Olmesartan

Identification

Summary

Olmesartan is an angiotensin receptor blocker (ARB) used in the treatment of hypertension.

Brand Names

Azor, Benicar, Benicar Hct, Olmetec, Olmetec Plus, Tribenzor

Generic Name

Olmesartan

DrugBank Accession Number

DB00275

Background

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.^3,18

Type

Small Molecule

Groups

Approved, Investigational

Structure

3D

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MOLSDF3D-SDFPDBSMILESInChI

Similar Structures

Structure for Olmesartan (DB00275)

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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

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Pharmacology

Indication

Olmesartan is indicated for the treatment of hypertension either alone or in combination with other antihypertensive agents.^23,24,7

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

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Age Group	Patient Characteristics	Dose Form
Management of	Diabetic nephropathy		••• •••••
Used in combination to manage	High blood pressure (hypertension)	Combination Product in combination with: Amlodipine (DB00381)	••••••••••••		•••••••• •••••••••••••••• ••••• •••••• ••••••••
Used in combination to manage	High blood pressure (hypertension)	Combination Product in combination with: Amlodipine (DB00381)	••••••••••••
Used in combination to manage	High blood pressure (hypertension)	Combination Product in combination with: Amlodipine (DB00381)	••••••••••••
Used in combination to manage	Hypertension	Combination Product in combination with: Hydrochlorothiazide (DB00999)	••••••••••••		•••••• ••••••• •••••••••

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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.^23,24

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.²⁴

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.^23,24

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.^23,24

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.^23,24

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.²³ 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

Target	Actions	Organism
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.²²

Volume of distribution

17 L²²

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.²²

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.²²

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

Pathways

Pathway	Category
Olmesartan Action Pathway	Drug action

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

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.

• Approved
• Vet approved
• Nutraceutical
• Illicit
• Withdrawn
• Investigational
• Experimental
• All Drugs

Drug	Interaction
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Abaloparatide	The risk or severity of adverse effects can be increased when Olmesartan is combined with Abaloparatide.
Acebutolol	Olmesartan may increase the hypotensive activities of Acebutolol.
Aceclofenac	The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Olmesartan is combined with Aceclofenac.
Acemetacin	The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Olmesartan is combined with Acemetacin.
Acetylsalicylic acid	The risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Olmesartan is combined with Acetylsalicylic acid.

Food Interactions

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

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Olmesartan medoxomil	6M97XTV3HD	144689-63-4	UQGKUQLKSCSZGY-UHFFFAOYSA-N

Product Images

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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

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Benicar	Tablet, film coated	20 mg/1	Oral	Remedy Repack	2013-10-04	2014-10-04
Benicar	Tablet, film coated	40 mg/1	Oral	bryant ranch prepack	2002-04-25	2017-12-31
Benicar	Tablet, film coated	20 mg/1	Oral	Med Pharma Co., Ltd.	2012-02-02	Not applicable
Benicar	Tablet, film coated	20 mg/1	Oral	Daiichi Sankyo, Inc.	2002-04-25	2024-03-31
Benicar	Tablet, film coated	20 mg/1	Oral	Physicians Total Care, Inc.	2004-01-30	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End	Region	Image
Ach-olmesartan	Tablet	40 mg	Oral	Accord Healthcare Inc	2020-05-06	Not applicable
Ach-olmesartan	Tablet	20 mg	Oral	Accord Healthcare Inc	2020-05-06	Not applicable
Ag-olmesartan	Tablet	40 mg	Oral	Angita Pharma Inc.	2018-09-06	Not applicable
Ag-olmesartan	Tablet	20 mg	Oral	Angita Pharma Inc.	2018-09-06	Not applicable
Apo-olmesartan	Tablet	20 mg	Oral	Apotex Corporation	2017-05-31	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End	Region	Image
Ach-olmesartan Hctz	Olmesartan medoxomil (20 mg) + Hydrochlorothiazide (12.5 mg)	Tablet	Oral	Accord Healthcare Inc	2019-06-27	Not applicable
Ach-olmesartan Hctz	Olmesartan medoxomil (40 mg) + Hydrochlorothiazide (12.5 mg)	Tablet	Oral	Accord Healthcare Inc	2019-06-27	Not applicable
Ach-olmesartan Hctz	Olmesartan medoxomil (40 mg) + Hydrochlorothiazide (25 mg)	Tablet	Oral	Accord Healthcare Inc	2019-06-27	Not applicable
Ag-olmesartan Hctz	Olmesartan medoxomil (40 mg) + Hydrochlorothiazide (12.5 mg)	Tablet	Oral	Angita Pharma Inc.	Not applicable	Not applicable
Ag-olmesartan Hctz	Olmesartan medoxomil (20 mg) + Hydrochlorothiazide (12.5 mg)	Tablet	Oral	Angita Pharma Inc.	Not applicable	Not applicable

