Telmisartan

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Telmisartan
Telmisartan.svg
Clinical data
Pronunciation /tɛlmɪˈsɑːrtən/
Trade names Micardis, Actavis, others
AHFS/Drugs.com Monograph
MedlinePlus a601249
License data
Pregnancy
category
  • AU:D
Routes of
administration 		By mouth
Drug class Angiotensin II receptor antagonist
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 42–100%
Protein binding >99.5%
Metabolism Minimal liver (glucuronidation)
Elimination half-life 24 hours
Excretion Feces 97%
Identifiers
  • 2-(4-{[4-Methyl-6-(1-methyl-1H-1,3-benzodiazol-2-yl)-2-propyl-1H-1,3-benzodiazol-1-yl]methyl}phenyl)benzoic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.149.347 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C33H30N4O2
Molar mass 514.629 g·mol−1
3D model (JSmol)
  • O=C(O)c1ccccc1c2ccc(cc2)Cn3c4cc(cc(c4nc3CCC)C)c5nc6ccccc6n5C
  • InChI=1S/C33H30N4O2/c1-4-9-30-35-31-21(2)18-24(32-34-27-12-7-8-13-28(27)36(32)3)19-29(31)37(30)20-22-14-16-23(17-15-22)25-10-5-6-11-26(25)33(38)39/h5-8,10-19H,4,9,20H2,1-3H3,(H,38,39) Yes check.svgY
  • Key:RMMXLENWKUUMAY-UHFFFAOYSA-N Yes check.svgY
   (verify)

Telmisartan, sold under the brand name Micardis among others, is a medication used to treat high blood pressure, heart failure, and diabetic kidney disease. [2] It is a reasonable initial treatment for high blood pressure. [2] It is taken by mouth. [2] Versions are available as the combination [3] telmisartan/hydrochlorothiazide, telmisartan/cilnidipine [4] and telmisartan/amlodipine. [2]

Contents

Common side effects include upper respiratory tract infections, diarrhea, and back pain. [2] Serious side effects may include kidney problems, low blood pressure, and angioedema. [2] Use in pregnancy may harm the baby and use when breastfeeding is not recommended. [5] It is an angiotensin II receptor antagonist and works by blocking the effects of angiotensin II. [2]

Telmisartan was patented in 1991 and came into medical use in 1999. [6] It is available as a generic medication. [7] In 2021, it was the 217th most commonly prescribed medication in the United States, with about 2 million prescriptions. [8]

Medical uses

Telmisartan is used to treat high blood pressure, heart failure, and diabetic kidney disease. [2] It is a reasonable initial treatment for high blood pressure. [2] [9] : 146 

Contraindications

Telmisartan is contraindicated during pregnancy. Like other drugs affecting the renin–angiotensin system (RAS), telmisartan can cause birth defects, stillbirths, and neonatal deaths. It is not known whether the drug passes into the breast milk. [10] Also it is contraindicated in bilateral renal artery stenosis in which it can cause kidney failure.

Side effects

Side effects are similar to other angiotensin II receptor antagonists and include tachycardia and bradycardia (fast or slow heartbeat), hypotension (low blood pressure) and edema (swelling of arms, legs, lips, tongue, or throat, the latter leading to breathing problems). Allergic reactions may also occur. [10]

Interactions

Due to its mechanism of action, telmisartan increases blood potassium levels. Combination with potassium preparations or potassium-sparing diuretics could cause hyperkalaemia (excessive potassium levels). Combination with NSAIDs, especially in patients with impaired kidney function, has a risk of causing (usually reversible) kidney failure. [11]

Pharmacology

Mechanism of action

Telmisartan is an angiotensin II receptor blocker that shows high affinity for the angiotensin II receptor type 1 (AT1), with a binding affinity 3000 times greater for AT1 than AT2.

In addition to blocking the renin–angiotensin system, telmisartan acts as a selective modulator of peroxisome proliferator-activated receptor gamma (PPAR-γ), a central regulator of insulin and glucose metabolism. It is believed that telmisartan's dual mode of action may provide protective benefits against the vascular and renal damage caused by diabetes and cardiovascular disease (CVD). [12]

Telmisartan's activity at the peroxisome proliferator-activated receptor delta (PPAR-δ) receptor has prompted speculation around its potential as a sport doping agent as an alternative to GW 501516. [13] Telmisartan activates PPAR-δ receptors in several tissues. [14] [15] [16] [17]

