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143322-58-1 molecular structure
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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 and InChIs

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

Cite this record

CBID:101 http://www.chembase.cn/molecule-101.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
5-[2-(benzenesulfonyl)ethyl]-3-{[(2R)-1-methylpyrrolidin-2-yl]methyl}-1H-indole
IUPAC Traditional name
relpax
eletriptan
Brand Name
Relpax
Synonyms
eletriptan
Eletriptan
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
CAS Number
143322-58-1
PubChem SID
46506380
160963564
PubChem CID
77993

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
TRC
E505000 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 17.110289  H Acceptors
H Donor LogD (pH = 5.5) 0.9913155 
LogD (pH = 7.4) 2.7574787  Log P 3.7732625 
Molar Refractivity 110.9416 cm3 Polarizability 44.744522 Å3
Polar Surface Area 53.17 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 3.84  LOG S -5.51 
Solubility (Water) 1.18e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Product Information Bioassay(PubChem)
Solubility
Chloroform expand Show data source
Methanol expand Show data source
Readily soluble as hydrobromide formulation expand Show data source
Apperance
Yellow Solid expand Show data source
Hydrophobicity(logP)
3.9 expand Show data source
Storage Condition
Hygroscopic, Refrigerator, Under Inert Atmosphere expand Show data source
MSDS Link
Download expand Show data source
Certificate of Analysis
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DETAILS

DETAILS

DrugBank DrugBank TRC TRC
DrugBank - DB00216 external link
Item Information
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 external link
A serotonin 5-HTIB/ID receptor agonist. Antimigrene.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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)
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PATENTS

PATENTS

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INTERNET

INTERNET

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