Categories

ATC Codes

C09DA08 — Olmesartan medoxomil and diuretics

• C09DA — Angiotensin II receptor blockers (ARBs) and diuretics
• C09D — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS
• C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
• C — CARDIOVASCULAR SYSTEM

C09DX03 — Olmesartan medoxomil, amlodipine and hydrochlorothiazide

• C09DX — Angiotensin II receptor blockers (ARBs), other combinations
• C09D — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS
• C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
• C — CARDIOVASCULAR SYSTEM

C09CA08 — Olmesartan medoxomil

• C09CA — Angiotensin II receptor blockers (ARBs), plain
• C09C — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), PLAIN
• C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
• C — CARDIOVASCULAR SYSTEM

C09DB02 — Olmesartan medoxomil and amlodipine

• C09DB — Angiotensin II receptor blockers (ARBs) and calcium channel blockers
• C09D — ANGIOTENSIN II RECEPTOR BLOCKERS (ARBs), COMBINATIONS
• C09 — AGENTS ACTING ON THE RENIN-ANGIOTENSIN SYSTEM
• C — CARDIOVASCULAR SYSTEM

Drug Categories

• Agents Acting on the Renin-Angiotensin System
• Agents causing hyperkalemia
• Angiotensin 2 Receptor Blocker
• Angiotensin II Antagonists and Calcium Channel Blockers
• Angiotensin II receptor antagonists
• Angiotensin II receptor blockers (ARBs) and calcium channel blockers
• Angiotensin II receptor blockers (ARBs) and diuretics
• Angiotensin II receptor blockers (ARBs), plain
• Angiotensin Receptor Antagonists
• Antihypertensive Agents
• Antihypertensive Agents Indicated for Hypertension
• BSEP/ABCB11 Inhibitors
• Cardiovascular Agents
• Hypotensive Agents
• Imidazoles
• OATP1B1/SLCO1B1 Substrates
• OATP1B3 substrates
• Tetrazoles

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 / Organonitrogen compounds / Organic oxides / Hydrocarbon derivatives / Aromatic alcohols

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Substituents

1,2,4,5-tetrasubstituted imidazole / Alcohol / Aromatic alcohol / Aromatic heteromonocyclic compound / Azacycle / Azole / Biphenyl / Carboxylic acid / Carboxylic acid derivative / Heteroaromatic compound / Hydrocarbon derivative / Imidazole / Imidazole-4-carbonyl group / Monocarboxylic acid or derivatives / N-substituted imidazole / Organic nitrogen compound / Organic oxide / Organic oxygen compound / Organoheterocyclic compound / Organonitrogen compound / Organooxygen compound / Organopnictogen compound / Phenyltetrazole / Tertiary alcohol / Tetrazole

show 15 more

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

biphenylyltetrazole (CHEBI:48416)

