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QuickView for telmisartan (compound)

Summary
General Info

PubChem

PubChem Compound 65999

Name:	telmisartan
PubChem Compound ID:	65999
Molecular formula:	C₃₃H₃₀N₄O₂
Molecular weight:	514.617 g/mol
Synonyms:	(1,1'-Biphenyl)-2-carboxylic acid, 4'-((1,4'-dimethyl-2'-propyl(2,6'-bi-1H-benzimidazol)-1'-yl)methyl)-; Kinzalmono; 144701-48-4; 4'-((4-Methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl)methyl)-2-biphenylcarboxylic acid; YM-086; KBio3_001958; Spectrum4_001261; Micardis (TN); Pritor; Spectrum2_001976. show more » (1,1'-Biphenyl)-2-carboxylic acid, 4'-((1,4'-dimethyl-2'-propyl(2,6'-bi-1H-benzimidazol)-1'-yl)methyl)-; Kinzalmono; 144701-48-4; 4'-((4-Methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl)methyl)-2-biphenylcarboxylic acid; YM-086; KBio3_001958; Spectrum4_001261; Micardis (TN); Pritor; Spectrum2_001976; BIBR 277; Telmisartan; BIBR 277SE; BIBR-277; Micardis; Telmisartan [INN]; Spectrum3_001089; D00627; BIBR-277-SE; LS-44263; KBioGR_001842; SPBio_002131; Telmisartan (JAN/USAN); C07710 show less «

DrugBank

Identification

Name:	telmisartan
Name (isomeric):	DB00966
Drug Type:	small molecule
Synonyms:	BIBR 277; BIBR 277SE
Brand:	Pritor, Micardis, Micardis HCT
Brand name mixture:	Micardis Plus(Hydrochlorothiazide + Telmisartan)
Category:	Angiotensin II Type 1 Receptor Blockers, Angiotensin-converting Enzyme Inhibitors
CAS number:	144701-48-4

Pharmacology

Indication:	Used alone or in combination with other classes of antihypertensives for the treatment of hypertension. Also used in the treatment of diabetic nephropathy in hypertensive patients with type 2 diabetes mellitus, as well as the treatment of congestive heart failure (only in patients who cannot tolerate ACE inhibitors).
Pharmacology:	Telmisartan is an orally active nonpeptide angiotensin II antagonist that acts on the AT₁ receptor subtype. It has the highest affinity for the AT₁ receptor among commercially available ARBS and has minimal affinity for the AT₂ receptor. New studies suggest that telmisartan may also have PPARγ agonistic proper... show more » Telmisartan is an orally active nonpeptide angiotensin II antagonist that acts on the AT₁ receptor subtype. It has the highest affinity for the AT₁ receptor among commercially available ARBS and has minimal affinity for the AT₂ receptor. New studies suggest that telmisartan may also have PPARγ agonistic properties that could potentially confer beneficial metabolic effects, as PPARγ is a nuclear receptor that regulates specific gene transcription, and whose target genes are involved in the regulation of glucose and lipid metabolism, as well as anti-inflammatory responses. This observation is currently being explored in clinical trials. Angiotensin II is formed from angiotensin I in a reaction catalyzed by angiotensin-converting enzyme (ACE, kininase II). Angiotensin II is the principal pressor agent of the renin-angiotensin system, with effects that include vasoconstriction, stimulation of synthesis and release of aldosterone, cardiac stimulation, and renal reabsorption of sodium. Telmisartan works by blocking the vasoconstrictor and aldosterone secretory effects of angiotensin II. show less «
Mechanism of Action:	Telmisartan interferes with the binding of angiotensin II to the angiotensin II AT₁-receptor by binding reversibly and selectively to the receptors in vascular smooth muscle and the adrenal gland. As angiotensin II is a vasoconstrictor, which also stimulates the synthesis and release of aldosterone, blockage of its effects results in dec... show more » Telmisartan interferes with the binding of angiotensin II to the angiotensin II AT₁-receptor by binding reversibly and selectively to the receptors in vascular smooth muscle and the adrenal gland. As angiotensin II is a vasoconstrictor, which also stimulates the synthesis and release of aldosterone, blockage of its effects results in decreases in systemic vascular resistance. Telmisartan does not inhibit the angiotensin converting enzyme, other hormone receptors, or ion channels. Studies also suggest that telmisartan is a partial agonist of PPARγ, which is an established target for antidiabetic drugs. This suggests that telmisartan can improve carbohydrate and lipid metabolism, as well as control insulin resistance without causing the side effects that are associated with full PPARγ activators. show less «
Absorption:	Absolute bioavailability depends on dosage. Food slightly decreases the bioavailability (a decrease of about 6% is seen when the 40-mg dose is administered with food).
Protein binding:	Highly bound to plasma proteins (>99.5%), mainly albumin and a1-acid glycoprotein. Binding is not dose-dependent.
Biotransformation:	Minimally metabolized by conjugation to form a pharmacologically inactive acylglucuronide; the glucuronide of the parent compound is the only metabolite that has been identified in human plasma and urine. The cytochrome P450 isoenzymes are not involved in the metabolism of telmisartan.
Route of elimination:	Following either intravenous or oral administration of 14C-labeled telmisartan, most of the administered dose (>97%) was eliminated unchanged in feces via biliary excretion; only minute amounts were found in the urine (0.91% and 0.49% of total radioactivity, respectively).
Half Life:	Bi-exponential decay kinetics with a terminal elimination half-life of approximately 24 hours.
Clearance:	>800 mL/min
Toxicity:	Intravenous LD₅₀ in rats is 150-200 mg/kg in males and 200 to 250 mg/kg in females. Acute oral toxicity is low: no deaths and no changes occurred in rats or dogs at 2000 mg/kg, the highest dose tested. Limited data are available with regard to overdosage in humans. The most likely manifestations of overdosage with telmisartan would be hypotension, dizziness and tachycardia; bradycardia could occur from parasympathetic (vagal) stimulation.
Affected organisms:	Humans and other mammals

