Eletriptan hydrobromide

Base Information

• Chemical Name: Eletriptan hydrobromide
• CAS No.: 177834-92-3
• Molecular Formula: C22H27BrN2O2S
• Molecular Weight: 463.439
• Hs Code.: 29339900
• European Community (EC) Number: 639-688-8
• UNII: M41W832TA3
• DSSTox Substance ID: DTXSID001016113
• Wikidata: Q27130865
• NCI Thesaurus Code: C47508
• RXCUI: 360288
• Metabolomics Workbench ID: 61504
• ChEMBL ID: CHEMBL1201003
• Mol file: 177834-92-3.mol

Synonyms:(R)-3-((1-methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1H-indole;(R)-3-((1-methyl-2-pyrrolidinyl)methyl)-5-(2-(phenylsulfonyl)ethyl)-1H-indole monohydrobromide;3-(1-methyl-2-pyrrolidinylmethyl)-5-(2-(phenylsulfonyl)ethyl)-1H-indole hydrobromide;eletriptan;eletriptan hydrobromide;Relpax;UK 166,044;UK 166044;UK-116,044-04;UK-116044-04;UK-166,044;UK-166044

Chemical Property of Eletriptan hydrobromide

Chemical Property:

• Appearance/Colour: Tan solid
• Vapor Pressure: 1.58E-16mmHg at 25°C
• Melting Point: 169-171 °C
• Boiling Point: 633.9 °C at 760 mmHg
• Flash Point: 337.2 °C
• PSA: 61.55000
• LogP: 4.83970
• Storage Temp.: Desiccate at RT
• Solubility.: DMSO: >10mg/mL
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 6
• Exact Mass: 462.09766
• Heavy Atom Count: 28
• Complexity: 582

Purity/Quality:

98% ^*data from raw suppliers

Relpax ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1CCCC1CC2=CNC3=C2C=C(C=C3)CCS(=O)(=O)C4=CC=CC=C4.Br
• Isomeric SMILES: CN1CCC[C@@H]1CC2=CNC3=C2C=C(C=C3)CCS(=O)(=O)C4=CC=CC=C4.Br
• Recent ClinicalTrials: Eletriptan Provides Consistent Migraine Relief: Results Of A Within-Patient Multiple-Dose Study
• Recent EU Clinical Trials: A randomised, double-blind, placebo- and active comparator-controlled, five parallel groups study to investigate the efficacy and safety of BI 44370 TA (50 mg, 200 mg, and 400 mg) administered orally once during an acute migraine attack of moderate or severe intensity
• Uses: Relpax is a second generation triptan drug used in the treatment of migraine headaches. antibiotic Eletriptan hydrobromide is a second generation triptan drug used in the treatment of migraine headaches.

Technology Process of Eletriptan hydrobromide

There total 27 articles about Eletriptan hydrobromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.34%

eletriptan (143322-58-1) → eletriptan hydrobromide (177834-92-3)

Guidance literature:

With hydrogen bromide; In acetone; at 20 ℃; for 0.25h; Product distribution / selectivity;

Reference yield: 88.33%

(R)-5-(2-phenylsulphonylethenyl)-3-(N-methylpyrrolidine-2-yl-methyl)-1H-indole hydrobromide (143577-60-0) → eletriptan hydrobromide (177834-92-3)

Guidance literature:

(R)-5-(2-phenylsulphonylethenyl)-3-(N-methylpyrrolidine-2-yl-methyl)-1H-indole hydrobromide; With hydrogen; palladium 10% on activated carbon; In methanol; at 40 ℃; under 3677.86 Torr;

With hydrogen bromide; In isopropyl alcohol; at 25 - 70 ℃; for 5h; Product distribution / selectivity;

Reference yield:

(R)-5-[(2-phenylsulfonyl)ethenyl]-3-(N-methylpyrrolidine-2-ylmethyl)-1H-indole (180637-89-2) → eletriptan hydrobromide (177834-92-3)

Guidance literature:

(R)-5-[(2-phenylsulfonyl)ethenyl]-3-(N-methylpyrrolidine-2-ylmethyl)-1H-indole; With methanesulfonic acid; hydrogen; 5%-palladium/activated carbon; In acetone;

With ammonia; In dichloromethane; water;

With hydrogen bromide; In dichloromethane; water; at 20 ℃; for 0.5h;

upstream raw materials:

eletriptan

3-(N-methyl-2(R)-pyrrolidinylmethyl)-5-(2-phenylsulphonylethyl)-1H-indole hydrobromide monohydrate

3-[[(R)-1-methyl-2-pyrrolidinyl]methyl]-5-[2-(phenyl-sulfonyl)ethyl]indole para-toluenesulfonate

5-bromo-3-(1-methylpyrrolidin-2(R)-ylmethyl)-1H-indole

Downstream raw materials:

3-(N-methyl-2(R)-pyrrolidinylmethyl)-5-(2-phenylsulphonylethyl)-1H-indole hydrobromide monohydrate

4-methyl-8-[2-(phenylsulfonyl)ethyl]-1,2,3,5,10,10a-hexahydropyrrolidino[3,2-b]indol-4-ium

Refernces

• 1、 Kumar, U. Sampath,Sankar, V. Ravi,Rao, M. Malleswara,Jaganathan,Buchi Reddy. "Investigational study into the formation of methoxy derivative and other impurities during the optimization of eletriptan hydrobromide". . p. 1917 - 1920. Retrieved 2013/03/13.
• 2、 -. "HIGHLY PURE ELETRIPTAN OR A PHARMACEUTICALLY ACCEPTABLE SALT THEREOF SUBSTANTIALLY FREE OF ELETRIPTAN N-OXIDE IMPURITY". Page/Page column 8. . Retrieved 2012/02/06.