Affected organisms

• Humans and other mammals

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-{[2'-(1H-1,2,3,4-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl]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. [Article]
2. Brunner HR: Olmesartan medoxomil: current status of its use in monotherapy. Vasc Health Risk Manag. 2006;2(4):327-40. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
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. [Article]
17. Health Canada Product Monograph: Olmesartan medoxomil oral tablets [Link]
18. FDA Approved Drug Products: Benicar (olmesartan medoxomil) oral tablets [Link]
19. FDA Approved Drug Products: Azor (amlodipine besylate/olmesartan medoxomil) tablets for oral use [Link]
20. FDA Approved Drug Products: Benicar HCT (olmesartan medoxomil/hydrochlorothiazide) tablets for oral use [Link]
21. FDA Approved Drug Products: Tribenzor (olmesartan medoxomil/amlodipine besylate/hydrochlorothiazide) tablets for oral use [Link]
22. FDA Clinical Pharmacology and Biopharmaceutics Review: Benicar (olmesartan medoximil) [Link]
23. FDA Label - Olmesartan [File]
24. Health Canada Monograph - Olmesartan [File]

External Links

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

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Olmesartan

PDB Entries

4zud

FDA label

Download (286 KB)

MSDS

Download (509 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Other	Dyslipidemia / Hypertension	1
4	Completed	Prevention	Cardiovascular Disease (CVD) / Diabetes / Hypertension	1
4	Completed	Prevention	Cardiovascular Disease (CVD) / Hypertension	1
4	Completed	Prevention	Hypertension / Obesity / Overweight / Prehypertension	1
4	Completed	Treatment	Angiotensin/Renin/Aldosterone Hypertension / Hypertension / Type 2 Diabetes Mellitus	1

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

Form	Route	Strength
Tablet	Oral	40.000 mg
Tablet	Oral
Tablet	Oral	10 mg
Tablet, coated	Oral
Tablet, film coated	Oral	5 mg
Tablet, film coated	Oral	10 mg
Tablet	Oral	12.500 mg
Tablet, film coated	Oral	20 mg/1
Tablet, film coated	Oral	40 mg/1
Tablet, film coated	Oral	5 mg/1
Tablet, film coated	Oral
Tablet	Oral	20.00 mg
Tablet	Oral	20.000 mg
Tablet, film coated	Oral
Tablet, film coated	Oral	10 MG
Tablet	Oral	20 mg/1
Tablet	Oral	40 mg/1
Tablet	Oral	5 mg/1
Tablet, coated	Oral	20 mg/1
Tablet, coated	Oral	40 mg/1
Tablet, coated	Oral	5 mg/1
Tablet, coated	Oral	4000000 mg
Tablet, film coated	Oral	20 MG
Tablet, film coated	Oral	40 MG
Tablet	Oral	20 mg
Tablet	Oral	40 mg
Tablet	Oral	5 mg
Tablet, film coated	Oral	20.00 mg
Tablet, film coated	Oral	40.00 mg
Tablet	Oral	40.00 mg
Tablet, coated	Oral	10 mg
Tablet, coated	Oral	20 mg
Tablet, coated	Oral	40 mg

Prices

Unit description	Cost	Unit
Benicar 5 mg tablet	12.81USD	tablet
Benicar hct 40-25 mg tablet	4.93USD	tablet
Benicar hct 40-12.5 mg tablet	4.67USD	tablet
Benicar hct 20-12.5 mg tablet	3.94USD	tablet
Benicar 40 mg tablet	3.74USD	tablet
Benicar 20 mg tablet	2.97USD	tablet
Olmetec 20 mg Tablet	1.04USD	tablet
Olmetec 40 mg Tablet	1.04USD	tablet

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)	Region
CA2061607	No	1999-01-19	2012-02-20
US5616599	Yes	1997-04-01	2016-10-25
US6878703	Yes	2005-04-12	2022-05-19

