Wikipedia:WikiProject Chemicals/Chembox validation/VerifiedDataSandbox and Olmesartan: Difference between pages

{{Short description|Angiotensin II receptor antagonist}}

{{Use dmy dates|date=November 2024}}

{{cs1 config|name-list-style=vanc|display-authors=6}}

{{Infobox drug

| verifiedrevid = 462265064

| image = Olmesartan.svg

| width =

| alt =

| caption =

<!-- Clinical data -->

| pronounce =

| DailyMedID = Olmesartan

| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->

| pregnancy_AU_comment =

| pregnancy_category =

| routes_of_administration = [[oral administration|Oral]]

| class =

| ATC_prefix = C09

| ATC_suffix = CA08

| ATC_supplemental = <br />{{ATC|C09|DA08}} (with [[diuretics]])<br />{{ATC|C09|DB02}} (with [[amlodipine]])

<!-- Legal status -->

| legal_AU = <!-- S2, S3, S4, S5, S6, S7, S8, S9 or Unscheduled -->

| legal_AU_comment =

| legal_BR = <!-- OTC, A1, A2, A3, B1, B2, C1, C2, C3, C4, C5, D1, D2, E, F -->

| legal_BR_comment =

| legal_CA = <!-- OTC, Rx-only, Schedule I, II, III, IV, V, VI, VII, VIII -->

| legal_CA_comment =

| legal_DE = <!-- Anlage I, II, III or Unscheduled -->

| legal_DE_comment =

| legal_NZ = <!-- Class A, B, C -->

| legal_NZ_comment =

| legal_UK = <!-- GSL, P, POM, CD, CD Lic, CD POM, CD No Reg POM, CD (Benz) POM, CD (Anab) POM or CD Inv POM / Class A, B, C -->

| legal_UK_comment =

| legal_US = Rx-only

| legal_US_comment = <ref name="Benicar FDA label">{{cite web | title=Benicar- olmesartan medoxomil tablet, film coated | website=DailyMed | date=7 September 2022 | url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5b6f8a18-8f8a-4521-81c3-3a39c73c6646 | access-date=14 April 2023}}</ref>

| legal_EU =

| legal_EU_comment =

| legal_UN = <!-- N I, II, III, IV / P I, II, III, IV -->

| legal_UN_comment =

<!-- Pharmacokinetic data -->

| metabolism = [[Liver]] (cannot be removed by hemodialysis)

| metabolites =

| onset =

| duration_of_action =

| excretion = [[Kidney]] 40%, [[bile duct]] 60%

<!-- Identifiers -->

| CAS_supplemental =

| IUPHAR_ligand = 591

| KEGG_Ref = {{keggcite|correct|kegg}}

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 31932

| ChEMBL = 1200692

| NIAID_ChemDB =

| PDB_ligand =

| synonyms = Olmesartan medoxomil

<!-- Chemical and physical data -->

| IUPAC_name = (5-methyl-2-oxo-2''H''-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(2''H''-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1''H''-imidazole-5-carboxylate

| C=29 | H=30 | N=6 | O=6

| SMILES = CCCc1nc(c(n1Cc2ccc(cc2)c3ccccc3c4[nH]nnn4)C(=O)OCc5c(oc(=O)o5)C)C(C)(C)O

| StdInChI_comment =

| density =

| density_notes =

| melting_point =

| melting_high =

| melting_notes =

| boiling_point =

| boiling_notes =

| solubility =

| sol_units =

| specific_rotation =

<!-- Definition and medical uses -->

'''Olmesartan''', sold under the brand name '''Benicar''' among others, is a [[medication]] used to treat high blood pressure ([[hypertension]]).<ref name="Benicar FDA label" /><ref name=AHFS2019/> It is taken [[oral administration|orally]] (swallowed by mouth).<ref name=AHFS2019/> Versions are available as the combination [[olmesartan/hydrochlorothiazide]] and [[olmesartan/amlodipine]].<ref name=AHFS2019/> It is available as a prodrug, olmesartan medoxomil.

<!-- Side effects and mechanisms -->

Common side effects include dizziness, [[headaches]], [[diarrhea]], and back pain.<ref name=AHFS2019/> Serious side effects may include [[kidney problems]], [[low blood pressure]], and [[angioedema]].<ref name=AHFS2019/> Use in [[pregnancy]] may harm the fetus and use when [[breastfeeding]] is not recommended.<ref name=Preg2019>{{cite web |title=Olmesartan Pregnancy and Breastfeeding Warnings |url=https://www.drugs.com/pregnancy/olmesartan.html |website=Drugs.com |access-date=3 March 2019 }}</ref> It is an [[angiotensin II receptor antagonist]] and works by blocking the effects of [[angiotensin II]].<ref name=AHFS2019>{{cite web |title=Olmesartan Medoxomil Monograph for Professionals |url=https://www.drugs.com/monograph/olmesartan-medoxomil.html |website=Drugs.com |publisher=American Society of Health-System Pharmacists |access-date=3 March 2019 }}</ref>

