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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:07:24
Primary Accession Number DB00966
Secondary Accession Number
  • APRD01247
Name Telmisartan
Drug Type
  • Approved
  • Investigational
  • Small Molecule
Description Telmisartan is an angiotensin II receptor antagonist (ARB) used in the management of hypertension. Generally, angiotensin II receptor blockers (ARBs) such as telmisartan bind to the angiotensin II type 1 (AT1) receptors with high affinity, causing inhibition of the action of angiotensin II on vascular smooth muscle, ultimately leading to a reduction in arterial blood pressure. Recent studies suggest that telmisartan may also have PPAR-gamma agonistic properties that could potentially confer beneficial metabolic effects.
Synonyms
  1. BIBR 277
  2. BIBR 277SE
  3. telmisartan
Brand Names
  1. Micardis
  2. Micardis HCT
  3. Pritor
Brand Mixtures
  1. Micardis Plus (Hydrochlorothiazide + Telmisartan)
Chemical IUPAC Name 2-[4-[[4-methyl-6-(1-methylbenzimidazol-2-yl)-2-propylbenzimidazol-1-yl]methyl]phenyl]benzoic acid
Chemical Formula C33H30N4O2
Chemical Structure Structure
CAS Registry Number 144701-48-4
InChI Identifier InChI=1/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)/f/h38H
InChI Key RMMXLENWKUUMAY-GLAYEKRECL
KEGG Drug D00627 Link Image
KEGG Compound C07710 Link Image
PubChem Compound 65999 Link Image
PubChem Substance 9912 Link Image
ChEBI ID Not Available
PharmGKB ID PA451605 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] 02240770 Link Image
RxList Link http://www.rxlist.com/cgi/generic2/telmisartan.htm Link Image
PDRhealth Link http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/mic1592.shtml Link Image
Wikipedia Link http://en.wikipedia.org/wiki/Telmisartan Link Image
FDA Label
Material Safety Data Sheet (MSDS)
Synthesis Reference Not Available
Average Molecular Weight 514.6169
Monoisotopic Molecular Weight 514.2369
State Solid
Melting Point 261-263oC
Experimental Water Solubility Practically insoluble Source: PhysProp
Predicted Water Solubility 3.51e-03 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 7.7 Source: PhysProp
Predicted LogP 6.66 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -5.17 Calculated using ALOGPS
Experimental Caco2 Permeability -4.82 [ADME Research, USCD]
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID Not Available
Isomeric SMILES CCCC1=NC2=C(C=C(C=C2C)C2=NC3=CC=CC=C3N2C)N1CC1=CC=C(C=C1)C1=CC=CC=C1C(O)=O
Canonical SMILES CCCC1=NC2=C(C=C(C=C2C)C2=NC3=CC=CC=C3N2C)N1CC1=CC=C(C=C1)C1=CC=CC=C1C(O)=O
Drug Category
  • Angiotensin II Type 1 Receptor Blockers
  • Angiotensin-converting Enzyme Inhibitors
ATC Codes
AHFS Codes
  • 24:32.08
Indication For the treatment of hypertension.
Pharmacology Telmisartan is an orally active nonpeptide angiotensin II antagonist that acts on the AT1 receptor subtype. New studies suggest that telmisartan may also have PPARγ agonistic properties that could potentially confer beneficial metabolic effects. 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.
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 decreases in systemic vascular resistance. Telmisartan does not inhibit the angiotensin converting enzyme, other hormone receptors, or ion channels.
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).
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.
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.
Half Life Bi-exponential decay kinetics with a terminal elimination half-life of approximately 24 hours.
Dosage Forms
Form Route
Tablet Oral
Patient Information Show Link Image
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions
Drug Interaction
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.
Amiloride Telmisartan may increase the hyperkalemic effect of Amiloride. Monitor for increased serum potassium concentrations during concomitant therapy.
Aspirin Concomitant use of Telmisartan and Aspirin may increase the risk of acute renal failure and hyperkalemia. Monitor renal function at the beginning and during treatment.
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.
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.
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.
Digoxin Telmisartan may increase plasma Digoxin concentrations. Monitor Digoxin levels and adjust dose as required if Telmisartan is initiated, discontinued or dose changed.
Drospirenone Telmisartan may increase the hyperkalemic effect of Drospirenone. Monitor for increased serum potassium concentrations during concomitant therapy.
