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
- External Links
- ChemSpider
- 30790735
- ChEMBL
- CHEMBL3039526
- Predicted Properties
Property Value Source Water Solubility 0.0175 mg/mL ALOGPS logP 2.76 ALOGPS logP 3.3 Chemaxon logS -4.3 ALOGPS pKa (Strongest Acidic) 12.23 Chemaxon pKa (Strongest Basic) 7.99 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 62.3 Å2 Chemaxon Rotatable Bond Count 11 Chemaxon Refractivity 96.15 m3·mol-1 Chemaxon Polarizability 35.6 Å3 Chemaxon Number of Rings 6 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon