U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C29H30N6O6
Molecular Weight 558.5851
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OLMESARTAN MEDOXOMIL

SMILES

CCCC1=NC(=C(N1CC2=CC=C(C=C2)C3=CC=CC=C3C4=NN=NN4)C(=O)OCC5=C(C)OC(=O)O5)C(C)(C)O

InChI

InChIKey=UQGKUQLKSCSZGY-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Molecular Formula C29H30N6O6
Molecular Weight 558.5851
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Olmesartan medoxomil, a prodrug, is hydrolyzed to olmesartan during absorption from the gastrointestinal tract. Olmesartan is a selective AT1 subtype angiotensin II receptor antagonist. Olmesartan blocks the vasoconstrictor effects of angiotensin II by selectively blocking the binding of angiotensin II to the AT1 receptor in vascular smooth muscle. Oral olmesartan medoxomil 10-40 mg once daily is recommended for the treatment of adult patients with hypertension, this dosage has consistently helped achieve a double-digit reduction both in systolic and diastolic blood pressure, a reduction which is maintained for one year. Extensive clinical evidence from several large well designed trials and the clinical practice setting has confirmed the antihypertensive efficacy and good tolerability profile of oral olmesartan medoxomil, as monotherapy in patients with hypertension. Olmesartan medoxomil has shown no clinically important pharmacokinetic interactions with digoxin, warfarin or antacid (aluminium magnesium hydroxide). Adverse events were infrequent in clinical studies of olmesartan medoxomil and were similar to those attributed to placebo.

CNS Activity

Originator

Approval Year

2002
55
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2491
Hypertension
 0.091 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Type-1 angiotensin II receptor
Approved
7883
BENICAR
Approved (off-label)
8
PubMed

PubMed

TitleDatePubMed
Adding hydrochlorothiazide to olmesartan dose dependently improves 24-h blood pressure and response rates in mild-to-moderate hypertension.
2005 Nov
Hydrochlorothiazide added to valsartan is more effective than when added to olmesartan in reducing blood pressure in moderately hypertensive patients inadequately controlled by monotherapy.
2006 Sep-Oct
Effect of olmesartan on oxidative stress in hemodialysis patients.
2007 May
Comparison of effects of olmesartan and telmisartan on blood pressure and metabolic parameters in Japanese early-stage type-2 diabetics with hypertension.
2008 Jan
Aldosterone induces interleukin-18 through endothelin-1, angiotensin II, Rho/Rho-kinase, and PPARs in cardiomyocytes.
2008 Sep
Olmesartan improves left ventricular function in pressure-overload hypertrophied rat heart by blocking angiotensin II receptor with synergic effects of upregulation of angiotensin converting enzyme 2.
2009 Apr
Olmesartan ameliorates myocardial function independent of blood pressure control in patients with mild-to-moderate hypertension.
2009 Jul
Culture period-dependent change of function and expression of ATP-binding cassette transporters in Caco-2 cells.
2009 Sep
Protective effects of angiotensin II type-1 receptor blockade with olmesartan on spinal cord ischemia-reperfusion injury: an experimental study on rats.
2010 Aug
Efficacy of Sevikar® compared to the combination of perindopril plus amlodipine on central arterial blood pressure in patients with moderate-to-severe hypertension: Rationale and design of the SEVITENSION study.
2011 Sep
Early treatment with olmesartan prevents juxtamedullary glomerular podocyte injury and the onset of microalbuminuria in type 2 diabetic rats.
2012 May
Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11).
2013 Dec
Modulation of carbon tetrachloride-induced hepatic oxidative stress, injury and fibrosis by olmesartan and omega-3.
2014 Jan 25
Patents

