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

• ChemBase ID: 72776
• Molecular Formular: C16H21N3O2
• Molecular Mass: 287.35684
• Monoisotopic Mass: 287.16337693
• SMILES: c1c(ccc2c1c(c[nH]2)CCN(C)C)C[C@@H]1NC(=O)OC1
• Canonical SMILES: CN(CCc1c[nH]c2c1cc(C[C@H]1COC(=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)/t13-/m0/s1
• InChIKey: ULSDMUVEXKOYBU-ZDUSSCGKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4S)-4-({3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-one
• IUPAC Traditional name: zomig
• Synonyms: Zomig; Zomigon; AscoTopand; Zomigoro; Zolmitriptan

Database IDs

• CAS Number: 139264-17-8
• PubChem SID: 162037697
• PubChem CID: 60857

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

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S1649

Research Area: Neurological Disease
Biological Activity:
Zolmitriptan(Zomig) is a selective serotonin receptor agonist. It is a triptan, used in the acute treatment of migraine attacks with or without aura and cluster headaches. Cytochrome 1A2 is likely to be the isoenzyme responsible for the metabolism of zolmitriptan. The increased exposure to zolmitriptan and 183C91 by cimetidine indicated that a reduction in the total daily recommended dose of zolmitriptan may be necessary when treating migraine patients who are taking nonspecific cytochrome P450 inhibitors or specific cytochrome 1A2 inhibitors. [1][2]

REFERENCES

• http://en.wikipedia.org/wiki/Zolmitriptan