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
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
CHEBI:63625
CAS Number
147127-20-6
DrugBank ID
DB14126
TTD ID
D0D9HW
VARIDT ID
DR00174
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

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)