Identification

Name
Olmesartan
Accession Number
DB00275
Description

Olmesartan belongs to the angiotensin II receptor blocker (ARB) family of drugs, which also includes telmisartan, candesartan, losartan, valsartan, and irbesartan. ARBs selectively bind to angiotensin receptor 1 (AT1) and prevent the protein angiotensin II from binding and exerting its hypertensive effects, which include vasoconstriction, stimulation and synthesis of aldosterone and ADH, cardiac stimulation, and renal reabsorption of sodium, among others. Overall, olmesartan's physiologic effects lead to reduced blood pressure, lower aldosterone levels, reduced cardiac activity, and increased excretion of sodium.

Olmesartan also affects the renin-angiotensin aldosterone system (RAAS), which plays an important role in hemostasis and regulation of kidney, vascular, and cardiac functions. Pharmacological blockade of RAAS via AT1 receptor blockade inhibits negative regulatory feedback within RAAS, which is a contributing factor to the pathogenesis and progression of cardiovascular disease, heart failure, and renal disease. In particular, heart failure is associated with chronic activation of RAAS, leading to inappropriate fluid retention, vasoconstriction, and ultimately a further decline in left ventricular function. ARBs have been shown to have a protective effect on the heart by improving cardiac function, reducing afterload, increasing cardiac output and preventing ventricular hypertrophy and remodelling.4

By comparison, the angiotensin-converting enzyme inhibitor (ACEi) class of medications (which includes drugs such as ramipril, lisinopril, and perindopril) inhibit the conversion of angiotensin I to angiotensin II through inhibition of the ACE enzyme. However, this does not prevent the formation of all angiotensin II within the body. The angiotensin II receptor blocker (ARB) family of drugs unique in that it blocks all angiotensin II activity, regardless of where or how it was synthesized.

Olmesartan is commonly used for the management of hypertension and Type 2 Diabetes-associated nephropathy, particularly in patients who are unable to tolerate ACE inhibitors. ARBs such as olmesartan have been shown in a number of large-scale clinical outcomes trials to improve cardiovascular outcomes including reducing risk of myocardial infarction, stroke, the progression of heart failure, and hospitalization.5,6,7,8,9,10,11,12 Like other ARBs, olmesartan blockade of RAAS slows the progression of diabetic nephropathy due to its renoprotective effects.13,14,15

Orally available olmesartan is produced as the prodrug olmesartan medoxomil which is rapidly converted in vivo to the pharmacologically active olmesartan.1 It was developed by Daiichi Sankyo Pharmaceuticals and approved in 2002.3

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 446.5016
Monoisotopic: 446.206638728
Chemical Formula
C24H26N6O3
Synonyms
  • 4-(1-hydroxy-1-methylethyl)-2-propyl-1-{[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylic acid
  • 4-(hydroxy-1-methylethyl)-2-propyl-1-{[2'-(1H-tetrazol-5-yl)-1,1'-biphenyl-4-yl]methyl}-1H-imidazole-5-carboxylic acid
  • Olmesartan
External IDs
  • DE-092
  • RNH-6270

Pharmacology

Indication

Olmesartan is indicated for the treatment of hypertension either alone or in combination with other antihypertensive agents.19,20,7

Olmesartan is also used off-label for the management Type 2 Diabetes-associated nephropathy, heart failure, and post-myocardial infarction, particularly in patients who are unable to tolerate ACE inhibitors.6,15,16 ARBs such as olmesartan have been shown in a number of large-scale clinical outcomes trials to improve cardiovascular outcomes including reducing risk of myocardial infarction, stroke, the progression of heart failure, and hospitalization.5,6,7,8,9,10,11,12 Like other ARBs, olmesartan blockade of RAAS slows the progression of diabetic nephropathy due to its renoprotective effects.13,14,15

Associated Conditions
Contraindications & Blackbox Warnings
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Pharmacodynamics

Overall, olmesartan's physiologic effects lead to reduced blood pressure, lower aldosterone levels, reduced cardiac activity, and increased excretion of sodium.