Interactions

Drug interaction:

Potassium	Potassium may increase the hyperkalemic effect of Telmisartan. Monitor serum potassium levels during concomitant use.
Trandolapril	The angiotensin II receptor blocker, Telmisartan, may increase the adverse effects of Trandolapril.
Piroxicam	Concomitant use of Telmisartan and Piroxicam may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Potassium Chloride	Potassium Chloride may increase the hyperkalemic effect of Telmisartan. Monitor serum potassium levels during concomitant use.
Nabumetone	Concomitant use of Telmisartan and Nabumetone may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.

Potassium	Potassium may increase the hyperkalemic effect of Telmisartan. Monitor serum potassium levels during concomitant use.
Trandolapril	The angiotensin II receptor blocker, Telmisartan, may increase the adverse effects of Trandolapril.
Piroxicam	Concomitant use of Telmisartan and Piroxicam may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Potassium Chloride	Potassium Chloride may increase the hyperkalemic effect of Telmisartan. Monitor serum potassium levels during concomitant use.
Nabumetone	Concomitant use of Telmisartan and Nabumetone may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Acetylsalicylic acid	Concomitant use of Telmisartan and Acetylsalicylic acid may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Meloxicam	Concomitant use of Telmisartan and Meloxicam may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Ketorolac	Concomitant use of Telmisartan and Ketorolac may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Sulindac	Concomitant use of Telmisartan and Sulindac may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Digoxin	Telmisartan may increase plasma Digoxin concentrations. Monitor Digoxin levels and adjust dose as required if Telmisartan is initiated, discontinued or dose changed.
Triamterene	Telmisartan may increase the hyperkalemic effect of Triamterene. Monitor for increased serum potassium concentrations during concomitant therapy.
Lithium	Telmisartan may increase serum Lithium concentrations. Monitor serum Lithium levels during concomitant therapy to avoid Lithium toxicity.
Oxaprozin	Concomitant use of Telmisartan and Oxaprozin may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Tobramycin	Increased risk of nephrotoxicity
Celecoxib	Concomitant use of Telmisartan and Celecoxib may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Treprostinil	Additive hypotensive effect. Monitor antihypertensive therapy during concomitant use.
Diflunisal	Concomitant use of Telmisartan and Diflunisal may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Drospirenone	Telmisartan may increase the hyperkalemic effect of Drospirenone. Monitor for increased serum potassium concentrations during concomitant therapy.
Rituximab	Telmisartan may increase the hypotensive effect of Rituximab. Telmisartan should be withheld prior to and throughout Rituximab administration.
Amifostine	Telmisartan may increase the hypotensive effect of Amifostine. At chemotherapeutic doses of Amifostine, Telmisartan should be withheld for 24 hours prior to Amifostine administration. Use caution at lower doses of Amifostine.
Ketoprofen	Concomitant use of Telmisartan and Ketoprofen may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Tolmetin	Concomitant use of Telmisartan and Tolmetin may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Diclofenac	Concomitant use of Telmisartan and Diclofenac may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Tiaprofenic acid	Concomitant use of Telmisartan and Tiaprofenic acid may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Meclofenamic acid	Concomitant use of Telmisartan and Meclofenamic acid may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Lumiracoxib	Concomitant use of Telmisartan and Lumiracoxib may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Naproxen	Concomitant use of Telmisartan and Naproxen may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Fenoprofen	Concomitant use of Telmisartan and Fenoprofen may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Amiloride	Telmisartan may increase the hyperkalemic effect of Amiloride. Monitor for increased serum potassium concentrations during concomitant therapy.
Flurbiprofen	Concomitant use of Telmisartan and Flurbiprofen may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Indomethacin	Concomitant use of Telmisartan and Indomethacin may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
Spironolactone	Telmisartan may increase the hyperkalemic effect of Spironolactone. Monitor for increased serum potassium concentrations during concomitant therapy.

