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158747-02-5 分子结构
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(3R)-3-(methylamino)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamide

ChemBase编号:871
分子式:C14H17N3O
平均质量:243.30428
单一同位素质量:243.13716218
SMILES和InChIs

SMILES:
O=C(N)c1cc2c3C[C@H](NC)CCc3[nH]c2cc1
Canonical SMILES:
CN[C@H]1Cc2c(CC1)[nH]c1c2cc(cc1)C(=O)N
InChI:
InChI=1S/C14H17N3O/c1-16-9-3-5-13-11(7-9)10-6-8(14(15)18)2-4-12(10)17-13/h2,4,6,9,16-17H,3,5,7H2,1H3,(H2,15,18)/t9-/m1/s1
InChIKey:
XPSQPHWEGNHMSK-SECBINFHSA-N

引用这个纪录

CBID:871 http://www.chembase.cn/molecule-871.html

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名称和登记号

名称和登记号

名称 登记号
IUPAC标准名
(3R)-3-(methylamino)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamide
IUPAC传统名
frovatriptan
商标名
Miguard
Frova
Frovelan
别名
Frovatriptan succinate
frovatriptan
Frovatriptan
CAS号
158747-02-5
PubChem SID
160964334
46506288
PubChem CID
77992

数据来源

数据来源

所有数据来源 商品来源 非商品来源
数据来源 数据ID
DrugBank DB00998 external link
PubChem 77992 external link
数据来源 数据ID 价格

理论计算性质

理论计算性质

JChem ALOGPS 2.1
Acid pKa 14.536194  质子受体
质子供体 LogD (pH = 5.5) -2.1550536 
LogD (pH = 7.4) -1.739132  Log P 1.077976 
摩尔折射率 71.8382 cm3 极化性 28.223196 Å3
极化表面积 70.91 Å2 可自由旋转的化学键
里宾斯基五规则 true 
Log P 1.2  LOG S -3.3 
溶解度 1.23e-01 g/l 

分子性质

分子性质

理化性质 生物活性(PubChem)
溶解度
Soluble expand 查看数据来源
疏水性(logP)
0.9 expand 查看数据来源

详细说明

详细说明

DrugBank DrugBank
DrugBank -  DB00998 external link
Item Information
Drug Groups approved; investigational
Description Frovatriptan (Frova?) is a triptan drug developed by Vernalis for the treatment of migraine headaches, in particular those associated with menstruation. The product is licensed to Endo Pharmaceuticals in North America and Menarini in Europe.[1] Frovatriptan causes vasoconstriction of arteries and veins that supply blood to the head. It is available as 2.5 mg tablets.

Frovatriptan has mean terminal elimination half-life of approximately 26 hours, which is substantially longer than other triptans.

