4-({3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-one

• ChemBase ID: 122733
• Molecular Formular: C16H21N3O2
• Molecular Mass: 287.35684
• Monoisotopic Mass: 287.16337693
• SMILES: C1(=O)NC(CO1)Cc1cc2c(c[nH]c2cc1)CCN(C)C
• Canonical SMILES: CN(CCc1c[nH]c2c1cc(CC1COC(=O)N1)cc2)C
• InChI: InChI=1S/C16H21N3O2/c1-19(2)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-21-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)
• InChIKey: ULSDMUVEXKOYBU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-({3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-one
• IUPAC Traditional name: 4-({3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-one
• Synonyms: 4-((3-(2-(dimethylamino)ethyl)-1H-indol-5-yl)methyl)oxazolidin-2-one; Zolmitriptan; (4S)-4-[[3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl]methyl-2-oxazolidinone; BW-311C90; Zomig; Zolmitriptan

Database IDs

• CAS Number: 139264-17-8; 139264-82-7
• PubChem SID: 162217086
• PubChem CID: 5731

CALCULATED PROPERTIES

• Acid pKa: 13.002183
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -1.3495891
• LogD (pH = 7.4): -0.08771248
• Log P: 2.0428753
• Molar Refractivity: 82.4392 cm^3
• Polarizability: 32.885002 Å^3
• Polar Surface Area: 57.36 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 139-141°C

Safety Information

• Storage Condition: Refrigerator

Pharmacology Properties

• Mechanism of Action: 5-Hydroxytryptamine (5HT1D) receptor agonist; Selective Serotonin receptor agonist

Product Information

• Application(s): Antimigraine agent

DETAILS

Toronto Research Chemicals - Z639000

A Serotonin 5HTID-receptor agonist.

REFERENCES

• Glen, R.C., et al.: J. Med. Chem., 38, 3566 (1995)
• Seaber, E., et al.: Brit. J. Clin. Pharmacol., 41, 141 (1995)
• Tepper, S.J., et al.: Curr. Med. Res. Opin., 15, 254 (1999)
• Pat. Coop. Treaty (WIPO), 1991, Wellcome, 91 18 897; CA, 116, 174136c, (synth, pharmacol)
• Goadsby, P.J. et al., Headache, 1994, 34, 394, (pharmacol)
• Glen, R.C. et al., J. Med. Chem., 1995, 38, 3566, (synth, pharmacol, sar)
• Buckingham, J. et al., J. Med. Chem., 1995, 38, 3566-3580, (synth, pharmacol)
• Dowson, A., Eur. Neurol., 1996, 36, 28-31, (pharmacol)
• MacGregor, E.A. et al., Drugs of the Future, 1998, 34, 1027-1033
• Spencer, C.M. et al., Drugs, 1999, 58, 347-374