Hypotension in Volume- or Salt-Depleted Patients

In patients with an activated renin-angiotensin aldosterone system, such as volume-and/or salt-depleted patients (e.g., those being treated with high doses of diuretics), symptomatic hypotension may be anticipated after initiation of treatment with olmesartan. Initiate treatment under close medical supervision. If hypotension does occur, place the patient in the supine position and, if necessary, give an intravenous infusion of normal saline. A transient hypotensive response is not a contraindication to further treatment, which usually can be continued without difficulty once the blood pressure has stabilized.19,20

Valvular Stenosis: there is concern on theoretical grounds that patients with aortic stenosis might be at a particular risk of decreased coronary perfusion, because they do not develop as much afterload reduction.20

Impaired Renal Function

As a consequence of inhibiting the renin-angiotensin-aldosterone system, changes in renal function may be anticipated in susceptible individuals treated with olmesartan. In patients whose renal function may depend upon the activity of the renin-angiotensin- aldosterone system (e.g., patients with severe congestive heart failure), treatment with angiotensin converting enzyme (ACE) inhibitors and angiotensin receptor antagonists has been associated with oliguria and/or progressive azotemia and rarely with acute renal failure and/or death. Similar results may be anticipated in patients treated with olmesartan.

In studies of ACE inhibitors in patients with unilateral or bilateral renal artery stenosis, increases in serum creatinine or blood urea nitrogen (BUN) have been reported. There has been no long-term use of olmesartan medoxomil in patients with unilateral or bilateral renal artery stenosis, but similar results may be expected.19,20

Sprue-like Enteropathy

Severe, chronic diarrhea with substantial weight loss has been reported in patients taking olmesartan months to years after drug initiation. Intestinal biopsies of patients often demonstrated villous atrophy. If a patient develops these symptoms during treatment with olmesartan, exclude other etiologies. Consider discontinuation of olmesartan medoxomil in cases where no other etiology is identified.19,20

Electrolyte Imbalances

Olmesartan medoxomil contains olmesartan, a drug that inhibits the renin-angiotensin system (RAS). Drugs that inhibit the RAS can cause hyperkalemia. Monitor serum electrolytes periodically.19,20

Mechanism of action

Olmesartan belongs to the angiotensin II receptor blocker (ARB) family of drugs, which also includes telmisartan, candesartan, losartan, valsartan, and irbesartan. ARBs selectively bind to angiotensin receptor 1 (AT1) and prevent the protein angiotensin II from binding and exerting its hypertensive effects. As the principal pressor agent of the renin-angiotensin system, Angiotensin II causes vasoconstriction, stimulation of synthesis and release of aldosterone, cardiac stimulation and renal reabsorption of sodium. Olmesartan blocks the vasoconstrictor effects of angiotensin II by selectively blocking the binding of angiotensin II to the AT1 receptor in vascular smooth muscle. Its action is, therefore, independent of the pathways for angiotensin II synthesis.19 Overall, olmesartan's physiologic effects lead to reduced blood pressure, lower aldosterone levels, reduced cardiac activity, and increased excretion of sodium.

Olmesartan also effects on the renin-angiotensin aldosterone system (RAAS) plays an important role in hemostasis and regulation of kidney, vascular, and cardiac functions. Pharmacological blockade of RAAS via AT1 receptor blockade inhibits negative regulatory feedback within RAAS, which is a contributing factor to the pathogenesis and progression of cardiovascular disease, heart failure, and renal disease. In particular, heart failure is associated with chronic activation of RAAS, leading to inappropriate fluid retention, vasoconstriction, and ultimately a further decline in left ventricular function. ARBs have been shown to have a protective effect on the heart by improving cardiac function, reducing afterload, increasing cardiac output and preventing ventricular hypertrophy and remodelling.4

TargetActionsOrganism
AType-1 angiotensin II receptor
antagonist
Humans
Absorption

When taken orally, the prodrug olmesartan medoxomil is rapidly absorbed in the gastrointestinal tract and metabolized to olmesartan. The esterification with medoxomil was created with the intention of increasing olmesartan bioavailability from 4.5% to 28.6%.1

Oral administration of 10-160 mg of olmesartan has been shown to reach peak plasma concentration of 0.22-2.1 mg/L after 1-3 hours with an AUC of 1.6-19.9mgh/L.2 The pharmacokinetic profile of olmesartan has been observed to be nearly linear and dose-dependent under the therapeutic range.1 The steady-state level of olmesartan is achieved after once a day dosing during 3 to 5 days.[L5566]

Volume of distribution

17 L[L5566]

Protein binding

Olmesartan is highly bound to plasma proteins. 99% of the administered dose is found in a bound state with no penetration in red blood cells.[L5566]

Metabolism

Olmesartan medoxomil is rapidly and completely bioactivated by ester hydrolysis to olmesartan during absorption from the gastrointestinal tract. This rapid first-pass metabolism was confirmed by the lack of measurable amounts of olmesartan medoxomil in plasma or excreta.1 This first-pass metabolism is not driven by cytochrome enzymes and hence it is not expected to interact with other drugs via this mechanism.2

