Irbesartan

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Irbesartan
Irbesartan skeletal.svg
Irbesartan-from-xtal-3D-bs-17.png
Clinical data
Pronunciation /ɜːrbəˈsɑːrtən/
Trade names Aprovel, Avapro, others
AHFS/Drugs.com Monograph
MedlinePlus a698009
License data
Pregnancy
category
Routes of
administration 		By mouth
Drug class Cardiovascular agent
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only) [2]
  • UK: POM (Prescription only)
  • US: WARNING [3] Rx-only
  • 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
  • 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 OOjs UI icon edit-ltr-progressive.svg
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) Yes check.svgY
  • Key:YOSHYTLCDANDAN-UHFFFAOYSA-N Yes check.svgY
   (verify)

Irbesartan, sold under the brand name Aprovel among others, is a medication used to treat 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]

Contents

Common side effects include dizziness, diarrhea, feeling tired, muscle pain, and heartburn. [5] [9] 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. [10] It is an angiotensin II receptor antagonist and works by blocking the effects of angiotensin II. [5]

Irbesartan was patented in 1990, and approved for medical use in 1997. [11] It is available as a generic medication. [9] In 2022, it was the 200th most commonly prescribed medication in the United States, with more than 2 million prescriptions. [12] [13]

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, [14] hypertension and microalbuminuria (>30 mg/24 h) or proteinuria (>900 mg/24 h). [15]

Combination with diuretic

Irbesartan is also available in a fixed-dose combination formulation with hydrochlorothiazide, a thiazide diuretic, to achieve an additive antihypertensive effect. [16] [17] [7] [18]

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. [6] [1]

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. [19] Health Canada also reported nitrosamine impurities. [20]

The FDA issued revised guidelines about nitrosamine impurities in September 2024. [21]

Related Research Articles

<span class="mw-page-title-main">Hydrochlorothiazide</span> Diuretic medication

Hydrochlorothiazide, sold under the brand name Hydrodiuril among others, is a diuretic medication used to treat hypertension and swelling due to fluid build-up. Other uses include treating diabetes insipidus and renal tubular acidosis and to decrease the risk of kidney stones in those with a high calcium level in the urine. Hydrochlorothiazide is taken by mouth and may be combined with other blood pressure medications as a single pill to increase effectiveness. Hydrochlorothiazide is a thiazide medication which inhibits reabsorption of sodium and chloride ions from the distal convoluted tubules of the kidneys, causing a natriuresis. This initially increases urine volume and lowers blood volume. It is believed to reduce peripheral vascular resistance.

<span class="mw-page-title-main">Angiotensin II receptor blocker</span> Group of pharmaceuticals that modulate the renin–angiotensin system

Angiotensin II receptor blockers (ARBs), formally angiotensin II receptor type 1 (AT1) antagonists, also known as angiotensin receptor blockers, angiotensin II receptor antagonists, or AT1 receptor antagonists, are a group of pharmaceuticals that bind to and inhibit the angiotensin II receptor type 1 (AT1) and thereby block the arteriolar contraction and sodium retention effects of renin–angiotensin system.

<span class="mw-page-title-main">Rimonabant</span> Chemical compound

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<span class="mw-page-title-main">Ranitidine</span> Medication that decreases stomach acid

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<span class="mw-page-title-main">Telmisartan</span> Blood pressure medication

Telmisartan, sold under the brand name Micardis among others, is a medication used to treat high blood pressure and heart failure. It is a reasonable initial treatment for high blood pressure. It is taken by mouth.

<span class="mw-page-title-main">Benazepril</span> Medication used to treat high blood pressure and heart failure

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<span class="mw-page-title-main">Losartan</span> Blood pressure medication

Losartan, sold under the brand name Cozaar among others, is a medication used to treat high blood pressure (hypertension). It is in the angiotensin receptor blocker (ARB) family of medication, and is considered protective of the kidneys. Besides hypertension, it is also used in diabetic kidney disease, heart failure, and left ventricular enlargement. It comes as a tablet that is taken by mouth. It may be used alone or in addition to other blood pressure medication. Up to six weeks may be required for the full effects to occur.

<span class="mw-page-title-main">Valsartan</span> Angiotensin II receptor antagonist

Valsartan, sold under the brand name Diovan among others, is a medication used to treat high blood pressure, heart failure, and diabetic kidney disease. It belongs to a class of medications referred to as angiotensin II receptor blockers (ARBs). It is a reasonable initial treatment for high blood pressure. It is taken by mouth.

<span class="mw-page-title-main">Olmesartan</span> Angiotensin II receptor antagonist

Olmesartan, sold under the brand name Benicar among others, is a medication used to treat high blood pressure (hypertension). It is taken orally. Versions are available as the combination olmesartan/hydrochlorothiazide and olmesartan/amlodipine. It is available as a prodrug, olmesartan medoxomil.

