Losartan

Base Information

• Chemical Name: Losartan
• CAS No.: 114798-26-4
• Molecular Formula: C22H23ClN6O
• Molecular Weight: 422.917
• Hs Code.: 2942000000
• European Community (EC) Number: 601-329-8
• NSC Number: 758699
• UNII: JMS50MPO89
• DSSTox Substance ID: DTXSID7023227
• Nikkaji Number: J276.444J
• Wikipedia: Losartan
• Wikidata: Q410074
• NCI Thesaurus Code: C66869
• RXCUI: 52175
• Pharos Ligand ID: D7KVGYDUG4PM
• Metabolomics Workbench ID: 42993
• ChEMBL ID: CHEMBL191
• Mol file: 114798-26-4.mol

Synonyms:2-Butyl-4-chloro-1-((2'-(1H-etrazol-5-yl) (1,1'-biphenyl)-4-yl)methyl)-1H-imidazole-5-methanol;Cozaar;DuP 753;DuP-753;DuP753;Losartan;Losartan Monopotassium Salt;Losartan Potassium;MK 954;MK-954;MK954;Monopotassium Salt, Losartan;Potassium, Losartan;Salt, Losartan Monopotassium

Chemical Property of Losartan

Chemical Property:

• Appearance/Colour: pale yellow solid
• Vapor Pressure: 8.63E-20mmHg at 25°C
• Melting Point: 183-184 °C
• Refractive Index: 1.68
• Boiling Point: 682 °C at 760mmHg
• PKA: 5-6(at 25℃)
• Flash Point: 366.3 °C
• PSA: 92.51000
• Density: 1.35 g/cm³
• LogP: 4.26680
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• Water Solubility.: 4.8mg/L at 20℃
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 8
• Exact Mass: 422.1621871
• Heavy Atom Count: 30
• Complexity: 520

Purity/Quality:

99% , ^*data from raw suppliers

Losartan ^*data from reagent suppliers

Safty Information:

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

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Angiotensin II Receptor Antagonists
• Canonical SMILES: CCCCC1=NC(=C(N1CC2=CC=C(C=C2)C3=CC=CC=C3C4=NNN=N4)CO)Cl
• Recent ClinicalTrials: Serial Measurements of Molecular and Architectural Responses to Therapy (SMMART) PRIME Trial
• Recent EU Clinical Trials: Randomised placebo controlled clinical trial of efficacy of MYOcardial protection in patients with postacute inFLAMmatory cardiac involvEment due to COVID-19 (MYOFLAME-19)
• Recent NIPH Clinical Trials: Drug-drug interactions study of TAS-115 in patients with solid tumors
• Uses: Losartan is a nonpeptide angiotensin II AT1-receptor antagonist. Antihypertensive. antihypertensive;antagonist of angiotensin type 1
• Therapeutic Function: Antihypertensive

Technology Process of Losartan

There total 76 articles about Losartan 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: 99.0%

2-n-Butyl-4-chloro-1-[(2'-cyanobiphenyl-4-yl)-methyl]-5-(hydroxymethyl)imidazole (114772-55-3) → lorsartan (114798-26-4)

Guidance literature:

With sodium azide; In 1-methyl-pyrrolidin-2-one;

Reference yield: 98.0%

methanol (67-56-1) + 2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol (124751-00-4) → methoxytriphenylmethane (596-31-6) + lorsartan (114798-26-4)

Guidance literature:

for 7h; Heating / reflux;

Reference yield: 97.0%

1-{[2′-(1-benzyl-1H-tetrazol-5-yl)-1,1′-biphenyl-4-yl]methyl}-2-butyl-4-chloro-1H-imidazole-5-carbaldehyde → lorsartan (114798-26-4)

Guidance literature:

With palladium 10% on activated carbon; hydrogen; at 20 ℃; for 24h; under 760.051 Torr;

DOI:10.1039/c4ob02453b

upstream raw materials:

2-n-Butyl-4-chloro-1-[(2'-(2-triphenylmethyl-2H-tetrazol-5-yl)-1,1'-biphenyl-4-yl)methyl]-1H-imidazole-5-carboxaldehyde

4-bromobenzyl acetate

4-bromobenzenemethanol

5-benzyl-1-phenyl-1H-tetrazole

Downstream raw materials:

3-nitrooxymethyl-benzoic acid 2-butyl-5-chloro-3-[2'-(1H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazol-4-ylmethyl ester

cozaar

2-Butyl-4-chloro-1-[[2'-[1-(triphenylmethyl)-1H-tetrazol-5-yl][1,1'-biphenyl]-4-yl]methyl]-1H-imidazole-5-methanol

2-butyl-4-chloro-5-(methoxymethyl)-1-[[2'-[tetrazole-5-yl]biphenyl-4-yl]methyl]imidazole

Refernces

• 1、 Larsen,King,Chen,Corley,Foster,Roberts,Yang,Lieberman,Reamer,Tschaen,Verhoeven,Reider,Lo,Rossano,Brookes,Meloni,Moore,Arnett. "Efficient synthesis of losartan, a nonpeptide angiotensin II receptor antagonist". . p. 6391 - 6394. Retrieved 1994.
• 2、 -. "Preparation method of losartan". Paragraph 0033-0042. . Retrieved 2021/04/21.
• 3、 -. "Preparation method of losartan". . . Retrieved 2019/11/29.