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.
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.
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.
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.
Lithium Telmisartan may increase serum Lithium concentrations. Monitor serum Lithium levels during concomitant therapy to avoid Lithium toxicity.
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.
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.
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.
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.
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.
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.
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 Potassium may increase the hyperkalemic effect of Telmisartan. Monitor serum potassium levels during concomitant use.
Potassium Chloride Potassium Chloride may increase the hyperkalemic effect of Telmisartan. Monitor serum potassium levels during concomitant use.
Rituximab Telmisartan may increase the hypotensive effect of Rituximab. Telmisartan should be withheld prior to and throughout Rituximab administration.
Spironolactone Telmisartan may increase the hyperkalemic effect of Spironolactone. Monitor for increased serum potassium concentrations during concomitant therapy.
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.
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.
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.
Triamterene Telmisartan may increase the hyperkalemic effect of Triamterene. Monitor for increased serum potassium concentrations during concomitant therapy.
Food Interactions Not Available
Pathways Not Available
General References
  1. Wikipedia Link Image
  2. RxList Link Image
  3. PDRhealth Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Type-1 angiotensin II receptor
Drug Target 1 [top]
Target 1 ID 70
Target 1 Name Type-1 angiotensin II receptor
Target 1 Synonyms
  1. AT1
  2. AT1AR
  3. AT1BR
Target 1 Gene Name AGTR1
Target 1 Protein Sequence >Type-1 angiotensin II receptor 
MILNSSTEDGIKRIQDDCPKAGRHNYIFVMIPTLYSIIFVVGIFGNSLVVIVIYFYMKLK
TVASVFLLNLALADLCFLLTLPLWAVYTAMEYRWPFGNYLCKIASASVSFNLYASVFLLT
CLSIDRYLAIVHPMKSRLRRTMLVAKVTCIIIWLLAGLASLPAIIHRNVFFIENTNITVC
AFHYESQNSTLPIGLGLTKNILGFLFPFLIILTSYTLIWKALKKAYEIQKNKPRNDDIFK
IIMAIVLFFFFSWIPHQIFTFLDVLIQLGIIRDCRIADIVDTAMPITICIAYFNNCLNPL
FYGFLGKKFKRYFLQLLKYIPPKAKSHSNLSTKMSTLSYRPSDNVSSSTKKPAPCFEVE
Target 1 Number of Residues 364
Target 1 Molecular Weight 41062
Target 1 Theoretical pI 9.71
Target 1 GO Classification
Function
G-protein chemoattractant receptor activity
chemokine receptor activity
C-X-C chemokine receptor activity
bradykinin receptor activity
signal transducer activity
receptor activity
transmembrane receptor activity
G-protein coupled receptor activity
rhodopsin-like receptor activity
peptide receptor activity, G-protein coupled
angiotensin receptor activity
angiotensin type II receptor activity
Process
cellular process
cell communication
signal transduction
cell surface receptor linked signal transduction
G-protein coupled receptor protein signaling pathway
Component
cell
membrane
intrinsic to membrane
integral to membrane
Target 1 General Function Involved in angiotensin type II receptor activity
Target 1 Specific Function Receptor for angiotensin II. Mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system
Target 1 Pathways Not Available
Target 1 Reactions Not Available
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • 28-52
  • 65-87
  • 103-124
  • 143-162
  • 193-214
  • 241-262
  • 276-296
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 179122 Link Image
