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I2286

Irbesartan

≥98% (HPLC), angiotensin II type 1 (AT1) receptor antagonist, powder

Synonym(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

Empirical Formula (Hill Notation):
C25H28N6O
CAS Number:
138402-11-6
Molecular Weight:
428.53
UNSPSC Code:
12352200
PubChem Substance ID:
329815365
NACRES:
NA.77
MDL number:
MFCD00864464
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
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Product Name

Irbesartan, ≥98% (HPLC), powder

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to off-white

solubility

DMSO: >25 mg/mL

originator

Bristol-Myers Squibb, Sanofi Aventis

storage temp.

2-8°C

SMILES string

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)

InChI key

YOSHYTLCDANDAN-UHFFFAOYSA-N

Gene Information

human ... AGTR1(185)

General description

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.

Biochem/physiol Actions

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.

Features and Benefits

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.

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Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Listings

Regulatory Listings are mainly provided for chemical products. Only limited information can be provided here for non-chemical products. No entry means none of the components are listed. It is the user’s obligation to ensure the safe and legal use of the product.

I2286-10MG: + I2286-VAR: + I2286-50MG: + I2286-BULK:

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I Van Liefde et al.
Molecular and cellular endocrinology, 302(2), 237-243 (2008-07-16)
Sartans are non-peptide AT(1) receptor antagonists used to treat hypertension and related pathologies. Their effects on the G protein-dependent responses of angiotensin II (Ang II) were the same in vascular tissues and in isolated cell systems. All are competitive but
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
Guru Prasad Sharma et al.
International journal of radiation oncology, biology, physics, 113(1), 177-191 (2022-01-31)
Radiation-induced lung injury is a major dose-limiting toxicity for thoracic radiation therapy patients. In experimental models, treatment with angiotensin converting enzyme (ACE) inhibitors mitigates radiation pneumonitis; however, the mechanism of action is not well understood. Here, we evaluate the direct
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