Irbesartan

Irbesartan

Clinical data
Pronunciation	/ɜːrbəˈsɑːrtən/
Trade names	Aprovel, others
AHFS/Drugs.com	Monograph
MedlinePlus	a698009
License data	US  DailyMed:  Irbesartan
Pregnancy category	AU:D [1]
Routes of administration	By mouth
Drug class	Cardiovascular agent
ATC code	C09CA04 ( WHO ) C09DA04 ( WHO )
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
Bioavailability	60% to 80%
Protein binding	~90%
Metabolism	Liver (CYP2C9)
Elimination half-life	11 h to 15 h
Excretion	Kidney 20%, feces 65%
Identifiers
IUPAC name 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	138402-11-6  Y
PubChem CID	3749
IUPHAR/BPS	589
DrugBank	DB01029  Y
ChemSpider	3618  Y
UNII	J0E2756Z7N
KEGG	D00523  Y
ChEBI	CHEBI:5959  Y
ChEMBL	ChEMBL1513  Y
CompTox Dashboard (EPA)	DTXSID0023169
ECHA InfoCard	100.119.966
Chemical and physical data
Formula	C25H28N6O
Molar mass	428.540 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C1N(\C(=N/C12CCCC2)CCCC)Cc5ccc(c3ccccc3c4n[nH]nn4)cc5
InChI 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) Y Key:YOSHYTLCDANDAN-UHFFFAOYSA-N Y
(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

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] [12] [7] [13]}

Side effects

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

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

History

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

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

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

References

1. "Irbesartan Pregnancy and Breastfeeding Warnings". Drugs.com. 16 August 2018. Archived from the original on 2 May 2019. Retrieved 19 March 2020.
2. "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 6 July 2023. Retrieved 30 March 2024.
3. "Avapro- irbesartan tablet, film coated". DailyMed. 9 May 2025. Retrieved 5 August 2025.
4. "Aprovel EPAR". European Medicines Agency (EMA). 27 August 1997. Archived from the original on 13 June 2024. Retrieved 13 June 2024.
5. "Irbesartan Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 30 November 2019. Retrieved 3 March 2019.
6. "Avalide- irbesartan and hydrochlorothiazide tablet, film coated". DailyMed. 31 July 2018. Archived from the original on 15 February 2018. Retrieved 19 March 2020.
7. "CoAprovel EPAR". European Medicines Agency (EMA). 15 October 1998. Archived from the original on 13 June 2024. Retrieved 13 June 2024.
8. "Karvezide EPAR". European Medicines Agency (EMA). 16 October 1998. Retrieved 30 August 2024.
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. "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 6 July 2023. Retrieved 30 March 2024.
12. "Irbesartan and Hydrochlorothiazide (Professional Patient Advice)". Drugs.com. 5 June 2019. Archived from the original on 20 March 2020. Retrieved 19 March 2020.
13. "Irbesartan and hydrochlorothiazide Advanced Patient Information". Drugs.com. 24 December 2019. Archived from the original on 20 March 2020. Retrieved 19 March 2020.
14. British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 175. ISBN   9780857113382.
15. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 470. ISBN   9783527607495.
16. "Top 300 of 2023". ClinCalc. Archived from the original on 12 August 2025. Retrieved 12 August 2025.
17. "Irbesartan Drug Usage Statistics, United States, 2013 - 2023". ClinCalc. Retrieved 18 August 2025.
18. "Recalls of Angiotensin II Receptor Blockers (ARBs) including Valsartan, Losartan and Irbesartan". U.S. Food and Drug Administration (FDA). 10 May 2021. Archived from the original on 13 October 2023. Retrieved 30 January 2023.
19. "Nitrosamine impurities in medications: Guidance". Health Canada . 4 April 2022. Archived from the original on 1 June 2024. Retrieved 24 April 2023.
20. "Control of Nitrosamine Impurities in Human Drugs". U.S. Food and Drug Administration. 24 February 2021. Retrieved 6 September 2024.