Tenofovir Disoproxil Fumarate

Base Information

• Chemical Name: Tenofovir Disoproxil Fumarate
• CAS No.: 202138-50-9
• Molecular Formula: C19H30N5O10P^.C4H4O4
• Molecular Weight: 635.522
• Hs Code.: 2933599550
• European Community (EC) Number: 687-766-5
• UNII: OTT9J7900I
• DSSTox Substance ID: DTXSID5050426
• Wikidata: Q27132754
• NCI Thesaurus Code: C47747
• RXCUI: 322248
• ChEMBL ID: CHEMBL1486
• Mol file: 202138-50-9.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 Disoproxil Fumarate

Chemical Property:

• Appearance/Colour: almost white crystalline
• Vapor Pressure: 2.06E-16mmHg at 25°C
• Melting Point: 219oC
• Boiling Point: 642.7 °C at 760 mmHg
• Flash Point: 342.5 °C
• PSA: 269.85000
• Density: 1.45 g/cm³
• LogP: 3.32860
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 18
• Rotatable Bond Count: 19
• Exact Mass: 635.18398777
• Heavy Atom Count: 43
• Complexity: 817

Purity/Quality:

99%, ^*data from raw suppliers

Tenofovir disoproxil fumarate ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

Useful:

• Canonical SMILES: CC(C)OC(=O)OCOP(=O)(COC(C)CN1C=NC2=C(N=CN=C21)N)OCOC(=O)OC(C)C.C(=CC(=O)O)C(=O)O
• Isomeric SMILES: C[C@H](CN1C=NC2=C(N=CN=C21)N)OCP(=O)(OCOC(=O)OC(C)C)OCOC(=O)OC(C)C.C(=C/C(=O)O)\C(=O)O
• Recent ClinicalTrials: Use of TDF in Patients With Inactive Chronic Hepatitis B Infection
• 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: Efficacy and safety of switching from entecavir to tenofovir for chronic hepatitis B patients with sustained viral supression: a randomized controlled trial
• Description: Tenofovir Disoproxil Fumarate (TDF) is a medication used for the management of HIV and hepatitis B virus (HBV). It is available in tablet form for oral administration.
• Chemical Composition: TDF is a prodrug of tenofovir, an antiretroviral medication. It is composed of tenofovir bound to a prodrug moiety, disoproxil fumarate.
• Uses: HIV Treatment:; TDF has been a mainstay in the treatment of HIV since its approval in 2001. It is used in combination with other antiretroviral medications to suppress viral replication.; ; HBV Treatment:; TDF is also approved for the treatment of HBV. It helps control HBV infection and reduces the risk of complications such as cirrhosis and hepatocellular carcinoma.
• Mechanism of Action: TDF is converted to tenofovir, which inhibits the action of reverse transcriptase, an enzyme necessary for the replication of HIV and HBV. TDF is orally administered and undergoes conversion to tenofovir in the body. It is eliminated primarily through the kidneys.
• References: [1] A Review and Clinical Understanding of Tenofovir: Tenofovir Disoproxil Fumarate versus Tenofovir Alafenamide; DOI 10.1177/2325958220919231; [2] Emtricitabine and tenofovir alafenamide vs emtricitabine and tenofovir disoproxil fumarate for HIV pre-exposure prophylaxis (DISCOVER): primary results from a randomised, double-blind, multicentre, active-controlled, phase 3, non-inferiority trial; DOI 10.1016/S0140-6736(20)31065-5; [3] Bictegravir, emtricitabine, and tenofovir alafenamide versus dolutegravir, emtricitabine, and tenofovir disoproxil fumarate for initial treatment of HIV-1 and hepatitis B coinfection (ALLIANCE): a double-blind, multicentre, randomised controlled, phase 3 non-inferiority trial; DOI 10.1016/S2352-3018(23)00151-0

Technology Process of Tenofovir Disoproxil Fumarate

There total 10 articles about Tenofovir Disoproxil Fumarate 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: 94.4%

(2E)-but-2-enedioic acid (110-17-8,26099-09-2) + tenofovir disoproxil (201341-05-1) → tenofovir disoproxyl fumarate (202138-50-9,1432630-26-6)

Guidance literature:

In isopropyl alcohol; at 50 - 55 ℃;

Reference yield: 90.0%

chloromethyl isopropyl carbonate (35180-01-9) + (2E)-but-2-enedioic acid (110-17-8,26099-09-2) + tenofovir (147127-20-6) → tenofovir disoproxyl fumarate (202138-50-9,1432630-26-6)

Guidance literature:

tenofovir; With triethylamine; In 1-methyl-pyrrolidin-2-one; at 63 ℃; for 0.5h;

chloromethyl isopropyl carbonate; In 1-methyl-pyrrolidin-2-one; at 63 ℃; for 4h;

(2E)-but-2-enedioic acid; In isopropyl alcohol; at 50 ℃; for 0.5h; Concentration;

Reference yield: 83.0%

9-[2-[(R)[[bis[[isopropoxycarbonyl]oxy]methoxy]phosphinyl]methoxy]propyl]adenine orotate + (2E)-but-2-enedioic acid (110-17-8,26099-09-2) → tenofovir disoproxyl fumarate (202138-50-9,1432630-26-6)

Guidance literature:

9-[2-[(R)[[bis[[isopropoxycarbonyl]oxy]methoxy]phosphinyl]methoxy]propyl]adenine orotate; With triethylamine; In dichloromethane; water; at 25 ℃;

(2E)-but-2-enedioic acid; In isopropyl alcohol; at 0 - 50 ℃;

upstream raw materials:

(2E)-but-2-enedioic acid

tenofovir disoproxil

adenine

(R)-9-(2-hydroxypropyl)adenine

Downstream raw materials:

tenofovir disoproxil

9-[(R)-2-[[bis[[ (isopropoxycarbonyl)oxy]methoxy]phosphinyl]-methoxy]propyl]adenine fumarate Tenofovir disoproxil fumarate

Refernces

• 1、 -. "A method for preparing for [...] (by machine translation)". Paragraph 0039-0041; 0058-0061. . Retrieved 2019/03/28.
• 2、 -. "Preparation method of high-purity tenofovir disoproxil fumarate". Paragraph 0020. . Retrieved 2018/12/02.