2-hydroxybutanedioic acid; dimethyl(2-{5-[(pyrrolidine-1-sulfonyl)methyl]-1H-indol-3-yl}ethyl)amine

• ChemBase ID: 159707
• Molecular Formular: C21H31N3O7S
• Molecular Mass: 469.55174
• Monoisotopic Mass: 469.18827135
• SMILES: C(C(O)C(=O)O)C(=O)O.c1c(cc2c(c1)[nH]cc2CCN(C)C)CS(=O)(=O)N1CCCC1
• Canonical SMILES: OC(=O)CC(C(=O)O)O.CN(CCc1c[nH]c2c1cc(cc2)CS(=O)(=O)N1CCCC1)C
• InChI: InChI=1S/C17H25N3O2S.C4H6O5/c1-19(2)10-7-15-12-18-17-6-5-14(11-16(15)17)13-23(21,22)20-8-3-4-9-20;5-2(4(8)9)1-3(6)7/h5-6,11-12,18H,3-4,7-10,13H2,1-2H3;2,5H,1H2,(H,6,7)(H,8,9)
• InChIKey: QHATUKWEVNMHRY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-hydroxybutanedioic acid; dimethyl(2-{5-[(pyrrolidine-1-sulfonyl)methyl]-1H-indol-3-yl}ethyl)amine
• IUPAC Traditional name: almotriptan; malic acid
• Synonyms: 1-[[[2-(Dimethyl-amino)ethyl]-1H-indol-5-yl]methyl]sulfonyl]pyrrolidine Malate; 1-[[3-(2-dimethylaminoethyl)-5-indolyl]methanesulphonyl]pyrrolidine Malate; LAS-31416 Malate; Almotriptan MalateSee: A575201; Almotriptan malate (Axert)

Database IDs

• CAS Number: 181183-52-8
• PubChem SID: 162253842
• PubChem CID: 123607

CALCULATED PROPERTIES

• Acid pKa: 17.136013
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -1.8689746
• LogD (pH = 7.4): -0.6067433
• Log P: 1.5233824
• Molar Refractivity: 94.5219 cm^3
• Polarizability: 38.129585 Å^3
• Polar Surface Area: 56.41 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow to Pale Orange Solid
• Melting Point: 102-109°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: 5-HT Receptor

Product Information

• Salt Data: Malate

DETAILS

Toronto Research Chemicals - A575200

Almotriptan is a serotonin 5HT1B /1D-receptor agonist used for treatment of migraine.

REFERENCES

• Fleishaker, J.C., et al.: Clin. Pharmacol. Ther., 67, 498 (2000)
• Kamali, F., et al.: Curr. Opin. Cent. Peripher. Nerv. Syst. Invest. Drugs, 2, 197 (2000)
• Dodick, D.W., et al.: Expert Opin.Pharmacother., 4, 1157 (2003)