Tenofovir-disoproxil
Tenofovir disoproxil is an organic phosphonate that is the disoproxil ester of tenofovir. A prodrug for tenofovir, an HIV-1 reverse transcriptase inhibitor, tenofovir disoproxil is used as the fumaric acid salt in combination therapy for the treatment of HIV infection. It has a role as an antiviral drug, a prodrug and a HIV-1 reverse transcriptase inhibitor. Prodrugs efficiently cross the cell membrane and undergo intracellular hydrolysis to release TFV, which is subsequently phosphorylated into the active metabolite TFV diphosphate (TFV-DP). TFV-DP inhibits viral replication by terminating viral DNA chain elongation
General
Type : Drug, Pro-Drug, Aminopurin, Propionate, Purine
Chemical_Nomenclature : [[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate
Canonical SMILES : C[C@H](CN1C=NC2=C(N=CN=C21)N)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C
InChI : InChI=1S\/C19H30N5O10P\/c1-12(2)33-18(25)28-9-31-35(27,32-10-29-19(26)34-13(3)4)11-30-14(5)6-24-8-23-15-16(20)21-7-22-17(15)24\/h7-8,12-14H,6,9-11H2,1-5H3,(H2,20,21,22)\/t14-\/m1\/s1
InChIKey : JFVZFKDSXNQEJW-CQSZACIVSA-N
Other name(s) : Tenofovir disoproxil || Bis(POC)PMPA || (r)-bis(poc)pmpa || bis-POC-PMPA || Viread || Tenofovir-disoproxil-fumarate || TDF || Tenofovir Disoproxil Fumarate || Tenofovir DF || PMPA prodrug || CHEBI:63717 || RefChem:187852 || CHEMBL1538 || SCHEMBL52793 || SCHEMBL29376425 || DB00300
MW : 519.4
Formula : C19H30N5O10P
CAS_number : 201341-05-1, 202138-50-9
UniChem : JFVZFKDSXNQEJW-CQSZACIVSA-N
Target
Structures : No structure
Families : Carb_B_Chordata
References (6)
| Title : A minimal physiologically based pharmacokinetic model for predicting the metabolism of tenofovir prodrugs in the liver of human with fibrosis - He_2026_Drug.Metab.Dispos_54_100263 |
| Author(s) : He H , Zhu J , Chen J , Guo H , Yu S , Hu H , Hong X , Yu H , Wang T , Wang G , Hao K , Zhang J |
| Ref : Drug Metabolism & Disposition: The Biological Fate of Chemicals , 54 :100263 , 2026 |
| Abstract : |
| PubMedSearch : He_2026_Drug.Metab.Dispos_54_100263 |
| PubMedID: 42085925 |
| Title : Simulating Intestinal Transporter and Enzyme Activity in a Physiologically Based Pharmacokinetic Model for Tenofovir Disoproxil Fumarate - Moss_2017_Antimicrob.Agents.Chemother_61_ |
| Author(s) : Moss DM , Domanico P , Watkins M , Park S , Randolph R , Wring S , Rajoli RKR , Hobson J , Rannard S , Siccardi M , Owen A |
| Ref : Antimicrobial Agents & Chemotherapy , 61 : , 2017 |
| Abstract : |
| PubMedSearch : Moss_2017_Antimicrob.Agents.Chemother_61_ |
| PubMedID: 28416547 |
| Title : Development of a Novel Formulation That Improves Preclinical Bioavailability of Tenofovir Disoproxil Fumarate - Watkins_2017_J.Pharm.Sci_106_906 |
| Author(s) : Watkins ME , Wring S , Randolph R , Park S , Powell K , Lutz L , Nowakowski M , Ramabhadran R , Domanico PL |
| Ref : J Pharm Sci , 106 :906 , 2017 |
| Abstract : |
| PubMedSearch : Watkins_2017_J.Pharm.Sci_106_906 |
| PubMedID: 27986599 |
| Title : Intestinal behavior of the ester prodrug tenofovir DF in humans - Geboers_2015_Int.J.Pharm_485_131 |
| Author(s) : Geboers S , Haenen S , Mols R , Brouwers J , Tack J , Annaert P , Augustijns P |
| Ref : Int J Pharm , 485 :131 , 2015 |
| Abstract : |
| PubMedSearch : Geboers_2015_Int.J.Pharm_485_131 |
| PubMedID: 25747454 |
| Title : Reversible inhibitory effects of saturated and unsaturated alkyl esters on the carboxylesterases activity in rat intestine - Li_2010_Lipids_45_603 |
| Author(s) : Li P , Zhu CL , Zhang XX , Gan L , Yu HZ , Gan Y |
| Ref : Lipids , 45 :603 , 2010 |
| Abstract : |
| PubMedSearch : Li_2010_Lipids_45_603 |
| PubMedID: 20532832 |