5-[2-(benzenesulfonyl)ethyl]-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole hydrobromide

• ChemBase ID: 154659
• Molecular Formular: C22H27BrN2O2S
• Molecular Mass: 463.43098
• Monoisotopic Mass: 462.09766111
• SMILES: CN1CCC[C@@H]1Cc1c[nH]c2c1cc(cc2)CCS(=O)(=O)c1ccccc1.Br
• Canonical SMILES: CN1CCC[C@@H]1Cc1c[nH]c2c1cc(cc2)CCS(=O)(=O)c1ccccc1.Br
• InChI: InChI=1S/C22H26N2O2S.BrH/c1-24-12-5-6-19(24)15-18-16-23-22-10-9-17(14-21(18)22)11-13-27(25,26)20-7-3-2-4-8-20;/h2-4,7-10,14,16,19,23H,5-6,11-13,15H2,1H3;1H/t19-;/m1./s1
• InChIKey: UTINOWOSWSPFLJ-FSRHSHDFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[2-(benzenesulfonyl)ethyl]-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole hydrobromide
• IUPAC Traditional name: eletriptan hydrobromide
• Synonyms: 3-[[(2R)-1-Methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-1H-indole Hydrobromide; Eletriptan Hydrobromide; (R)-5-[2-(Benzenesulfonyl)ethyl]-3-[(N-methylpyrrolidin-2-yl)methyl]-1H-indole Hydrobromide; Relert; UK 116044-04; RelpaxAlso see: E505000; Eletriptan hydrobromide

Database IDs

• CAS Number: 177834-92-3
• MDL Number: MFCD08141806
• PubChem SID: 162248797
• PubChem CID: 656631

CALCULATED PROPERTIES

• Acid pKa: 17.110289
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 0.9913155
• LogD (pH = 7.4): 2.7574787
• Log P: 3.7732625
• Molar Refractivity: 110.9416 cm^3
• Polarizability: 44.744522 Å^3
• Polar Surface Area: 53.17 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; DMSO: >10 mg/mL; Methanol
• Apperance: off-white to light tan powder; Tan Solid
• Melting Point: 169-171°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H319
• GHS Precautionary statements: P305 + P351 + P338
• Storage Temperature: room temp

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C22H26N2O2S · HBr

DETAILS

Sigma Aldrich - PZ0011

Biochem/physiol Actions
Eletriptan hydrobromide is a serotonin 5-HT1B/1D receptor agonist; second generation anti-migraine drug.
Legal Information
Sold for research purposes under agreement from Pfizer Inc.

Toronto Research Chemicals - R143400

A second generation triptan drug used in the treatment of migraine headaches.

REFERENCES

• McCormack, P.L. et al.: Drugs, 66, 1129 (2006)
• Goadsby, P.J. et al.: Neurology, 54, 156 (2006)
• Napier, C. et al.: Eur. J. Pharmacol., 368, 259 (2006)