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Details

Stereochemistry ACHIRAL
Molecular Formula C24H26N6O3.H2O
Molecular Weight 464.5178
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of OLMESARTAN MONOHYDRATE

SMILES

CCCc1nc(c(C(=O)O)n1Cc2ccc(cc2)-c3ccccc3-c4n[nH]nn4)C(C)(C)O.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 446.5026
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
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 No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021286s023lbl.pdf https://www.ncbi.nlm.nih.gov/pubmed/19033634 https://www.ncbi.nlm.nih.gov/pubmed/12076183

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

Curator's Comment:: Olmesartan in a dose dependent manner showed increase in antiepileptic activity toward chemically induced seizure model in mice. Human data not available.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
0.091 nM [Kd]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BENICAR

Approved Use

Benicar is indicated for the treatment of hypertension, to lower blood pressure. Lowering blood pressure reduces the risk of fatal and nonfatal cardiovascular events, primarily strokes and myocardial infarctions. These benefits have been seen in controlled trials of antihypertensive drugs from a wide variety of pharmacologic classes including the class to which this drug principally belongs. There are no controlled trials demonstrating risk reduction with Benicar. Control of high blood pressure should be part of comprehensive cardiovascular risk management, including, as appropriate, lipid control, diabetes management, antithrombotic therapy, smoking cessation, exercise, and limited sodium intake. Many patients will require more than one drug to achieve blood pressure goals. For specific advice on goals and management, see published guidelines, such as those of the National High Blood Pressure Education Program’s Joint National Committee on Prevention, Detection, Evaluation, and Treatment of High Blood Pressure (JNC). Numerous antihypertensive drugs, from a variety of pharmacologic classes and with different mechanisms of action, have been shown in randomized controlled trials to reduce cardiovascular morbidity and mortality, and it can be concluded that it is blood pressure reduction, and not some other pharmacologic property of the drugs, that is largely responsible for those benefits. The largest and most consistent cardiovascular outcome benefit has been a reduction in the risk of stroke, but reductions in myocardial infarction and cardiovascular mortality also have been seen regularly. Elevated systolic or diastolic pressure causes increased cardiovascular risk, and the absolute risk increase per mmHg is greater at higher blood pressures, so that even modest reductions of severe hypertension can provide substantial benefit. Relative risk reduction from blood pressure reduction is similar across populations with varying absolute risk, so the absolute benefit is greater in patients who are at higher risk independent of their hypertension (for example, patients with diabetes or hyperlipidemia), and such patients would be expected to benefit from more aggressive treatment to a lower blood pressure goal. Some antihypertensive drugs have smaller blood pressure effects (as monotherapy) in black patients, and many antihypertensive drugs have additional approved indications and effects (e.g., on angina, heart failure, or diabetic kidney disease). These considerations may guide selection of therapy. It may be used alone or in combination with other antihypertensive agents.

Launch Date

1.01969278E12
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2204 ng/mL
8 mg single, intravenous
dose: 8 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
OLMESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
5975 ng × h/mL
8 mg single, intravenous
dose: 8 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
OLMESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
14.5 h
8 mg single, intravenous
dose: 8 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
OLMESARTAN plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
80 mg 1 times / day multiple, oral
Highest studied dose
Dose: 80 mg, 1 times / day
Route: oral
Route: multiple
Dose: 80 mg, 1 times / day
Sources:
unhealthy, 65-75 years
n = 12
Health Status: unhealthy
Condition: hypertension
Age Group: 65-75 years
Sex: M+F
Population Size: 12
Sources:
320 mg single, oral
Highest studied dose
Dose: 320 mg
Route: oral
Route: single
Dose: 320 mg
Sources:
healthy
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
weak [Inhibition 10 uM]
weak [Inhibition 500 uM]
weak [Inhibition 500 uM]
weak [Inhibition 500 uM]
weak [Inhibition 500 uM]
weak [Inhibition 500 uM]
weak [Inhibition 500 uM]
Drug as victim
PubMed

PubMed

TitleDatePubMed
Effects of temocapril and olmesartan on myocardial sympathetic nervous activity and fatty acid metabolism in rats with chronic beta-adrenergic stimulation.
2003 Jan
Irbesartan: a review of its use in hypertension and in the management of diabetic nephropathy.
2004
Olmesartan improves endothelin-induced hypertension and oxidative stress in rats.
2004 Jul
Angiotensin II infusion increases hepatic triglyceride production via its type 2 receptor in rats.
2005 Aug
Mechanism of permeability-enhancing effect of EDTA and boric acid on the corneal penetration of 4-[1-hydroxy-1-methylethyl]-2-propyl-1-[4-[2-[tetrazole-5-yl]phenyl]phenyl] methylimidazole-5-carboxylic acid monohydrate (CS-088).
2005 Aug 11
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
Enhanced intrarenal angiotensinogen contributes to early renal injury in spontaneously hypertensive rats.
2005 Jul
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
Pravastatin enhances beneficial effects of olmesartan on vascular injury of salt-sensitive hypertensive rats, via pleiotropic effects.
2007 Mar
Improvement of stunned myocardium in dogs with olmesartan, an angiotensin II type 1 receptor antagonist, is independent of type 2 receptors.
2008
Inhibition of advanced glycation end products: an implicit goal in clinical medicine for the treatment of diabetic nephropathy?
2008 Apr
Reduction of albuminuria by angiotensin receptor blocker beyond blood pressure lowering: evaluation in megsin/receptor for advanced glycation end products/inducible nitric oxide synthase triple transgenic diabetic nephropathy mouse model.
2008 Dec
Comparison of effects of olmesartan and telmisartan on blood pressure and metabolic parameters in Japanese early-stage type-2 diabetics with hypertension.
2008 Jan
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

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
Pre-treatment with 100 nM olmesartan abolished Ang II-induced apoptosis in cultured mouse podocytes
Substance Class Chemical
Created
by admin
on Sat Jun 26 15:10:30 UTC 2021
Edited
by admin
on Sat Jun 26 15:10:30 UTC 2021
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
FDA UNII
DJD559V57Z
Created by admin on Sat Jun 26 15:10:30 UTC 2021 , Edited by admin on Sat Jun 26 15:10:30 UTC 2021
PRIMARY
CAS
913529-31-4
Created by admin on Sat Jun 26 15:10:30 UTC 2021 , Edited by admin on Sat Jun 26 15:10:30 UTC 2021
PRIMARY
PUBCHEM
9934159
Created by admin on Sat Jun 26 15:10:30 UTC 2021 , Edited by admin on Sat Jun 26 15:10:30 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE