Sumatriptan

Molecular formula Ci4H2,N302S Molecular weight 295.4 

Sample preparation Condition a Bond-Elut C2 SPE cartridge with two 1 mL portions of MeOH and two 1 mL portions of water. 1 mL Plasma -I- 100 p-L 100 ng/mL IS in water, vortex briefly, add to the SPE cartridge at 2 mL/min, wash with 1 mL water, wash with two 1 mL portions of MeOH water 30 70, elute with 1 mL MeOH 10 mM pH 5.0 ammonium acetate 60 40, evaporate the eluate to dryness under reduced pressure at 50°, reconstitute with 200 p-L mobile phase, sonicate for 10 min, vortex, inject a 25 p-L aliquot. 

Mobile phase MeCN MeOH water trifluoroacetic acid 36 6 58 0.1 

Detector MS, Sciex Model API III triple quadrupole, nebulizer probe 500°, nebulizing gas 80 psi, auxiliary flow 2 L/min, corona discharge needle -1-3 p,A, 0.1143 mm orifice, orifice 40 V, collision gas argon 

Internal standard 3-[2-(diethylamino)ethyl)-N-methyl-lH-indole-5-methanesulfonamide (L-737,404, Merck) (3.35) 

McLou in, DA. Olah, T.Y. Ellis, J.D. Gilbert, J.D. Halpin, R.A Quantitation of the 5HT,d agonists MK-462 and sumatriptan in plasma by liqvdd chromatography-atmospheric pressure chemical ionization mass spectrometry. J.Chromatogr.A, 1996, 726, 115-124 

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Among the indole derivatives which have found use as drugs are indo-methacin, one of the first non-steroidal anti-inflammatory agentsfll], sumatriptan, which is used in the treatment of migraine headaches[12] and pindolol[13], one of the p-adrenergic blockers. 

Imitrex (Sumatriptan) 82 is the first selective 5-HTid agonist developed by Glaxo for the treatment of migraine. The synthesis of Imitrex has been carried out by several different routes all of which involved a Fischer indolization reaction as the key step. Outlined below is one of the synthetic routes. 

Perez, M., Pauwels, P. J., Fourrier, C., Chopin, P., Valentin, J.-P., John, G. W., Marien, M., and Halazy, S. (1998). Dimerization of sumatriptan as an efficienct way to design a potent, centrally and orally active 5-HT1B agonist. Bioorg. Med. Chem. Lett. 8 675-680. 

C14H17N3O4S 103628-49-5) see Sumatriptan dimethyl A -methylcarbonimidodithioate (C4H9NS2 18805-25-9) see Ranitidine (E)-A, Af-dimethyl-3-(4-methylphenyl)-3-phenyl-2-propen-1-amine... 

C 2H, N05 39562-27-7) see Aranidipine 4-nitrophenyl-iV-methylmethanesulfonamide (CjHk,N204S 85952-29-0) see Sumatriptan... 

C2CI2O2 79-37-8) see Cefuroxime Diclofenae Dorzolamide Fexofenadine hydroehloride Granisetron Gusperimus trihydrochloride Indoramin Maprotiline Micinicate Ritonavir Saquinavir Sumatriptan Tacrolimus Tirofiban hydrochloride Tropisetron Viminol... 

C17H21NO2S 1227-99-2) see Tiemonium iodide (phenylthio)acetaldehyde (CgHjOS 66303-55-7) see Sumatriptan (4-phenylthiobenzoyl)dithioacetic acid (C15H12OS3 41054-41-5) see Tibezonium iodide... 

Interest in this receptor has been generated by the possibility that its activation accounts for the anti-migraine effects of the non-selective 5-HTib/id agonist, sumatriptan. The exact process(es) that account for this action are unresolved but... 

Sumatriptan is an agonist at 5-HTib and 5-HTid receptors. It has three distinct pharmacological actions. 

Direct vasoconstriction is mediated by the stimulation of vascular 5-HTib receptors. These receptors are also found systemically, so coronary arteries also undergo vasoconstriction. Sumatriptan constricts cerebral arteries, but if the vasculature is normal, this does not affect rCBF. 

PE Warner, KLR Brouwer, EK Hussey, GE Dukes, WD Heizer, KH Donn, IM Davis, JR Powell. Sumatriptan absorption from different regions of the human gastrointestinal tract. Pharmaceut Res 12 138-143, 1995. 

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