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72956-09-3 分子结构
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[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl][2-(2-methoxyphenoxy)ethyl]amine

ChemBase编号:1007
分子式:C24H26N2O4
平均质量:406.47424
单一同位素质量:406.18925732
SMILES和InChIs

SMILES:
O(c1c2c3c([nH]c2ccc1)cccc3)CC(O)CNCCOc1c(OC)cccc1
Canonical SMILES:
COc1ccccc1OCCNCC(COc1cccc2c1c1ccccc1[nH]2)O
InChI:
InChI=1S/C24H26N2O4/c1-28-21-10-4-5-11-22(21)29-14-13-25-15-17(27)16-30-23-12-6-9-20-24(23)18-7-2-3-8-19(18)26-20/h2-12,17,25-27H,13-16H2,1H3
InChIKey:
OGHNVEJMJSYVRP-UHFFFAOYSA-N

引用这个纪录

CBID:1007 http://www.chembase.cn/molecule-1007.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
[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl][2-(2-methoxyphenoxy)ethyl]amine
IUPAC传统名
carvedilol
[3-(9H-carbazol-4-yloxy)-2-hydroxypropyl][2-(2-methoxyphenoxy)ethyl]amine
商标名
Coreg
Coreg CR
别名
Carvedilolum [Latin]
carvedilol
Carvedilol
Coreg
Dilatrend
1-(9H-Carbazol-4-yloxy)-3-[[2-(2-methoxyphenoxy)ethyl]amino]-2-propanol
BM-14190
Carvedilol
Artist
BM 14190
Cadilan
Carca
Cardivas
Carloc
Carvas
Carvediol
DQ 2466
Dimitone
Eucardic
Korvasan
Kredex
Querto
SKF 105517
Talliton
1-((9H-carbazol-4-yl)oxy)-3-((2-(2-methoxyphenoxy)ethyl)amino)propan-2-ol
CAS号
72956-09-3
MDL号
MFCD00864692
PubChem SID
160964470
46505146
PubChem CID
2585