Target 1 UniProtKB/Swiss-Prot ID P30556 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name AGTR1_HUMAN Link Image
Target 1 PDB ID Not Available
Target 1 Cellular Location
  • Membrane
  • multi-pass membrane protein
Target 1 Gene Sequence >1080 bp 
ATGATTCTCAACTCTTCTACTGAAGATGGTATTAAAAGAATCCAAGATGATTGTCCCAAA
GCTGGAAGGCATAATTACATATTTGTCATGATTCCTACTTTATACAGTATCATCTTTGTG
GTGGGAATATTTGGAAACAGCTTGGTGGTGATAGTCATTTACTTTTATATGAAGCTGAAG
ACTGTGGCCAGTGTTTTTCTTTTGAATTTAGCACTGGCTGACTTATGCTTTTTACTGACT
TTGCCACTATGGGCTGTCTACACAGCTATGGAATACCGCTGGCCCTTTGGCAATTACCTA
TGTAAGATTGCTTCAGCCAGCGTCAGTTTCAACCTGTACGCTAGTGTGTTTCTACTCACG
TGTCTCAGCATTGATCGATACCTGGCTATTGTTCACCCAATGAAGTCCCGCCTTCGACGC
ACAATGCTTGTAGCCAAAGTCACCTGCATCATCATTTGGCTGCTGGCAGGCTTGGCCAGT
TTGCCAGCTATAATCCATCGAAATGTATTTTTCATTGAGAACACCAATATTACAGTTTGT
GCTTTCCATTATGAGTCCCAAAATTCAACCCTCCCGATAGGGCTGGGCCTGACCAAAAAT
ATACTGGGTTTCCTGTTTCCTTTTCTGATCATTCTTACAAGTTATACTCTTATTTGGAAG
GCCCTAAAGAAGGCTTATGAAATTCAGAAGAACAAACCAAGAAATGATGATATTTTTAAG
ATAATTATGGCAATTGTGCTTTTCTTTTTCTTTTCCTGGATTCCCCACCAAATATTCACT
TTTCTGGATGTATTGATTCAACTAGGCATCATACGTGACTGTAGAATTGCAGATATTGTG
GACACGGCCATGCCTATCACCATTTGTATAGCTTATTTTAACAATTGCCTGAATCCTCTT
TTTTATGGCTTTCTGGGGAAAAAATTTAAAAGATATTTTCTCCAGCTTCTAAAATATATT
CCCCCAAAAGCCAAATCCCACTCAAACCTTTCAACAAAAATGAGCACGCTTTCCTACCGC
CCCTCAGATAATGTAAGCTCATCCACCAAGAAGCCTGCACCATGTTTTGAGGTTGAGTGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID AGTR1 Link Image
Target 1 GenAtlas ID AGTR1 Link Image
Target 1 HGNC ID HGNC:336 Link Image
Target 1 Chromosome Location 3
Target 1 Locus 3q21-q25
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Mauzy CA, Hwang O, Egloff AM, Wu LH, Chung FZ: Cloning, expression, and characterization of a gene encoding the human angiotensin II type 1A receptor. Biochem Biophys Res Commun. 1992 Jul 15;186(1):277-84. [PubMed Link Image]
  2. Curnow KM, Pascoe L, White PC: Genetic analysis of the human type-1 angiotensin II receptor. Mol Endocrinol. 1992 Jul;6(7):1113-8. [PubMed Link Image]
  3. Furuta H, Guo DF, Inagami T: Molecular cloning and sequencing of the gene encoding human angiotensin II type 1 receptor. Biochem Biophys Res Commun. 1992 Feb 28;183(1):8-13. [PubMed Link Image]
  4. Takayanagi R, Ohnaka K, Sakai Y, Nakao R, Yanase T, Haji M, Inagami T, Furuta H, Gou DF, Nakamuta M, et al.: Molecular cloning, sequence analysis and expression of a cDNA encoding human type-1 angiotensin II receptor. Biochem Biophys Res Commun. 1992 Mar 16;183(2):910-6. [PubMed Link Image]
  5. Bergsma DJ, Ellis C, Kumar C, Nuthulaganti P, Kersten H, Elshourbagy N, Griffin E, Stadel JM, Aiyar N: Cloning and characterization of a human angiotensin II type 1 receptor. Biochem Biophys Res Commun. 1992 Mar 31;183(3):989-95. [PubMed Link Image]
  6. Nawata H, Takayanagi R, Ohnaka K, Sakai Y, Imasaki K, Yanase T, Ikuyama S, Tanaka S, Ohe K: Type 1 angiotensin II receptors of adrenal tumors. Steroids. 1995 Jan;60(1):28-34. [PubMed Link Image]
  7. Konishi H, Kuroda S, Inada Y, Fujisawa Y: Novel subtype of human angiotensin II type 1 receptor: cDNA cloning and expression. Biochem Biophys Res Commun. 1994 Mar 15;199(2):467-74. [PubMed Link Image]
Target 1 Drug References
  1. 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. [PubMed Link Image]
  2. 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. [PubMed Link Image]
  3. 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. [PubMed Link Image]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed Link Image]
  5. 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. [PubMed Link Image]
  6. 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. [PubMed Link Image]

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