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药品详细

Sumatriptan(舒马曲坦)

化学结构式图
中文名
舒马曲坦
英文名
Sumatriptan
分子式
C14H21N3O2S
化学名
1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide
分子量
Average: 295.4
Monoisotopic: 295.135447621
CAS号
103628-46-2
ATC分类
N02C 未知
药物类型
small molecule
阶段
approved
商品名
同义名
基本介绍

A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of migraine disorders. A transdermal patch version of sumatriptan is currently in phase I trials in the U.S. under the code name NP101 (NuPathe).

生产厂家
  • App pharmaceuticals llc
  • Aurobindo pharma ltd
  • Bedford laboratories
  • Bedford laboratories div ben venue laboratories inc
  • Dr reddys laboratories inc
  • Glaxosmithkline
  • Jhp pharmaceuticals llc
  • King pharmaceuticals inc
  • Mylan pharmaceuticals inc
  • Orchid healthcare
  • Par pharmaceutical inc
  • Ranbaxy laboratories ltd
  • Roxane laboratories inc
  • Sagent strides llc
  • Sandoz canada inc
  • Sandoz inc
  • Sun pharmaceutical industries ltd
  • Teva parenteral medicines inc
  • Teva pharmaceuticals usa inc
  • Watson laboratories inc
  • Wockhardt ltd
  • Zogenix inc
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Nikai T, Basbaum AI, Ahn AH: Profound reduction of somatic and visceral pain in mice by intrathecal administration of the anti-migraine drug, sumatriptan. Pain. 2008 Oct 31;139(3):533-40. Epub 2008 Aug 23. Pubmed
剂型
规格
化合物类型
Type small molecule
Classes
  • Tryptamines and Derivatives
Substructures
  • Indoles and Indole Derivatives
  • Pyrroles
  • Sulfonyls
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Heterocyclic compounds
  • Aromatic compounds
  • Tryptamines and Derivatives
  • Sulfonamides
适应症
药理
Indication For the treatment of migraine attacks with or without aura.
Pharmacodynamics Sumatriptan, an antimigraine drug, is a selective agonist of vascular serotonin ((5-hydroxytryptamine; 5-HT) type 1-like receptors, likely the 5-HT1D and 5-HT1B subtypes. It has no significant affinity (as measured using standard radioligand binding assays) or pharmacological activity at 5-HT2, 5-HT3 receptor subtypes or at alpha1-, alpha2-, or beta-adrenergic; dopamine1; dopamine2; muscarinic; or benzodiazepine receptors.
Mechanism of action The 5-HT1B and 5-HT1D receptors function as autoreceptors, which inhibit the firing of serotonin neurons and a reduction in the synthesis and release of serotonin upon activation. After sumatriptan binds to these receptors, adenylate cyclase activity is inhibited via regulatory G proteins, incrases intracellular calcium, and affects other intracellular events. This results in vasoconstriction and inhibtion of sensory nociceptive (trigeminal) nerve firing and vasoactive neuropeptide release.
Absorption Approximately 15%
Volume of distribution
  • 2.7 L/kg [subcutaneous dosing]
Protein binding 14%-21%
Metabolism
Hepatic. In vitro studies with human microsomes suggest that sumatriptan is metabolized by monoamine oxidase (MAO), predominantly the A isoenzyme.
Route of elimination Only 3% of the dose is excreted in the urine as unchanged sumatriptan; 42% of the dose is excreted as the major metabolite, the indole acetic acid analogue of sumatriptan.
Half life 2.5 hours
Clearance
  • 1200 mL/min [Following a 6-mg SC injection]
Toxicity Symptoms of overdose include convulsions, tremor, paralysis, inactivity, ptosis, erythema of the extremities, abnormal respiration, cyanosis, ataxia, mydriasis, salivation, and lacrimation.
Affected organisms
  • Humans and other mammals
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 169-171 °C Not Available
water solubility 21.4 mg/ml Not Available
logP 0.93 ADLARD,M ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 1.27e-01 g/l ALOGPS
logP 1.17 ALOGPS
logP 0.74 ChemAxon
logS -3.4 ALOGPS
pKa (strongest acidic) 11.24 ChemAxon
pKa (strongest basic) 9.54 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 65.2 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 82.08 ChemAxon
polarizability 32.31 ChemAxon
药物相互作用
Drug Interaction
Citalopram Increased risk of CNS adverse effects
Desvenlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Dihydroergotamine Possible severe and prolonged vasoconstriction
Ergotamine Possible severe and prolonged vasoconstriction
Escitalopram Increased risk of CNS adverse effects
Fluoxetine Increased risk of CNS adverse effects
Fluvoxamine Increased risk of CNS adverse effects
Isocarboxazid The MAO inhibitor, isocarboxazid, may decrease the metabolism and clearance of the serotonin 5-HT receptor agonist, sumatriptan. Concomitant therapy is contraindicated.
Lithium Possible serotoninergic syndrome with this combination
Methysergide Possible severe and prolonged vasoconstriction
Nefazodone Increased risk of CNS adverse effects
Paroxetine Increased risk of CNS adverse effects
Phenelzine The MAO inhibitor, phenelzine, may decrease the metabolism and clearance of the serotonin 5-HT receptor agonist, sumatriptan. Concomitant therapy is contraindicated.
Tramadol Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Tranylcypromine The MAO inhibitor, Tranylcypromine, may reduce the metabolism and clearance of the serotonin 5-HT1D receptor agonist, Sumatriptan. Risk of serotonin syndrome and Sumatriptan toxicity. Concomitant therapy should be avoided.
Trazodone Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Trimipramine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Venlafaxine Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Vilazodone Increased risk of serotonin syndrome
Zolmitriptan Concomitant use of two serotonin 5-HT1D receptor agonists, such as zolmitriptan and sumatriptan, may result in additive vasoconstrictive effects. Concomitant use within 24 hours is contraindicated.
食物相互作用
Not Available

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