(3R)-3-(methylamino)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamide butanedioic acid hydrate

• ChemBase ID: 169461
• Molecular Formular: C18H25N3O6
• Molecular Mass: 379.4076
• Monoisotopic Mass: 379.17433554
• SMILES: C(CC(=O)O)C(=O)O.O.c1(ccc2c(c1)c1c([nH]2)CC[C@H](C1)NC)C(=O)N
• Canonical SMILES: OC(=O)CCC(=O)O.CN[C@@H]1CCc2c(C1)c1cc(ccc1[nH]2)C(=O)N.O
• InChI: InChI=1S/C14H17N3O.C4H6O4.H2O/c1-16-9-3-5-13-11(7-9)10-6-8(14(15)18)2-4-12(10)17-13;5-3(6)1-2-4(7)8;/h2,4,6,9,16-17H,3,5,7H2,1H3,(H2,15,18);1-2H2,(H,5,6)(H,7,8);1H2/t9-;;/m1../s1
• InChIKey: CUETXFMONOSVJA-KLQYNRQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (3R)-3-(methylamino)-2,3,4,9-tetrahydro-1H-carbazole-6-carboxamide butanedioic acid hydrate
• IUPAC Traditional name: frovatriptan succinic acid hydrate
• Synonyms: (3R)-2,3,4,9-Tetrahydro-3-(methylamino)-1H-carbazole-6-carboxamide Butanedioic Acid Monohydrate; Frova; Frovelan; Migard; Miguard; Frovatriptan Succinate Monohydrate

Database IDs

• CAS Number: 158930-17-7
• PubChem SID: 162263593
• PubChem CID: 152943

CALCULATED PROPERTIES

• Acid pKa: 14.536194
• H Acceptors: 2
• H Donor: 3
• LogD (pH = 5.5): -2.1550536
• LogD (pH = 7.4): -1.739132
• Log P: 1.077976
• Molar Refractivity: 71.8382 cm^3
• Polarizability: 28.223196 Å^3
• Polar Surface Area: 70.91 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol; Water
• Apperance: White to Off-White Solid
• Melting Point: 150-153°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - F768500

Serotonin 5-HT1B/1D receptor agonist. It is a triptan drug for the treatment of migraine headaches. Frovatriptan causes vasoconstriction of arteries and veins that supply blood to the head.

REFERENCES

• Parsons, A.A., et al.: J. Cardiovasc. Pharmacol., 30, 136 (1997)
• Siow, C.H., et al.: Cephalalgia, 24, 1045 (1997)
• Poolsup, N., et al.: J. Clin. Pharm. Ther., 30, 521 (1997)