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Sumatriptan (Molecule of the Month for June 2007)

Imitrex, Imigran,Imigran Recovery



Sumatriptan is a triptan drug including a sulfonamide group which was originally developed by Glaxo for the treatment of migraine headaches. Sumatriptan is also shown to decrease the activity of the trigeminal nerve, which probably accounts for Sumatriptan's efficacy in treating cluster headaches. The injectable form of the drug has been shown to abort a cluster headache within fifteen minutes in 96% of cases. This type of headache is extremely painful and debilitating, and sumatriptan injection is currently the only truly effective acute treatment.

Often, serotonin levels in the brain become extremely erratic before the onset of a migraine. In an attempt to stabilize this, sumatriptan is administered to help aid in leveling the serotonin levels in the brain. Sumatriptan is structurally similar to serotonin, and is a 5-HT (5-HT1D) agonist, which is one of the receptors to which serotonin binds.

A team of Canadian surgeons got a shock when the patient they were operating on began shedding dark greenish-black blood, the Lancet reports. The man emulated Star Trek's Mr Spock - the Enterprise's science officer who supposedly had green Vulcan blood. This is due to large doses of sumatripan (200 mg/day) can cause sulfhemoglobinemia, a rare condition in which the blood changes from red to greenish-black, due to the integration of sulfur into the hemoglobin molecule. If sumatripan is discontinued, the condition reverses within a few weeks.

Formal Chemical Name (IUPAC)
N,N-dimethyl-2-(5-((methylamino)methylsulfonyl)-1H-indol-3-yl)ethanamine

References

http://en.wikipedia.org/wiki/Sumatriptan

http://news.bbc.co.uk/1/hi/health/6733203.stm

Picture of Sumatriptan

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Sumatriptan structure
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Picture of Sumatriptan

C14 H21 N3 O2 S



Update by Karl Harrison
(Molecule of the Month for June 2007 )