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144701-48-4 分子结构
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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编号:841
分子式:C33H30N4O2
平均质量:514.6169
单一同位素质量:514.23687622
SMILES和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

引用这个纪录

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

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
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传统名
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
商标名
Micardis
Micardis HCT
Pritor
别名
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号
144701-48-4
MDL号
MFCD00918125
PubChem SID
160964304
46505370
PubChem CID
65999

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 3.645957  质子受体
质子供体 LogD (pH = 5.5) 6.091965 
LogD (pH = 7.4) 5.0242934  Log P 6.040852 
摩尔折射率 164.4888 cm3 极化性 63.009975 Å3
极化表面积 72.94 Å2 可自由旋转的化学键
里宾斯基五规则 false 
Log P 6.66  LOG S -5.17 
溶解度 3.50e-03 g/l 

分子性质

分子性质

理化性质 安全信息 药理学性质 产品相关信息 生物活性(PubChem)
溶解度
Chloroform expand 查看数据来源
DMSO: >5 mg/mL at 60 °C expand 查看数据来源
H2O: insoluble expand 查看数据来源
Practically insoluble expand 查看数据来源
外观
white solid expand 查看数据来源
White Solid expand 查看数据来源
熔点
261-263°C expand 查看数据来源
疏水性(logP)
7.7 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
Hygroscopic, -20°C Freezer, Under Inert Atmosphere expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
下载链接 expand 查看数据来源
德国WGK号
2 expand 查看数据来源
TSCA收录
false expand 查看数据来源
个人保护装置
Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter expand 查看数据来源
生物活性机理
Angiotensin II (AT 1 ) receptor antagonist expand 查看数据来源
纯度
≥98% (HPLC) expand 查看数据来源
95+% expand 查看数据来源
98% expand 查看数据来源
成盐信息
Free Base expand 查看数据来源
质检报告
下载链接 expand 查看数据来源
应用领域
Antihypertensive agent expand 查看数据来源
Empirical Formula (Hill Notation)
C33H30N4O2 expand 查看数据来源

详细说明

详细说明

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.

参考文献

参考文献

供应商提供 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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