({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid

• ChemBase ID: 185
• Molecular Formular: C9H14N5O4P
• Molecular Mass: 287.212321
• Monoisotopic Mass: 287.07834058
• SMILES: P(=O)(O)(O)CO[C@@H](Cn1c2ncnc(N)c2nc1)C
• Canonical 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
• InChIKey: SGOIRFVFHAKUTI-ZCFIWIBFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid
• IUPAC Traditional name: ({[(2R)-1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonic acid; tenofovir
• Brand Name: Apropovir; Viread
• Synonyms: (R)-9-(2-Phosphonomethoxypropyl)adenine; Apropovir; 9-[2-(Phosphonomethoxy)propyl]adenine; Tenofovir; Tenofovir disoproxil; Tenofovir disoproxil fumarate; D,L-Tenofovir; TDF; PMPA; Tenofovir; Viread; PMPA; [[(1R)-2(6-Amino-9H-purin-9-yl)-1-methylethoxy]methyl]phosphonic Acid; (R)-9-(2-Phosphonomethoxypropyl)adenine; (R)-PMPA; GS-1278; 泰诺福韦

Database IDs

• CAS Number: 147127-20-6; 147127-20-6
• MDL Number: MFCD00943794
• PubChem SID: 160963648; 46508131
• PubChem CID: 464205

CALCULATED PROPERTIES

JChem

• Acid pKa: 1.3504745
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -3.55535
• LogD (pH = 7.4): -3.5490735
• Log P: -4.1293006
• Molar Refractivity: 67.535 cm^3
• Polarizability: 25.71448 Å^3
• Polar Surface Area: 136.38 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -1.51
• LOG S: -2.19
• Solubility (Water): 1.87e+00 g/l

PROPERTIES

Physical Property

• Solubility: 13.4 mg/mL in distilled water at 25oC (disoproxil fumarate salt); Warm DMSO; Warm Water
• Apperance: White to Off-White Solid
• Melting Point: 280-282°C
• Hydrophobicity(logP): -1.6

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• Storage Warning: IRRITANT
• TSCA Listed: false

Pharmacology Properties

• Target: Reverse transcriptase
• Mechanism of Action: Reverse transcriptase inhibitor

Product Information

• Purity: 95+%
• Salt Data: Free Base
• Application(s): Anti-HIV agent; Antiretroviral drugs

DETAILS

DrugBank - DB00300

• Drug Groups: approved; investigational
• Description: Tenofovir, marketed by Gilead Sciences under the trade name Viread®, belongs to a class of antiretroviral drugs known as nucleotide analogue reverse transcriptase inhibitors (nRTIs), which block reverse transcriptase, an enzyme crucial to viral production in HIV-infected people. [Wikipedia]
• Indication: For use, in combination with other antiretroviral agents, for the treatment of HIV-1 infection.
• Pharmacology: Tenofovir belongs to a class of antiretroviral drugs known as nucleotide analogue reverse transcriptase inhibitors (NtRTIs), which block reverse transcriptase, an enzyme crucial to viral production in HIV-infected people. Tenofovir is currently in late-stage clinical trials for the treatment of hepatitis B. Tenofovir disoproxil fumarate is an acyclic nucleoside phosphonate diester analog of adenosine monophosphate. Tenofovir requires initial diester hydrolysis for conversion to tenofovir and subsequent phosphorylations by cellular enzymes to form tenofovir diphosphate. Tenofovir diphosphate is a weak inhibitor of mammalian DNA polymerases α, β, and mitochondrial DNA polymerase γ.
• Toxicity: Limited clinical experience at doses higher than the therapeutic dose of tenofovir 300 mg is available. In Study 901 tenofovir disoproxil fumarate 600 mg was administered to 8 patients orally for 28 days. No severe adverse reactions were reported. The effects of higher doses are not known.
• Affected Organisms: Human Immunodeficiency Virus
• Biotransformation: Neither tenofovir disoproxil nor tenofovir are substrates of CYP450 enzymes.
• Absorption: The oral bioavailability in fasted patients is approximately 25%. Administration of food (high fat meal containing 40 to 50% fat) increases the oral bioavailability, with an increase in the AUC of approximately 40%.
• Half Life: Approximately 17 hours.
• Protein Binding: Very low: < 0.7% to human plasma proteins and < 7.2% to serum proteins
• Distribution: * 1.3 ± 0.6 L/kg [tenofovir 1.0 mg/kg]; * 1.2 ± 0.4 L/kg [tenofovir 3.0 mg/kg]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Selleck Chemicals - S1401

Research Area: Infection
Biological Activity:
Tenofovir (Viread) is a drug used to treat human immunodeficiency virus (HIV) infection. Tenofovir is an antiviral drug called a nucleotide reverse transcriptase inhibitor. Tenofovir may reduce the amount of HIV in the blood and increase the number of CD4 cells (T-cells) in the blood. Tenofovir is used in combination with other drugs to treat the HIV virus. Tenofovir will not cure or prevent HIV infection or AIDS. [1]

Toronto Research Chemicals - T018500

Acyclic phosphonate nucleotide analogue; reverse transcriptase inhibitor. Used as an anti-HIV agent. Antiviral.

REFERENCES

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