Irbesartan

Base Information

• Chemical Name: Irbesartan
• CAS No.: 138402-11-6
• Molecular Formula: C25H28N6O
• Molecular Weight: 428.537
• Hs Code.: 29332900
• European Community (EC) Number: 604-078-2
• NSC Number: 758696
• UNII: J0E2756Z7N
• DSSTox Substance ID: DTXSID0023169
• Nikkaji Number: J549.417F
• Wikipedia: Irbesartan
• Wikidata: Q947266
• NCI Thesaurus Code: C29130
• RXCUI: 83818
• Pharos Ligand ID: 24QDP6NHFGA9
• Metabolomics Workbench ID: 43271
• ChEMBL ID: CHEMBL1513
• Mol file: 138402-11-6.mol

Synonyms:2-n-butyl-3-((2'-(1H-tetrazol-5-yl)biphenyl-4-yl)methyl)-1,3-diazaspiro(4,4)non-1-en-4-one;Aprovel;Avapro;BMS 186295;BMS-186295;irbesartan;Karvea;SR 47436;SR-47436;SR47436

Chemical Property of Irbesartan

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 1.05E-16mmHg at 25°C
• Melting Point: 180-181 °C
• Refractive Index: 1.689
• Boiling Point: 648.6 °C at 760 mmHg
• PKA: 4.16±0.10(Predicted)
• Flash Point: 346 °C
• PSA: 87.13000
• Density: 1.3 g/cm³
• LogP: 4.15090
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO: >25mg/mL
• XLogP3: 4.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 7
• Exact Mass: 428.23245954
• Heavy Atom Count: 32
• Complexity: 682

Purity/Quality:

99% ^*data from raw suppliers

Irbesartan ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 26-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Angiotensin II Receptor Antagonists
• Canonical SMILES: CCCCC1=NC2(CCCC2)C(=O)N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NNN=N5
• Recent ClinicalTrials: A Study to Evaluate the Effect of Sodium Zirconium Cyclosilicate on Chronic Kidney Disease (CKD) Progression in Participants With CKD and Hyperkalaemia or at Risk of Hyperkalaemia
• Recent EU Clinical Trials: A Phase 3, International, Randomised, Double-blind, Placebo-controlled Study to Evaluate the Effect of Sodium Zirconium Cyclosilicate on Chronic Kidney Disease (CKD) Progression in Participants with CKD and Hyperkalaemia or at Risk of Hyperkalaemia
• Recent NIPH Clinical Trials: Feasible study of the effect of irbesartan on psoriasis
• Uses: Antihypertensive drugs. Angiotensin Ⅱ-l (Ⅱ 1 A) receptor antagonist. Used to treat high blood pressure. An angiotensin II type 1 (AII1)-receptor antagonist antidepressant For the treatment of hypertension, as well as diabetic nephropathy with an elevated serum creatinine and proteinuria (>300 mg/day) in patients with type 2 diabetes and hypertension. Irbesartan is also used as a second line agent in the treatment of conges
• Production Method: Methods 1: 1-(fluorene methoxy carbonyl amino) ring e carboxylic acid (I) benzylamine reaction with 4-(2-phenyl cyano) amidation, product (Ⅲ) and water release N to produce compound (Ⅳ). (Ⅳ) and Triethyl orthobutyrate condensation, cyclization to compound (V), then azide to formation tetrazolium with sodium reaction to obtain Telmisartan. Methods 2: 1-(fluorene methoxyl carbonyl amino) ring e carboxylic acid (I) condensation with compound(Ⅳ), the product remove N protection based to compound (Ⅷ), reacts with Triethyl orthobutyrate, obtain the product.
• Description: Avapro was launched in Germany, the UK and the US for hypertension. It can be prepared in six steps starting with cyclopentanone or in three steps from 1- aminocyclopentanecarboxylic acid ethyl ester and pentanimidic ethyl ester. Avapro is an angiotensin Ⅱ receptor antagonist that is non-competitive and selective for AT, subtypes and has no AT2 activity at postsynaptic receptors compared to presynatpic. It has no affinity for various non angiotensin Ⅱ receptor types in binding, no interaction with calcium channels or antiports, and no affinity for α1- and α2--adrenoreceptors, serotonergic receptors, muscarinic m1 and m2 or other receptors. It is as potent as saralasin but with no agonist activity and is 10 times more potent than DuP753 in rats. It is similar in efficacy to enalapril (in those with severe hypertension) and atenolol, while more effective than losartan for mild to moderate hypertension.
• Therapeutic Function: Antihypertensive
• Clinical Use: Angiotensin-II receptor antagonist: Hypertension Diabetic nephropathy
• Drug interactions: Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect. Analgesics: antagonism of hypotensive effect and increased risk of renal impairment with NSAIDs; hyperkalaemia with ketorolac and other NSAIDs. Antihypertensives: increased risk of hyperkalaemia hypotension and renal impairment with ACE-Is and aliskiren. Ciclosporin: increased risk of hyperkalaemia and nephrotoxicity. Diuretics: enhanced hypotensive effect; hyperkalaemia with potassium-sparing diuretics. ESAs: increased risk of hyperkalaemia; antagonism of hypotensive effect. Lithium: reduced excretion (possibility of enhanced lithium toxicity). Potassium salts: increased risk of hyperkalaemia. Tacrolimus: increased risk of hyperkalaemia and nephrotoxicity.