The pharmacologically active moiety does not appear to undergo further metabolism.1,18

Route of elimination

The main elimination route of olmesartan is in the unchanged form through the feces. From the systemically bioavailable dose, about 10-16% is eliminated in the urine.1

Half-life

The mean plasma olmesartan half-life is reported to be from 10-15 hours after multiple oral administration.1

Clearance

Total plasma clearance is 1.3 L/h and the renal clearance is 0.6 L/h.[L5566]

Adverse Effects
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Toxicity

The reported LD50 of olmesartan in dogs was reported to be greater of 1500 mg/kg. Overdose is expressed as hypotension, tachycardia, and bradycardia when there is parasympathetic stimulation. In case of overdose, supportive treatment is recommended.Label

Olmesartan was shown to be safe on carcinogenic and fertility studies. However, in in vitro mutagenic studies showed a potential to induce chromosomal aberrations in cells and it tested positive for thymidine kinase mutations in the mouse lymphoma assay.Label

Affected organisms
  • Humans and other mammals
Pathways
PathwayCategory
Olmesartan Action PathwayDrug action
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AcebutololThe risk or severity of hyperkalemia can be increased when Olmesartan is combined with Acebutolol.
AceclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Olmesartan is combined with Aceclofenac.
AcemetacinThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Olmesartan is combined with Acemetacin.
Acetylsalicylic acidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Olmesartan is combined with Acetylsalicylic acid.
AlclofenacThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Olmesartan is combined with Alclofenac.
AldesleukinThe risk or severity of adverse effects can be increased when Aldesleukin is combined with Olmesartan.
AlfentanilAlfentanil may decrease the antihypertensive activities of Olmesartan.
AlfuzosinAlfuzosin may increase the hypotensive activities of Olmesartan.
AliskirenThe risk or severity of hyperkalemia can be increased when Aliskiren is combined with Olmesartan.
AlmotriptanAlmotriptan may decrease the antihypertensive activities of Olmesartan.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Take with or without food. Food does not affect absorption.

