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药品详细

Naratriptan(那拉曲坦)

化学结构式图
中文名
那拉曲坦
英文名
Naratriptan
分子式
C17H25N3O2S
化学名
N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethane-1-sulfonamide
分子量
Average: 335.464
Monoisotopic: 335.166747749
CAS号
121679-13-8
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

Naratriptan is a triptan drug used for the treatment of migraine headaches. It is a selective 5-hydroxytryptamine1 receptor subtype agonist.

生产厂家
  • Glaxosmithkline
  • Paddock laboratories inc
  • Roxane laboratories inc
  • Sandoz inc
  • Teva pharmaceuticals usa
封装厂家
参考
Synthesis Reference Not Available
General Reference
  1. Massiou H: Naratriptan. Curr Med Res Opin. 2001;17 Suppl 1:s51-3. Pubmed
  2. Lambert GA: Preclinical neuropharmacology of naratriptan. CNS Drug Rev. 2005 Autumn;11(3):289-316. Pubmed
  3. Villalon CM, Centurion D, Valdivia LF, de Vries P, Saxena PR: Migraine: pathophysiology, pharmacology, treatment and future trends. Curr Vasc Pharmacol. 2003 Mar;1(1):71-84. 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
  • Tryptamines and Derivatives
  • Aliphatic and Aryl Amines
  • Heterocyclic compounds
  • Aromatic compounds
  • Sulfonamides
  • Piperidines
适应症
药理
Indication For the acute treatment of migraine attacks with or without aura in adults.
Pharmacodynamics Naratriptan 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 agonist. Naratriptan has only a weak affinity for 5-HT1A, 5-HT5A, 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 Naratriptan 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 Naratriptan in humans.
Mechanism of action Three distinct pharmacological actions have been implicated in the antimigraine effect of the triptans: (1) stimulation of presynaptic 5-HT1D receptors, which serves to inhibit both dural vasodilation and inflammation; (2) direct inhibition of trigeminal nuclei cell excitability via 5-HT1B/1D receptor agonism in the brainstem and (3) vasoconstriction of meningeal, dural, cerebral or pial vessels as a result of vascular 5-HT1B receptor agonism.
Absorption Well absorbed (74% oral biovaility), absorption is rapid with peak plasma concentrations after 2-5 hours. The rate of absorption is slower during a migraine attack.
Volume of distribution
  • 170 L
Protein binding 28%-31% (over the concentration range of 50 to 1000 ng/mL)
Metabolism
Primarily hepatic. In vitro, naratriptan is metabolized by a wide range of cytochrome P450 isoenzymes into a number of inactive metabolites.
Route of elimination Not Available
Half life 5-8 hours
Clearance
  • 6.6 mL/min/kg
Toxicity Symptoms of overdose include light-headedness, loss of coordination, tension in the neck, and tiredness.
Affected organisms
  • Humans and other mammals
Pathways Not Available
理化性质
Properties
State solid
Experimental Properties
Property Value Source
melting point 246 °C (HCl salt) Not Available
water solubility 35 mg/mL Not Available
logP 1.6 Not Available
Predicted Properties
Property Value Source
water solubility 1.14e-01 g/l ALOGPS
logP 2.16 ALOGPS
logP 1.44 ChemAxon
logS -3.5 ALOGPS
pKa (strongest acidic) 11.55 ChemAxon
pKa (strongest basic) 9.18 ChemAxon
physiological charge 1 ChemAxon
hydrogen acceptor count 3 ChemAxon
hydrogen donor count 2 ChemAxon
polar surface area 65.2 ChemAxon
rotatable bond count 4 ChemAxon
refractivity 94.26 ChemAxon
polarizability 38 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 Naratriptan, a serotonin 5-HT1D receptor agonists, may increase the vasoconstricting effect of dihydroergotamine. Concomitant use of these two agents within 24 hours is contraindicated.
Dihydroergotoxine Possible severe and prolonged vasocontriction
Ergonovine Possible severe and prolonged vasocontriction
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 use of two serotonin modulators increases the risk of serotonin syndrome. Consider alternate therapy or monitor for signs and symptoms of serotonin syndrome.
Methylergonovine Possible severe and prolonged vasocontriction
Methysergide Possible severe and prolonged vasoconstriction.
Nefazodone Increased risk of CNS adverse effects
Paroxetine Increased risk of CNS adverse effects
Phenelzine The use of two serotonin modulators increases the risk of serotonin syndrome. Consider alternate therapy or monitor for signs and symptoms of serotonin syndrome.
Sertraline Increased risk of CNS adverse effects
Sibutramine Increased risk of CNS adverse effects
Tramadol Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Tranylcypromine Increased risk of serotonin syndrome. Use caution during concomitant therapy and monitor for symptoms of serotonin syndrome.
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 naratriptan, may result in additive vasoconstrictive effects. Concomitant use within 24 hours is contraindicated.
食物相互作用
  • Take without regard to meals.

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