Olmesartan

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Olmesartan
Olmesartan.png
Clinical data
Trade names Benicar
Other namesOlmesartan medoxomil
AHFS/Drugs.com Monograph
MedlinePlus a603006
License data
Routes of
administration
By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 26%
Metabolism Liver (cannot be removed by hemodialysis)
Elimination half-life 13 hours
Excretion Kidney 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 InfoCard 100.174.243 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C29H30N6O6
Molar mass 558.595 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) Yes check.svgY
  • Key:UQGKUQLKSCSZGY-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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 by mouth. [2] Versions are available as the combination olmesartan/hydrochlorothiazide and olmesartan/amlodipine. [2]

Contents

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 2020, it was the 139th most commonly prescribed medication in the United States, with more than 4 million prescriptions, [6] ranking 3rd among ARB's after Losartan (9th overall) and Valsartan (123rd overall). [7]

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. [1]

Olmesartan is used for the treatment of hypertension. It may be used alone or in combination with other antihypertensive agents. [8] 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. [9]

Contraindications

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. [10]

Adverse effects

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. [11] 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. [12] 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

An ester prodrug, it is completely and rapidly hydrolyzed to its active acid form. [13] The metabolites in this process are carbon dioxide and 2,3-dione.[ citation needed ]

History

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

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. [14]

Several preparations containing olmesartan and other antihypertensives are available. Teva Pharmaceuticals produces a formulation containing olmesartan, amlodipine, and hydrochlorothiazide. [15] 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. [16] This effect was also observed in a high-cholesterol primate test model. [17]

Related Research Articles

<span class="mw-page-title-main">Hydrochlorothiazide</span> Diuretic medication

Hydrochlorothiazide, sold under the brand name Hydrodiuril among others, is a diuretic medication used to treat hypertension and swelling due to fluid build-up. Other uses include treating diabetes insipidus and renal tubular acidosis and to decrease the risk of kidney stones in those with a high calcium level in the urine. Hydrochlorothiazide is taken by mouth and may be combined with other blood pressure medications as a single pill to increase effectiveness. Hydrochlorothiazide is a thiazide medication which inhibits reabsorption of sodium and chloride ions from the distal convoluted tubules of the kidneys, causing a natriuresis. This initially increases urine volume and lowers blood volume. It is believed to reduce peripheral vascular resistance.

Antihypertensives are a class of drugs that are used to treat hypertension. Antihypertensive therapy seeks to prevent the complications of high blood pressure, such as stroke, heart failure, kidney failure and myocardial infarction. Evidence suggests that reduction of the blood pressure by 5 mmHg can decrease the risk of stroke by 34% and of ischaemic heart disease by 21%, and can reduce the likelihood of dementia, heart failure, and mortality from cardiovascular disease. There are many classes of antihypertensives, which lower blood pressure by different means. Among the most important and most widely used medications are thiazide diuretics, calcium channel blockers, ACE inhibitors, angiotensin II receptor antagonists (ARBs), and beta blockers.

<span class="mw-page-title-main">Amlodipine</span> Medication against high blood pressure

Amlodipine, sold under the brand name Norvasc among others, is a calcium channel blocker medication used to treat high blood pressure, coronary artery disease (CAD) and variant angina. It is taken orally.

<span class="mw-page-title-main">Angiotensin II receptor blocker</span> Group of pharmaceuticals that modulate the renin–angiotensin system

Angiotensin II receptor blockers (ARBs), formally angiotensin II receptor type 1 (AT1) antagonists, also known as angiotensin receptor blockers, angiotensin II receptor antagonists, or AT1 receptor antagonists, are a group of pharmaceuticals that bind to and inhibit the angiotensin II receptor type 1 (AT1) and thereby block the arteriolar contraction and sodium retention effects of renin–angiotensin system.

<span class="mw-page-title-main">Irbesartan</span> Chemical compound

Irbesartan, sold under the brand name Avapro among others, is a medication used to treat high blood pressure, heart failure, and diabetic kidney disease. It is a reasonable initial treatment for high blood pressure. It is taken by mouth. Versions are available as the combination irbesartan/hydrochlorothiazide.

<span class="mw-page-title-main">Eprosartan</span> Angiotensin II receptor antagonist

Eprosartan, sold under the brand name Teveten among others, is an angiotensin II receptor antagonist used for the treatment of high blood pressure.

<span class="mw-page-title-main">Candesartan</span> Angiotensin II receptor antagonist

Candesartan is an angiotensin receptor blocker used mainly for the treatment of high blood pressure and congestive heart failure. Candesartan has a very low maintenance dose. Like Olmesartan, the metabolism of the drug is unusual as it is a cascading prodrug. Candesartan has good bioavailibility and is the most potent by weight of the AT-1 receptor antagonists.

<span class="mw-page-title-main">Telmisartan</span> Angiotensin II receptor antagonist

Telmisartan, sold under the brand name Micardis among others, is a medication used to treat high blood pressure, heart failure, and diabetic kidney disease. It is a reasonable initial treatment for high blood pressure. It is taken by mouth. Versions are available as the combination telmisartan/hydrochlorothiazide, telmisartan/cilnidipine and telmisartan/amlodipine.

