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66104-23-2 分子结构
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(2R,4R,7R)-4-[(methylsulfanyl)methyl]-6-propyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraene

ChemBase编号:1057
分子式:C19H26N2S
平均质量:314.48814
单一同位素质量:314.18166984
SMILES和InChIs

SMILES:
S(C[C@@H]1C[C@H]2[C@H](N(C1)CCC)Cc1c3c2cccc3[nH]c1)C
Canonical SMILES:
CCCN1C[C@H](CSC)C[C@H]2[C@H]1Cc1c[nH]c3c1c2ccc3
InChI:
InChI=1S/C19H26N2S/c1-3-7-21-11-13(12-22-2)8-16-15-5-4-6-17-19(15)14(10-20-17)9-18(16)21/h4-6,10,13,16,18,20H,3,7-9,11-12H2,1-2H3/t13-,16-,18-/m1/s1
InChIKey:
YEHCICAEULNIGD-MZMPZRCHSA-N

引用这个纪录

CBID:1057 http://www.chembase.cn/molecule-1057.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
(2R,4R,7R)-4-[(methylsulfanyl)methyl]-6-propyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),9,12,14-tetraene
(2R,4R,7R)-4-[(methylsulfanyl)methyl]-6-propyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),9,12,14-tetraene
IUPAC传统名
pergolide
商标名
Permax
别名
Pergolida [INN-Spanish]
Pergolide Mesylate
Pergolide Methanesulfonate
Pergolidum [INN-Latin]
Pergolide
(8β)-8-[(Methylthio)methyl]-6-propylergoline Mesylate
Celance
Permax
Nopar
LY-127809
Pergolide Mesylate
CAS号
66104-23-2
66104-22-1
PubChem SID
160964520
46507604
PubChem CID
47811

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 价格
TRC
P287200 external link 加入购物车 请登录

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 17.350344  质子受体
质子供体 LogD (pH = 5.5) 0.84682393 
LogD (pH = 7.4) 2.1517017  Log P 4.22529 
摩尔折射率 97.0167 cm3 极化性 38.847607 Å3
极化表面积 19.03 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 4.17  LOG S -5.73 
溶解度 5.84e-04 g/l 

