(4R)-4-({3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-one

• ChemBase编号: 200
• 分子式: C16H21N3O2
• 平均质量: 287.35684
• 单一同位素质量: 287.16337693
• SMILES: O1C[C@H](NC1=O)Cc1cc2c(CCN(C)C)c[nH]c2cc1
• Canonical SMILES: CN(CCc1c[nH]c2c1cc(C[C@@H]1COC(=O)N1)cc2)C
• InChI: InChI=1S/C16H21N3O2/c1-19(2)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-21-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)/t13-/m1/s1
• InChIKey: ULSDMUVEXKOYBU-CYBMUJFWSA-N

名称和登记号

名称

• IUPAC标准名: (4R)-4-({3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-one
• IUPAC传统名: zolmitriptan
• 商标名: Zomig; Zomigon; AscoTop; Zomig Rapimelt
• 别名: ZMT; zolmitriptan; Zolmitriptan

登记号

• CAS号: 139264-17-8
• PubChem SID: 160963663
• PubChem CID: 441240

理论计算性质

JChem

• Acid pKa: 13.002183
• 质子受体: 2
• 质子供体: 2
• LogD (pH = 5.5): -1.3495891
• LogD (pH = 7.4): -0.08771248
• Log P: 2.0428753
• 摩尔折射率: 82.4392 cm^3
• 极化性: 32.885002 Å^3
• 极化表面积: 57.36 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.25
• LOG S: -3.18
• 溶解度: 1.90e-01 g/l

分子性质

理化性质

• 疏水性(logP): 1.6

详细说明

DrugBank - DB00315

• Drug Groups: approved; investigational
• Description: Zolmitriptan is a synthetic tryptamine derivative and appears as a white powder that is readily soluble in water. [Wikipedia]
• Indication: For the acute treatment of adult migraine with or without auras.
• Pharmacology: Zolmitriptan is a selective agonist of serotonin (5-hydroxytryptamine; 5-HT) type 1B and 1D receptors. It is structurally and pharmacologically related to other selective 5-HT1B/1D receptor agonists, and has only a weak affinity for 5-HT_1A, 5-HT_5A, and 5-HT₇ receptors and no significant affinity or pharmacological activity at 5-HT₂, 5-HT₃ or 5-HT₄ receptor subtypes or at alpha1-, alpha2-, or beta-adrenergic, dopamine1,; dopamine2; muscarinic, or benzodiazepine receptors. This action in humans correlates with the relief of migraine headache. In addition to causing vasoconstriction, experimental data from animal studies show that Zolmitriptan also activates 5-HT₁ receptors on peripheral terminals of the trigeminal nerve innervating cranial blood vessels, which may also contribute to the antimigrainous effect of Zolmitriptan in humans.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. There have been three metabolites identified: indole acetic acid, N -oxide, and N-desmethyl metabolites. However, the N-desmethyl is the only active metabolite.
• Absorption: Mean absolute oral bioavailability is approximately 40%. Food has no affect on the rate and extent of absorption.
• Half Life: The mean elimination half-life of zolmitriptan and of the active N-desmethyl metabolite is 3 hours.
• Protein Binding: 25%
• Distribution: * 8.4±3.3 L/kg
• Clearance: * 25.9 mL/min/kg
• References: Pascual J: [Mechanism of action of zolmitriptan] Neurologia. 1998 Oct;13 Suppl 2:9-15. [Pubmed] ; Martin GR: Pre-clinical pharmacology of zolmitriptan (Zomig; formerly 311C90), a centrally and peripherally acting 5HT1B/1D agonist for migraine. Cephalalgia. 1997 Oct;17 Suppl 18:4-14. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Pascual J: [Mechanism of action of zolmitriptan] Neurologia. 1998 Oct;13 Suppl 2:9-15. Pubmed
• Martin GR: Pre-clinical pharmacology of zolmitriptan (Zomig; formerly 311C90), a centrally and peripherally acting 5HT1B/1D agonist for migraine. Cephalalgia. 1997 Oct;17 Suppl 18:4-14. Pubmed