Also, telmisartan has a PPAR-γ agonist activity. [9] : 171 

Pharmacokinetics

The substance is quickly but to varying degrees absorbed from the gut. The average bioavailability is about 50% (42–100%). Food intake has no clinically relevant influence on the kinetics of telmisartan. Plasma protein binding is over 99.5%, mainly to albumin and alpha-1-acid glycoprotein. [11] It has the longest half-life of any angiotensin II receptor blocker (ARB) (24 hours) [18] [12] and the largest volume of distribution among ARBs (500 liters). [19] [20] Less than 3% of telmisartan is inactivated by glucuronidation in the liver, and over 97% is eliminated in unchanged form via bile and faeces. [2] [11]

History

Society and culture

Telmisartan is available as a generic medication. [7]

Related Research Articles

<span class="mw-page-title-main">ACE inhibitor</span> Class of medications used primarily to treat high blood pressure

Angiotensin-converting-enzyme inhibitors are a class of medication used primarily for the treatment of high blood pressure and heart failure. This class of medicine works by causing relaxation of blood vessels as well as a decrease in blood volume, which leads to lower blood pressure and decreased oxygen demand from the heart.

<span class="mw-page-title-main">Angiotensin</span> Group of peptide hormones in mammals

Angiotensin is a peptide hormone that causes vasoconstriction and an increase in blood pressure. It is part of the renin–angiotensin system, which regulates blood pressure. Angiotensin also stimulates the release of aldosterone from the adrenal cortex to promote sodium retention by the kidneys.

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">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">Amiloride</span> Medication

Amiloride, sold under the trade name Midamor among others, is a medication typically used with other medications to treat high blood pressure or swelling due to heart failure or cirrhosis of the liver. Amiloride is classified as a potassium-sparing diuretic. Amiloride is often used together with another diuretic, such as a thiazide or loop diuretic. It is taken by mouth. Onset of action is about two hours and it lasts for about a day.

<span class="mw-page-title-main">Ramipril</span> ACE inhibitor

Ramipril, sold under the brand name Altace among others, is an ACE inhibitor type medication used to treat high blood pressure, heart failure, and diabetic kidney disease. It can also be used as a preventative medication in patients over 55 years old to reduce the risk of having a heart attack, stroke or cardiovascular death in patients shown to be at high risk, such as some diabetics and patients with vascular disease. It is a reasonable initial treatment for high blood pressure. It is taken by mouth.

<span class="mw-page-title-main">Losartan</span> Blood pressure medication

Losartan, sold under the brand name Cozaar among others, is a medication used to treat high blood pressure (hypertension). It is in the angiotensin receptor blocker (ARB) family of medication, and is considered protective of the kidneys. Besides hypertension, it is also used in diabetic kidney disease, heart failure, and left ventricular enlargement. It comes as a tablet that is taken by mouth. It may be used alone or in addition to other blood pressure medication. Up to six weeks may be required for the full effects to occur.

<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">Olmesartan</span> Angiotensin II receptor antagonist

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

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

Penbutolol is a medication in the class of beta blockers, used in the treatment of high blood pressure. Penbutolol is able to bind to both beta-1 adrenergic receptors and beta-2 adrenergic receptors, thus making it a non-selective β blocker. Penbutolol is a sympathomimetic drug with properties allowing it to act as a partial agonist at β adrenergic receptors.

<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">Azilsartan</span> Chemical compound

Azilsartan, sold under the brand name Edarbi among others, is used for the treatment of hypertension. It is used as the prodrug azilsartan medoxomil, is an angiotensin II receptor antagonist, and was developed by Takeda.

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].

Telmisartan/hydrochlorothiazide, sold under the brand name Micardis HCT among others, is a fixed-dose combination medication used to treat high blood pressure. It is a combination of telmisartan an angiotensin II receptor antagonist with hydrochlorothiazide a diuretic. It may be used if telmisartan by itself is not sufficient. It is taken by mouth.

<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.

<span class="mw-page-title-main">Sacubitril/valsartan</span> Combination medication

Sacubitril/valsartan, sold under the brand name Entresto, is a fixed-dose combination medication for use in heart failure. It consists of the neprilysin inhibitor sacubitril and the angiotensin receptor blocker valsartan. The combination is sometimes described as an "angiotensin receptor-neprilysin inhibitor" (ARNi). In 2016, the American College of Cardiology/American Heart Association Task Force recommended it as a replacement for an ACE inhibitor or an angiotensin receptor blocker in people with heart failure with reduced ejection fraction.

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

Fimasartan is a non-peptide angiotensin II receptor antagonist (ARB) used for the treatment of hypertension and heart failure. Through oral administration, fimasartan blocks angiotensin II receptor type 1 (AT1 receptors), reducing pro-hypertensive actions of angiotensin II, such as systemic vasoconstriction and water retention by the kidneys. Concurrent administration of fimasartan with diuretic hydrochlorothiazide has shown to be safe in clinical trials. Fimasartan was approved for use in South Korea on September 9, 2010, and is available under the brand name Kanarb through Boryung Pharmaceuticals, who are presently seeking worldwide partnership.

