158930-09-7 Usage
Description
Frovatriptan Succinate, also known as Frova, is a medication belonging to the "triptan" class, specifically designed as an oral treatment for acute migraine attacks in adults, with or without aura. It is a conformationally-restricted analog of the 5-HT1-receptor agonist 5-carboxytryptamine and acts as a dual 5-HT1D/1B receptor partial agonist. Frovatriptan Succinate is characterized by its high and selective affinity for 5HT1B and 5-HT1D receptors in cranial vessels, its long half-life (25 hours), and excellent tolerance profile.
Uses
Used in Pharmaceutical Industry:
Frovatriptan Succinate is used as an oral treatment for acute migraine attacks in adults, providing relief from the symptoms associated with migraines. Its application is based on its ability to act as a dual 5-HT1D/1B receptor partial agonist, selectively targeting receptors in cranial vessels without significant activity at other receptors such as 5-HT2, 5-HT3, 5-HT4, α-adrenergic, histaminergic, or GABAA receptors.
Additionally, Frovatriptan Succinate is used as a moderately potent full agonist at 5-HT7 receptors, which have a dilatory action and are expressed in the human coronary artery. This feature contributes to its functional selectivity for the cerebral circulation, as demonstrated by in vitro studies comparing its effects on basilar and coronary arteries.
Frovatriptan Succinate is also notable for its low headache recurrence rate, which is one of the lowest among triptans, and its excellent tolerance profile. This is likely due to its long half-life and the fact that it has no significant effect on the cardiovascular system, even after administration of a single oral dose that is 14 times the therapeutic dose.
Originator
GlaxoSmithKlineNernaIis (UK)
Therapeutic Function
Migraine therapy
Synthesis
The synthesis of frovatriptan (11)
appeared in a patent in multi-kilo scale.
Cyclohexanedione monoketal (121) was converted to amine
122 by reductive amination. The Fischer indolization of
amine 122 with hydrazine 123 furnished indole nitrile 124
in 72% yield. The desired R isomer of the indole nitrile was
obtained via a chiral salt formation/recrystallization process
using chiral lactam 125 and isolated as a L-pyroglutamic
acid salt 126. Hydrolysis of the nitrile functional group in
126 provided carboxamido indole 127, which was converted
to succinate 11 in situ.
Check Digit Verification of cas no
The CAS Registry Mumber 158930-09-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,5,8,9,3 and 0 respectively; the second part has 2 digits, 0 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 158930-09:
(8*1)+(7*5)+(6*8)+(5*9)+(4*3)+(3*0)+(2*0)+(1*9)=157
157 % 10 = 7
So 158930-09-7 is a valid CAS Registry Number.
InChI:InChI=1/C14H17N3O.C4H6O4/c1-16-9-3-5-13-11(7-9)10-6-8(14(15)18)2-4-12(10)17-13;5-3(6)1-2-4(7)8/h2,4,6,9,16-17H,3,5,7H2,1H3,(H2,15,18);1-2H2,(H,5,6)(H,7,8)/t9-;/m1./s1
