Details
Stereochemistry | ACHIRAL |
Molecular Formula | C24H26N6O3 |
Molecular Weight | 446.5016 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
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=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)
Molecular Formula | C24H26N6O3 |
Molecular Weight | 446.5016 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/18547134Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18547134
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25478368
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.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL227 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17572702 |
0.091 nM [Kd] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | BENICAR Approved UseBenicar 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 Date2002 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2204 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11451211 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
5975 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11451211 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
14.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/11451211 |
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
Dose | Population | Adverse 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 Health Status: healthy Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as perpetrator
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 14.0 |
no | |||
yes [Km 20 uM] | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Olmesartan improves endothelin-induced hypertension and oxidative stress in rats. | 2004 Jul |
|
Clinical and experimental aspects of olmesartan medoxomil, a new angiotensin II receptor antagonist. | 2004 Winter |
|
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 |
|
The regressive effect of an angiotensin II receptor blocker on formed fatty streaks in monkeys fed a high-cholesterol diet. | 2005 Oct |
|
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 |
|
Inhibition of advanced glycation end products: an implicit goal in clinical medicine for the treatment of diabetic nephropathy? | 2008 Apr |
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Olmesartan ameliorates myocardial function independent of blood pressure control in patients with mild-to-moderate hypertension. | 2009 Jul |
|
Protective effects of angiotensin II type-1 receptor blockade with olmesartan on spinal cord ischemia-reperfusion injury: an experimental study on rats. | 2010 Aug |
|
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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23800993
Pre-treatment with 100 nM olmesartan abolished Ang II-induced apoptosis in cultured mouse podocytes
Substance Class |
Chemical
Created
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Record UNII |
8W1IQP3U10
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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WHO-ATC |
C09DB02
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NDF-RT |
N0000175561
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NCI_THESAURUS |
C66930
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LIVERTOX |
NBK548153
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NDF-RT |
N0000000070
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CHEMBL1516
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DB00275
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C66253
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759810
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8214
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158781
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100000086475
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OLMESARTAN
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144689-24-7
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321064
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591
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8W1IQP3U10
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8612
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m8203
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SUB20707
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8W1IQP3U10
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NN-36
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C437965
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Olmesartan
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DTXSID2040571
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48416
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Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR | |||
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SALT/SOLVATE -> PARENT | |||
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TARGET -> INHIBITOR |
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BINDER->LIGAND |
BINDING
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BINDER->LIGAND |
BINDING
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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
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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
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SOLVATE->ANHYDROUS | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
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PRODRUG -> METABOLITE ACTIVE |
Related Record | Type | Details | ||
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IMPURITY GENOTOXIC->PARENT |
NDMA is an organic chemical that is in a family of potent carcinogens.
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
Probable human carcinogen.
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IMPURITY -> PARENT |
Priority toxic pollutant.
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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