(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: 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

名称和登记号

名称

• IUPAC标准名: (4R,7R)-N-[(2S)-1-hydroxybutan-2-yl]-6,11-dimethyl-6,11-diazatetracyclo[7.6.1.0^2,^7.0^1^2,^1^6]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

登记号

• 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

理论计算性质

JChem

• Acid pKa: 15.006512
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): -0.5095057
• LogD (pH = 7.4): 1.2321609
• Log P: 1.8168944
• 摩尔折射率: 104.4726 cm^3
• 极化性: 41.054924 Å^3
• 极化表面积: 57.5 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.22
• LOG S: -3.2
• 溶解度: 2.24e-01 g/l

分子性质

理化性质

• 疏水性(logP): 1.5

药理学性质

• 妊娠期药物分类: X

详细说明

DrugBank - DB00247

• 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