分子性质

分子性质

理化性质 安全信息 产品相关信息 生物活性(PubChem)
溶解度
DMSO expand 查看数据来源
Methanol (Sparingly) expand 查看数据来源
外观
White to Off-White Solid expand 查看数据来源
熔点
>232°C (dec.) expand 查看数据来源
疏水性(logP)
4 expand 查看数据来源
保存条件
-20°C Freezer expand 查看数据来源
MSDS下载
下载链接 expand 查看数据来源
质检报告
下载链接 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank TRC TRC
DrugBank -  DB01186 external link
Item Information
Drug Groups approved; withdrawn
Description Pergolide is a long-acting dopamine agonist approved in 1982 for the treatment of Parkinson’s Disease. It is an ergot derivative that acts on the dopamine D2 and D3, alpha2- and alpha1-adrenergic, and 5-hydroxytryptamine (5-HT) receptors. It was indicated as adjunct therapy with levodopa/carbidopa in the symptomatic treatment of parkinsonian syndrome. It was later found that pergolide increased the risk of cardiac valvulopathy. The drug was withdrawn from the US market in March 2007 and from the Canadian market in August 2007.
Indication Indicated as adjunctive treatment to levodopa/carbidopa in the management of the signs and symptoms of Parkinson's disease. It was withdrawn from the US and Canadian markets in 2007 due to an increased risk of cardiac valvulopathy.
Pharmacology Pergolide stimulates centrally-located dopaminergic receptors resulting in a number of pharmacologic effects. Five dopamine receptor types from two dopaminergic subfamilies have been identified. The dopaminergic D1 receptor subfamily consists of D1 and D5 subreceptors and are associated with dyskinesias. The dopaminergic D2 receptor subfamily consists of D2, D3 and D4 subreceptors and has been associated with improvement of symptoms of movement disorders. Thus, agonist activity specific for D2 subfamily receptors, primarily D2 and D3 receptor subtypes, are the primary targets of dopaminergic antiparkinsonian agents. It is thought that postsynaptic D2 stimulation is primarily responsible for the antiparkinsonian effect of dopamine agonists, while presynaptic D2 stimulation confers neuroprotective effects. This semisynthetic ergot derivative exhibits potent agonist activity on dopamine D2- and D3-receptors. It also exhibits agonist activity on dopamine D4, D1, and D5, 5-hydroxytryptamine (5-HT)1A, 5-HT1B, 5-HT1D, 5-HT2A, 5-HT2B, 5-HT2C, α2A-, α2B-, α2C-, α1A-, α1B-, and α1D-adrenergic receptors. Parkinsonian Syndrome manifests when approximately 80% of dopaminergic activity in the nigrostriatal pathway of the brain is lost. As this striatum is involved in modulating the intensity of coordinated muscle activity (e.g. movement, balance, walking), loss of activity may result in dystonia (acute muscle contraction), Parkinsonism (including symptoms of bradykinesia, tremor, rigidity, and flattened affect), akathesia (inner restlessness), tardive dyskinesia (involuntary muscle movements usually associated with long-term loss of dopaminergic activity), and neuroleptic malignant syndrome, which manifests when complete blockage of nigrostriatal dopamine occurs. High dopaminergic activity in the mesolimbic pathway of the brain causes hallucinations and delusions; these side effects of dopamine agonists are manifestations seen in patients with schizophrenia who have overractivity in this area of the brain. The hallucinogenic side effects of dopamine agonists may also be due to 5-HT2A agonism. The tuberoinfundibular pathway of the brain originates in the hypothalamus and terminates in the pituitary gland. In this pathway, dopamine inhibits lactotrophs in anterior pituitary from secreting prolactin. Increased dopaminergic activity in the tuberoinfundibular pathway inhibits prolactin secretion. Pergolide also causes transient increases in somatotropin (growth hormone) secretion and decreases in luteinizing hormone (LH) concentrations.
Toxicity Oral, rat LD50: 15 mg/kg. Symptoms of overdose include nausea, vomiting, convulsions, decreased blood pressure, and CNS stimulation.
Affected Organisms
Humans and other mammals
Biotransformation Extensively hepatic.
Absorption Significant amount may be absorbed (evidence on bioavailability still lacking).
Half Life 27 hours
Protein Binding 90%
Elimination The major route of excretion is the kidney.
References
Schade R, Andersohn F, Suissa S, Haverkamp W, Garbe E: Dopamine agonists and the risk of cardiac-valve regurgitation. N Engl J Med. 2007 Jan 4;356(1):29-38. [Pubmed]
Breitenstein C, Korsukewitz C, Floel A, Kretzschmar T, Diederich K, Knecht S: Tonic dopaminergic stimulation impairs associative learning in healthy subjects. Neuropsychopharmacology. 2006 Nov;31(11):2552-64. Epub 2006 Jul 26. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com
Toronto Research Chemicals -  P287200 external link
A dopaminergic agonist that also decrease plasma prolactin concentrations. An antiparkinsonian agent.

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Schade R, Andersohn F, Suissa S, Haverkamp W, Garbe E: Dopamine agonists and the risk of cardiac-valve regurgitation. N Engl J Med. 2007 Jan 4;356(1):29-38. Pubmed
  • Breitenstein C, Korsukewitz C, Floel A, Kretzschmar T, Diederich K, Knecht S: Tonic dopaminergic stimulation impairs associative learning in healthy subjects. Neuropsychopharmacology. 2006 Nov;31(11):2552-64. Epub 2006 Jul 26. Pubmed
  • Lemberger, L. and Crabtree, R.E.: Science, 205, 1151 (1979)
  • Koller, W.C.: Neuropharmacology, 19, 831 (1979)
  • Francks, S., et al.: Lancet, 2, 659 (1979)
  • Kleinberg, D.L., et al.: N. Engl. J. Med., 309, 704 (1983)
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专利

专利

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