Products

Product Ingredients
IngredientUNIICASInChI Key
Olmesartan medoxomil6M97XTV3HD144689-63-4UQGKUQLKSCSZGY-UHFFFAOYSA-N
Product Images
International/Other Brands
Erastapex (Apex Pharma) / Golme (Golgi USA Research Laboratories Ltd) / Olmy (Zydus Cadila) / Olsar (Unichem Laboratories) / Olvance (Ranbaxy Laboratories Ltd) / WinBP (Abbott Healthcare Pvt Ltd)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Act OlmesartanTabletOralTEVA Canada Limited2017-05-01Not applicableCanada flag
Act OlmesartanTabletOralTEVA Canada Limited2017-05-01Not applicableCanada flag
BenicarTablet, film coated40 mg/1OralCardinal Health2002-04-252018-10-31US flag55154 612720180913 8702 xha09y
BenicarTablet, film coated20 mg/1OralA-S Medication Solutions2002-04-25Not applicableUS flag54569 560620180907 15195 1hjkrfq
BenicarTablet, film coated40 mg/1OralPD-Rx Pharmaceuticals, Inc.2002-04-252019-09-12US flag
BenicarTablet, film coated20 mg/1OralCardinal Health2002-04-252017-05-31US flag55154 613020180913 8702 kx05re
BenicarTablet, film coated40 mg/1OralMed Pharma Co., Ltd.2012-02-02Not applicableUS flag65597 0104 90 nlmimage10 14130a78
BenicarTablet, film coated40 mg/1OralDaiichi Sankyo Inc.2002-04-25Not applicableUS flag
BenicarTablet, film coated40 mg/1OralPhysicians Total Care, Inc.2003-08-06Not applicableUS flag54868 488520180906 25352 kzz46a
BenicarTablet, film coated20 mg/1OralA-S Medication Solutions2002-04-25Not applicableUS flag50090 087720180913 8702 ab5pq4
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Ach-olmesartanTabletOralAccord Healthcare Inc2020-05-06Not applicableCanada flag
Ach-olmesartanTabletOralAccord Healthcare Inc2020-05-06Not applicableCanada flag
Ag-olmesartanTabletOralAngita Pharma Inc.2018-09-06Not applicableCanada flag
Ag-olmesartanTabletOralAngita Pharma Inc.2018-09-06Not applicableCanada flag
Apo-olmesartanTabletOralApotex Corporation2017-05-30Not applicableCanada flag
Apo-olmesartanTabletOralApotex Corporation2017-05-31Not applicableCanada flag
Apo-olmesartanTabletOralApotex CorporationNot applicableNot applicableCanada flag
Auro-olmesartanTabletOralAuro Pharma IncNot applicableNot applicableCanada flag
Auro-olmesartanTabletOralAuro Pharma Inc2017-05-01Not applicableCanada flag
Auro-olmesartanTabletOralAuro Pharma Inc2017-05-01Not applicableCanada flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Ach-olmesartan HctzOlmesartan medoxomil (40 mg) + Hydrochlorothiazide (12.5 mg)TabletOralAccord Healthcare Inc2019-06-27Not applicableCanada flag
Ach-olmesartan HctzOlmesartan medoxomil (20 mg) + Hydrochlorothiazide (12.5 mg)TabletOralAccord Healthcare Inc2019-06-27Not applicableCanada flag
Ach-olmesartan HctzOlmesartan medoxomil (40 mg) + Hydrochlorothiazide (25 mg)TabletOralAccord Healthcare Inc2019-06-27Not applicableCanada flag
Act Olmesartan HCTOlmesartan medoxomil (40 mg) + Hydrochlorothiazide (12.5 mg)TabletOralTEVA Canada Limited2017-05-01Not applicableCanada flag
Act Olmesartan HCTOlmesartan medoxomil (20 mg) + Hydrochlorothiazide (12.5 mg)TabletOralTEVA Canada Limited2017-05-01Not applicableCanada flag
Act Olmesartan HCTOlmesartan medoxomil (40 mg) + Hydrochlorothiazide (25 mg)TabletOralTEVA Canada Limited2017-05-01Not applicableCanada flag
Ag-olmesartan HctzOlmesartan medoxomil (40 mg) + Hydrochlorothiazide (12.5 mg)TabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Ag-olmesartan HctzOlmesartan medoxomil (40 mg) + Hydrochlorothiazide (25 mg)TabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Ag-olmesartan HctzOlmesartan medoxomil (20 mg) + Hydrochlorothiazide (12.5 mg)TabletOralAngita Pharma Inc.Not applicableNot applicableCanada flag
Amlodipine and Olmesartan MedoxomilOlmesartan medoxomil (20 mg/1) + Amlodipine (5 mg/1)TabletOralTorrent Pharmaceuticals Limited2016-11-25Not applicableUS flag

Categories

ATC Codes
C09DA08 — Olmesartan medoxomil and diureticsC09DX03 — Olmesartan medoxomil, amlodipine and hydrochlorothiazideC09CA08 — Olmesartan medoxomilC09DB02 — Olmesartan medoxomil and amlodipine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as biphenyls and derivatives. These are organic compounds containing to benzene rings linked together by a C-C bond.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Biphenyls and derivatives
Direct Parent
Biphenyls and derivatives
Alternative Parents
Phenyltetrazoles and derivatives / 1,2,4,5-tetrasubstituted imidazoles / Carbonylimidazoles / N-substituted imidazoles / Tertiary alcohols / Heteroaromatic compounds / Monocarboxylic acids and derivatives / Carboxylic acids / Azacyclic compounds / Organopnictogen compounds
show 4 more
Substituents
1,2,4,5-tetrasubstituted imidazole / Alcohol / Aromatic alcohol / Aromatic heteromonocyclic compound / Azacycle / Azole / Biphenyl / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound
show 15 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
biphenylyltetrazole (CHEBI:48416)

Chemical Identifiers

UNII
8W1IQP3U10
CAS number
144689-24-7
InChI Key
VTRAEEWXHOVJFV-UHFFFAOYSA-N
InChI
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)
IUPAC Name
4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(1H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylic acid
SMILES
CCCC1=NC(=C(N1CC1=CC=C(C=C1)C1=C(C=CC=C1)C1=NN=NN1)C(O)=O)C(C)(C)O