Patents

5744612
10
6040454
8
JP2006290899A
4

Sample Use Guides

In Vivo Use Guide
BENICAR (olmesartan med oxomil) tablets dosage. Adult hypertension: Starting dose - 20 mg once daily (dose range 20 - 40 mg once daily). Pediatric hypertension (6 - 16 years): Starting dose for patients with body weight 20 to <35 kg - 10 mg once daily, if body weight >35 kg - 20 mg once daily (dose range 10 - 20 mg once daily and 20 - 40 mg once daily, respectively)
Route of Administration: Oral
In Vitro Use Guide
Pre-treatment with 100 nM olmesartan abolished Ang II-induced apoptosis in cultured mouse podocytes
Substance Class Chemical
Created
by admin
on Tue Oct 22 00:04:38 UTC 2019
Edited
by admin
on Tue Oct 22 00:04:38 UTC 2019
Record UNII
6M97XTV3HD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OLMESARTAN MEDOXOMIL
INN   JAN   MART.   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
OLMESARTAN MEDOXOMIL COMPONENT OF TRIBENZOR
Brand Name English
OLMESARTAN MEDOXOMIL [ORANGE BOOK]
Common Name English
AZOR COMPONENT OLMESARTAN MEDOXOMIL
Common Name English
OLMESARTAN MEDOXOMIL [USP-RS]
Common Name English
OLMESARTAN MEDOXOMIL [INN]
Common Name English
OLMESARTAN MEDOXOMIL [VANDF]
Common Name English
BENICAR
Brand Name English
OLMESARTAN MEDOXOMIL COMPONENT OF BENICAR HCT
Common Name English
CS-866
Code English
OLMESARTAN MEDOXOMIL [JAN]
Common Name English
OLMESARTAN MEDOXOMIL [USAN]
Common Name English
OLMESARTAN MEDOXOMIL [MART.]
Common Name English
BENICAR HCT COMPONENT OLMESARTAN MEDOXOMIL
Common Name English
1H-IMIDAZOLE-5-CARBOXYLIC ACID, 4-(1-HYDROXY-1-METHYLETHYL)-2-PROPYL-1-((2'-(1H-TETRAZOL-5-YL)(1,1'-BIPHENYL)-4-YL)METHYL)-, (5-METHYL-2-OXO-1,3- DIOXOL-4-YL)METHYL ESTER
Common Name English
OLMESARTAN MEDOXOMIL [WHO-DD]
Common Name English
OLMESARTAN MEDOXOMIL COMPONENT OF AZOR
Common Name English
OLMETEC
Brand Name English
TRIBENZOR COMPONENT OLMESARTAN MEDOXOMIL
Brand Name English
Classification Tree Code System Code
WHO-ATC C09DA08
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
WHO-ATC C09DX03
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
WHO-ATC C09CA08
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
NCI_THESAURUS C66930
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
WHO-VATC QC09CA08
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
WHO-VATC QC09DB02
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
WHO-VATC QC09DA08
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
WHO-ATC C09DB02
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
Code System Code Type Description
MESH
C097933
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
PRIMARY
PUBCHEM
130881
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
PRIMARY
ChEMBL
CHEMBL1200692
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
PRIMARY
EPA CompTox
144689-63-4
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
PRIMARY
MERCK INDEX
M8203
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
PRIMARY
RXCUI
118463
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
PRIMARY RxNorm
NCI_THESAURUS
C47640
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
PRIMARY
CAS
144689-63-4
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
PRIMARY
INN
7787
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
PRIMARY
DRUG BANK
DB00275
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
PRIMARY
EVMPD
SUB03508MIG
Created by admin on Tue Oct 22 00:04:38 UTC 2019 , Edited by admin on Tue Oct 22 00:04:38 UTC 2019
PRIMARY
Related Record Type Details
Structure of OLMESARTAN MEDOXOMIL
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
Related Record Type Details
Structure of TRITYLOLMESARTAN MEDOXOMIL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of N2-TRITYLOLMESARTAN MEDOXOMIL
IMPURITY -> PARENT
UNSPECIFIED
EP
Structure of DES(1-HYDROXY-1-METHYLETHYL)-(1-METHYLETHENYL)-OLMESARTAN MEDOXOMIL
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of OLMESARTAN
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of OLMESARTAN LACTONE
IMPURITY -> PARENT
UNSPECIFIED
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
Structure of OLMESARTAN
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966