinico-pathological study.
Clin J Am Soc Nephrol, 8 (6): 930-8. [PMID:23430209]
8. Zhu W, Chen CZ, Gorshkov K, Xu M, Lo DC, Zheng W. (2020)
RNA-Dependent RNA Polymerase as a Target for COVID-19 Drug Discovery.
SLAS Discov, 25 (10): 1141-1151. [PMID:32660307]