References

Synthesis Reference
US20060069141
General References
  1. Brunner HR: The new oral angiotensin II antagonist olmesartan medoxomil: a concise overview. J Hum Hypertens. 2002 May;16 Suppl 2:S13-6. doi: 10.1038/sj.jhh.1001391. [PubMed:11967728]
  2. Brunner HR: Olmesartan medoxomil: current status of its use in monotherapy. Vasc Health Risk Manag. 2006;2(4):327-40. [PubMed:17323586]
  3. Gonakoti S, Khullar S, Rajkumar A: Olmesartan Associated Enteropathy: A Rare Underdiagnosed Cause of Diarrhea and Weight Loss. Am J Case Rep. 2019 Jan 26;20:111-116. doi: 10.12659/AJCR.913207. [PubMed:30683835]
  4. Akazawa H, Yabumoto C, Yano M, Kudo-Sakamoto Y, Komuro I: ARB and cardioprotection. Cardiovasc Drugs Ther. 2013 Apr;27(2):155-60. doi: 10.1007/s10557-012-6392-2. [PubMed:22538956]
  5. Black HR, Bailey J, Zappe D, Samuel R: Valsartan: more than a decade of experience. Drugs. 2009;69(17):2393-414. doi: 10.2165/11319460-000000000-00000. [PubMed:19911855]
  6. Ezekowitz JA, O'Meara E, McDonald MA, Abrams H, Chan M, Ducharme A, Giannetti N, Grzeslo A, Hamilton PG, Heckman GA, Howlett JG, Koshman SL, Lepage S, McKelvie RS, Moe GW, Rajda M, Swiggum E, Virani SA, Zieroth S, Al-Hesayen A, Cohen-Solal A, D'Astous M, De S, Estrella-Holder E, Fremes S, Green L, Haddad H, Harkness K, Hernandez AF, Kouz S, LeBlanc MH, Masoudi FA, Ross HJ, Roussin A, Sussex B: 2017 Comprehensive Update of the Canadian Cardiovascular Society Guidelines for the Management of Heart Failure. Can J Cardiol. 2017 Nov;33(11):1342-1433. doi: 10.1016/j.cjca.2017.08.022. Epub 2017 Sep 6. [PubMed:29111106]
  7. Leung AA, Daskalopoulou SS, Dasgupta K, McBrien K, Butalia S, Zarnke KB, Nerenberg K, Harris KC, Nakhla M, Cloutier L, Gelfer M, Lamarre-Cliche M, Milot A, Bolli P, Tremblay G, McLean D, Tran KC, Tobe SW, Ruzicka M, Burns KD, Vallee M, Prasad GVR, Gryn SE, Feldman RD, Selby P, Pipe A, Schiffrin EL, McFarlane PA, Oh P, Hegele RA, Khara M, Wilson TW, Penner SB, Burgess E, Sivapalan P, Herman RJ, Bacon SL, Rabkin SW, Gilbert RE, Campbell TS, Grover S, Honos G, Lindsay P, Hill MD, Coutts SB, Gubitz G, Campbell NRC, Moe GW, Howlett JG, Boulanger JM, Prebtani A, Kline G, Leiter LA, Jones C, Cote AM, Woo V, Kaczorowski J, Trudeau L, Tsuyuki RT, Hiremath S, Drouin D, Lavoie KL, Hamet P, Gregoire JC, Lewanczuk R, Dresser GK, Sharma M, Reid D, Lear SA, Moullec G, Gupta M, Magee LA, Logan AG, Dionne J, Fournier A, Benoit G, Feber J, Poirier L, Padwal RS, Rabi DM: Hypertension Canada's 2017 Guidelines for Diagnosis, Risk Assessment, Prevention, and Treatment of Hypertension in Adults. Can J Cardiol. 2017 May;33(5):557-576. doi: 10.1016/j.cjca.2017.03.005. Epub 2017 Mar 10. [PubMed:28449828]
  8. Lee VC, Rhew DC, Dylan M, Badamgarav E, Braunstein GD, Weingarten SR: Meta-analysis: angiotensin-receptor blockers in chronic heart failure and high-risk acute myocardial infarction. Ann Intern Med. 2004 Nov 2;141(9):693-704. doi: 10.7326/0003-4819-141-9-200411020-00011. [PubMed:15520426]
  9. Brenner BM, Cooper ME, de Zeeuw D, Keane WF, Mitch WE, Parving HH, Remuzzi G, Snapinn SM, Zhang Z, Shahinfar S: Effects of losartan on renal and cardiovascular outcomes in patients with type 2 diabetes and nephropathy. N Engl J Med. 2001 Sep 20;345(12):861-9. doi: 10.1056/NEJMoa011161. [PubMed:11565518]
  10. Yusuf S, Teo KK, Pogue J, Dyal L, Copland I, Schumacher H, Dagenais G, Sleight P, Anderson C: Telmisartan, ramipril, or both in patients at high risk for vascular events. N Engl J Med. 2008 Apr 10;358(15):1547-59. doi: 10.1056/NEJMoa0801317. Epub 2008 Mar 31. [PubMed:18378520]
