Benicar

Olmesartan medoxomil

Clinical data
Trade names	Olmecip.
AHFS/Drugs.com	Monograph
MedlinePlus	a603006
Pregnancy category	C (D if used in second or third trimester)
Routes of administration	Oral
ATC code	C09CA08 (WHO) C09DA08 (WHO) (with diuretics) C09DB02 (WHO) (with amlodipine)
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Bioavailability	26%
Metabolism	Hepatic (cannot be removed by hemodialysis)
Biological half-life	13 hours
Excretion	Renal 40%, biliary 60%
Identifiers
IUPAC name (5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylate
CAS Number	144689-63-4 Y
PubChem CID	130881
IUPHAR/BPS	591
DrugBank	DB00275 Y
ChemSpider	115748 Y
UNII	6M97XTV3HD
KEGG	D01204 Y
ChEMBL	CHEMBL1516 N
ECHA InfoCard	100.126.511
Chemical and physical data
Formula	C29H30N6O6
Molar mass	558.585 g/mol
3D model (Jmol)	Interactive image
SMILES O=C1O/C(=C(\O1)C)COC(=O)c2c(nc(n2Cc5ccc(c4ccccc4c3nnnn3)cc5)CCC)C(O)(C)C
InChI InChI=1S/C29H30N6O6/c1-5-8-23-30-25(29(3,4)38)24(27(36)39-16-22-17(2)40-28(37)41-22)35(23)15-18-11-13-19(14-12-18)20-9-6-7-10-21(20)26-31-33-34-32-26/h6-7,9-14,38H,5,8,15-16H2,1-4H3,(H,31,32,33,34) Y Key:UQGKUQLKSCSZGY-UHFFFAOYSA-N Y
NY (what is this?)

Olmesartan medoxomil is an angiotensin II receptor antagonist which has been used for the treatment of high blood pressure. It was developed by Sankyo in 1995, and is sold under the trade name Benicar Olmecip(Cipla)Olsar (Unichem Laboratories). An ester prodrug, it is completely and rapidly hydrolyzed to the active acid form, olmesartan (RNH-6270).

Olmesartan is indicated for the treatment of hypertension. It may be used alone or in combination with other antihypertensive agents. The U.S. Food and Drug Administration (FDA) has determined that the benefits of Benicar continue to outweigh its potential risks when used for the treatment of patients with high blood pressure according to the drug label.

Contraindications for treatment with olmesartan include biliary obstruction. Another major contraindication is pregnancy; reports in the scientific literature reveal fetal malformations for pregnant women taking sartan-derived drugs.

The incidence of adverse effects with Benicar (the US trade name for olmesartan medoxomil) is reported as similar to placebo; the only adverse effect that occurred in >1% of patients treated with it and more frequently than placebo was dizziness (3% vs 1%). The full prescribing information for Benicar notes as with all drugs that act directly on the renin-angiotensin system, olmesartan is contraindicated in pregnancy and can cause injury and even death to the developing fetus. In studies of angiotensin II receptor antagonists such as olmesartan, patients with unilateral or bilateral renal artery stenosis, increases in serum creatinine or blood urea nitrogen have been reported. There has been no long-term use of olmesartan medoxomil in patients with unilateral or bilateral renal artery stenosis, but similar results may be expected. Rarely, olmesartan can cause severe gastrointestinal issues. The symptoms, which include nausea, vomiting, diarrhea, weight loss, and electrolyte abnormalities, are common among those who have celiac disease. Recent studies suggested this form of sprue-like enteropathy could be caused by the inhibition of TGF-β, a polypeptide cytokine that maintains intestinal homeostasis. However, it is still unclear why this action was never observed with other ARBs.