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73963-72-1 分子结构
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6-[4-(1-cyclohexyl-1H-1,2,3,4-tetrazol-5-yl)butoxy]-1,2,3,4-tetrahydroquinolin-2-one

ChemBase编号:1037
分子式:C20H27N5O2
平均质量:369.46068
单一同位素质量:369.21647513
SMILES和InChIs

SMILES:
O(CCCCc1n(nnn1)C1CCCCC1)c1cc2CCC(=O)Nc2cc1
Canonical SMILES:
O=C1CCc2c(N1)ccc(c2)OCCCCc1nnnn1C1CCCCC1
InChI:
InChI=1S/C20H27N5O2/c26-20-12-9-15-14-17(10-11-18(15)21-20)27-13-5-4-8-19-22-23-24-25(19)16-6-2-1-3-7-16/h10-11,14,16H,1-9,12-13H2,(H,21,26)
InChIKey:
RRGUKTPIGVIEKM-UHFFFAOYSA-N

引用这个纪录

CBID:1037 http://www.chembase.cn/molecule-1037.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
6-[4-(1-cyclohexyl-1H-1,2,3,4-tetrazol-5-yl)butoxy]-1,2,3,4-tetrahydroquinolin-2-one
IUPAC传统名
pletal
cilostazol
商标名
Pletaal
Pletal
别名
Cilostazolum [INN-Latin]
Cilostazole
Cilostazol
Pletal
Cilostazol
6-[4-(1-Cyclohexyl-1H-tetrazol-5-yl)butoxy]-2-oxo-1,2,3,4-tetrahydroquinoline
6-[4-(1-Cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydroquinolin-2(1H)-one
6-[4-(1-Cyclohexyl-1H-tetrazol-5-yl)-butoxy]-3,4-dihydro-2(1H)-quinolinone
OPC 13013
OPC 21
Pletaal
Cilostazol
6-[4-(1-Cyclohexyl-1H-tetrazol-5-yl)butoxy]-3,4-dihydro-2(1H)-quinolinone
OPC-13013
CAS号
73963-72-1
MDL号
MFCD00866780
PubChem SID
46506317
24278291
160964500
PubChem CID
2754
CHEBI ID
31401
ATC码
B01AC23
CHEMBL
799
Chemspider ID
2652
DrugBank ID
DB01166
KEGG ID
D01896
美国药典/FDA物质标识码
N7Z035406B
维基百科标题
Cilostazol
Medline Plus
a601038

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 14.416321  质子受体
质子供体 LogD (pH = 5.5) 3.3055658 
LogD (pH = 7.4) 3.305566  Log P 3.305566 
摩尔折射率 117.1349 cm3 极化性 39.19583 Å3
极化表面积 81.93 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 3.38  LOG S -4.06 
溶解度 3.24e-02 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
Dimethyl Sulfoxide expand 查看数据来源
DMSO: soluble18 mg/mL expand 查看数据来源
Ethanol expand 查看数据来源
Methanol expand 查看数据来源
外观
off-white solid expand 查看数据来源
White Solid expand 查看数据来源
熔点
159-160°C expand 查看数据来源
疏水性(logP)
2.3 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
VC8277500 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
德国WGK号
2 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
作用靶点
PDE expand 查看数据来源
给药途径
Oral expand 查看数据来源
排泄
Renal expand 查看数据来源
半衰期
11–13 hours expand 查看数据来源
代谢
Hepatic (CYP3A4- and CYP2C19-mediated) expand 查看数据来源
蛋白结合率
95–98% expand 查看数据来源
妊娠期药物分类
C (US) expand 查看数据来源
相关基因信息
human ... PDE3A(5139), PDE3B(5140) expand 查看数据来源
纯度
>99% (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
Empirical Formula (Hill Notation)
C20H27N5O2 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Selleck Chemicals Selleck Chemicals Wikipedia Wikipedia Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank -  DB01166 external link
Item Information
Drug Groups approved
Description Cilostazol is a medication used in the alleviation of the symptom of intermittent claudication in individuals with peripheral vascular disease. It is manufactured by Otsuka Pharmaceutical Co. under the trade name Pletal. Although drugs similar to cilostazol have increased the risk of death in patients with congestive heart failure, studies of significant size have not addressed people without the disease. [Wikipedia]
Indication For the reduction of symptoms of intermittent claudication (pain in the legs that occurs with walking and disappears with rest).
Pharmacology Cilostazol is a quinolinone derivative indicated for the reduction of symptoms of intermittent claudication, as indicated by an increased walking distance. Intermittent claudication is pain in the legs that occurs with walking and disappears with rest. The pain occurs due to reduced blood flow to the legs.
Toxicity Information on acute overdosage with cilostazol in humans is limited. The signs and symptoms of an acute overdose can be anticipated to be those of excessive pharmacologic effect: severe headache, diarrhea, hypotension, tachycardia, and possibly cardiac arrhythmias. The oral LD50 of cilostazol is >5.0 g/kg in mice and rats and >2.0 g/kg in dogs.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic. Cilostazol is extensively metabolized by hepatic cytochrome P-450 enzymes, mainly 3A4, and, to a lesser extent, 2C19, with metabolites largely excreted in urine. Two metabolites are active, with one metabolite appearing to account for at least 50% of the pharmacologic (PDE III inhibition) activity after administration of cilostazol.
Absorption Cilostazol is absorbed after oral administration. A high fat meal increases absorption, with an approximately 90% increase in Cmax and a 25% increase in AUC. Absolute bioavailability is not known.
Half Life 11-13 hours.
Protein Binding 95-98%
Elimination Cilostazol is extensively metabolized by hepatic cytochrome P-450 enzymes, mainly 3A4, and, to a lesser extent, 2C19, with metabolites largely excreted in urine. Cilostazol is eliminated predominately by metabolism and subsequent urinary excretion of metabolites. The primary route of elimination was via the urine (74%), with the remainder excreted in feces (20%). No measurable amount of unchanged cilostazol was excreted in the urine, and less than 2% of the dose was excreted as 3,4-dehydro-cilostazol.
About 30% of the dose was excreted in urine as 4'-trans-hydroxy-cilostazol.
External Links
Wikipedia
RxList
Drugs.com
Selleck Chemicals -  S1294 external link
Research Area: Cardiovascular Disease
Biological Activity:
Cilostazol is a medication used in the alleviation of the symptom of intermittent claudication in individuals with peripheral vascular disease. Cilostazol is a phosphodiesterase inhibitor with therapeutic focus on cAMP. It inhibits platelet aggregation and is a direct arterial vasodilator. Its main effects are dilation of the arteries supplying blood to the legs and decreasing platelet coagulation. [1]
Sigma Aldrich -  C0737 external link
Biochem/physiol Actions
Phosphodiesterase III (PDE3) inhibitor
Toronto Research Chemicals -  C441500 external link
A potent phosphodiesterase III A (PDE3A) inhibitor (IC50=0.2uM) and inhibitor of adenosine uptake. Has antimitogeni, antithrombotic, vasodilatory and cardiotonic properties in vivo. Also affects lipid levels in vivo.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • http://en.wikipedia.org/wiki/Cilostazol
  • Suri, A., et al.: J. Clin. Pharmacol., 38, 144 (1998)
  • Park, S.-W., et al.: Am. J. Cardiol., 84, 511 (1998)
  • Tsuchikane, E., et al.: Circulation, 100, 21 (1998)
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专利

专利

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