Irbesartan

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Irbesartan
File:Irbesartan skeletal.svg
File:Irbesartan-from-xtal-3D-bs-17.png
Clinical data
Pronunciation/ɜːrbəˈsɑːrtən/
Trade namesAprovel, others
AHFS/Drugs.comMonograph
MedlinePlusa698009
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classCardiovascular agent
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)[2]
  • UK: POM (Prescription only)
  • US: ℞-only[3]
  • EU: Rx-only[4]
  • In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability60% to 80%
Protein binding~90%
MetabolismLiver (CYP2C9)
Elimination half-life11 h to 15 h
ExcretionKidney 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
E number{{#property:P628}}
CompTox Dashboard (EPA)
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Chemical and physical data
FormulaC25H28N6O
Molar mass428.540 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) checkY
  • Key:YOSHYTLCDANDAN-UHFFFAOYSA-N checkY
  (verify)

Irbesartan, sold under the brand name Aprovel among others, is a medication used to treat hypertension (high blood pressure), heart failure, and diabetic kidney disease.[5] It is a reasonable initial treatment for high blood pressure.[5] It is taken by mouth.[5] Versions are available as the combination irbesartan/hydrochlorothiazide.[5][6][7][8]

Medical uses

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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,[9] hypertension and microalbuminuria (>30 mg/24 h) or proteinuria (>900 mg/24 h).[10]

Combination with diuretic

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Irbesartan is also available in a fixed-dose combination formulation with hydrochlorothiazide, a thiazide diuretic, to achieve an additive antihypertensive effect.[11][12][7][13]

Side effects

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Common side effects include dizziness, diarrhea, feeling tired, muscle pain, and heartburn.[5][14] Serious side effects may include kidney problems, low blood pressure, and angioedema.[5] Use in pregnancy may harm the baby and use when breastfeeding is not recommended.[1]

Mechanism of action

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Irbesartan is an angiotensin II receptor antagonist and works by blocking the effects of angiotensin II.[5]

History

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Irbesartan 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.[3][1]

It was patented in 1990, and approved for medical use in 1997.[15] It is available as a generic medication.[14] In 2023, it was the 134th most commonly prescribed medication in the United States, with more than 4 million prescriptions.[16][17]

Society and culture

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Recalls

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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.[18] Health Canada also reported nitrosamine impurities.[19]

The FDA issued revised guidelines about nitrosamine impurities in September 2024.[20]

References

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