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
• General Description: Losartan is an angiotensin II receptor antagonist, originally developed as DuP 753, that serves as a therapeutic agent for conditions such as hypertension by blocking the effects of angiotensin II. The study explored novel derivatives, including triazole, sulfur-containing diazole, and N-phenylthiatriazole biphenyltetrazoles, to identify compounds with comparable or improved efficacy, with one derivative showing promising in vitro activity. However, losartan remains a well-established reference in this class of medications. **Final paragraph (conclusion):** Losartan is a clinically effective angiotensin II receptor antagonist used primarily for hypertension management, with its structure serving as a basis for developing newer derivatives aimed at enhancing therapeutic potential.

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:

cozaar

(S)-(1-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-2-butyl-4-chloro-1H-imidazol-5-yl)methyl 2-(tert-butoxycarbonyl)aminopropanoate

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

2-n-butyl-5-chloro-3-[2'-(2H-tetrazol-5-yl)-biphenyl-4-ylmethyl]-3H-imidazole-4-carboxylic acid

Refernces

The Syntheses of Triazole, Sulfur-Containing Diazole and N-Phenylthiatriazole Biphenyltetrazoles as Potential Angiotensin II Receptor Antagonists

10.1002/jccs.199600014

The study focuses on the synthesis of novel triazole, sulfur-containing diazole, and N-phenylthiatriazole biphenyltetrazole derivatives as potential angiotensin II receptor antagonists. This research was inspired by the success of the angiotensin II receptor antagonist losartan (DuP 753) and aimed to explore alternative heterocycles that could maintain or enhance its efficacy. Chemicals such as methyl valerimidate hydrochloride, thionyl chloride, N-methylmorpholine, cesium carbonate, and Lawesson's reagent were used in the synthetic processes. Among the synthesized compounds, 5-butyl-3-[(2-trifluoromethyl)phenyl]-2,1,3,4-1H-thiatriazole-2-one biphenyltetrazole demonstrated promising in vitro activity, suggesting its potential for further pharmaceutical development?.