Irbesartan

Irbesartan
Clinical data
Pronunciation
Trade names Avapro, others
AHFS/Drugs.com Monograph
MedlinePlus a698009
License data
Pregnancy
category
  • AU: D
Routes of
administration		 By mouth
Drug class Cardiovascular agent
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: WARNINGRx-only
  • EU: Rx-only
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability 60% to 80%
Protein binding ~90%
Metabolism Liver (CYP2C9)
Elimination half-life 11 h to 15 h
Excretion Kidney 20%, feces 65%
Identifiers
  • 2-butyl-3-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1,3-diazaspiro[4.4]non-1-en-4-one
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.119.966
Chemical and physical data
Formula C25H28N6O
Molar mass 428.540 g·mol−1
3D model (JSmol)
  • O=C1N(\C(=N/C12CCCC2)CCCC)Cc5ccc(c3ccccc3c4n[nH]nn4)cc5
  • 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) check
  • Key:YOSHYTLCDANDAN-UHFFFAOYSA-N check
  (verify)

Irbesartan, sold under the brand name Avapro among others, is a medication used to treat high blood pressure, heart failure, and diabetic kidney disease. It is a reasonable initial treatment for high blood pressure. It is taken by mouth. Versions are available as the combination irbesartan/hydrochlorothiazide.

Common side effects include dizziness, diarrhea, feeling tired, muscle pain, and heartburn. Serious side effects may include kidney problems, low blood pressure, and angioedema. Use in pregnancy may harm the baby and use when breastfeeding is not recommended. It is an angiotensin II receptor antagonist and works by blocking the effects of angiotensin II.

Irbesartan was patented in 1990, and approved for medical use in 1997. It is available as a generic medication. In 2020, it was the 148th most commonly prescribed medication in the United States, with more than 4 million prescriptions.

Structure activity relationship

Irbesartan has the common structural features seen within the Angiotensin-II Receptor blockers or ARB medications. The medicine has an extended diphenyl group with a tetrazole at the 2-prime position. At the 4'prime position, the molecule has a diazaspiro04-none, which is on a methyl.

Medical uses

Irbesartan is used for the treatment of hypertension. It may also delay progression of diabetic nephropathy and is also indicated for the reduction of renal disease progression in patients with type 2 diabetes, hypertension and microalbuminuria (>30 mg/24 h) or proteinuria (>900 mg/24 h).

Combination with diuretic

Irbesartan is also available in a fixed-dose combination formulation with hydrochlorothiazide, a thiazide diuretic, to achieve an additive antihypertensive effect. Irbesartan/hydrochlorothiazide combination preparations are marketed under various brand names.

Society and culture

Brand names

It was developed by Sanofi Research (part of Sanofi-Aventis). It is jointly marketed by Sanofi-Aventis and Bristol-Myers Squibb under the brand names Aprovel, Karvea, and Avapro.

Recalls

See also: Valsartan § recalls, and Angiotensin II receptor blocker § recalls

In 2018, the US Food and Drug Administration (FDA) reported that some versions of the angiotensin II receptor blocker medicines (including valsartan, losartan, irbesartan and other "-sartan" drugs) contain nitrosamine impurities.