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 14.030432  质子受体
质子供体 LogD (pH = 5.5) 0.48382187 
LogD (pH = 7.4) 2.069334  Log P 3.4248545 
摩尔折射率 115.6377 cm3 极化性 47.905235 Å3
极化表面积 75.74 Å2 可自由旋转的化学键 10 
里宾斯基五规则 true 
Log P 3.05  LOG S -4.96 
溶解度 4.44e-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 expand 查看数据来源
DMSO: >20 mg/mL expand 查看数据来源
Methanol expand 查看数据来源
Practically insoluble (0.583 mg/L) expand 查看数据来源
外观
White Solid expand 查看数据来源
white to off-white solid expand 查看数据来源
熔点
114-115°C expand 查看数据来源
疏水性(logP)
3.8 expand 查看数据来源
保存条件
-20°C expand 查看数据来源
-20°C Freezer expand 查看数据来源
保存注意事项
IRRITANT expand 查看数据来源
RTECS编号
UA8670000 expand 查看数据来源
欧盟危险性物质标志
环境危害性(Nature polluting) 环境危害性(Nature polluting) (N) expand 查看数据来源
联合国危险货物编号
3077 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
3 expand 查看数据来源
联合国危险货物等级
9 expand 查看数据来源
联合国危险货物包装类别(PG)
3 expand 查看数据来源
危险公开号
51/53 expand 查看数据来源
安全公开号
61 expand 查看数据来源
TSCA收录
false expand 查看数据来源
GHS危险品标识
GHS09 expand 查看数据来源
GHS危险声明
H411 expand 查看数据来源
GHS警示性声明
P273 expand 查看数据来源
个人保护装置
Eyeshields, Gloves expand 查看数据来源
RID/ADR
UN 3077 9/PG 3 expand 查看数据来源
作用靶点
adrenergic receptor expand 查看数据来源
生物活性机理
Beta-Adrenoceptor blocker expand 查看数据来源
Calcium channel blocker expand 查看数据来源
纯度
>98% expand 查看数据来源
≥98% (HPLC) 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
Vasodilator expand 查看数据来源
Empirical Formula (Hill Notation)
C24H26N2O4 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 -  DB01136 external link
Item Information
Drug Groups approved; investigational
Description Carvedilol is a non-selective beta blocker indicated in the treatment of mild to moderate congestive heart failure (CHF). It blocks beta-1 and beta-2 adrenergic receptors as well as the alpha-1 adrenergic receptors.
Indication For the treatment of mild or moderate (NYHA class II or III) heart failure of ischemic or cardiomyopathic origin.
Pharmacology Carvedilol is a nonselective beta-adrenergic blocking agent with alpha1-blocking activity and is indicated for the treatment of hypertension and mild or moderate (NYHA class II or III) heart failure of ischemic or cardiomyopathic origin. Carvedilol is a racemic mixture in which nonselective b-adrenoreceptor blocking activity is present in the S(-) enantiomer and a-adrenergic blocking activity is present in both R(+) and S(-) enantiomers at equal potency. Carvedilol has no intrinsic sympathomimetic activity. The effect of carvedilol's b-adrenoreceptor blocking activity has been demonstrated in animal and human studies showing that carvedilol (1) reduces cardiac output in normal subjects; (2) reduces exercise-and/or isoproterenol-induced tachycardia and (3) reduces reflex orthostatic tachycardia.
Toxicity Not expected to be toxic following ingestion.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Carvedilol is metabolized primarily by aromatic ring oxidation and glucuronidation. The oxidative metabolites are further metabolized by conjugation via glucuronidation and sulfation. Demethylation and hydroxylation at the phenol ring produce three active metabolites with b-receptor blocking activity. The 4'-hydroxyphenyl metabolite is approximately 13 times more potent than carvedilol for b-blockade.
Absorption Carvedilol is rapidly and extensively absorbed following oral administration, with an absolute bioavailability of approximately 25% to 35% due to a significant degree of first-pass metabolism.
Half Life 7-10 hours
Protein Binding 98%
Elimination Carvedilol is extensively metabolized. Less than 2% of the dose was excreted unchanged in the urine.
Carvedilol is metabolized primarily by aromatic ring oxidation and glucuronidation. The oxidative metabolites are further metabolized by conjugation via glucuronidation and sulfation. The metabolites of carvedilol are excreted primarily via the bile into the feces.
Distribution * 115 L
Clearance * 500-700 mL/min
References
Packer M, Fowler MB, Roecker EB, Coats AJ, Katus HA, Krum H, Mohacsi P, Rouleau JL, Tendera M, Staiger C, Holcslaw TL, Amann-Zalan I, DeMets DL: Effect of carvedilol on the morbidity of patients with severe chronic heart failure: results of the carvedilol prospective randomized cumulative survival (COPERNICUS) study. Circulation. 2002 Oct 22;106(17):2194-9. [Pubmed]
Packer M, Coats AJ, Fowler MB, Katus HA, Krum H, Mohacsi P, Rouleau JL, Tendera M, Castaigne A, Roecker EB, Schultz MK, DeMets DL: Effect of carvedilol on survival in severe chronic heart failure. N Engl J Med. 2001 May 31;344(22):1651-8. [Pubmed]
Vanderhoff BT, Ruppel HM, Amsterdam PB: Carvedilol: the new role of beta blockers in congestive heart failure. Am Fam Physician. 1998 Nov 1;58(7):1627-34, 1641-2. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S1831 external link
Biological Activity:
Carvedilol is a non-selective beta blocker/alpha-1 blocker with an IC50 of 3.8 μM for inhibition of LDL oxidation. [1] Norepinephrine stimulates the nerves that control the muscles of the heart by binding to the β1- and β2-adrenergic receptors. Carvedilol blocks the binding to those receptors, which both slows the heart rhythm and reduces the force of the heart’s pumping. This lowers blood pressure and reduces heart failure. Norepinephrine also binds to the α1-adrenergic receptors on blood vessels, causing them to constrict and raise blood pressure. Carvedilol blocks this binding to the α1-adrenergic receptors too, which also lowers blood pressure. [2]
Sigma Aldrich -  C3993 external link
Biochem/physiol Actions
Cavedilol is a non-selective β-adrenergic blocker with α1 blocking activity. Carvedilol is used specifically for the treatment of heart failure and high blood pressure. It has been shown to improve left ventricular ejection fraction and may reduce mortality.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. C3993.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.
Toronto Research Chemicals -  C184625 external link
Carvedilol is a nonselective β-adrenergic blocker with α1-blocking activity. Carvedilol is an antihypertensive used in the treatment of congestive heart failure.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Packer M, Fowler MB, Roecker EB, Coats AJ, Katus HA, Krum H, Mohacsi P, Rouleau JL, Tendera M, Staiger C, Holcslaw TL, Amann-Zalan I, DeMets DL: Effect of carvedilol on the morbidity of patients with severe chronic heart failure: results of the carvedilol prospective randomized cumulative survival (COPERNICUS) study. Circulation. 2002 Oct 22;106(17):2194-9. Pubmed
  • Packer M, Coats AJ, Fowler MB, Katus HA, Krum H, Mohacsi P, Rouleau JL, Tendera M, Castaigne A, Roecker EB, Schultz MK, DeMets DL: Effect of carvedilol on survival in severe chronic heart failure. N Engl J Med. 2001 May 31;344(22):1651-8. Pubmed
  • Vanderhoff BT, Ruppel HM, Amsterdam PB: Carvedilol: the new role of beta blockers in congestive heart failure. Am Fam Physician. 1998 Nov 1;58(7):1627-34, 1641-2. Pubmed
  • http://en.wikipedia.org/wiki/Carvedilol
  • Hirohashi, M., et al.: Arzneim.-Forsch., 40, 735 (1990)
  • Packer, M., et al.: N. Engl. J. Med., 334, 1349 (1990)
  • Ger. Pat., 1984, 2 815 926; CA, 92, 128716e, (synth)
  • Ger. Pat., 1984, 3 319 027; CA, 102, 113292, (resoln)
  • Cubeddu, L.X. et al., Clin. Pharmacol. Ther. (St. Louis), 1987, 41, 31, (pharmacol)
  • Abshagen, U., J. Cardiovasc. Pharmacol., (Suppl. 11), 1987, 10, S23, (rev, pharmacol)
  • Sponer, G. et al., J. Cardiovasc. Pharmacol., (Suppl. 11), 1987, 10, S49, (pharmacol)
  • Reiff, K., J. Chromatogr., 1987, 413, 355, (hplc)
  • Neugebauer, G. et al., Eur. J. Clin. Pharmacol., 1990, 38, S108, (pharmacol, isomers)
  • Ruffolo, R.R. et al., Cardiovasc. Drug Rev., 1992, 10, 127, (rev)
  • McTavish, D. et al., Drugs, 1993, 45, 232, (rev)
  • Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 632
  • Beta-blockers in Clinical Practice, (Eds. Cruickshank, J.M. et al), 2nd edn., Churchill Livingstone, 1994, 1119, (book)
  • Dunn, C.J., Drugs, 1997, 53, 161-185, (rev)
  • Rabasseda, X. et al., Drugs of Today (Barcelona), 1998, 34, 905-926
  • Wood, A.J.J. et al., N. Engl. J. Med., 1998, 339, 1759-1765, (rev)
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