Details of the Drug

General Information of Drug (ID: DM1IS6U)

Drug Name
Tenofovir
Synonyms
Apropovir; PMPA; TFV; Tenefovir; GS 1275; GS 1278; GS1278; GNA & Tenofovir; HHA & Tenofovir; KS-5021; Viread (TN); Viread, Tenofovir; D,L-Tenofovir; PMPA-(R); Phosphonic acid, [[2-(6-amino-9H-purin-9; [(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethylphosphonic acid; Phosphonic acid, [[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]-(9CI); Phosphonic acid, [[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]-& Galanthus nivalis agglutinin (GNA); Phosphonic acid, [[(1R)-2-(6-amino-9H-purin-9-yl)-1-methylethoxy]methyl]-& Hippeastrum hybrid agglutinin(HHA); (R)-9-(2-Phosphonomethoxypropyl)adenine; (R)-9-(2-Phosphonylmethoxypropyl)adenine; (R)-PMPA
Indication
Disease Entry ICD 11 Status REF
Chronic hepatitis B virus infection N.A. Approved [1]
Hepatitis B virus infection 1E51.0 Approved [1]
Human immunodeficiency virus infection 1C62 Approved [2]
Therapeutic Class
Anti-HIV Agents
Affected Organisms
Herpes simplex virusHIV-1Hepatitis B virus
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 287.21
Logarithm of the Partition Coefficient (xlogp) -1.6
Rotatable Bond Count (rotbonds) 5
Hydrogen Bond Donor Count (hbonddonor) 3
Hydrogen Bond Acceptor Count (hbondacc) 8
ADMET Property
Absorption AUC
The area under the plot of plasma concentration (AUC) of drug is 4800 mcgh/L [3]
Absorption Cmax
The maximum plasma concentration (Cmax) of drug is 2500 mcg/L [3]
Clearance
The clearance of drug is 134 mL/min [4]
Half-life
The concentration or amount of drug in body reduced by one-half in 32 hours [5]
Metabolism
The drug is metabolized via a bi-phosphorylation which in order forms the biologically active compound tenofovir biphosphate [3]
Unbound Fraction
The unbound fraction of drug in plasma is 0.93% [6]
Vd
The volume of distribution (Vd) of drug is 0.813 L/kg [3]
Chemical Identifiers
Formula
C9H14N5O4P
IUPAC Name
[(2R)-1-(6-aminopurin-9-yl)propan-2-yl]oxymethylphosphonic acid
Canonical SMILES
C[C@H](CN1C=NC2=C(N=CN=C21)N)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
InChIKey
SGOIRFVFHAKUTI-ZCFIWIBFSA-N
Cross-matching ID
PubChem CID
464205
ChEBI ID
CHEMBL483
CAS Number
147127-20-6
UNII
W4HFE001U5
DrugBank ID
DB14126
TTD ID
D0D9HW
VARIDT ID
DR00174
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Drug Pharmacogenomic Perturbation (DPP)NEW Click to Jump to the Detailed DPP Information of This Drug
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Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Human immunodeficiency virus Reverse transcriptase (HIV RT) TT84ETX POL_HV1B1 Inhibitor [7]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
Multidrug resistance-associated protein 7 (ABCC10) DTPS120 MRP7_HUMAN Substrate [8]
Multidrug resistance-associated protein 8 (ABCC11) DTWN7FC ABCCB_HUMAN Substrate [9]
Multidrug resistance-associated protein 4 (ABCC4) DTCSGPB MRP4_HUMAN Substrate [10]
Breast cancer resistance protein (ABCG2) DTI7UX6 ABCG2_HUMAN Substrate [11]
Organic anion transporter 1 (SLC22A6) DTQ23VB S22A6_HUMAN Substrate [12]
Organic anion transporter 3 (SLC22A8) DTVP67E S22A8_HUMAN Substrate [13]
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [14]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

References

1 Tenofovir FDA Label
2 Anti-hepatitis B virus activity in vitro of combinations of tenofovir with nucleoside/nucleotide analogues. Antivir Chem Chemother. 2009;19(4):165-76.
3 Olkkola KT, Brunetto AV, Mattila MJ: Pharmacokinetics of oxicam nonsteroidal anti-inflammatory agents. Clin Pharmacokinet. 1994 Feb;26(2):107-20.
4 Kearney BP, Yale K, Shah J, Zhong L, Flaherty JF: Pharmacokinetics and dosing recommendations of tenofovir disoproxil fumarate in hepatic or renal impairment. Clin Pharmacokinet. 2006;45(11):1115-24. doi: 10.2165/00003088-200645110-00005.
5 Bictegravir/Emtricitabine/Tenofovir Alafenamide: A Review in HIV-1 Infection. Drugs. 2018 Nov;78(17):1817-1828. doi: 10.1007/s40265-018-1010-7.
6 Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
7 Antiviral drugs in current clinical use. J Clin Virol. 2004 Jun;30(2):115-33.
8 Genetic variants of ABCC10, a novel tenofovir transporter, are associated with kidney tubular dysfunction. J Infect Dis. 2011 Jul 1;204(1):145-53.
9 Tenofovir Disoproxil Fumarate Is a New Substrate of ATP-Binding Cassette Subfamily C Member 11. Antimicrob Agents Chemother. 2017 Mar 24;61(4). pii: e01725-16.
10 Functional involvement of multidrug resistance-associated protein 4 (MRP4/ABCC4) in the renal elimination of the antiviral drugs adefovir and tenofovir. Mol Pharmacol. 2007 Feb;71(2):619-27.
11 KEGG: new perspectives on genomes, pathways, diseases and drugs. Nucleic Acids Res. 2017 Jan 4;45(D1):D353-D361. (dg:DG01913)
12 Human renal organic anion transporter 1 (hOAT1) and its role in the nephrotoxicity of antiviral nucleotide analogs. Nucleosides Nucleotides Nucleic Acids. 2001 Apr-Jul;20(4-7):641-8.
13 Tenofovir alafenamide is not a substrate for renal organic anion transporters (OATs) and does not exhibit OAT-dependent cytotoxicity. Antivir Ther. 2014;19(7):687-92.
14 KEGG: new perspectives on genomes, pathways, diseases and drugs. Nucleic Acids Res. 2017 Jan 4;45(D1):D353-D361. (dg:DG01665)