Irbesartan

Irbesartan, sold under the brand name Avapro among others, is a medication used to treat high blood pressure, heart failure, and diabetic kidney disease.[2] It is a reasonable initial treatment for high blood pressure.[2] It is taken by mouth.[2] Versions are available as the combination irbesartan/hydrochlorothiazide.[2][3]

Irbesartan
Clinical data
Pronunciation/ɜːrbəˈsɑːrtən/
Trade namesAvapro, 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)
  • UK: POM (Prescription only)
  • US: ℞-only
  • EU: Rx-only
  • 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
CompTox Dashboard (EPA)
ECHA InfoCard100.119.966
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)

Common side effects include dizziness, diarrhea, feeling tired, muscle pain, and heartburn.[2][4] Serious side effects may include kidney problems, low blood pressure, and angioedema.[2] Use in pregnancy may harm the baby and use when breastfeeding is not recommended.[5] It is an angiotensin II receptor antagonist and works by blocking the effects of angiotensin II.[2]

Irbesartan was patented in 1990, and approved for medical use in 1997.[6] It is available as a generic medication.[4] In 2020, it was the 148th most commonly prescribed medication in the United States, with more than 4 million prescriptions.[7][8]

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

Combination with diuretic

Irbesartan is also available in a fixed-dose combination formulation with hydrochlorothiazide, a thiazide diuretic, to achieve an additive antihypertensive effect. [11] Irbesartan/hydrochlorothiazide combination preparations are marketed under various brand names.[12]

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.[3][1]

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.[13]

References
  1. "Irbesartan (Avapro) Use During Pregnancy". Drugs.com. 16 August 2018. Retrieved 19 March 2020.
  2. "Irbesartan Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  3. "Avalide- irbesartan and hydrochlorothiazide tablet, film coated". DailyMed. 31 July 2018. Retrieved 19 March 2020.
  4. British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 175. ISBN 9780857113382.
  5. "Irbesartan Pregnancy and Breastfeeding Warnings". Drugs.com. Retrieved 3 March 2019.
  6. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 470. ISBN 9783527607495.
  7. "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  8. "Irbesartan - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  9. Lewis EJ, Hunsicker LG, Clarke WR, Berl T, Pohl MA, Lewis JB, et al. (September 2001). "Renoprotective effect of the angiotensin-receptor antagonist irbesartan in patients with nephropathy due to type 2 diabetes". The New England Journal of Medicine. 345 (12): 851–860. doi:10.1056/NEJMoa011303. hdl:2445/122787. PMID 11565517.
  10. Rossi S, ed. (2006). Australian Medicines Handbook. Adelaide: Australian Medicines Handbook. ISBN 0-9757919-2-3.
  11. "Irbesartan and Hydrochlorothiazide (Professional Patient Advice)". Drugs.com. 5 June 2019. Retrieved 19 March 2020.
  12. "Irbesartan and hydrochlorothiazide Advanced Patient Information". Drugs.com. 24 December 2019. Retrieved 19 March 2020.
  13. "Recalls of Angiotensin II Receptor Blockers (ARBs) including Valsartan, Losartan and Irbesartan". U.S. Food and Drug Administration (FDA). 10 May 2021.
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