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361-37-5 分子结构
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(4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide

ChemBase编号:132
分子式:C21H27N3O2
平均质量:353.45798
单一同位素质量:353.21032712
SMILES和InChIs

SMILES:
O=C(N[C@@H](CC)CO)[C@H]1CN([C@H]2C(=C1)c1c3c(C2)cn(c3ccc1)C)C
Canonical SMILES:
CC[C@H](NC(=O)[C@H]1CN(C)[C@H]2C(=C1)c1cccc3c1c(C2)cn3C)CO
InChI:
InChI=1S/C21H27N3O2/c1-4-15(12-25)22-21(26)14-8-17-16-6-5-7-18-20(16)13(10-23(18)2)9-19(17)24(3)11-14/h5-8,10,14-15,19,25H,4,9,11-12H2,1-3H3,(H,22,26)/t14-,15+,19-/m1/s1
InChIKey:
KPJZHOPZRAFDTN-ZRGWGRIASA-N

引用这个纪录

CBID:132 http://www.chembase.cn/molecule-132.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
(4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.02,7.012,16]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
(4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^{2,7}.0^{12,16}]hexadeca-1(16),2,9,12,14-pentaene-4-carboxamide
IUPAC传统名
methysergide
商标名
Deseril
Desernil
Desernyl
Deseryl
Sansert
别名
Methyllysergic acid butanolamide
Methysergid
Methysergidum [INN-Latin]
Metisergide [DCIT]
Metisergido [INN-Spanish]
N-(1-(Hydroxymethyl)propyl)-1-methyl-dextro-(+)-lysergamide
N-(alpha-(Hydroxymethyl)propyl)-1-methyl-dextro-lysergamide
Methysergide
CAS号
361-37-5
PubChem SID
160963595
PubChem CID
9681
ATC码
N02CA04
CHEMBL
1065
Chemspider ID
9300
DrugBank ID
DB00247
IUPHAR配体索引
134
KEGG ID
D02357
美国药典/FDA物质标识码
XZA9HY6Z98
维基百科标题
Methysergide
Medline Plus
a603022

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

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 15.006512  质子受体
质子供体 LogD (pH = 5.5) -0.5095057 
LogD (pH = 7.4) 1.2321609  Log P 1.8168944 
摩尔折射率 104.4726 cm3 极化性 41.054924 Å3
极化表面积 57.5 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 2.22  LOG S -3.2 
溶解度 2.24e-01 g/l 

分子性质

分子性质

理化性质 药理学性质 生物活性(PubChem)
疏水性(logP)
1.5 expand 查看数据来源
妊娠期药物分类
X expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank Wikipedia Wikipedia
DrugBank -  DB00247 external link
Item Information
Drug Groups approved
Description An ergot derivative that is a congener of lysergic acid diethylamide. It antagonizes the effects of serotonin in blood vessels and gastrointestinal smooth muscle, but has few of the properties of other ergot alkaloids. Methysergide is used prophylactically in migraine and other vascular headaches and to antagonize serotonin in the carcinoid syndrome. [PubChem]
Indication For the treatment of vascular headache
Pharmacology Methysergide has been shown, in vitro and in vivo, to inhibit or block the effects of serotonin, a substance which may be involved in the mechanism of vascular headaches. Serotonin has been variously described as a central neurohumoral agent or chemical mediator, as a "headache substance" acting directly or indirectly to lower pain threshold, as an intrinsic "motor hormone" of the gastrointestinal tract, and as a "hormone" involved in connective tissue reparative processes.
Toxicity Few cases of acute methysergide intoxication have been reported. The possible symptom complex is therefore not fully known. The following symptoms are based on these few case reports. Euphoria, hyperactivity, tachycardia, dilated pupils, and dizziness have been reported in a child with a dose of 20-24 mg of methysergide. In adults, peripheral vasospasm, with diminished or absent pulses, coldness, mottling and cyanosis, has been observed at a dose of 200 mg. Ischemic tissue damage has not been reported in acute overdosage with methysergide.
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption Rapid
External Links
Wikipedia
RxList

参考文献

参考文献

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专利

专利

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互联网资源

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