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Olmesartan

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Olmesartan
Clinical data
Trade namesBenicar
Other namesOlmesartan medoxomil
AHFS/Drugs.comMonograph
MedlinePlusa603006
License data
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability26%
MetabolismLiver (cannot be removed by hemodialysis)
Elimination half-life13 hours
ExcretionKidney 40%, bile duct 60%
Identifiers
  • (5-methyl-2-oxo-2H-1,3-dioxol-4-yl)methyl 4-(2-hydroxypropan-2-yl)-2-propyl-1-({4-[2-(2H-1,2,3,4-tetrazol-5-yl)phenyl]phenyl}methyl)-1H-imidazole-5-carboxylate
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.174.243 Edit this at Wikidata
Chemical and physical data
FormulaC29H30N6O6
Molar mass558.595 g·mol−1
3D model (JSmol)
  • CCCc1nc(c(n1Cc2ccc(cc2)c3ccccc3c4[nH]nnn4)C(=O)OCc5c(oc(=O)o5)C)C(C)(C)O
  • InChI=1S/C29H30N6O6/c1-5-8-23-30-25(29(3,4)38)24(27(36)39-16-22-17(2)40-28(37)41-22)35(23)15-18-11-13-19(14-12-18)20-9-6-7-10-21(20)26-31-33-34-32-26/h6-7,9-14,38H,5,8,15-16H2,1-4H3,(H,31,32,33,34) checkY
  • Key:UQGKUQLKSCSZGY-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Olmesartan, sold under the brand name Benicar among others, is a medication used to treat high blood pressure (hypertension).[1][2] It is taken orally (swallowed by mouth).[2] Versions are available as the combination olmesartan/hydrochlorothiazide and olmesartan/amlodipine.[2] It is available as a prodrug, olmesartan medoxomil.

Common side effects include dizziness, headaches, diarrhea, and back pain.[2] Serious side effects may include kidney problems, low blood pressure, and angioedema.[2] Use in pregnancy may harm the fetus and use when breastfeeding is not recommended.[3] It is an angiotensin II receptor antagonist and works by blocking the effects of angiotensin II.[2]

It was patented in 1991 and came into medical use in 2002.[4] It is available as a generic medication.[5] In 2022, it was the 97th most commonly prescribed medication in the United States, with more than 6 million prescriptions.[6][7]

Medical uses

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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.[1]

Olmesartan is used for the treatment of hypertension. It may be used alone or in combination with other antihypertensive agents.[8]

Contraindications

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Contraindications 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.[9]

Adverse effects

[edit]

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.[10][11]

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.[12] Recent studies suggested this form of sprue-like enteropathy could be caused by the inhibition of TGF-β, a polypeptide cytokine that maintains intestinal homeostasis. However, it is still unclear why this action was never observed with other ARBs.[13] 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.[1]

Chemistry

[edit]
Olmesartan medoxomil, the prodrug.

Olmesartan medoxomil, an ester prodrug, is completely and rapidly hydrolyzed to its active acid form, olmesartan.[14]

Olmesartan medoxomil metabolism.[15]

History

[edit]
See also: Discovery and development of angiotensin receptor blockers

It was patented in 1991 and came into medical use in 2002.[4]

Society and culture

[edit]

Brand names

[edit]

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.[16]

Several preparations containing olmesartan and other antihypertensives are available. Teva Pharmaceuticals produces a formulation containing olmesartan, amlodipine, and hydrochlorothiazide.[17] 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

[edit]

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.[18] This effect was also observed in a high-cholesterol primate test model.[19]

References

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  1. ^ a b c d "Benicar- olmesartan medoxomil tablet, film coated". DailyMed. 7 September 2022. Retrieved 14 April 2023.
  2. ^ a b c d e f "Olmesartan Medoxomil Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  3. ^ "Olmesartan Pregnancy and Breastfeeding Warnings". Drugs.com. Retrieved 3 March 2019.
  4. ^ a b Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 471. ISBN 9783527607495.
  5. ^ British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 177. ISBN 9780857113382.
  6. ^ "The Top 300 of 2022". ClinCalc. Archived from the original on 30 August 2024. Retrieved 30 August 2024.
  7. ^ "Olmesartan Drug Usage Statistics, United States, 2013 - 2022". ClinCalc. Retrieved 30 August 2024.
  8. ^ "Benicar (olmesartan medoxomil)". RxList Inc. 5 July 2007. Retrieved 22 July 2010.
  9. ^ Hünseler C, Paneitz A, Friedrich D, Lindner U, Oberthuer A, Körber F, et al. (January 2011). "Angiotensin II receptor blocker induced fetopathy: 7 cases". Klinische Padiatrie. 223 (1): 10–14. doi:10.1055/s-0030-1269895. PMID 21271514. S2CID 260206339.
  10. ^ "FDA Alert: Benicar (olmesartan): Ongoing Safety Review". Drugs.com. Retrieved 27 June 2013.
  11. ^ "FDA Drug Safety Communication: FDA review of cardiovascular risks for diabetics taking hypertension drug olmesartan not conclusive; label updates required". U.S. Food and Drug Administration (FDA). 24 June 2014.
  12. ^ De Petris G, Caldero SG, Chen L, Xiao SY, Dhungel BM, Spizcka AJ, et al. (May 2014). "Histopathological changes in the gastrointestinal tract due to medications: an update for the surgical pathologist (part II of II)". International Journal of Surgical Pathology. 22 (3): 202–211. doi:10.1177/1066896913502230. PMID 24021900. S2CID 20614874.
  13. ^ Rubio-Tapia A, Herman ML, Ludvigsson JF, Kelly DG, Mangan TF, Wu TT, et al. (August 2012). "Severe spruelike enteropathy associated with olmesartan". Mayo Clinic Proceedings. 87 (8): 732–738. doi:10.1016/j.mayocp.2012.06.003. PMC 3538487. PMID 22728033.
  14. ^ Aulakh GK, Sodhi RK, Singh M (August 2007). "An update on non-peptide angiotensin receptor antagonists and related RAAS modulators". Life Sciences. 81 (8): 615–639. doi:10.1016/j.lfs.2007.06.007. PMID 17692338.
  15. ^ Ishizuka T, Fujimori I, Kato M, Noji-Sakikawa C, Saito M, Yoshigae Y, et al. (April 2010). "Human carboxymethylenebutenolidase as a bioactivating hydrolase of olmesartan medoxomil in liver and intestine". The Journal of Biological Chemistry. 285 (16): 11892–11902. doi:10.1074/jbc.M109.072629. PMC 2852926. PMID 20177059.
  16. ^ "Cosette Pharmaceuticals Acquires Rights to Eight Branded Products from Daiichi Sankyo". Cosette Pharma (Press release). 18 January 2022. Retrieved 14 April 2023.
  17. ^ "OLMESARTAN MEDOXOMIL, AMLODIPINE AND HYDROCHLOROTHIAZIDE – olmesartan medoxomil, amlodipine and hydrochlorothiazide tablet, film coated". DailyMed. U.S. National Library of Medicine.
  18. ^ Omboni S, Volpe M (December 2018). "Management of arterial hypertension with angiotensin receptor blockers: Current evidence and the role of olmesartan". Cardiovascular Therapeutics. 36 (6): e12471. doi:10.1111/1755-5922.12471. PMC 6587798. PMID 30358114.
  19. ^ Miyazaki M, Takai S (May 2002). "Anti-atherosclerotic efficacy of olmesartan". Journal of Human Hypertension. 16 (Suppl 2): S7-12. doi:10.1038/sj.jhh.1001393. PMID 11967727. S2CID 23755806.
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