Tenofovir

Base Information

• Chemical Name: Tenofovir
• CAS No.: 147127-20-6
• Molecular Formula: C9H14N5O4P
• Molecular Weight: 287.215
• Hs Code.: 29339900
• European Community (EC) Number: 604-571-2
• UNII: W4HFE001U5
• DSSTox Substance ID: DTXSID9040132
• Nikkaji Number: J540.142I
• Wikipedia: Tenofovir_disoproxil
• Wikidata: Q155954
• NCI Thesaurus Code: C170540
• RXCUI: 1546017
• Metabolomics Workbench ID: 42689
• ChEMBL ID: CHEMBL483
• Mol file: 147127-20-6.mol

Synonyms:(R)-9-(2-phosphonylmethoxypropyl)adenine;9-(2-phosphonomethoxypropyl)adenine;9-(2-phosphonylmethoxypropyl)adenine;9-(2-phosphonylmethoxypropyl)adenine, (+-)-isomer;9-(2-Phosphonylmethoxypropyl)adenine, (R)-isomer - T357098;9-(2-phosphonylmethoxypropyl)adenine, (S)-isomer;9-PMPA (tenofovir);Disoproxil Fumarate, Tenofovir;Disoproxil, Tenofovir;Fumarate, Tenofovir Disoproxil;tenofovir;tenofovir disoproxil;tenofovir disoproxil fumarate;Viread

Chemical Property of Tenofovir

Chemical Property:

• Appearance/Colour: white crystalline solid
• Melting Point: 276-280 °C
• Boiling Point: 616.1 °C at 760 mmHg
• PKA: 2.36±0.10(Predicted)
• Flash Point: 326.4 °C
• PSA: 146.19000
• Density: 1.79 g/cm³
• LogP: 0.53000
• Storage Temp.: Store at -20°C
• Solubility.: Aqueous Acid (Sparingly), DMSO (Slightly, Heated), Water (Slightly, Heated)
• Water Solubility.: 13.4 mg/mL (25 ºC)
• XLogP3: -1.6
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 5
• Exact Mass: 287.07834094
• Heavy Atom Count: 19
• Complexity: 354

Purity/Quality:

99% ^*data from raw suppliers

Tenofovir ^*data from reagent suppliers

Safty Information:

• Pictogram(s): C
• Hazard Codes: C

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antiviral Agents
• Canonical SMILES: CC(CN1C=NC2=C(N=CN=C21)N)OCP(=O)(O)O
• Isomeric SMILES: C[C@H](CN1C=NC2=C(N=CN=C21)N)OCP(=O)(O)O
• Recent ClinicalTrials: ANRS 12372 MODERATO Study
• Recent EU Clinical Trials: A randomised non-inferiority trial with nested PK to assess DTG/3TC fixed dose formulations for the maintenance of virological suppression in children
• Recent NIPH Clinical Trials: A Study of JNJ-73763989, Pegylated Interferon Alpha-2a and Nucleos(t)ide Analogs in Participants With Chronic Hepatitis B Virus Infection
• Uses: Tenofovir is an acyclic phosphonate nucleotide analogue and reverse transcriptase inhibitor. It is used as an anti-HIV agent. Antiviral. Tenofovir is a drug used for the treatment of chronic heptatitis B as well as prevention and treatment of HIV/AIDS. It is a kind of nucleotide analog, acting as the reverse-transcriptase inhibitor (NtRTI). It inhibits the activity of HIV reverse transcriptase through competing with the natural substrate deoxyadenosine 5’-triphosphate, causing the termination of DNA chain.
• Description: Tenofovir is an analog of adenosine monophosphate that has antiviral activity. It is converted by cellular enzymes to tenofovir diphosphate, an obligate chain terminator that inhibits the activity of HIV reverse transcriptase and hepatitis B virus polymerase. Tenofovir diphosphate is a weak inhibitor of mammalian DNA polymerases α and β and mitochondrial DNA polymerase γ. For in vivo and cell culture use, tenofovir is supplied as a water soluble prodrug in the form of tenofovir disoproxil (fumarate) , which increases the intracellular diphosphorylated compound >1,000-fold above the level attained with unmodified tenofovir.
• Indications: Tenofovir disoproxil fumarate (Viread) is a prodrug of tenofovir, a phosphorylated adenosine nucleoside analogue, and is the only available agent of its class. It is converted by cellular enzymes to tenofovir diphosphate, which competes with deoxyadenosine triphosphate (dATP) for access to reverse transcriptase and causes chain termination following its incorporation. Tenofovir was approved as part of a combination therapy for HIV in adults who failed treatment with other regimens; it appears to be effective against HIV strains that are resistant to NRTIs.
• Clinical Use: Chronic hepatitis B infection

Technology Process of Tenofovir

There total 62 articles about Tenofovir which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

(R)-diethyl (((1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphonate (180587-75-1) → tenofovir (147127-20-6)

Guidance literature:

With hydrogenchloride; In N,N-dimethyl-formamide; at 130 ℃; for 0.0416667h; under 7500.75 Torr; Solvent; Pressure; Temperature; Inert atmosphere;

Reference yield: 91.8%

(R)-[1-iodo(2-propoxy)]methylphosphonic acid + adenine (66224-66-6,66224-67-7,66224-68-8,66224-69-9,134434-48-3,134434-49-4,134454-76-5,134461-75-9) → tenofovir (147127-20-6)

Guidance literature:

With sodium hydroxide; In water; for 5h; Reflux;

Reference yield: 91.0%

bis(2-propyl) (R)-9-(2-phosphonomethoxypropyl)adenine (160616-04-6) → tenofovir (147127-20-6)

Guidance literature:

With hydrogenchloride; In water; at 130 - 140 ℃; Microwave irradiation; Sealed tube;

DOI:10.1039/c2gc35547g

upstream raw materials:

methyl hydrogen ({[1-(6-amino-9H-purin-9-yl)propan-2-yl]oxy}methyl)phosphonate

N'-[9-(2-Hydroxy-propyl)-9H-purin-6-yl]-N,N-dimethyl-formamidine

6-amino-α-methyl-9H-purine-9-ethanol

6-chloro-7H-purine

Downstream raw materials:

((((R)-1-(6-amino-9H-purin-9-yl)propan-2-yl)oxy)methyl)phosphoric acid monophenyl ester

hexadecyloxypropyl tenofovir

Refernces

• 1、 -. "Green and environment-friendly preparation method of tenofovir". Paragraph 0051-0062; 0075-0080. . Retrieved 2021/08/07.
• 2、 -. "Synthesis process of antiviral drug". Paragraph 0041-0049. . Retrieved 2020/11/26.