<!-- Society and culture -->

It was patented in 1991 and came into medical use in 2002.<ref name=Fis2006>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=471 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA471 }}</ref> It is available as a [[generic medication]].<ref name=BNF76>{{cite book|title=British national formulary : BNF 76|date=2018|publisher=Pharmaceutical Press|isbn=9780857113382|pages=177|edition=76}}</ref> In 2022, it was the 97th most commonly prescribed medication in the United States, with more than 6{{nbsp}}million prescriptions.<ref>{{cite web | title=The Top 300 of 2022 | url=https://clincalc.com/DrugStats/Top300Drugs.aspx | website=ClinCalc | access-date=30 August 2024 | archive-date=30 August 2024 | archive-url=https://web.archive.org/web/20240830202410/https://clincalc.com/DrugStats/Top300Drugs.aspx | url-status=live }}</ref><ref>{{cite web | title = Olmesartan Drug Usage Statistics, United States, 2013 - 2022 | website = ClinCalc | url = https://clincalc.com/DrugStats/Drugs/Olmesartan | access-date = 30 August 2024 }}</ref>

==Medical uses==

In the United States, olmesartan is [[indicated]] for the treatment of hypertension in people aged six years of age and older to lower blood pressure.<ref name="Benicar FDA label" />

Olmesartan is used for the treatment of hypertension. It may be used alone or in combination with other antihypertensive agents.<ref name=RxList>{{cite web|date=5 July 2007| url=http://www.rxlist.com/benicar-drug.htm| title=Benicar (olmesartan medoxomil)| publisher=[[RxList|RxList Inc.]]| access-date=22 July 2010}}</ref>

==Contraindications==

[[Contraindication]]s for treatment with olmesartan include [[biliary obstruction]]. Another major contraindication is pregnancy; reports in the scientific literature reveal fetal malformations for pregnant women taking sartan-derived drugs.<ref>{{cite journal | vauthors = Hünseler C, Paneitz A, Friedrich D, Lindner U, Oberthuer A, Körber F, Schmitt K, Welzing L, Müller A, Herkenrath P, Hoppe B, Gortner L, Roth B, Kattner E, Schaible T | title = Angiotensin II receptor blocker induced fetopathy: 7 cases | journal = Klinische Padiatrie | volume = 223 | issue = 1 | pages = 10–14 | date = January 2011 | pmid = 21271514 | doi = 10.1055/s-0030-1269895 | s2cid = 260206339 }}</ref>

==Adverse effects==

The US [[Food and Drug Administration]] (FDA) has determined that the benefits of olmesartan continue to outweigh its potential risks when used for the treatment of people with high blood pressure according to the drug label.<ref>{{cite web|url=https://www.drugs.com/fda/benicar-olmesartan-ongoing-safety-review-12946.html |title=FDA Alert: Benicar (olmesartan): Ongoing Safety Review |publisher=Drugs.com |access-date=27 June 2013}}</ref><ref>{{cite web |date=24 June 2014|title=FDA Drug Safety Communication: FDA review of cardiovascular risks for diabetics taking hypertension drug olmesartan not conclusive; label updates required |url=https://www.fda.gov/drugs/drug-safety-and-availability/fda-drug-safety-communication-fda-review-cardiovascular-risks-diabetics-taking-hypertension-drug |website=U.S. [[Food and Drug Administration]] (FDA) }}</ref>

The incidence of adverse effects with olmesartan is reported as similar to placebo; the only adverse effect that occurred in >1% of patients treated with it and more frequently than placebo was [[dizziness]] (3% vs 1%). Rarely, olmesartan can cause severe [[gastrointestinal issues]]. The symptoms, which include nausea, vomiting, diarrhea, weight loss, and [[electrolyte abnormalities]], are common among those who have [[celiac disease]].<ref>{{cite journal | vauthors = De Petris G, Caldero SG, Chen L, Xiao SY, Dhungel BM, Spizcka AJ, Lam-Himlin D | title = Histopathological changes in the gastrointestinal tract due to medications: an update for the surgical pathologist (part II of II) | journal = International Journal of Surgical Pathology | volume = 22 | issue = 3 | pages = 202–211 | date = May 2014 | pmid = 24021900 | doi = 10.1177/1066896913502230 | s2cid = 20614874 }}</ref> Recent studies suggested this form of sprue-like [[enteropathy]] could be caused by the inhibition of [[Transforming growth factor beta|TGF-β]], a [[polypeptide cytokine]] that maintains intestinal [[homeostasis]]. However, it is still unclear why this action was never observed with other ARBs.<ref>{{cite journal | vauthors = Rubio-Tapia A, Herman ML, Ludvigsson JF, Kelly DG, Mangan TF, Wu TT, Murray JA | title = Severe spruelike enteropathy associated with olmesartan | journal = Mayo Clinic Proceedings | volume = 87 | issue = 8 | pages = 732–738 | date = August 2012 | pmid = 22728033 | pmc = 3538487 | doi = 10.1016/j.mayocp.2012.06.003 }}</ref> In studies of angiotensin II receptor antagonists such as olmesartan, patients with unilateral or bilateral [[renal artery stenosis]], increases in [[serum creatinine]] or [[blood urea nitrogen]] 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.<ref name="Benicar FDA label" />

==Chemistry==

[[File:Olmesartan medoxomil.svg|thumb|left|Olmesartan medoxomil, the [[prodrug]].]]

