您当前所在的位置:首页 > 产品中心 > 产品详细信息
106650-56-0 分子结构
点击图片或这里关闭

{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}dimethylamine

ChemBase编号:976
分子式:C17H26ClN
平均质量:279.84804
单一同位素质量:279.17537752
SMILES和InChIs

SMILES:
Clc1ccc(C2(CCC2)C(N(C)C)CC(C)C)cc1
Canonical SMILES:
CC(CC(C1(CCC1)c1ccc(cc1)Cl)N(C)C)C
InChI:
InChI=1S/C17H26ClN/c1-13(2)12-16(19(3)4)17(10-5-11-17)14-6-8-15(18)9-7-14/h6-9,13,16H,5,10-12H2,1-4H3
InChIKey:
UNAANXDKBXWMLN-UHFFFAOYSA-N

引用这个纪录

CBID:976 http://www.chembase.cn/molecule-976.html

Collapse All Expand All

名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
{1-[1-(4-chlorophenyl)cyclobutyl]-3-methylbutyl}dimethylamine
IUPAC传统名
sibutramine
商标名
Medaria
Meridia
Reductil
Butramin
别名
Sibutramina [Spanish]
Sibutraminum [Latin]
Sibutramine
CAS号
106650-56-0
PubChem SID
160964439
46507740
PubChem CID
5210

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB01105 external link
PubChem 5210 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
质子受体 质子供体
LogD (pH = 5.5) 1.7681136  LogD (pH = 7.4) 2.8568501 
Log P 5.20185  摩尔折射率 83.9214 cm3
极化性 33.18467 Å3 极化表面积 3.24 Å2
可自由旋转的化学键 里宾斯基五规则 false 
Log P 5.05  LOG S -5.47 
溶解度 9.40e-04 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
溶解度
2.9 mg/mL (in pH 5.2 water) expand 查看数据来源
疏水性(logP)
5.2 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB01105 external link
Item Information
Drug Groups illicit; approved; withdrawn; investigational
Description Sibutramine (trade name Meridia in the USA, Reductil in Europe and other countries), usually as sibutramide hydrochloride monohydrate, is an orally administered agent for the treatment of obesity. It is a centrally acting stimulant chemically related to amphetamines. Sibutramine is classified as a Schedule IV controlled substance in the United States. In October 2010, Sibutramine was withdrawn from Canadian and U.S. markets due to concerns that the drug increases the risk of heart attack and stroke in patients with a history of heart disease.
Indication For the treatment of obesity.
Pharmacology Sibutramine is an orally administered agent for the treatment of obesity. Sibutramine exerts its pharmacological actions predominantly via its secondary (M1) and primary (M2) amine metabolites. The parent compound, sibutramine, is a potent inhibitor of serotonin and norepinephrine reuptake in vivo, but not in vitro. However, metabolites M1 and M2 inhibit the reuptake of these neurotransmitters both in vitro and in vivo. In human brain tissue, M1 and M2 also inhibit dopamine reuptake in vitro, but with ~3-fold lower potency than for the reuptake inhibition of serotonin or norepinephrine. Sibutramine, M1 and M2 exhibit no evidence of anticholinergic or antihistaminergic actions. In addition, receptor binding profiles show that sibutramine, M1 and M2 have low affinity for serotonin (5-HT1, 5-HT1A, 5-HT1B, 5-HT2A, 5-HT2C), norepinephrine (b, b1, b3, a1 and a2), dopamine (D1 and D2), benzodiazepine, and glutamate (NMDA) receptors. These compounds also lack monoamine oxidase inhibitory activity in vitro and in vivo.
Toxicity Side effects include dry mouth, anorexia, insomnia, constipation and headache.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Rapid absorption following oral administration. Absolute bioavailability is not known, but at least 77% of a single oral dose of sibutramine is absorbed.
Half Life 1.1 hours
Protein Binding 97% (to human plasma proteins)
Elimination Sibutramine is metabolized in the liver principally by the cytochrome P450 (3A4) isoenzyme, to desmethyl metabolites, M1 and M2. These active metabolites are further metabolized by hydroxylation and conjugation to pharmacologically inactive metabolites, M5 and M6. Approximately 85% (range 68-95%) of a single orally administered radiolabeled dose was excreted in urine and feces over a 15-day collection period with the majority of the dose (77%) excreted in the urine. The primary route of excretion for M1 and M2 is hepatic metabolism and for M5 and M6 is renal excretion.
Clearance * Oral cl=1750 L/h [oral administration]
References
Sharma B, Henderson DC: Sibutramine: current status as an anti-obesity drug and its future perspectives. Expert Opin Pharmacother. 2008 Aug;9(12):2161-73. [Pubmed]
Tziomalos K, Krassas GE, Tzotzas T: The use of sibutramine in the management of obesity and related disorders: an update. Vasc Health Risk Manag. 2009;5(1):441-52. [Pubmed]
Heal DJ, Aspley S, Prow MR, Jackson HC, Martin KF, Cheetham SC: Sibutramine: a novel anti-obesity drug. A review of the pharmacological evidence to differentiate it from d-amphetamine and d-fenfluramine. Int J Obes Relat Metab Disord. 1998 Aug;22 Suppl 1:S18-28; discussion S29. [Pubmed]
Stock MJ: Sibutramine: a review of the pharmacology of a novel anti-obesity agent. Int J Obes Relat Metab Disord. 1997 Mar;21 Suppl 1:S25-9. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Sharma B, Henderson DC: Sibutramine: current status as an anti-obesity drug and its future perspectives. Expert Opin Pharmacother. 2008 Aug;9(12):2161-73. Pubmed
  • Tziomalos K, Krassas GE, Tzotzas T: The use of sibutramine in the management of obesity and related disorders: an update. Vasc Health Risk Manag. 2009;5(1):441-52. Pubmed
  • Heal DJ, Aspley S, Prow MR, Jackson HC, Martin KF, Cheetham SC: Sibutramine: a novel anti-obesity drug. A review of the pharmacological evidence to differentiate it from d-amphetamine and d-fenfluramine. Int J Obes Relat Metab Disord. 1998 Aug;22 Suppl 1:S18-28; discussion S29. Pubmed
  • Stock MJ: Sibutramine: a review of the pharmacology of a novel anti-obesity agent. Int J Obes Relat Metab Disord. 1997 Mar;21 Suppl 1:S25-9. Pubmed
正在搜索,请耐心等待...(如果遇到网页错误或者长时间没有结果,请刷新页面[F5])

专利

专利

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

互联网资源

互联网资源

百度图标百度 google iconGoogle