Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00729)
Name
Tenofovir disoproxil
Synonyms    Click to Show/Hide the Synonyms of This API
Tenofovir disoproxil; 201341-05-1; PMPA prodrug; Bis(POC)PMPA; Tenofovir (Disoproxil); UNII-F4YU4LON7I; 9-((R)-2-((Bis(((isopropoxycarbonyl)oxy)methoxy)phosphinyl)methoxy)propyl)adenine; Tenofovir Disoproxil Fumarate; F4YU4LON7I; tenofovir bis(isopropyloxycarbonyloxymethyl) ester; CHEBI:63717; 201341-05-1 (free); Tenofovirdisoproxil; (R)-(((((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphoryl)bis(oxy))bis(methylene) diisopropyl bis(carbonate); 2,4,6,8-Tetraoxa-5-phosphanonanedioic acid, 5-[[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]-, 1,9-bis(1-methylethyl) ester, 5-oxide; bis({[(propan-2-yloxy)carbonyl]oxy}methyl) ({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonate; 9-[(r)-2-[[bis[[(isopropoxycarbonyl)oxy]methoxy]phosphinyl]methoxy]propyl]adenine; C19H30N5O10P; tenofovir-disoproxil; [[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethyl-(propan-2-yloxycarbonyloxymethoxy)phosphoryl]oxymethyl propan-2-yl carbonate; 202138-50-9; CHEMBL1538; SCHEMBL52793; cc-668; MLS006010919; DTXSID5052757; BDBM77145; Bis(POC)-PMPA;GS 4331; Bis(isopropyloxymethylcarbonyl)PMPA; AMY11134; ZINC3929022; HY-13782A; MFCD00952920; AKOS015895093; Viread(TM) (*1:1 Fumarate salt*); CS-5922; DB00300; NCGC00183876-02; [[(1R)-2-(6-aminopurin-9-yl)-1-methyl-ethoxy]methyl-(isopropoxycarbonyloxymethoxy)phosphoryl]oxymethyl isopropyl carbonate; SMR004701787; GS 4331-05 (*1:1 Fumarate salt*); W4257; C13480; AB01568241_01; 138T509; J-519478; Q27132753; 9-[(R)-2-[[Bis[[(isopropoxycarbonyl)oxy] methoxy]phosphinyl]methoxy]propyl]adenine; (R)-(((1-(6-amino-9H-purin-9-yl)propan-2-yloxy)methyl)phosphoryl)bis(oxy)bis(methylene) isopropyl dicarbonate
Clinical Status
Approved
Disease Indication Human immunodeficiency virus infection ICD-11: 1C60 [1]
PubChem CID
5481350
Formula
C19H30N5O10P
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
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=5481350"></iframe>
3D MOL is unavailable 2D MOL
Physicochemical Properties Molecular Weight 519.4 Topological Polar Surface Area 185
XlogP 1.6 Complexity 698
Heavy Atom Count 35 Rotatable Bond Count 17
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 14
Full List of Drug Formulations (DFMs) Containing This API
          Tenofovir disoproxil 300 mg tablet Click to Show/Hide the Full List of Formulation(s):          3 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c red no. 40; Fd&c blue no. 2; Indigotindisulfonate sodium; Magnesium stearate; Mannitol; Talc; Titanium dioxide; Povidone k30; Silicon dioxide; Crospovidone, unspecified; Polyethylene glycol, unspecified; Polyvinyl alcohol, unspecified
                   Dosage Form Oral Tablet
                   Company RemedyRepack; Teva Pharmaceuticals
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 4.7 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Mannitol DIG Info Glycine receptor alpha-1 (EC50 = 12589.25 nM) [3]
Allura red AC dye DIG Info Solute carrier SLCO2B1 (Ki = 2.59 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c blue no. 2; Magnesium stearate; Titanium dioxide; Triacetin; Croscarmellose sodium; Aluminum oxide; Cellulose, microcrystalline; Hypromellose 2910 (15000 mpa.s); Starch, corn
                   Dosage Form Oral Tablet
                   Company A-S Medication Solutions; Avera McKennan Hospital; RemedyRepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
             Drug Formulation 3 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Fd&c blue no. 2; Magnesium stearate; Titanium dioxide; Triacetin; Croscarmellose sodium; Aluminum oxide; Hypromellose 2910 (15000 mpa.s); Microcrystalline cellulose; Starch, corn
                   Dosage Form Oral Tablet
                   Company A-S Medication Solutions; Gilead Sciences; RemedyRepack
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
          Tenofovir disoproxil 150 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Triacetin; Croscarmellose sodium; Hypromellose 2910 (15000 mpa.s); Microcrystalline cellulose; Starch, corn
                   Dosage Form Oral Tablet
                   Company Gilead Sciences
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
          Tenofovir disoproxil 200 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Triacetin; Croscarmellose sodium; Hypromellose 2910 (15000 mpa.s); Microcrystalline cellulose; Starch, corn
                   Dosage Form Oral Tablet
                   Company Gilead Sciences
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
          Tenofovir disoproxil 250 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Triacetin; Croscarmellose sodium; Hypromellose 2910 (15000 mpa.s); Microcrystalline cellulose; Starch, corn
                   Dosage Form Oral Tablet
                   Company Gilead Sciences
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [5]
References
1 FDA label for approved tenofovir disoproxil from the official website of the U.S. Food and Drug Administration.
2 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
3 Pharmacological property optimization for allosteric ligands: A medicinal chemistry perspective. Bioorg Med Chem Lett. 2017 Jun 1; 27(11):2239-2258.
4 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
5 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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