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144701-48-4 molecular structure
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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

ChemBase ID: 841
Molecular Formular: C33H30N4O2
Molecular Mass: 514.6169
Monoisotopic Mass: 514.23687622
SMILES and InChIs

SMILES:
OC(=O)c1c(c2ccc(Cn3c4c(nc3CCC)c(cc(c4)c3n(c4c(n3)cccc4)C)C)cc2)cccc1
Canonical SMILES:
CCCc1nc2c(n1Cc1ccc(cc1)c1ccccc1C(=O)O)cc(cc2C)c1nc2c(n1C)cccc2
InChI:
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)
InChIKey:
RMMXLENWKUUMAY-UHFFFAOYSA-N

Cite this record

CBID:841 http://www.chembase.cn/molecule-841.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
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
IUPAC Traditional name
telmisartan
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
Brand Name
Micardis
Micardis HCT
Pritor
Synonyms
Micardis
Targit
Temax
BIBR277
4'-((1,7'-Dimethyl-2'-propyl-1H,3'H-[2,5'-bibenzo[d]imidazol]-3'-yl)methyl)-[1,1'-biphenyl]-2-carboxylic acid
BIBR 277
BIBR 277SE
telmisartan
Telmisartan
4′[(1,4′-Dimethyl-2′-propyl[2,6′-bi-1H-benzimidazol]-1′-yl)methyl][1,1′-biphenyl]-2-carboxylic acid
Telmisartan
Kinzal
Telma
Teleact D
4’-[(1,4’-Dimethyl-2’-propyl[2,6’-bi-H-benzimidazol]-1’-yl)methyl][1,1’-biphenyl]-2-carboxylic Acid
4'-[[4-Methyl-6-(1-methyl-2-benzimidazolyl)-2-propyl-1-benzimidazolyl]methyl]-2-biphenylcarboxylic Acid
Pritor
CAS Number
144701-48-4
MDL Number
MFCD00918125
PubChem SID
46505370
160964304
PubChem CID
65999

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.645957  H Acceptors
H Donor LogD (pH = 5.5) 6.091965 
LogD (pH = 7.4) 5.0242934  Log P 6.040852 
Molar Refractivity 164.4888 cm3 Polarizability 63.009975 Å3
Polar Surface Area 72.94 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P 6.66  LOG S -5.17 
Solubility (Water) 3.50e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
DMSO: >5 mg/mL at 60 °C expand Show data source
H2O: insoluble expand Show data source
Practically insoluble expand Show data source
Apperance
white solid expand Show data source
White Solid expand Show data source
Melting Point
261-263°C expand Show data source
Hydrophobicity(logP)
7.7 expand Show data source
Storage Condition
-20°C expand Show data source
Hygroscopic, -20°C Freezer, Under Inert Atmosphere expand Show data source
Storage Warning
IRRITANT expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
TSCA Listed
false expand Show data source
Personal Protective Equipment
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand Show data source
Mechanism of Action
Angiotensin II (AT 1 ) receptor antagonist expand Show data source
Purity
≥98% (HPLC) expand Show data source
95+% expand Show data source
98% expand Show data source
Salt Data
Free Base expand Show data source
Certificate of Analysis
Download expand Show data source
Application(s)
Antihypertensive agent expand Show data source
Empirical Formula (Hill Notation)
C33H30N4O2 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00966 external link
Item Information
Drug Groups approved; investigational
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.
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 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.
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
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.
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).
Half Life Bi-exponential decay kinetics with a terminal elimination half-life of approximately 24 hours.
Protein Binding Highly bound to plasma proteins (>99.5%), mainly albumin and a1-acid glycoprotein. Binding is not dose-dependent.
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).
Distribution * 500 L
Clearance * >800 mL/min
References
Sharpe M, Jarvis B, Goa KL: Telmisartan: a review of its use in hypertension. Drugs. 2001;61(10):1501-29. [Pubmed]
Smith DH: Treatment of hypertension with an angiotensin II-receptor antagonist compared with an angiotensin-converting enzyme inhibitor: a review of clinical studies of telmisartan and enalapril. Clin Ther. 2002 Oct;24(10):1484-501. [Pubmed]
Kumar AS, Ghosh S, Mehta GN: Efficient and improved synthesis of Telmisartan. Beilstein J Org Chem. 2010 Mar 11;6:25. [Pubmed]
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. [Pubmed]
Kumar AS, Ghosh S, Mehta GN: Efficient and improved synthesis of Telmisartan. Beilstein J Org Chem. 2010 Mar 11;6:25. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com
Selleck Chemicals - S1738 external link
Research Area: Cardiovascular Disease
Biological Activity:
Telmisartan o(Micardis) is an angiotensin II receptor antagonist (ARB) used in the management of hypertension. In addition to blocking the Renin-Angiotensin System (RAS), telmisartan acts as a selective modulator of Peroxisome proliferator-activated receptor gamma (PPAR-γ), a central regulator of insulin and glucose metabolism. Telmisartan has binding affinity 3000 times greater for AT1 than AT2 receptors. Telmisartan also has the longest half life (24 hrs) of all angiotensin II type 1 receptor antagonists. [1]
Sigma Aldrich - T8949 external link
Biochem/physiol Actions
Telmisartan is a non-peptide AT1 angiotensin receptor antagonist.
Toronto Research Chemicals - T017000 external link
Telmisartan is an angiotensin II receptor antagonist.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Sharpe M, Jarvis B, Goa KL: Telmisartan: a review of its use in hypertension. Drugs. 2001;61(10):1501-29. Pubmed
  • • Smith DH: Treatment of hypertension with an angiotensin II-receptor antagonist compared with an angiotensin-converting enzyme inhibitor: a review of clinical studies of telmisartan and enalapril. Clin Ther. 2002 Oct;24(10):1484-501. Pubmed
  • • Kumar AS, Ghosh S, Mehta GN: Efficient and improved synthesis of Telmisartan. Beilstein J Org Chem. 2010 Mar 11;6:25. Pubmed
  • • 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. PubmedKumar AS, Ghosh S, Mehta GN: Efficient and improved synthesis of Telmisartan. Beilstein J Org Chem. 2010 Mar 11;6:25. Pubmed
  • • http://en.wikipedia.org/wiki/Telmisartan
  • • Wienen, W., et al.: Brit. J. Pharmacol., 110, 245 (1993)
  • • Neutel, J.M., and Smith, D.H.G.: Adv. Ther., 15, 206 (1998)
  • • Eur. Pat., 1992, Thomae, 502 314; CA, 117, 251352v, (synth, pharmacol)
  • • Wienen, W. et al., Br. J. Pharmacol., 1993, 110, 245, (pharmacol)
  • • Ries, U.J. et al., J. Med. Chem., 1993, 36, 4040, (synth, pmr, pharmacol)
  • • Su, C.A.P.F. et al., Clin. Pharmacol. Ther. (St. Louis), 1994, 55, 205, (pharmacol)
  • • Bhm, M. et al., J. Hypertens., 1995, 13, 891, (pharmacol)
  • • van Meel, J.C.A. et al., Arzneim.-Forsch., 1996, 46, 755, (pharmacol)
  • • McClellan, K.J. et al., Drugs, 1998, 56, 1039-1044, (rev)
  • • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 951
  • • Gavras, I. et al., Cardiovasc. Rev. Rep., 2000, 21, 76
  • • Sharpe, M. et al., Drugs, 2001, 61, 1501-1529, (rev)
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