  11. Pfeffer MA, McMurray JJ, Velazquez EJ, Rouleau JL, Kober L, Maggioni AP, Solomon SD, Swedberg K, Van de Werf F, White H, Leimberger JD, Henis M, Edwards S, Zelenkofske S, Sellers MA, Califf RM: Valsartan, captopril, or both in myocardial infarction complicated by heart failure, left ventricular dysfunction, or both. N Engl J Med. 2003 Nov 13;349(20):1893-906. doi: 10.1056/NEJMoa032292. Epub 2003 Nov 10. [PubMed:14610160]
  12. O'Gara PT, Kushner FG, Ascheim DD, Casey DE Jr, Chung MK, de Lemos JA, Ettinger SM, Fang JC, Fesmire FM, Franklin BA, Granger CB, Krumholz HM, Linderbaum JA, Morrow DA, Newby LK, Ornato JP, Ou N, Radford MJ, Tamis-Holland JE, Tommaso CL, Tracy CM, Woo YJ, Zhao DX: 2013 ACCF/AHA guideline for the management of ST-elevation myocardial infarction: a report of the American College of Cardiology Foundation/American Heart Association Task Force on Practice Guidelines. J Am Coll Cardiol. 2013 Jan 29;61(4):e78-e140. doi: 10.1016/j.jacc.2012.11.019. Epub 2012 Dec 17. [PubMed:23256914]
  13. Si X, Li P, Zhang Y, Zhang Y, Lv W, Qi D: Renoprotective effects of olmesartan medoxomil on diabetic nephropathy in streptozotocin-induced diabetes in rats. Biomed Rep. 2014 Jan;2(1):24-28. doi: 10.3892/br.2013.183. Epub 2013 Oct 9. [PubMed:24649063]
  14. Takami T, Okada S, Saito Y, Nishijima Y, Kobori H, Nishiyama A: Effects of Olmesartan and Azilsartan on Albuminuria and the Intrarenal Renin-Angiotensin System. World J Res Rev. 2018 Jan;6(1):7-10. [PubMed:29683146]
  15. Haller H, Ito S, Izzo JL Jr, Januszewicz A, Katayama S, Menne J, Mimran A, Rabelink TJ, Ritz E, Ruilope LM, Rump LC, Viberti G: Olmesartan for the delay or prevention of microalbuminuria in type 2 diabetes. N Engl J Med. 2011 Mar 10;364(10):907-17. doi: 10.1056/NEJMoa1007994. [PubMed:21388309]
  16. Stevens PE, Levin A: Evaluation and management of chronic kidney disease: synopsis of the kidney disease: improving global outcomes 2012 clinical practice guideline. Ann Intern Med. 2013 Jun 4;158(11):825-30. doi: 10.7326/0003-4819-158-11-201306040-00007. [PubMed:23732715]
  17. Health Canada Product Monograph: Olmesartan medoxomil oral tablets [Link]
  18. FDA Approved Drug Products: Benicar (olmesartan medoxomil) oral tablets [Link]
  19. FDA Label - Olmesartan [File]
  20. Health Canada Monograph - Olmesartan [File]
Human Metabolome Database
HMDB0014420
KEGG Drug
D01204
PubChem Compound
158781
PubChem Substance
46508275
ChemSpider
139674
BindingDB
50241364
RxNav
321064
ChEBI
48416
ChEMBL
CHEMBL1516
ZINC
ZINC000000538621
Therapeutic Targets Database
DAP001412
PharmGKB
PA164742950
PDBe Ligand
OLM
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Olmesartan
AHFS Codes
  • 24:32.08 — Angiotensin Ii Receptor Antagonists
PDB Entries
4zud
FDA label
Download (286 KB)
MSDS
Download (509 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentCongestive Cardiomyopathy1
4CompletedNot AvailableHigh Blood Pressure (Hypertension)1
4CompletedOtherDyslipidemia / High Blood Pressure (Hypertension)1
4CompletedPreventionBMI >27 kg/m2 / High Blood Pressure (Hypertension) / Obese / Prehypertension1
4CompletedPreventionCardiovascular Heart Disease / Diabetes / High Blood Pressure (Hypertension)1
4CompletedPreventionCardiovascular Heart Disease / High Blood Pressure (Hypertension)1
4CompletedTreatmentCardiovascular Heart Disease / Chronic Kidney Disease (CKD) / Hypertension,Essential / Stroke1
4CompletedTreatmentDrug Interaction of Olmesartan in Healthy Chinese Volunteers1
4CompletedTreatmentEssential,Hypertension / Hypertension,Essential1
4CompletedTreatmentHealthy Volunteers1