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Targets

Type-1 angiotensin II receptor

Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system

UniProt ID:

P30556

Gene:

AGTR1

Actions:

antagonist

References:

Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5.
View Article

Karlberg BE, Lins LE, Hermansson K: Efficacy and safety of telmisartan, a selective AT1 receptor antagonist, compared with enalapril in elderly patients with primary hypertension. TEES Study Group. J Hypertens. 1999 Feb;17(2):293-302.
View Article

Balt JC, Mathy MJ, Nap A, Pfaffendorf M, van Zwieten PA: Effect of the AT1-receptor antagonists losartan, irbesartan, and telmisartan on angiotensin II-induced facilitation of sympathetic neurotransmission in the rat mesenteric artery. J Cardiovasc Pharmacol. 2001 Jul;38(1):141-8.
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Gohlke P, Weiss S, Jansen A, Wienen W, Stangier J, Rascher W, Culman J, Unger T: AT1 receptor antagonist telmisartan administered peripherally inhibits central responses to angiotensin II in conscious rats. J Pharmacol Exp Ther. 2001 Jul;298(1):62-70.
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Strohmenger HU, Lindner KH, Wienen W, Vogt J: Effects of the AT1-selective angiotensin II antagonist, telmisartan, on hemodynamics and ventricular function after cardiopulmonary resuscitation in pigs. Resuscitation. 1997 Aug;35(1):61-8.
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Fujimoto M, Masuzaki H, Tanaka T, Yasue S, Tomita T, Okazawa K, Fujikura J, Chusho H, Ebihara K, Hayashi T, Hosoda K, Nakao K: An angiotensin II AT1 receptor antagonist, telmisartan augments glucose uptake and GLUT4 protein expression in 3T3-L1 adipocytes. FEBS Lett. 2004 Oct 22;576(3):492-7.
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Sharpe M, Jarvis B, Goa KL: Telmisartan: a review of its use in hypertension. Drugs. 2001;61(10):1501-29.
View Article

McClellan KJ, Markham A: Telmisartan. Drugs. 1998 Dec;56(6):1039-44; discussion 1045-6.
View Article

Galzerano D, Capogrosso C, Di Michele S, Galzerano A, Paparello P, Lama D, Gaudio C: New standards in hypertension and cardiovascular risk management: focus on telmisartan. Vasc Health Risk Manag. 2010 Mar 24;6:113-33.
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Tagami T, Yamamoto H, Moriyama K, Sawai K, Usui T, Shimatsu A, Naruse M: A selective peroxisome proliferator-activated receptor-gamma modulator, telmisartan, binds to the receptor in a different fashion from thiazolidinediones. Endocrinology. 2009 Feb;150(2):862-70. Epub 2009 Jan 15.
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Imayama I, Ichiki T, Inanaga K, Ohtsubo H, Fukuyama K, Ono H, Hashiguchi Y, Sunagawa K: Telmisartan downregulates angiotensin II type 1 receptor through activation of peroxisome proliferator-activated receptor gamma. Cardiovasc Res. 2006 Oct 1;72(1):184-90. Epub 2006 Jul 21.
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Kurtz TW: Beyond the classic angiotensin-receptor-blocker profile. Nat Clin Pract Cardiovasc Med. 2008 Jul;5 Suppl 1:S19-26.
View Article

Yamagishi S, Takeuchi M: Telmisartan is a promising cardiometabolic sartan due to its unique PPAR-gamma-inducing property. Med Hypotheses. 2005;64(3):476-8.
View Article

Yamagishi S, Nakamura K, Matsui T: Potential utility of telmisartan, an angiotensin II type 1 receptor blocker with peroxisome proliferator-activated receptor-gamma (PPAR-gamma)-modulating activity for the treatment of cardiometabolic disorders. Curr Mol Med. 2007 Aug;7(5):463-9.
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Peroxisome proliferator-activated receptor gamma

Receptor that binds peroxisome proliferators such as hypolipidemic drugs and fatty acids. Once activated by a ligand, the receptor binds to a promoter element in the gene for acyl-CoA oxidase and activates its transcription. It therefore controls the peroxisomal beta-oxidation pathway of fatty acids. Key regulator of adipocyte differentiation and glucose homeostasis

UniProt ID:

P37231

Gene:

PPARG

Actions:

partial agonist

References:

Kurtz TW: Beyond the classic angiotensin-receptor-blocker profile. Nat Clin Pract Cardiovasc Med. 2008 Jul;5 Suppl 1:S19-26.
View Article

Yamagishi S, Takeuchi M: Telmisartan is a promising cardiometabolic sartan due to its unique PPAR-gamma-inducing property. Med Hypotheses. 2005;64(3):476-8.
View Article

Kurtz TW: Treating the metabolic syndrome: telmisartan as a peroxisome proliferator-activated receptor-gamma activator. Acta Diabetol. 2005 Apr;42 Suppl 1:S9-16.
View Article

Yamagishi S, Takenaka K, Inoue H: Role of insulin-sensitizing property of telmisartan, a commercially available angiotensin II type 1 receptor blocker in preventing the development of atrial fibrillation. Med Hypotheses. 2006;66(1):118-20. Epub 2005 Sep 12.
View Article

Enzymes

Cytochrome P450 2C19

Transporters

Multidrug resistance protein 1

Canalicular multispecific organic anion transporter 1

ATP-binding cassette sub-family G member 2