Frovatriptan is available only by prescription in the United States, where a secondary New Drug Approval (sNDA) was filed in July 2006[2] and which is currently pending.[3] The FDA anticipates completing its review of this application on or before the current PDUFA (Prescription Drug User Fee Act) review date of August 19, 2007. If the sNDA is approved, Frova? will be the only medication indicated in the U.S. for the short-term prevention of menstrual migraine (MM).
Indication For the acute treatment of migraine attacks with or without aura in adults.
Pharmacology Frovatriptan is a second generation triptan 5-HT receptor agonist that binds with high affinity for 5-HT1B and 5-HT1D receptors. It is structurally distinct from, but pharmacologically related to other selective 5-HT1B/1D receptor agonists. Frovatriptan has no significant effects on GABAA mediated channel activity and has no significant affinity for benzodiazepine binding sites. Frovatriptan is believed to act on extracerebral, intracranial arteries and to inhibit excessive dilation of these vessels in migraine. Research has shown that migraine can be caused by the swelling of blood vessels around the brain. Frovatriptan eases the pain associated with migraine by narrowing these blood vessels. Frovatriptan has one of the highest affinities for the 5-HT1B of the second-generation triptan agonists.
Toxicity There is no direct experience of any patient taking an overdose of Frovatriptan. The maximum single dose of frovatriptan given to male and female patients with migraine was 40 mg (16 times the clinical dose) and the maximum single dose given to healthy male subjects was 100 mg (40 times the clinical dose) without significant adverse events.
Affected Organisms
Humans and other mammals
Biotransformation In vitro, cytochrome P450 1A2 appears to be the principal enzyme involved in the metabolism of frovatriptan to several metabolites including hydroxylated frovatriptan, N-acetyl desmethyl frovatriptan, hydroxylated N-acetyl desmethyl frovatriptan and desmethyl frovatriptan, and several other minor metabolites. Desmethyl frovatriptan has lower affinity for 5-HT1B/1D receptors compared to the parent compound. The N-acetyl desmethyl metabolite has no significant affinity for 5-HT receptors. The activity of the other metabolites is unknown.
Absorption Frovatriptan is rapidly absorbed from the duodenum, but has low oral bioavailability.
Half Life 26 hours
Protein Binding Binding to serum proteins is low (approximately 15%). Reversible binding to blood cells at equilibrium is approximately 60%.
Elimination Radiolabeled compounds excreted in urine were unchanged frovatriptan, hydroxylated frovatriptan, N-acetyl desmethyl frovatriptan, hydroxylated N-acetyl desmethyl frovatriptan and desmethyl frovatriptan, together with several other minor metabolites. Less than 10% of frovatriptan was excreted in urine after an oral dose.
Distribution * 4.2 L/kg [males]
* 3 L/kg [females]
Clearance * 220 mL/min [male receiving IV dose of 0.8 mg]
* 130 mL/min [Female receiving IV dose of 0.8 mg]
References
Markus F, Mikko K: Frovatriptan review. Expert Opin Pharmacother. 2007 Dec;8(17):3029-33. [Pubmed]
Easthope SE, Goa KL: Frovatriptan. CNS Drugs. 2001;15(12):969-76; discussion 977-8. [Pubmed]
Balbisi EA: Frovatriptan: a review of pharmacology, pharmacokinetics and clinical potential in the treatment of menstrual migraine. Ther Clin Risk Manag. 2006 Sep;2(3):303-8. [Pubmed]
Balbisi EA: Frovatriptan succinate, a 5-HT1B/1D receptor agonist for migraine. Int J Clin Pract. 2004 Jul;58(7):695-705. [Pubmed]
Elkind AH, Wade A, Ishkanian G: Pharmacokinetics of frovatriptan in adolescent migraineurs. J Clin Pharmacol. 2004 Oct;44(10):1158-65. [Pubmed]
Jhee SS, Shiovitz T, Crawford AW, Cutler NR: Pharmacokinetics and pharmacodynamics of the triptan antimigraine agents: a comparative review. Clin Pharmacokinet. 2001;40(3):189-205. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

参考文献

参考文献

供应商提供 Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • Balbisi EA: Frovatriptan: a review of pharmacology, pharmacokinetics and clinical potential in the treatment of menstrual migraine. Ther Clin Risk Manag. 2006 Sep;2(3):303-8. Pubmed
  • Balbisi EA: Frovatriptan succinate, a 5-HT1B/1D receptor agonist for migraine. Int J Clin Pract. 2004 Jul;58(7):695-705. Pubmed
  • Elkind AH, Wade A, Ishkanian G: Pharmacokinetics of frovatriptan in adolescent migraineurs. J Clin Pharmacol. 2004 Oct;44(10):1158-65. Pubmed
  • Jhee SS, Shiovitz T, Crawford AW, Cutler NR: Pharmacokinetics and pharmacodynamics of the triptan antimigraine agents: a comparative review. Clin Pharmacokinet. 2001;40(3):189-205. Pubmed
  • Markus F, Mikko K: Frovatriptan review. Expert Opin Pharmacother. 2007 Dec;8(17):3029-33. Pubmed
  • Easthope SE, Goa KL: Frovatriptan. CNS Drugs. 2001;15(12):969-76; discussion 977-8. Pubmed
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