Olmesartan medoxomil, an ester [[prodrug]], is completely and rapidly [[hydrolyzed]] to its active acid form, olmesartan.<ref name=Aulakh_2007>{{cite journal | vauthors = Aulakh GK, Sodhi RK, Singh M | title = An update on non-peptide angiotensin receptor antagonists and related RAAS modulators | journal = Life Sciences | volume = 81 | issue = 8 | pages = 615–639 | date = August 2007 | pmid = 17692338 | doi = 10.1016/j.lfs.2007.06.007 }}</ref>

[[File:Olmesartan medoxomil metabolism.svg|thumb|600px|left|Olmesartan medoxomil metabolism.<ref>{{cite journal | vauthors = Ishizuka T, Fujimori I, Kato M, Noji-Sakikawa C, Saito M, Yoshigae Y, Kubota K, Kurihara A, Izumi T, Ikeda T, Okazaki O | title = Human carboxymethylenebutenolidase as a bioactivating hydrolase of olmesartan medoxomil in liver and intestine | journal = The Journal of Biological Chemistry | volume = 285 | issue = 16 | pages = 11892–11902 | date = April 2010 | pmid = 20177059 | pmc = 2852926 | doi = 10.1074/jbc.M109.072629 | doi-access = free }}</ref>]]

==History==

{{see also|Discovery and development of angiotensin receptor blockers}}

It was patented in 1991 and came into medical use in 2002.<ref name=Fis2006/>

==Society and culture==

=== Brand names ===

Olmesartan and Sevikar HCT combined is marketed worldwide by [[Daiichi Sankyo]], in India by Abbott Healthcare Pvt. Ltd. under the trade name WinBP, by Zydus Cadila under the trade name Olmy, by Ranbaxy Laboratories Ltd. under the trade name Olvance, Olsar by Unichem Laboratories and in Canada by Schering-Plough as Olmetec. The marketing rights to the brand names Benicar, Benicar HCT, Azor, and Tribenzor in the United States were transferred from Daiichi Sankyo to Cosette in January 2022.<ref>{{cite press release | title=Cosette Pharmaceuticals Acquires Rights to Eight Branded Products from Daiichi Sankyo | website=Cosette Pharma | date=18 January 2022 | url=https://cosettepharma.com/cosette-pharmaceuticals-acquires-rights-to-eight-branded-products-from-daiichi-sankyo/ | access-date=14 April 2023}}</ref>

Several preparations containing olmesartan and other antihypertensives are available. Teva Pharmaceuticals produces a formulation containing olmesartan, [[amlodipine]], and [[hydrochlorothiazide]].<ref>{{cite web |url=https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=5c128ef2-60a6-40f3-b37f-ee139fe27987 |title=OLMESARTAN MEDOXOMIL, AMLODIPINE AND HYDROCHLOROTHIAZIDE – olmesartan medoxomil, amlodipine and hydrochlorothiazide tablet, film coated |website=DailyMed |publisher=U.S. National Library of Medicine }}</ref> [[Benicar HCT]] is the brand name of a medication containing [[olmesartan medoxomil with hydrochlorothiazide]]. Benitec H, another medication containing olmesartan medoxomil and hydrochlorothiazide, is marketed by GlaxoSmithKline in India.

== Research ==

Olmesartan has demonstrated potential benefits in reducing the progression of atherosclerotic buildup in arteries. In large randomized placebo-controlled or active drug-controlled studies conducted in participants with hypertension, stable angina, or type 2 diabetes, long-term treatment with olmesartan has been shown to reduce the levels of markers of vascular inflammation.<ref>{{cite journal | vauthors = Omboni S, Volpe M | title = Management of arterial hypertension with angiotensin receptor blockers: Current evidence and the role of olmesartan | journal = Cardiovascular Therapeutics | volume = 36 | issue = 6 | pages = e12471 | date = December 2018 | pmid = 30358114 | pmc = 6587798 | doi = 10.1111/1755-5922.12471 }}</ref> This effect was also observed in a high-cholesterol primate test model.<ref>{{cite journal | vauthors = Miyazaki M, Takai S | title = Anti-atherosclerotic efficacy of olmesartan | journal = Journal of Human Hypertension | volume = 16 | issue = Suppl 2 | pages = S7-12 | date = May 2002 | pmid = 11967727 | doi = 10.1038/sj.jhh.1001393 | s2cid = 23755806 }}</ref>

== References ==

{{reflist}}

{{Angiotensin II receptor antagonists}}

{{Angiotensin receptor modulators}}

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[[Category:Angiotensin II receptor antagonists]]

[[Category:Imidazoles]]

[[Category:Tetrazoles]]

[[Category:Carboxylate esters]]

[[Category:Tertiary alcohols]]

[[Category:Biphenyls]]

[[Category:1995 in biotechnology]]

[[Category:Daiichi Sankyo]]

[[Category:Drugs developed by Merck & Co.]]

[[Category:Wikipedia medicine articles ready to translate]]