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<span class="mw-page-title-main">Amlodipine/valsartan</span> Antihypertensive medication

Amlodipine/valsartan, sold under the brand name Exforge among others, is a blood pressure lowering combination drug. It contains amlodipine, as the besilate, a dihydropyridine-type calcium channel blocker, and valsartan, an angiotensin II receptor antagonist. This combination is usually well tolerated and effective for the reduction of blood pressure.

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<i>N</i>-Nitrosodimethylamine Chemical compound

N-Nitrosodimethylamine (NDMA), also known as dimethylnitrosamine (DMN), is an organic compound with the formula (CH3)2NNO. It is one of the simplest members of a large class of nitrosamines. It is a volatile yellow oil. NDMA has attracted wide attention as being highly hepatotoxic and a known carcinogen in laboratory animals.

<i>N</i>-Nitrosodiethylamine Chemical compound

N-Nitrosodiethylamine (NDEA) is an organic compound with the formula Et2NNO (Et = C2H5). A member of the nitrosamines, it is a light-sensitive, volatile, clear yellow oil that is soluble in water, lipids, and other organic solvents. It has an amine or aromatic odor. It is used as gasoline and lubricant additive, antioxidant, and stabilizer for industry materials. When heated to decomposition, N-nitrosodiethylamine emits toxic fumes of nitrogen oxides. N-Nitrosodiethylamine affects DNA integrity, probably by alkylation, and is used in experimental research to induce liver tumorigenesis. It is carcinogenic and mutagenic. NDEA has also been found to perturb amino acid biosynthesis including arginine, as well as DNA damage repair and mitochondrial genome maintenance in yeast.

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The angiotensin receptor blockers (ARBs), also called angiotensin (AT1) receptor antagonists or sartans, are a group of antihypertensive drugs that act by blocking the effects of the hormone angiotensin II in the body, thereby lowering blood pressure. Their structure is similar to Ang II and they bind to Ang II receptors as inhibitors, e.g., [T24 from Rhys Healthcare].

<span class="mw-page-title-main">Valsartan/hydrochlorothiazide</span> Chemical compound

Valsartan/hydrochlorothiazide, sold under the brand name Diovan HCT among others, is a medication used to treat high blood pressure when valsartan is not sufficient. It is a combination of valsartan, an angiotensin receptor blocker with hydrochlorothiazide, a diuretic. It is taken by mouth.

Losartan/hydrochlorothiazide, sold under the brand name Hyzaar among others, is a fixed-dose combination medication used to treat high blood pressure when losartan is not sufficient. It consists of losartan, an angiotensin II receptor blocker; and hydrochlorothiazide, a thiazide diuretic. It is taken by mouth.

<span class="mw-page-title-main">Sacubitril/valsartan</span> Combination medication

Sacubitril/valsartan, sold under the brand name Entresto among others, is a fixed-dose combination medication for use in heart failure. It consists of the neprilysin inhibitor sacubitril and the angiotensin receptor blocker valsartan. The combination is sometimes described as an "angiotensin receptor-neprilysin inhibitor" (ARNi). In 2016, the American College of Cardiology/American Heart Association Task Force recommended it as a replacement for an ACE inhibitor or an angiotensin receptor blocker in people with heart failure with reduced ejection fraction.

References

  1. 1 2 "Irbesartan (Avapro) Use During Pregnancy". 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. ↑ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA . Retrieved 22 October 2023.
  4. ↑ "Aprovel EPAR". European Medicines Agency. 27 August 1997. Archived from the original on 13 June 2024. Retrieved 13 June 2024.
  5. 1 2 3 4 5 6 7 "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. 1 2 "Avalide- irbesartan and hydrochlorothiazide tablet, film coated". DailyMed. 31 July 2018. Archived from the original on 15 February 2018. Retrieved 19 March 2020.
  7. 1 2 "CoAprovel EPAR". European Medicines Agency. 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. 1 2 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 175. ISBN   9780857113382.
  10. ↑ "Irbesartan Pregnancy and Breastfeeding Warnings". Drugs.com. Archived from the original on 2 May 2019. Retrieved 3 March 2019.
  11. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 470. ISBN   9783527607495.
  12. ↑ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  13. ↑ "Irbesartan Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  14. ↑ 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.
  15. ↑ Rossi S, ed. (2006). Australian Medicines Handbook . Adelaide: Australian Medicines Handbook. ISBN   0-9757919-2-3.
  16. ↑ "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.
  17. ↑ "Irbesartan and Hydrochlorothiazide (Professional Patient Advice)". Drugs.com. 5 June 2019. Archived from the original on 20 March 2020. Retrieved 19 March 2020.
  18. ↑ "Irbesartan and hydrochlorothiazide Advanced Patient Information". Drugs.com. 24 December 2019. Archived from the original on 20 March 2020. Retrieved 19 March 2020.
  19. ↑ "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.
  20. ↑ "Nitrosamine impurities in medications: Guidance". Health Canada . 4 April 2022. Archived from the original on 1 June 2024. Retrieved 24 April 2023.
  21. ↑ "Control of Nitrosamine Impurities in Human Drugs". U.S. Food and Drug Administration. 24 February 2021. Retrieved 6 September 2024.
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