Tìm theo
Naratriptan
Các tên gọi khác (3) :
  • N-Methyl-2-(3-(1-methylpiperiden-4-yl)indole-5-yl)ethanesulfonamide
  • N-Methyl-2-[3-(1-methyl-4-piperidyl)-1H-indol-5-yl]-ethanesulfonamide
  • Naratriptanum
serotonin antagonists, serotonin receptor agonists
Thuốc Gốc
Small Molecule
CAS: 121679-13-8
ATC: N02CC02
ĐG : GlaxoSmithKline Inc. , http://www.gsk.com
CTHH: C17H25N3O2S
PTK: 335.464
Naratriptan is a triptan drug used for the treatment of migraine headaches. It is a selective 5-hydroxytryptamine1 receptor subtype agonist.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C17H25N3O2S
Phân tử khối
335.464
Monoisotopic mass
335.166747749
InChI
InChI=1S/C17H25N3O2S/c1-18-23(21,22)10-7-13-3-4-17-15(11-13)16(12-19-17)14-5-8-20(2)9-6-14/h3-4,11-12,14,18-19H,5-10H2,1-2H3
InChI Key
InChIKey=AMKVXSZCKVJAGH-UHFFFAOYSA-N
IUPAC Name
N-methyl-2-[3-(1-methylpiperidin-4-yl)-1H-indol-5-yl]ethane-1-sulfonamide
Traditional IUPAC Name
naratriptan
SMILES
CNS(=O)(=O)CCC1=CC2=C(NC=C2C2CCN(C)CC2)C=C1
Độ tan chảy
246 °C (HCl salt)
Độ hòa tan
35 mg/mL
logP
1.6
logS
-3.5
pKa (strongest acidic)
11.55
pKa (Strongest Basic)
9.18
PSA
65.2 Å2
Refractivity
94.26 m3·mol-1
Polarizability
38 Å3
Rotatable Bond Count
4
H Bond Acceptor Count
3
H Bond Donor Count
2
Physiological Charge
1
Number of Rings
3
Bioavailability
1
Rule of Five
true
Ghose Filter
true
Dược Lực Học : 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.
Cơ Chế Tác Dụng : Naratriptan is a triptan drug used for the treatment of migraine headaches. It is a selective 5-hydroxytryptamine1 receptor subtype agonist. 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.
Dược Động Học :
▧ 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.
▧ Half Life :
5-8 hours
▧ Clearance :
* 6.6 mL/min/kg
Độc Tính : Symptoms of overdose include light-headedness, loss of coordination, tension in the neck, and tiredness.
Chỉ Định : For the acute treatment of migraine attacks with or without aura in adults.
Tương Tác Thuốc :
  • 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.
  • 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.
  • Methylergometrine 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.
Liều Lượng & Cách Dùng : Tablet - Oral
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Amerge
  • Công ty :
    Sản phẩm biệt dược : Naramig
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00952
PubChem Compound
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=4440
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46507243
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C07792
ChemSpider
http://www.chemspider.com/Chemical-Structure.4287.html
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/0173-0561-00
PharmGKB
http://www.pharmgkb.org/drug/PA450597
Wikipedia
http://en.wikipedia.org/wiki/Naratriptan
RxList
http://www.rxlist.com/cgi/generic2/naratript.htm
PDRhealth
http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ame1018.shtml
Drugs.com
http://www.drugs.com/cdi/naratriptan.html
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