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

• ChemBase ID: 101
• Molecular Formular: C22H26N2O2S
• Molecular Mass: 382.51904
• Monoisotopic Mass: 382.17149908
• SMILES: S(=O)(=O)(CCc1cc2c(C[C@@H]3N(CCC3)C)c[nH]c2cc1)c1ccccc1
• Canonical SMILES: CN1CCC[C@@H]1Cc1c[nH]c2c1cc(cc2)CCS(=O)(=O)c1ccccc1
• InChI: InChI=1S/C22H26N2O2S/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/t19-/m1/s1
• InChIKey: PWVXXGRKLHYWKM-LJQANCHMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-[2-(benzenesulfonyl)ethyl]-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole
• IUPAC Traditional name: eletriptan; relpax
• Brand Name: Relpax
• Synonyms: 3-[[(2R)-1-Methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-1H-indole; (R)-5-[2-(Benzenesulfonyl)ethyl]-3-[(N-methylpyrrolidin-2-yl)methyl]-1H-indole; UK-116044; Relpax free amine; EletriptanAlso see: R143400; eletriptan; Eletriptan

Database IDs

• CAS Number: 143322-58-1
• PubChem SID: 46506380; 160963564
• PubChem CID: 77993

CALCULATED PROPERTIES

JChem

• 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

ALOGPS 2.1

• Log P: 3.84
• LOG S: -5.51
• Solubility (Water): 1.18e-03 g/l

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol; Readily soluble as hydrobromide formulation
• Apperance: Yellow Solid
• Hydrophobicity(logP): 3.9

Safety Information

• Storage Condition: Hygroscopic, Refrigerator, Under Inert Atmosphere

DETAILS

DrugBank - DB00216

• Drug Groups: approved; investigational
• Description: Eletriptan is a second generation triptan drug developed by Pfizer Inc for the treatment of migraine headaches. [Wikipedia]
• Indication: For the acute treatment of migraine with or without aura in adults.
• Pharmacology: Eletriptan is a selective 5-hydroxytryptamine 1B/1D receptor agonist. In the anesthetized dog, eletriptan has been shown to reduce carotid arterial blood flow, with only a small increase in arterial blood pressure at high doses. While the effect on blood flow was selective for the carotid arterial bed, decreases in coronary artery diameter were observed. Eletriptan has also been shown to inhibit trigeminal nerve activity in the rat.
• Toxicity: Based on the pharmacology of the 5-HT1B/1D agonists, hypertension or other more serious cardiovascular symptoms could occur on overdose.
• Affected Organisms: Humans and other mammals
• Biotransformation: In vitro studies indicate that eletriptan is primarily metabolized by cytochrome P-450 enzyme CYP3A4. The N-demethylated metabolite of eletriptan is the only known active metabolite.
• Absorption: Well absorbed after oral administration with a mean absolute bioavailability of approximately 50%.
• Half Life: The terminal elimination half-life of eletriptan is approximately 4 hours.
• Protein Binding: Plasma protein binding is moderate and approximately 85%.
• Distribution: * 138 L
• Clearance: * Renal cl=3.9 L/h
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - E505000

A serotonin 5-HTIB/ID receptor agonist. Antimigrene.

REFERENCES

• Willems, E., et al.: Arch. Pharmacol., 358, 212 (1998)
• Napier, C., et al.: Eur. J. Pharmacol., 368, 259 (1998)
• Goadsby, P.J., et al.: Neurology, 54, 156 (2000)