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	177.6 ºC	'MSDS'
boiling point (°C)	800 ºC at 760 mm Hg	'MSDS'
water solubility	Insoluble	FDA Chemical report
logP	0.73	FDA Pharmacological report
pKa	4.3	FDA Chemical report

Predicted Properties

Property	Value	Source
Water Solubility	0.0105 mg/mL	ALOGPS
logP	2.98	ALOGPS
logP	2.16	Chemaxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	0.89	Chemaxon
pKa (Strongest Basic)	5.33	Chemaxon
Physiological Charge	-2	Chemaxon
Hydrogen Acceptor Count	7	Chemaxon
Hydrogen Donor Count	3	Chemaxon
Polar Surface Area	129.81 Å2	Chemaxon
Rotatable Bond Count	8	Chemaxon
Refractivity	137.32 m3·mol-1	Chemaxon
Polarizability	47.52 Å3	Chemaxon
Number of Rings	4	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	-	0.8719
Caco-2 permeable	-	0.6865
P-glycoprotein substrate	Substrate	0.7247
P-glycoprotein inhibitor I	Non-inhibitor	0.5917
P-glycoprotein inhibitor II	Inhibitor	0.6029
Renal organic cation transporter	Non-inhibitor	0.807
CYP450 2C9 substrate	Non-substrate	0.7429
CYP450 2D6 substrate	Non-substrate	0.8602
CYP450 3A4 substrate	Non-substrate	0.5149
CYP450 1A2 substrate	Non-inhibitor	0.782
CYP450 2C9 inhibitor	Inhibitor	0.5816
CYP450 2D6 inhibitor	Non-inhibitor	0.8059
CYP450 2C19 inhibitor	Inhibitor	0.6604
CYP450 3A4 inhibitor	Inhibitor	0.7409
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.8396
Ames test	Non AMES toxic	0.6203
Carcinogenicity	Non-carcinogens	0.6871
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.6599 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9254
hERG inhibition (predictor II)	Non-inhibitor	0.6427

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	splash10-003i-3062900000-66da1fa4f726bf91355c
LC-MS/MS Spectrum - LC-ESI-qTof , Positive	LC-MS/MS	splash10-0a6r-0692700000-11f020dfbb889ac85e4e
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0a6r-0692700000-11f020dfbb889ac85e4e
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004j-0000900000-d0b22250ac21ac982cf8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0f8a-0009600000-6b2b23946e595b98bdbf
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0f6x-2005900000-2f57c6fcf964ca35983a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0udi-1307900000-3f26a136174a103a1e01
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-0670-0469300000-e907b91e5008c3dba3f9
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0uxr-0923400000-4b6213d47a6a5ca04a9d
Predicted 1H NMR Spectrum	1D NMR	Not Applicable
Predicted 13C NMR Spectrum	1D NMR	Not Applicable

Chromatographic Properties

Collision Cross Sections (CCS)

Adduct	CCS Value (Å2)	Source type	Source
[M-H]-	222.5781516	predicted	DarkChem Lite v0.1.0
[M-H]-	228.1091516	predicted	DarkChem Lite v0.1.0
[M-H]-	204.16579	predicted	DeepCCS 1.0 (2019)
[M+H]+	223.3477516	predicted	DarkChem Lite v0.1.0
[M+H]+	228.5559516	predicted	DarkChem Lite v0.1.0
[M+H]+	206.56136	predicted	DeepCCS 1.0 (2019)
[M+Na]+	222.1791516	predicted	DarkChem Lite v0.1.0
[M+Na]+	227.3897516	predicted	DarkChem Lite v0.1.0
[M+Na]+	212.47716	predicted	DeepCCS 1.0 (2019)

Targets

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Details1. Type-1 angiotensin II receptor

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. [Article]
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. [Article]
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. [Article]
4. Warner GT, Jarvis B: Olmesartan medoxomil. Drugs. 2002;62(9):1345-53; discussion 1354-6. [Article]
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. [Article]
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. [Article]

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Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:55