103628-46-2

• 常用中文名：舒马曲坦
• 常用英文名：Sumatriptan
• CAS号：103628-46-2
• 分子式：C₁₄H₂₁N₃O₂S
• 分子量：295.400
• 相关类别： 原料药 解热镇痛药 抗偏头痛药
• 发布时间：2018-07-20 14:27:55
• 更新时间：2026-07-01 06:12:04
• 舒马曲普坦(GR 43175游离碱)是一种口服活性5-HT1受体激动剂,5-HT1D、5-HT1B和5-HT1A受体的Kis分别为17 nM、27 nM和100 nM。舒马曲普坦可用于偏头痛研究[1][2]。

名称

• 中文名: 磺马曲坦
• 英文名: sumatriptan
• 中文别名: 舒马普坦杂质5; 3-[2-(二甲氨基)乙基]-N-甲基-1H-吲哚-5-甲烷碘酰胺; 琥珀酸盐; 3-[2-(二甲胺基)乙基]-N-甲基-1H-吲哚-5-甲基磺酰胺; 3-[2-(二甲胺基)乙基]-N-甲基-1H-吲哚-5-甲磺酰胺; 舒马曲坦碱; 1-[3-[2-(二甲氨基)乙基]-5-吲哚基]-N-甲基甲磺酰胺; 舒马曲坦 标准品; 舒马曲坦系统适应性 标准品; 4-苯肼-N-甲基甲烷磺; 舒马曲坦杂质H; 舒马坦; 舒马坦琥珀酸; 琥珀酸舒马普坦(注射剂); 舒巴曲坦; 1-(3-(2-(二甲氨基)乙基)-1H-吲哚-5-基)-N-甲基甲磺酰胺; 舒马曲坦 化学名
• 英文别名: Sumatriptan for system suitability CRS; 3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide; 43175; 1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide; Sumatriptan (base and/or unspecified salts); 4-HYDRAZINE-N-METHYLBENZENE METHANE SULFONAMIDE; IMIGRAN; Sumatriptan (50 mg); 3-(2-(dimethylamino)ethyl)-n-methyl-1h-indole-5-methanesulfonamid; 3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulfonamide; Sumatriptan - Bio-X; methylene (2S,5R,6R)-6-[[(2R)-[[[(2S,5R,6R)-6-[[(2R)- aminophenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia- 1-azabicyclo[3.2.0]ht-2-yl]carbonyl]amino]- phenylacetyl]amino]-3,3-dimethyl-7-oxo-4-thia-1- azabicyclo[3.2.0]htane-2-cboxylate (2S,5R)-3,3-dimethyl-4,4,7-trioxo-4λ6-thia-1-azabicyclo[3.2.0]htane-2-cboxylate (ampicillin sultamicillin amide); [3-(2-Dimethylaminoethyl)-1H-indole-5-yl]-N-methylmethanesulfonamide; (3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamide; 1-[3-[2-(Dimethylamino)ethyl]-5-indolyl]-N-methylmethanesulfonamide; Sumatriptan //BP; 43175x; sumatriptan hemisuccinate; SuMatriptan IMpurity H; GR 43175C; IMITREX; 1H-Indole-5-methanesulfonamide, -(dimethylamino)ethyl-N-methyl; Imian，Imitrex; 3-[2-(DIMETHYLAMINO)ETHYL]-N-METHYL-1H-INDOLE-5-METHANESULFONAMIDE, SUCCINATE; SumatriptanQ: What is Sumatriptan Q: What is the CAS Number of Sumatriptan Q: What is the storage condition of Sumatriptan; 3-[2-(Dimethyl amino) ethyl -1H-indol-5-yl -N-methyl methane sulphonamide; SuMatriptan Succinate Inj; SuMatriptan Maxalt; SUMATRIPTAN BASE; MFCD00902856; IMIAN; 1-{3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide; SumatriptanSuccinateBase

物化性质

• 密度: 1.2±0.1 g/cm3
• 沸点: 497.7±55.0 °C at 760 mmHg
• 熔点: 169-171°C
• 分子式: C₁₄H₂₁N₃O₂S
• 分子量: 295.400
• 闪点: 254.8±31.5 °C
• 精确质量: 295.135437
• PSA: 73.58000
• LogP: 0.67
• 外观性状: 白色至灰白色结晶粉末
• 蒸汽压: 0.0±1.3 mmHg at 25°C
• 折射率: 1.610
• 储存条件: 2-8°C
• 水溶解性: 21.4 mg/mL
• 分子结构:

  1、 摩尔折射率：82.35

  2、 摩尔体积（cm³/mol）：237.6

  3、 等张比容（90.2K）：640.3

  4、 表面张力（dyne/cm）：52.7

  5、 极化率（10-24cm3）：32.64

• 计算化学:

  1.疏水参数计算参考值（XlogP）:无

  2.氢键供体数量:2

  3.氢键受体数量:4

  4.可旋转化学键数量:6

  5.互变异构体数量:无

  6.拓扑分子极性表面积73.6

  7.重原子数量:20

  8.表面电荷:0

  9.复杂度:405

  10.同位素原子数量:0

  11.确定原子立构中心数量:0

  12.不确定原子立构中心数量:0

  13.确定化学键立构中心数量:0

  14.不确定化学键立构中心数量:0

  15.共价键单元数量:1

• 更多:

