Lasmiditan

Lasmiditan

Systematic (IUPAC) name
2,4,6-Trifluoro-N-[6-[(1-methyl-4-piperidinyl)carbonyl]-2-pyridinyl]benzamide
Clinical data
Routes of administration	Oral, intravenous
Legal status	Investigational
Identifiers
ATC code	none
PubChem	CID 11610526
IUPHAR/BPS	3928
ChemSpider	9785281
UNII	760I9WM792
Chemical data
Formula	C19H18F3N3O2
Molar mass	377.36 g/mol
SMILES CN3CCC(CC3)C(=O)c(n2)cccc2NC(=O)c1c(F)cc(F)cc1F
InChI InChI=1S/C19H18F3N3O2/c1-25-7-5-11(6-8-25)18(26)15-3-2-4-16(23-15)24-19(27)17-13(21)9-12(20)10-14(17)22/h2-4,9-11H,5-8H2,1H3,(H,23,24,27) Key:XEDHVZKDSYZQBF-UHFFFAOYSA-N
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Lasmiditan (codenamed COL-144) is an investigational drug for the treatment of acute migraine. It was discovered by Eli Lilly and Company and is being developed by CoLucid Pharmaceuticals. Phase II clinical trial for dose finding purposes were completed in 2007 for an intravenous^[1] and in early 2010 for an oral application form.^[2]

Mechanism of action

Lasmiditan is a serotonin receptor agonist that, like the unsuccessful LY-334,370, selectively binds to the 5-HT_1F receptor subtype. A number of triptans have been shown to act on this subtype as well, but only after their affinity for 5-HT_1B and 5-HT_1D has been made responsible for their anti-migraine activity. The lack of affinity for these receptors might result in fewer side-effects related to vasoconstriction compared to triptans.^[3] A 1998 review has found such side-effects to rarely occur in patients taking triptans,^[4] but they are contraindicated for patients with ischaemic heart disease, Raynaud's phenomenon or after a myocardial infarction.^[5]

References

1. Clinical trial number NCT00384774 for "A Placebo-Controlled Adaptive Treatment Assignment Study of Intravenous COL-144 in the Acute Treatment of Migraine" at ClinicalTrials.gov
2. Clinical trial number NCT00883051 for "Dose-ranging Study of Oral COL-144 in Acute Migraine Treatment" at ClinicalTrials.gov
3. "Molecule of the Month July 2010: Lasmiditan hydrochloride". Prous Science. Retrieved 2011-08-03.
4. Dahlöf, CG; Mathew, N (1998). "Cardiovascular safety of 5HT1B/1D agonists--is there a cause for concern?". Cephalalgia : an international journal of headache 18 (8): 539–45. doi:10.1046/j.1468-2982.1998.1808539.x. PMID 9827245.
5. Mutschler, Ernst; Geisslinger, Gerd; Kroemer, Heyo K.; Schäfer-Korting, Monika (2001). Arzneimittelwirkungen (in German) (8th ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. p. 265. ISBN 978-3-8047-1763-3. OCLC 47700647.