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Details

Stereochemistry ACHIRAL
Molecular Formula C24H26N6O3
Molecular Weight 446.5016
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OLMESARTAN

SMILES

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

InChI

InChIKey=VTRAEEWXHOVJFV-UHFFFAOYSA-N
InChI=1S/C24H26N6O3/c1-4-7-19-25-21(24(2,3)33)20(23(31)32)30(19)14-15-10-12-16(13-11-15)17-8-5-6-9-18(17)22-26-28-29-27-22/h5-6,8-13,33H,4,7,14H2,1-3H3,(H,31,32)(H,26,27,28,29)

HIDE SMILES / InChI
Molecular Formula C24H26N6O3
Molecular Weight 446.5016
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
Olmesartan improves endothelin-induced hypertension and oxidative stress in rats.
2004 Jul
Self-association properties of 4-[1-hydroxy-1-methylethyl]-2-propyl-1-[4-[2-[tetrazole-5-yl]phenyl]phenyl] methylimidazole-5-carboxylic acid monohydrate (CS-088), an antiglaucoma ophthalmic agent.
2005 Aug 11
Renin-angiotensin system modulates oxidative stress-induced endothelial cell apoptosis in rats.
2005 Jun
Adding hydrochlorothiazide to olmesartan dose dependently improves 24-h blood pressure and response rates in mild-to-moderate hypertension.
2005 Nov
The regressive effect of an angiotensin II receptor blocker on formed fatty streaks in monkeys fed a high-cholesterol diet.
2005 Oct
Role of AT1 receptor in isoproterenol-induced cardiac hypertrophy and oxidative stress in mice.
2007 Apr
Effect of olmesartan on oxidative stress in hemodialysis patients.
2007 May
Inhibition of Fas-associated apoptosis in granulation tissue cells accompanies attenuation of postinfarction left ventricular remodeling by olmesartan.
2007 May
Improvement of stunned myocardium in dogs with olmesartan, an angiotensin II type 1 receptor antagonist, is independent of type 2 receptors.
2008
Comparison of effects of olmesartan and telmisartan on blood pressure and metabolic parameters in Japanese early-stage type-2 diabetics with hypertension.
2008 Jan
Culture period-dependent change of function and expression of ATP-binding cassette transporters in Caco-2 cells.
2009 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 Mon Oct 21 21:29:26 UTC 2019
Edited
by admin
on Mon Oct 21 21:29:26 UTC 2019
Record UNII
8W1IQP3U10
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OLMESARTAN
INN   MI   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
OLMESARTAN MEDOXOMIL SPECIFIED IMPURITY A [EP]
Common Name English
OLMESARTAN [INN]
Common Name English
OLMESARTAN MEDOXOMIL IMPURITY, OLMESARTAN- [USP]
Common Name English
OLMESARTAN [MI]
Common Name English
RNH-6270
Code English
OLMESARTAN [USAN]
Common Name English
OLMESARTAN [WHO-DD]
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)-
Common Name English
OLMESARTAN [VANDF]
Common Name English
Classification Tree Code System Code
WHO-ATC C09DB02
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
NDF-RT N0000175561
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
NCI_THESAURUS C66930
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
LIVERTOX 706
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
NDF-RT N0000000070
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
Code System Code Type Description
ChEMBL
CHEMBL1516
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
PRIMARY
NCI_THESAURUS
C66253
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
PRIMARY
HSDB
144689-24-7
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
PRIMARY
PUBCHEM
158781
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
PRIMARY
WIKIPEDIA
OLMESARTAN
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
PRIMARY
CAS
144689-24-7
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
PRIMARY
RXCUI
321064
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
PRIMARY RxNorm
IUPHAR
591
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
PRIMARY
INN
8612
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
PRIMARY
MERCK INDEX
M8203
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
PRIMARY Merck Index
EVMPD
SUB20707
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
PRIMARY
MESH
C437965
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
PRIMARY
LactMed
144689-24-7
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
PRIMARY
EPA CompTox
144689-24-7
Created by admin on Mon Oct 21 21:29:26 UTC 2019 , Edited by admin on Mon Oct 21 21:29:26 UTC 2019
PRIMARY
Related Record Type Details
Structure of OLMESARTAN MONOHYDRATE
SALT/SOLVATE -> PARENT
TYPE-1 ANGIOTENSIN II RECEPTOR
TARGET -> INHIBITOR
OAT-1
TRANSPORTER -> INHIBITOR
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
OAT-3
TRANSPORTER -> INHIBITOR
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
BINDING
OAT-4
TRANSPORTER -> INHIBITOR
CYTOCHROME P450 2J2
METABOLIC ENZYME -> INHIBITOR
As there is almost a negligible accumulation of olmesartan ain the liver it is thought not to inhibit the production of eicosanoids.
IC50
CYTOCHROME P450 2C9
METABOLIC ENZYME -> INHIBITOR
As there is almost a negligible accumulation of olmesartan ain the liver it is thought not to inhibit the production of eicosanoids.
IC50
Related Record Type Details
Structure of N-NITROSODIMETHYLAMINE
IMPURITY GENOTOXIC->PARENT
NDMA is an organic chemical that is in a family of potent carcinogens.
Structure of OLMESARTAN MEDOXOMIL
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Structure of N-NITROSODIETHYLAMINE
IMPURITY -> PARENT
Probable human carcinogen.
Structure of BENZYL(METHYL)NITROSAMINE
IMPURITY -> PARENT
Priority toxic pollutant.
Related Record Type Details
Structure of OLMESARTAN
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC
NIH
NCATS
PRIVACY ACT
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