  1.性状：白色结晶性粉末。

  2.熔点：169～171℃。

  3.溶解度：易溶于水。

生物活性

• 描述: 舒马曲普坦(GR 43175游离碱)是一种口服活性5-HT1受体激动剂,5-HT1D、5-HT1B和5-HT1A受体的Kis分别为17 nM、27 nM和100 nM。舒马曲普坦可用于偏头痛研究[1][2]。
• 相关类别:
  研究领域 >> 神经疾病
  信号通路 >> G 蛋白偶联受体/G 蛋白 >> 5-HT受体
  信号通路 >> 神经信号通路 >> 5-HT受体
• 靶点:

  5-HT1A Receptor:100 nM (Ki)

  5-HT1B Receptor:27 nM (Ki)

  5-HT1D Receptor:17 nM (Ki)

• 参考文献:

  [1]. S J Peroutka, et al. Sumatriptan (GR 43175) interacts selectively with 5-HT1B and 5-HT1D binding sites. Eur J Pharmacol. 1989 Apr 12;163(1):133-6.

  [2]. K L Dechant, et al. Sumatriptan. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in the acute treatment of migraine and cluster headache. Drugs. 1992 May;43(5):776-98.

毒性和生态

CHEMICAL IDENTIFICATION RTECS NUMBER : NL9482200 CHEMICAL NAME : 1H-Indole-5-methanesulfonamide, 3-(2-(dimethylamino)ethyl)-N-methyl- CAS REGISTRY NUMBER : 103628-46-2 LAST UPDATED : 199612 DATA ITEMS CITED : 11 MOLECULAR FORMULA : C14-H21-N3-O2-S MOLECULAR WEIGHT : 295.44 HEALTH HAZARD DATA ACUTE TOXICITY DATA TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Human - man DOSE/DURATION : 86 mg/kg TOXIC EFFECTS : Cardiac - arrhythmias (including changes in conduction) Cardiac - EKG changes not diagnostic of specified effects REFERENCE : BMJOAE British Medical Journal. (British Medical Assoc., BMA House, Tavistock Sq., London WC1H 9JR, UK) V.1- 1857- Volume(issue)/page/year: 304,1415,1992 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Human - man DOSE/DURATION : 429 ug/kg/2W-I TOXIC EFFECTS : Behavioral - muscle weakness REFERENCE : LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 341,1091,1993 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Human - woman DOSE/DURATION : 120 ug/kg TOXIC EFFECTS : Behavioral - muscle weakness REFERENCE : LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 341,1091,1993 TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Human - woman DOSE/DURATION : 240 ug/kg/1H-I TOXIC EFFECTS : Peripheral Nerve and Sensation - sensory change involving peripheral nerve Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - hallucinations, distorted perceptions REFERENCE : LANCAO Lancet. (7 Adam St., London WC2N 6AD, UK) V.1- 1823- Volume(issue)/page/year: 343,1105,1994 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >2 gm/kg TOXIC EFFECTS : Sense Organs and Special Senses (Eye) - lacrimation Behavioral - ataxia Skin and Appendages - dermatitis, other (after systemic exposure) REFERENCE : HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 14,959,1995 TYPE OF TEST : LD - Lethal dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >1 gm/kg TOXIC EFFECTS : Behavioral - tremor Lungs, Thorax, or Respiration - respiratory depression Skin and Appendages - dermatitis, other (after systemic exposure) REFERENCE : HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 14,959,1995 TYPE OF TEST : LD - Lethal dose ROUTE OF EXPOSURE : Intravenous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : >20 mg/kg TOXIC EFFECTS : Sense Organs and Special Senses (Eye) - effect, not otherwise specified Lungs, Thorax, or Respiration - respiratory stimulation Skin and Appendages - dermatitis, other (after systemic exposure) REFERENCE : HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 14,959,1995 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >500 mg/kg TOXIC EFFECTS : Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Behavioral - ataxia Skin and Appendages - dermatitis, other (after systemic exposure) REFERENCE : HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 14,959,1995 TYPE OF TEST : LDLo - Lowest published lethal dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - mouse DOSE/DURATION : >100 mg/kg TOXIC EFFECTS : Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Gastrointestinal - changes in structure or function of salivary glands Skin and Appendages - dermatitis, other (after systemic exposure) REFERENCE : HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 14,959,1995 ** OTHER MULTIPLE DOSE TOXICITY DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Subcutaneous SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 11648 mg/kg/26W-I TOXIC EFFECTS : Skin and Appendages - dermatitis, other (after systemic exposure) REFERENCE : HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 14,959,1995 ** TUMORIGENIC DATA ** TYPE OF TEST : TDLo - Lowest published toxic dose ROUTE OF EXPOSURE : Oral SPECIES OBSERVED : Rodent - rat DOSE/DURATION : 146 gm/kg/2Y-I TOXIC EFFECTS : Tumorigenic - Carcinogenic by RTECS criteria Endocrine - tumors Reproductive - Tumorigenic effects - testicular tumors REFERENCE : HETOEA Human & Experimental Toxicology. (Macmillan Press Ltd., Brunel Road, Houndmills, Basingstoke, Hampshire, RG21 2XS, UK) V.9- 1990- Volume(issue)/page/year: 14,959,1995

安全

• 危害码 (欧洲): Xi
• 风险声明 (欧洲): R36/37/38
• 安全声明 (欧洲): S26-S36/37/39-S45-S28A
• 危险品运输编码: UN 3261 8/PG 2
• WGK德国: 3
• RTECS号: NL9482200
• 海关编码: 29280090

合成路线

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制备

下列腈化物在二甲胺的甲醇溶液中，10%钯-炭催化下，室温氢化24h，得舒马普坦。

海关

海关编码	29280090