<span class="mw-page-title-main">Valsartan</span> Angiotensin II receptor antagonist

Valsartan, sold under the brand name Diovan among others, is a medication used to treat high blood pressure, heart failure, and diabetic kidney disease. It belongs to a class of medications referred to as angiotensin II receptor blockers (ARBs). It is a reasonable initial treatment for high blood pressure. It is taken by mouth. Versions are available as the combination valsartan/hydrochlorothiazide, valsartan/amlodipine, valsartan/amlodipine/hydrochlorothiazide, or valsartan/sacubitril.

<span class="mw-page-title-main">Perindopril</span> High blood pressure medication

Perindopril is a medication used to treat high blood pressure, heart failure, or stable coronary artery disease.

<span class="mw-page-title-main">Aliskiren</span> Medication

Aliskiren is the first in a class of drugs called direct renin inhibitors. It is used for essential (primary) hypertension. While used for high blood pressure, other better studied medications are typically recommended due to concerns of higher side effects and less evidence of benefit.

<span class="mw-page-title-main">Amlodipine/valsartan</span> Antihypertensive medication

Amlodipine/valsartan, sold under the brand name Exforge among others, is a blood pressure lowering combination drug. It contains amlodipine, as the besilate, a dihydropyridine-type calcium channel blocker, and valsartan, an angiotensin II receptor antagonist. This combination is usually well tolerated and effective for the reduction of blood pressure.

Amlodipine/olmesartan, sold under the brand name Azor, among others is a fixed-dose combination medication used to treat high blood pressure. It contains amlodipine, as the besilate, a dihydropyridine calcium channel blocker, and olmesartan medoxomil, an angiotensin II receptor blocker.

The angiotensin receptor blockers (ARBs), also called angiotensin (AT1) receptor antagonists or sartans, are a group of antihypertensive drugs that act by blocking the effects of the hormone angiotensin II in the body, thereby lowering blood pressure. Their structure is similar to Ang II and they bind to Ang II receptors as inhibitors, e.g., [T24 from Rhys Healthcare].

<span class="mw-page-title-main">Valsartan/hydrochlorothiazide</span> Chemical compound

Valsartan/hydrochlorothiazide, sold under the brand name Diovan HCT among others, is a medication used to treat high blood pressure when valsartan is not sufficient. It is a combination of valsartan, an angiotensin receptor blocker with hydrochlorothiazide, a diuretic. It is taken by mouth.

Losartan/hydrochlorothiazide, sold under the brand name Hyzaar among others, is a fixed-dose combination medication used to treat high blood pressure when losartan is not sufficient. It consists of losartan and hydrochlorothiazide. It is taken by mouth.

An ACE inhibitor and thiazide combination is a drug combination used to treat hypertension. They are given by mouth. ACE inhibitors reduce the activity of angiotensin-converting enzyme (ACE) which produces angiotensin II, a hormone that constricts blood vessels. Thiazides are a class of diuretics that inhibit the thiazide receptor, thereby increasing urine production and reducing excess water and salt in the body. Several organizations recommend combination therapy for hypertension in cases of failure of a single drug to achieve target blood pressure, or even as a first line treatment for some patients.

Olmesartan/hydrochlorothiazide, sold under the brand name Benicar HCT among others, is a fixed-dose combination medication used to treat high blood pressure. It is a combination of olmesartan medoxomil, an angiotensin II receptor blocker and hydrochlorothiazide, a diuretic. It may be used if olmesartan is not sufficient to manage blood pressure. It is taken by mouth.

Olmesartan/amlodipine/hydrochlorothiazide, sold under the brand name Tribenzor among others, is a fixed-dose combination medication used to treat high blood pressure. It contains olmesartan medoxomil, an angiotensin II receptor blocker, amlodipine, as the besilate, a calcium channel blocker, and hydrochlorothiazide, a thiazide diuretic. It is taken by mouth.

References

  1. 1 2 3 4 "Benicar- olmesartan medoxomil tablet, film coated". DailyMed. 7 September 2022. Retrieved 14 April 2023.
  2. 1 2 3 4 5 6 "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. 1 2 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. "Olmesartan - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
  7. "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  8. "Benicar (olmesartan medoxomil)". RxList Inc. 5 July 2007. Retrieved 22 July 2010.
  9. "FDA Alert: Benicar (olmesartan): Ongoing Safety Review". Drugs.com. Retrieved 27 June 2013.
  10. 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.
  11. De Petris G, Caldero SG, Chen L, Xiao SY, Dhungel BM, Spizcka AJ, Lam-Himlin D (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.
  12. Rubio-Tapia A, Herman ML, Ludvigsson JF, Kelly DG, Mangan TF, Wu TT, Murray JA (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.
  13. 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.
  14. "Cosette Pharmaceuticals Acquires Rights to Eight Branded Products from Daiichi Sankyo". Cosette Pharma (Press release). 18 January 2022. Retrieved 14 April 2023.
  15. "OLMESARTAN MEDOXOMIL, AMLODIPINE AND HYDROCHLOROTHIAZIDE – olmesartan medoxomil, amlodipine and hydrochlorothiazide tablet, film coated". DailyMed. U.S. National Library of Medicine.
  16. 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.
  17. 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.