Azilsartan

Azilsartan

Systematic (IUPAC) name
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-1-([2'-(5-oxo-4,5-dihydro-1,2,4-oxadiazol-3-yl)biphenyl-4-yl]methyl)-1H-benzimidazole-7-carboxylate
Clinical data
Trade names	Edarbi
AHFS/Drugs.com	Consumer Drug Information
MedlinePlus	a611028
Licence data	US FDA:link
Pregnancy category	C (1st trimester) D (2nd/3rd trimester) (US)
Legal status	UK: POM (Prescription only) US: ℞-only
Routes of administration	Oral
Identifiers
CAS Number	147403-03-0 N
ATC code	C09CA09 (WHO)
PubChem	CID: 9825285
IUPHAR/BPS	6900
ChemSpider	9413866 Y
UNII	F9NUX55P23 Y
ChEBI	CHEBI:68845 N
ChEMBL	CHEMBL57242 N
Synonyms	Azilsartan medoxomil
Chemical data
Formula	C25H20N4O5
Molecular mass	456.46 g/mol
SMILES O=C1O/C(=C(\O1)C)COC(=O)c3cccc2nc(OCC)n(c23)Cc6ccc(c5ccccc5C\4=N\C(=O)ON/4)cc6
InChI 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) Y Key:QJFSABGVXDWMIW-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Azilsartan (INN, codenamed TAK-536) is an angiotensin II receptor antagonist used in the treatment of hypertension, developed by Takeda.

It is marketed in tablet form under the trade name Edarbi as the prodrug azilsartan medoxomil (INN, codenamed TAK-491). On 25 February 2011, the U.S. Food and Drug Administration approved azilsartan medoxomil for the treatment of high blood pressure in adults. On March 8, 2012, Health Canada approved the drug for mild to moderate essential hypertension.

Contraindications

Azilsartan should not be used with aliskiren, a renin inhibitor, in patients with diabetes as this increases the risk of serious adverse effects.

Mechanism of action

Main article: Angiotensin II receptor antagonist

Azilsartan medoxomil lowers blood pressure by blocking the action of angiotensin II, a vasopressor hormone.

Azilsartan medoxomil, the prodrug used, Edarbi