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

Forasartan, otherwise known as the compound SC-52458, is a nonpeptide angiotensin II receptor antagonist (ARB, AT1 receptor blocker).

<span class="mw-page-title-main">GW0742</span> PPAR β/δ receptor Agonist compound

GW0742 is a PPARδ/β agonist that has been investigated for drug use by GlaxoSmithKline.

References

  1. ↑ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA . Retrieved 22 October 2023.
  2. 1 2 3 4 5 6 7 8 9 10 "Telmisartan Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 3 March 2019.
  3. ↑ Golwala D. "Formulation and Evaluation of Mouth Dissolving Tablets of Telmisartan". Inventi Journals. Retrieved 18 July 2020.[ permanent dead link ]
  4. ↑ "Cilacar T". Medical Dialogues. Retrieved 23 February 2021.
  5. ↑ "Telmisartan Pregnancy and Breastfeeding Warnings". Drugs.com. Retrieved 3 March 2019.
  6. ↑ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 471. ISBN   9783527607495.
  7. 1 2 British national formulary : BNF 76 (76 ed.). Pharmaceutical Press. 2018. p. 178. ISBN   9780857113382.
  8. ↑ "The Top 300 of 2021". clincalc.com. Retrieved 25 January 2024.
  9. 1 2 Opie LH, Gersh BJ (2009). Drugs for the heart (seventh ed.). Saunders. ISBN   978-1-4160-6158-8.
  10. 1 2 Drugs.com: Micardis
  11. 1 2 3 Haberfeld, H, ed. (2015). Austria-Codex (in German). Vienna: Österreichischer Apothekerverlag.
  12. 1 2 Benson SC, Pershadsingh HA, Ho CI, Chittiboyina A, Desai P, Pravenec M, et al. (May 2004). "Identification of telmisartan as a unique angiotensin II receptor antagonist with selective PPARgamma-modulating activity". Hypertension. 43 (5): 993–1002. doi: 10.1161/01.HYP.0000123072.34629.57 . PMID   15007034.
  13. ↑ Sanchis-Gomar F, Lippi G (March 2012). "Telmisartan as metabolic modulator: a new perspective in sports doping?". Journal of Strength and Conditioning Research. 26 (3): 608–10. doi: 10.1519/JSC.0b013e31824301b6 . PMID   22130396.
  14. ↑ Cytoplasmic and Nuclear Receptors: Advances in Research and Application: 2011 Edition. ScholarlyEditions. 2012. pp. 21–. ISBN   978-1-464-93110-9 . Retrieved 2 April 2013.
  15. ↑ Feng X, Luo Z, Ma L, Ma S, Yang D, Zhao Z, et al. (July 2011). "Angiotensin II receptor blocker telmisartan enhances running endurance of skeletal muscle through activation of the PPAR-δ/AMPK pathway". Journal of Cellular and Molecular Medicine. 15 (7): 1572–81. doi:10.1111/j.1582-4934.2010.01085.x. PMC   3823201 . PMID   20477906.
  16. ↑ He H, Yang D, Ma L, Luo Z, Ma S, Feng X, et al. (April 2010). "Telmisartan prevents weight gain and obesity through activation of peroxisome proliferator-activated receptor-delta-dependent pathways". Hypertension. 55 (4): 869–79. doi: 10.1161/HYPERTENSIONAHA.109.143958 . PMID   20176998.
  17. ↑ Li L, Luo Z, Yu H, Feng X, Wang P, Chen J, et al. (March 2013). "Telmisartan improves insulin resistance of skeletal muscle through peroxisome proliferator-activated receptor-δ activation". Diabetes. 62 (3): 762–74. doi:10.2337/db12-0570. PMC   3581229 . PMID   23238297.
  18. ↑ Pritor prescribing information
  19. ↑ Stangier J, Su CA, Roth W (2000). "Pharmacokinetics of orally and intravenously administered telmisartan in healthy young and elderly volunteers and in hypertensive patients". The Journal of International Medical Research. 28 (4): 149–67. doi:10.1177/147323000002800401. PMID   11014323. S2CID   33299699.
  20. ↑ Gosse P (September 2006). "A review of telmisartan in the treatment of hypertension: blood pressure control in the early morning hours". Vascular Health and Risk Management. 2 (3): 195–201. doi: 10.2147/vhrm.2006.2.3.195 . PMC   1993985 . PMID   17326326.

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