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Details

Stereochemistry ACHIRAL
Molecular Formula C24H26N6O3.H2O
Molecular Weight 464.5169
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OLMESARTAN MONOHYDRATE

SMILES

O.CCCC1=NC(=C(N1CC2=CC=C(C=C2)C3=C(C=CC=C3)C4=NN=NN4)C(O)=O)C(C)(C)O

InChI

InChIKey=CBVAUXGQUBKMCU-UHFFFAOYSA-N
InChI=1S/C24H26N6O3.H2O/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);1H2

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

Molecular Formula H2O
Molecular Weight 18.0153
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.091 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BENICAR
PubMed

PubMed

TitleDatePubMed
Angiotensin II infusion increases hepatic triglyceride production via its type 2 receptor in rats.
2005 Aug
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
Pravastatin enhances beneficial effects of olmesartan on vascular injury of salt-sensitive hypertensive rats, via pleiotropic effects.
2007 Mar
Effect of olmesartan on oxidative stress in hemodialysis patients.
2007 May
Inhibition of advanced glycation end products: an implicit goal in clinical medicine for the treatment of diabetic nephropathy?
2008 Apr
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

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 18:15:44 UTC 2019
Edited
by admin
on Tue Oct 22 18:15:44 UTC 2019
Record UNII
DJD559V57Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
OLMESARTAN MONOHYDRATE
Common Name English
1H-IMIDAZOLE-5-CARBOXYLIC ACID, 4-(1-HYDROXY-1-METHYLETHYL)-2-PROPYL-1-((2'-(2H-TETRAZOL-5-YL)(1,1'-BIPHENYL)-4-YL)METHYL)-, HYDRATE (1:1)
Systematic Name English
Code System Code Type Description
CAS
913529-31-4
Created by admin on Tue Oct 22 18:15:44 UTC 2019 , Edited by admin on Tue Oct 22 18:15:44 UTC 2019
PRIMARY
PUBCHEM
9934159
Created by admin on Tue Oct 22 18:15:44 UTC 2019 , Edited by admin on Tue Oct 22 18:15:44 UTC 2019
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE