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I2286

Sigma-Aldrich

Irbesartan

≥98% (HPLC), powder

Synonyme(s) :

2-Butyl-3-[[2′-(2H-tetrazol-5-yl)[1,1′-biphenyl]-4-yl]methyl]-1,3-diazaspiro[4.4]non-1-en-4-one, Avapro, BMS-186295, SR-47436

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About This Item

Formule empirique (notation de Hill) :
C25H28N6O
Numéro CAS:
138402-11-6
Poids moléculaire :
428.53
Numéro MDL:
MFCD00864464
Code UNSPSC :
12352200
ID de substance PubChem :
329815365
Nomenclature NACRES :
NA.77

Essai

≥98% (HPLC)

Forme

powder

Couleur

white to off-white

Solubilité

DMSO: >25 mg/mL

Auteur

Bristol-Myers Squibb
Sanofi Aventis

Température de stockage

2-8°C

Chaîne SMILES 

CCCCC1=NC2(CCCC2)C(=O)N1Cc3ccc(cc3)-c4ccccc4-c5nnn[nH]5

InChI

1S/C25H28N6O/c1-2-3-10-22-26-25(15-6-7-16-25)24(32)31(22)17-18-11-13-19(14-12-18)20-8-4-5-9-21(20)23-27-29-30-28-23/h4-5,8-9,11-14H,2-3,6-7,10,15-17H2,1H3,(H,27,28,29,30)

Clé InChI

YOSHYTLCDANDAN-UHFFFAOYSA-N

Informations sur le gène

human ... AGTR1(185)

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Description générale

Irbesartan comprises bipentyl-tetrazole side chain. It is an imidazole derivative with high bioavailability and is metabolized by the enzyme cytochrome P450 2C9 isoenzyme in liver to be majorly eliminated by oxidation and glucuronidation.

Application

Irbesartan has been used as an angiotensin II receptor type 1 (ATR1) blocker in carotid atheroma tissue. It may be used to test its effect on allergic asthma in rat and mice mast cells.

Actions biochimiques/physiologiques

Irbesartan is an angiotensin II type 1 (AT1) receptor antagonist with antihypertensive activity. It also elicits selective peroxisome proliferator-activated receptor γ (PPARγ)-modulating activity and possesses anti-inflammatory properties. Irbesartan shows protective cardiovascular effects and provides protection against chronic glomerulonephritis.

Caractéristiques et avantages

This compound is featured on the Angiotensin Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.
This compound was developed by Bristol-Myers Squibb and Sanofi Aventis. To browse the list of other pharma-developed compounds, Approved Drugs, and Drug Candidates, click here.

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

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Certificats d'analyse (COA)

Lot/Batch Number
0000426827
0000288821
0000288821
0000288819
0000288819

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Irbesartan impurity A European Pharmacopoeia (EP) Reference Standard

Y0001156

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Ross T Campbell et al.
Journal of the American College of Cardiology, 60(23), 2349-2356 (2012-11-13)
Examination of patients with reduced and preserved ejection fraction in the DIG (Digitalis Investigation Group) trials and the CHARM (Candesartan in Heart Failure: Assessment of Reduction in Mortality and Morbidity) trials provides comparisons of outcomes in each of these types
Koen Verdonk et al.
Hypertension (Dallas, Tex. : 1979), 60(3), 722-729 (2012-07-18)
Angiotensin II type 2 (AT(2)) receptor stimulation has been linked to vasodilation. Yet, AT(2) receptor-independent hypertension and hypotension (or no effect on blood pressure) have been observed in vivo after application of the AT(2) receptor agonist compound 21 (C21). We
Crina L Burlacu et al.
Therapeutics and clinical risk management, 4(2), 381-392 (2008-08-30)
In recent years levobupivacaine, the pure S (-)-enantiomer of bupivacaine, emerged as a safer alternative for regional anesthesia than its racemic parent. It demonstrated less affinity and strength of depressant effects onto myocardial and central nervous vital centers in pharmacodynamic
Marie Hudson et al.
Pharmacotherapy, 27(4), 526-534 (2007-03-27)
To examine the class effect of angiotensin II receptor blockers (ARBs) on mortality in patients with heart failure who were aged 65 years or older. Retrospective population-based study. Administrative database that stores information on hospital discharge summaries for the Canadian
Paula Clancy et al.
Journal of atherosclerosis and thrombosis, 23(7), 773-791 (2016-03-08)
Matrix metalloproteinases (MMPs), angiotensin II (AII) and its receptors are implicated in atherosclerotic plaque instability, however the roles of the two receptor subtypes, ATR1 and ATR2, in MMP regulation remain uncertain. In this study, we investigated the effect of ATR1
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