Azilsartan

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Azilsartan
Clinical data
Trade namesEdarbi, Azilva
Other namesTAK-536, TAK-491
AHFS/Drugs.comMonograph
MedlinePlusa611028
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability60%
MetabolismCYP2C9
Elimination half-life11 hrs
Excretion55% feces, 42% urine
Identifiers
  • 2-Ethoxy-1-{[2'-(5-oxo-2,5-dihydro-1,2,4-oxadiazol-3-yl)-4-biphenylyl]methyl}-1H-benzimidazole-7-carboxylic acid
JSmol)
  • CCOC1=NC2=CC=CC(=C2N1CC3=CC=C(C=C3)C4=CC=CC=C4C5=NOC(=O)N5)C(=O)O
  • InChI=InChI=1S/C25H20N4O5/c1-2-33-24-26-20-9-5-8-19(23(30)31)21(20)29(24)14-15-10-12-16(13-11-15)17-6-3-4-7-18(17)22-27-25(32)34-28-22/h3-13H,2,14H2,1H3,(H,30,31)(H,27,28,32) ☒N
  • Key:KGSXMPPBFPAXLY-UHFFFAOYSA-N ☒N

  • as medoxomil: InChI=1S/C30H24N4O8 /c1-3-38-28-31-23-10-6-9-22(27(35)39-16-24-17(2)40-30(37)41-24)25(23)34(28)15-18-11-13-19(14-12-18)20-7-4-5-8-21(20)26-32-29(36)42-33-26/h4-14H,3,15-16H2,1-2H3,(H,32,33,36)
  • Key:QJFSABGVXDWMIW-UHFFFAOYSA-N
 ☒NcheckY (what is this?)  (verify)

Azilsartan, sold under the brand name Edarbi among others, is used for the treatment of

angiotensin II receptor antagonist,[5] and was developed by Takeda
.

The most common adverse reaction in adults is diarrhea.[2]

It is available as a

generic medication.[6] It is also sold as a combination drug with chlortalidone under the brand name Edarbyclor.[7]

Structure activity relationship

Like other ARBs, azilsartan has an extended diphenyl group within the structure. An interesting aspect of the molecule is that unlike other ARBs which have a tetrazole attached to the molecule, azilsartan has an oxadiazole, which has an acidic proton at the nitrogen. The tetrazole represents a non-classical bio-isostere. The carboxylate seen in the molecule is the active moiety after the molecule has been metabolized. Azilsartan is a pro-drug.[medical citation needed]

Medical uses

Azilsartan is used for the treatment of hypertension in adults.[5][8][2] One of the benefits of the medication is that Azilsartan does not need dose adjustments for patients with renal or hepatic dysfunction.

Contraindications

Azilsartan must not be used with aliskiren, a renin inhibitor, in patients with diabetes as this increases the risk of serious adverse effects.[5][2] Like other antihypertensive drugs acting on the renin–angiotensin system, it is contraindicated during the second and third trimesters of pregnancy.[5][8][9] It should not be used during pregnancy.[2][10]

Interactions

No relevant drug interactions have been found in studies.

potassium sparing diuretics.[8][9]

Pharmacology

Mechanism of action

Main article:
Angiotensin II receptor antagonist

Azilsartan medoxomil lowers blood pressure by blocking the action of

AT1 receptor, a hormone that contracts blood vessels and reduces water excretion through the kidneys.[8]

Pharmacokinetics

Azilsartan medoxomil is quickly absorbed from the gut, independently of food intake. Maximal

Elimination half life is about 11 hours. 55% are excreted via the feces, and 42% via the urine, of which 15% are present as azilsartan and the rest in form of the metabolites.[9]

Chemistry

Azilsartan medoxomil, the prodrug

The drug formulation contains the

lipophilic
than azilsartan itself.

History

In February 2011, the U.S. Food and Drug Administration (FDA) approved azilsartan medoxomil for the treatment of high blood pressure in adults.[11][12] In July 2011, azilsartan medoxomil was approved in the European Union for the treatment of essential hypertension.[5] In March 2012, Health Canada approved the drug for mild to moderate essential hypertension.[13]

In December 2014, Valeant Canada acquired the marketing rights to Edarbi and Edarbyclor from Takeda Pharmaceutical.[14]

References

  1. ^ "Product monograph brand safety updates". Health Canada. February 2024. Retrieved 24 March 2024.
  2. ^ a b c d e "Edarbi- azilsartan kamedoxomil tablet". DailyMed. 26 July 2019. Retrieved 9 March 2020.
  3. PMID 30860708
    .
  4. PMID 31885897
    .
  5. ^ a b c d e "Edarbi EPAR". European Medicines Agency (EMA). 18 May 2018. Retrieved 9 March 2020.
  6. ^ "2022 First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). 3 March 2023. Archived from the original on 30 June 2023. Retrieved 30 June 2023.
  7. ^ "Drug Approval Package:Edarbyclor (azilsartan medoxomil and chlorthalidone) NDA #202331". U.S. Food and Drug Administration (FDA). 16 August 2012. Retrieved 11 March 2020.
  8. ^ a b c d e Haberfeld H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag. Edarbi-Tabletten.
  9. ^
    ISBN 978-3-7741-9846-3
    .
  10. ^ "Azilsartan medoxomil (Edarbi) Use During Pregnancy". Drugs.com. 28 February 2020. Retrieved 9 March 2020.
  11. ^ "Drug Approval Package: Edarbi (azilsartan medoxomil) NDA 200796". U.S. Food and Drug Administration (FDA). 4 April 2011. Retrieved 9 March 2020.
  12. ^ "FDA approves Edarbi to treat high blood pressure" (Press release). U.S. Food and Drug Administration. 25 February 2011. Archived from the original on 18 January 2017. Retrieved 1 March 2011.
  13. ^ "Summary Basis of Decision - Edarbi - Health Canada". Government of Canada. 26 June 2012. Retrieved 6 March 2021.
  14. ^ "Valeant Canada acquires rights to Edarbi and Edarbyclor for the Canadian market" (Press release). Valeant Canada. 17 December 2014. Retrieved 9 March 2020 – via Cision.
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