Pharmacoeconomics

Manufacturers
  • Daiichi sankyo inc
  • Daiichi Sankyo
Packagers
  • Bryant Ranch Prepack
  • Cardinal Health
  • Daiichi Sankyo
  • DispenseXpress Inc.
  • Dispensing Solutions
  • Lake Erie Medical and Surgical Supply
  • Murfreesboro Pharmaceutical Nursing Supply
  • Physicians Total Care Inc.
  • Quality Care
  • Resource Optimization and Innovation LLC
  • Schering-Plough Inc.
  • Southwood Pharmaceuticals
Dosage Forms
FormRouteStrength
TabletOral
Tablet, film coatedOral40 MG
Tablet, film coatedOral20 mg/1
Tablet, film coatedOral40 mg/1
Tablet, film coatedOral5 mg/1
Tablet, film coatedOral
Tablet, film coated10 mg
Tablet, film coated20 mg
Tablet, film coated40 mg
Tablet, coated10 mg
Tablet, coated20 mg
Tablet, coated40 mg
Tablet, coated2.5 mg
Tablet, coated5 mg
Tablet, film coatedOral10 MG
Tablet, film coatedOral20 MG
Tablet, coatedOral10 mg
Tablet, film coatedOral5 mg
Tablet, coatedOral5 mg
TabletOral12.5 mg
Tablet, coatedOral20 mg
TabletOral20 mg/1
TabletOral40 mg/1
TabletOral5 mg/1
Tablet, coatedOral20 mg/1
Tablet, coatedOral40 mg/1
Tablet, coatedOral5 mg/1
TabletOral40 mg
Tablet, film coatedOral13.88 mg
TabletOral
Tablet
Tablet, coatedOral12.5 mg
Tablet, film coated5 mg
TabletOral20 mg
Tablet, coatedOral40 mg
Prices
Unit descriptionCostUnit
Benicar 5 mg tablet12.81USD tablet
Benicar hct 40-25 mg tablet4.93USD tablet
Benicar hct 40-12.5 mg tablet4.67USD tablet
Benicar hct 20-12.5 mg tablet3.94USD tablet
Benicar 40 mg tablet3.74USD tablet
Benicar 20 mg tablet2.97USD tablet
Olmetec 20 mg Tablet1.04USD tablet
Olmetec 40 mg Tablet1.04USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
CA2061607No1999-01-192012-02-20Canada flag
US5616599Yes1997-04-012016-10-25US flag
US6878703Yes2005-04-122022-05-19US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)177.6 ºC'MSDS'
boiling point (°C)800 ºC at 760 mm Hg'MSDS'
water solubilityInsolubleFDA Chemical report
logP0.73FDA Pharmacological report
pKa4.3FDA Chemical report
Predicted Properties
PropertyValueSource
Water Solubility0.0105 mg/mLALOGPS
logP2.98ALOGPS
logP2.14ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)0.91ChemAxon
pKa (Strongest Basic)5.57ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area129.81 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity137.32 m3·mol-1ChemAxon
Polarizability47.46 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier-0.8719
Caco-2 permeable-0.6865
P-glycoprotein substrateSubstrate0.7247
P-glycoprotein inhibitor INon-inhibitor0.5917
P-glycoprotein inhibitor IIInhibitor0.6029
Renal organic cation transporterNon-inhibitor0.807
CYP450 2C9 substrateNon-substrate0.7429
CYP450 2D6 substrateNon-substrate0.8602
CYP450 3A4 substrateNon-substrate0.5149
CYP450 1A2 substrateNon-inhibitor0.782
CYP450 2C9 inhibitorInhibitor0.5816
CYP450 2D6 inhibitorNon-inhibitor0.8059
CYP450 2C19 inhibitorInhibitor0.6604
CYP450 3A4 inhibitorInhibitor0.7409
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8396
Ames testNon AMES toxic0.6203
CarcinogenicityNon-carcinogens0.6871
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6599 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9254
hERG inhibition (predictor II)Non-inhibitor0.6427
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a6r-0692700000-11f020dfbb889ac85e4e