Technology Process of Irbesartan

There total 55 articles about Irbesartan 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: 100.0%

3-{[2′-(1-benzyl-1H-tetrazol-5-yl)-1,1′-biphenyl-4-yl]methyl}-2-butyl-1,3-diazaspiro[4.4]non-1-en-4-one → 2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one (138402-11-6)

Guidance literature:

With 5% palladium on barium sulphate; ammonium formate; In water; isopropyl alcohol; at 25 - 55 ℃; for 3.5h;

DOI:10.1055/s-0034-1378585

Reference yield: 98.75%

trityl irbesartan (138402-10-5) → 2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one (138402-11-6)

Guidance literature:

trityl irbesartan; With hydrogenchloride; In water; acetone; at 35 - 45 ℃; for 1.5 - 2h;

In water; acetone; at 15 ℃; pH=11 - 13; Alkaline aqueous solution;

Reference yield: 95.0%

4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile (138401-24-8) → 2-butyl-3-{4-[2-(1H-tetrazol-5-yl)phenyl]benzyl}-1,3-diazaspiro[4.4]non-1-en-4-one (138402-11-6)

Guidance literature:

With sodium azide; tributyltin chloride; In o-xylene; Heating;

DOI:10.1515/HC.2006.12.5.323

upstream raw materials:

4'-[(2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl]-[1,1'-biphenyl]-2-carbonitrile

3-[4-bromobenzyl]-2-n-butyl-1,3-diazaspiro[4.4]non-1-en-4-one

2-(N-triphenylmethyl-tetrazol-5-yl)-phenylboronic acid

2-n-butyl-3-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one hydrobromide

Downstream raw materials:

2-(tetrazol-5-yl)-4'-methyl-1,1'-biphenyl

2-n-butyl-4-spirocyclopentane-1-[((2'-tetrazol-5-yl)biphenyl-4-yl)methyl]-2-imidazolin-5-one hydrochloride

Refernces

• 1、 -. "Method for treating azide ions, non-genotoxic impurity Sartan raw material medicine and immediate thereof". Paragraph 0099; 0100; 0101; 0109. . Retrieved 2019/05/28.
• 2、 Thorat, Vijaykumar H.,Upadhyay, Nitinkumar Satyadev,Cheng, Chien-Hong. "Nickel-Catalyzed Denitrogenative ortho-Arylation of Benzotriazinones with Organic Boronic Acids: an Efficient Route to Losartan and Irbesartan Drug Molecules". supporting information. p. 4784 - 4789. Retrieved 2018/11/10.