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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

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Certificates of Analysis (COA)

Lot/Batch Number
0000486124
0000486124
0000426827
0000288821
0000288821

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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
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
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
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