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Protein heterodimerization activity
Specific Function
Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system.
Gene Name
AGTR1
Uniprot ID
P30556
Uniprot Name
Type-1 angiotensin II receptor
Molecular Weight
41060.53 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
  2. Koike H, Sada T, Mizuno M: In vitro and in vivo pharmacology of olmesartan medoxomil, an angiotensin II type AT1 receptor antagonist. J Hypertens Suppl. 2001 Jun;19(1):S3-14. [PubMed:11451212]
  3. Ochiai K, Hu Q, Lee J, Mansoor A, Liu J, Wang X, Gong G, Murakami Y, Ishibashi Y, Shimada T, Zhang J: Functional and bioenergetic consequences of AT1 antagonist olmesartan medoxomil in hearts with postinfarction LV remodeling. J Cardiovasc Pharmacol. 2006 May;47(5):686-94. [PubMed:16775509]
  4. Warner GT, Jarvis B: Olmesartan medoxomil. Drugs. 2002;62(9):1345-53; discussion 1354-6. [PubMed:12076183]
  5. Mire DE, Silfani TN, Pugsley MK: A review of the structural and functional features of olmesartan medoxomil, an angiotensin receptor blocker. J Cardiovasc Pharmacol. 2005 Nov;46(5):585-93. [PubMed:16220064]
  6. Kreutz R, Bolbrinker J, Huber M: Pharmacokinetics of olmesartan medoxomil plus hydrochlorothiazide combination in healthy subjects. Clin Drug Investig. 2006;26(1):29-34. [PubMed:17163232]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Organic anion transmembrane transporter activity
Specific Function
Mediates hepatobiliary excretion of numerous organic anions. May function as a cellular cisplatin transporter.
Gene Name
ABCC2
Uniprot ID
Q92887
Uniprot Name
Canalicular multispecific organic anion transporter 1
Molecular Weight
174205.64 Da
References
  1. Weiss J, Sauer A, Divac N, Herzog M, Schwedhelm E, Boger RH, Haefeli WE, Benndorf RA: Interaction of angiotensin receptor type 1 blockers with ATP-binding cassette transporters. Biopharm Drug Dispos. 2010 Mar;31(2-3):150-61. doi: 10.1002/bdd.699. [PubMed:20222053]
  2. Nakagomi-Hagihara R, Nakai D, Kawai K, Yoshigae Y, Tokui T, Abe T, Ikeda T: OATP1B1, OATP1B3, and mrp2 are involved in hepatobiliary transport of olmesartan, a novel angiotensin II blocker. Drug Metab Dispos. 2006 May;34(5):862-9. Epub 2006 Feb 24. [PubMed:16501004]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
Gene Name
SLCO1B3
Uniprot ID
Q9NPD5
Uniprot Name
Solute carrier organic anion transporter family member 1B3
Molecular Weight
77402.175 Da
References
  1. Nakagomi-Hagihara R, Nakai D, Kawai K, Yoshigae Y, Tokui T, Abe T, Ikeda T: OATP1B1, OATP1B3, and mrp2 are involved in hepatobiliary transport of olmesartan, a novel angiotensin II blocker. Drug Metab Dispos. 2006 May;34(5):862-9. Epub 2006 Feb 24. [PubMed:16501004]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
Gene Name
SLCO1B1
Uniprot ID
Q9Y6L6
Uniprot Name
Solute carrier organic anion transporter family member 1B1
Molecular Weight
76447.99 Da
References
  1. Nakagomi-Hagihara R, Nakai D, Kawai K, Yoshigae Y, Tokui T, Abe T, Ikeda T: OATP1B1, OATP1B3, and mrp2 are involved in hepatobiliary transport of olmesartan, a novel angiotensin II blocker. Drug Metab Dispos. 2006 May;34(5):862-9. Epub 2006 Feb 24. [PubMed:16501004]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Involved in the ATP-dependent secretion of bile salts into the canaliculus of hepatocytes.
Gene Name
ABCB11
Uniprot ID
O95342
Uniprot Name
Bile salt export pump
Molecular Weight
146405.83 Da
References
  1. Pedersen JM, Matsson P, Bergstrom CA, Hoogstraate J, Noren A, LeCluyse EL, Artursson P: Early identification of clinically relevant drug interactions with the human bile salt export pump (BSEP/ABCB11). Toxicol Sci. 2013 Dec;136(2):328-43. doi: 10.1093/toxsci/kft197. Epub 2013 Sep 6. [PubMed:24014644]

Drug created on June 13, 2005 07:24 / Updated on September 27, 2020 08:17

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