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I2286

Sigma-Aldrich

Irbesartan

≥98% (HPLC), powder

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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
Empirical Formula (Hill Notation):
C25H28N6O
CAS Number:
Molecular Weight:
428.53
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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)

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This Item
1347700Y0001166BP1093
Irbesartan ≥98% (HPLC), powder

I2286

Irbesartan

Irbesartan United States Pharmacopeia (USP) Reference Standard

1347700

Irbesartan

Irbesartan European Pharmacopoeia (EP) Reference Standard

Y0001166

Irbesartan

Irbesartan British Pharmacopoeia (BP) Reference Standard

BP1093

Irbesartan

assay

≥98% (HPLC)

assay

-

assay

-

assay

-

storage temp.

2-8°C

storage temp.

-

storage temp.

-

storage temp.

2-8°C

solubility

DMSO: >25 mg/mL

solubility

-

solubility

-

solubility

-

originator

Bristol-Myers Squibb, Sanofi Aventis

originator

-

originator

-

originator

-

color

white to off-white

color

-

color

-

color

-

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.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable


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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
Ross T Campbell et al.
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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
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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.
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There are few sex-specific outcome data in heart failure with preserved ejection fraction. We assessed sex differences in baseline characteristics and outcomes among 4128 patients with heart failure with preserved ejection fraction in the Irbesartan in Heart Failure with Preserved

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