138402-11-6 Irbesartan AKSci J10394
 
 
Loading Please Wait...
  J10394    AKSci Reference Standard
Irbesartan
, >98% (HPLC), powder
 
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




IDENTITY
CAS Number:138402-11-6
MDL Number:MFCD00864464
MF:C25H28N6O
MW:428.53
BRN:6620400
SPECIFICATIONS & PROPERTIES
Purity:>98% (HPLC), powder
Spectra:LCMS, HPLC
Physical Form:White to off-white crystalline powder
Melting Point:180-190°C
Long-Term Storage:Store long-term at 2-8°C

BIOLOGICAL INFO
Solubility:Insoluble in water; Very soluble in DMSO; Slightly soluble in hot methanol
Application(s):Angiotensin II type 1 (AT1) receptor antagonist
Form:Free Base

REVIEW

 Irbesartan is a nonpeptide tetrazole derivative and an angiotensin II antagonist that selectively blocks the binding of angiotensin II to the AT1 receptor. In the renin-angiotensin system, angiotensin I is converted by angiotensin-converting enzyme (ACE) to form angiotensin II. Angiotensin II stimulates the adrenal cortex to synthesize and secrete aldosterone, which decreases the excretion of sodium and increases the excretion of potassium. Angiotensin II also acts as a vasoconstrictor in vascular smooth muscle. Irbesartan, by blocking the binding of angiotensin II to the AT1 receptor, promotes vasodilation and decreases the effects of aldosterone. The negative feedback regulation of angiotensin II on renin secretion is also inhibited, but the resulting rise in plasma renin concentrations and consequent rise in angiotensin II plasma concentrations do not counteract the blood pressure-lowering effect that occurs. The action of ARBs is different from ACE inhibitors, which block the conversion of angiotensin I to angiotensin II, meaning that the production of angiotensin II is not completely inhibited, as the hormone can be formed via other enzymes. Also, unlike ACE inhibitors, irbesartan and other ARBs do not interfere with response to bradykinins and substance P, which allows for the absence of adverse effects that are present in ACE inhibitors (eg. dry cough).

REFERENCES
[1]Lewis EJ, Hunsicker LG, Clarke WR, Berl T, Pohl MA, Lewis JB, Ritz E, Atkins RC, Rohde R, Raz I; Collaborative Study Group. (2001). Renoprotective effect of the angiotensin-receptor antagonist irbesartan in patients with nephropathy due to type 2 diabetes. N Engl J Med 345 (12): 851-60. doi:10.1056/NEJMoa011303. PMID 11565517.
[2] Rossi S, editor. Australian Medicines Handbook 2006. Adelaide: Australian Medicines Handbook; 2006. ISBN 0-9757919-2-3
[3] Massie BM, Carson PE, McMurray JJ, Komajda M, McKelvie R, Zile MR, Anderson S, Donovan M, Iverson E, Staiger C, Ptaszynska A (December 2008). Irbesartan in patients with heart failure and preserved ejection fraction. N. Engl. J. Med. 359 (23): 2456-67. doi:10.1056/NEJMoa0805450. PMID 19001508.

GHS

Pictograms

Signal Word
Warning

Hazard Statements
H315; H319; H335

Precautionary Statements
P261; P264; P271; P280; P302+P352; P304+P340; P305+P351+P338; P312; P321; P332+P313; P337+P313; P362; P403+P233; P405; P501


Current as of August 21, 2019

AKSci Reference Standards are high-purity, low-impurity compounds suitable for use as standards.


Download SDS

For research use only. Not for diagnostic or therapeutic use.
Not for human use.


CATEGORIES

 APIs and Bioactives > Angiotensin Receptor Blockers


PubChem