Lasmiditan succinateProduct ingredient for Lasmiditan

Name
Lasmiditan succinate
Drug Entry
Lasmiditan

Lasmiditan is an oral medication used in the termination of migraine headaches that was first approved for use in the United States in October 2019.7,9 It was also approved by the European Commission on August 17, 2022.12

Traditionally, the triptan class of anti-migraine medications (e.g. sumatriptan) have seen preferential use in the acute treatment of migraines due to their relatively favourable efficacy and safety. Their use is not devoid of concerns, however, and their vasoconstrictive activity can lead to blood pressure lability and other cardiovascular side effects - for this reason, these medications are less suitable for use in patients with pre-existing cardiovascular disorders.4 Triptans abort migraines via action at several serotonin receptors, including 5-HT1D and 5-HT1B receptors, and activity at the 5-HT1B receptor has been specifically implicated in their vasoconstrictive activity.4,6

Lasmiditan, in contrast, is a highly selective agonist of 5-HT1F receptors, carrying virtually no affinity for other receptors which appear to be largely responsible for the adverse effect profile of its predecessors - in other words, lasmiditan’s selectivity allows for the successful termination of migraines without causing vasoconstriction.6,5 Selectivity for 5-HT1F, a lack of vasoconstrictive activity, and the ability to terminate migraines through neuronal inhibition has resulted in the creation of a new class of anti-migraine medications in which lasmiditan is the first and only member: the neurally-acting anti-migraine medications (NAAMAs).6,1

Accession Number
DBSALT002893
Structure
Synonyms
Lasmiditan hemisuccinate
External IDs
LY-573144 / LY-683974 / LY573144 / LY683974
UNII
W64YBJ346B
CAS Number
439239-92-6
Weight
Average: 872.822
Monoisotopic: 872.296831314
Chemical Formula
C42H42F6N6O8
InChI Key
MSOIHUHNGPOCTH-UHFFFAOYSA-N
InChI
InChI=1S/2C19H18F3N3O2.C4H6O4/c2*1-25-7-5-11(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;5-3(6)1-2-4(7)8/h2*2-4,9-11H,5-8H2,1H3,(H,23,24,27);1-2H2,(H,5,6)(H,7,8)
IUPAC Name
bis(2,4,6-trifluoro-N-[6-(1-methylpiperidine-4-carbonyl)pyridin-2-yl]benzamide); butanedioic acid
SMILES
OC(=O)CCC(O)=O.CN1CCC(CC1)C(=O)C1=CC=CC(NC(=O)C2=C(F)C=C(F)C=C2F)=N1.CN1CCC(CC1)C(=O)C1=CC=CC(NC(=O)C2=C(F)C=C(F)C=C2F)=N1
ChemSpider
30790735
ChEMBL
CHEMBL3039526
Predicted Properties
PropertyValueSource
Water Solubility0.0175 mg/mLALOGPS
logP2.76ALOGPS
logP3.3Chemaxon
logS-4.3ALOGPS
pKa (Strongest Acidic)12.23Chemaxon
pKa (Strongest Basic)7.99Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area62.3 Å2Chemaxon
Rotatable Bond Count11Chemaxon
Refractivity96.15 m3·mol-1Chemaxon
Polarizability35.6 Å3Chemaxon
Number of Rings6Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon