Eletriptan hydrobromide CAS 177834-92-3
Introduction：Basic information about Eletriptan hydrobromide CAS 177834-92-3, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.
Eletriptan hydrobromide Basic information
| Product Name: | Eletriptan hydrobromide |
| Synonyms: | Unii-m41W832ta3;RelpaxAlso see: E505000;Eletriptan HCl;1H-Indole,3-[[(2R)-1-methyl-2-pyrrolidinyl]methyl]-5-[2-(phenylsulfonyl)ethyl]-,hydrobromide;(R)-5-[2-(Benzenesulfonyl)ethyl]-3-[(N-Methylpyrrolidin-2-yl)Methyl]-1H-indole hydrobroMide;Relert;(R)-3-((1-Methylpyrrolidin-2-yl)Methyl)-5-(2-(phenylsulfonyl)ethyl)-1H-indole hydrobroMide;eletriptan hydrobromide |
| CAS: | 177834-92-3 |
| MF: | C22H27BrN2O2S |
| MW: | 463.43 |
| EINECS: | 639-688-8 |
| Product Categories: | Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pfizer compounds;Pharmaceuticals |
| Mol File: | 177834-92-3.mol |
Eletriptan hydrobromide Chemical Properties
| Melting point | 169-171?C |
| storage temp. | Keep in dark place,Inert atmosphere,Store in freezer, under -20°C |
| solubility | DMSO: >10mg/mL |
| form | powder |
| color | off-white to light tan |
| InChIKey | PWVXXGRKLHYWKM-IBGZPJMESA-N |
| SMILES | C([C@H]1CCCN1C)C1=CNC2C=CC(CCS(C3C=CC=CC=3)(=O)=O)=CC1=2.Br |&1:1,r| |
Safety Information
| Hazard Codes | Xi |
| Risk Statements | 36 |
| Safety Statements | 26 |
| WGK Germany | 3 |
| HS Code | 29339900 |
| Storage Class | 11 - Combustible Solids |
| Hazard Classifications | Acute Tox. 4 Oral Aquatic Chronic 3 Eye Dam. 1 |
| Chemical Properties | Eletriptan hydrobromide is Tan Solid |
| Originator | Relpax,Pfizer |
| Uses | Relpax is a second generation triptan drug used in the treatment of migraine headaches. |
| Uses | antibiotic |
| Uses | Eletriptan hydrobromide is a second generation triptan drug used in the treatment of migraine headaches. |
| Definition | ChEBI: Eletriptan hydrobromide is a hydrobromide. It has a role as a serotonergic agonist, a vasoconstrictor agent and a non-steroidal anti-inflammatory drug. It contains an eletriptan(1+). |
| Manufacturing Process | A mixture of the appropriate phenyl vinyl sulfone, tri-o-tolylphosphine,palladium (II) acetate, triethlamine and (R)-5-bromo-3-(Nmethylpyrrolidinylmethyl)-1H-indole in anhydrous acetonitrle was heated atreflux under nitrogen. The resultant reaction mixture was evaporated underreduced pressure, and the residue was column chromatographed using silicagel and elution with methylene chloride/absolute ethanol/ammonia to affordthe (R )-5-trans-(2-phenylsulfonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole. A solution of (R)-5-trans-(2-phenylsulfonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole and 10% Pd/C in ethanolic hydrogen chloride (preparedfrom absolute ethanol and acetyl chloride and N,N-dimethylformamide wasshaken under a hydrogen atmosphere at room temperature). The resultantreaction mixture was filtered through diatomaceous earth (Celite trademark),washed with absolute ethanol, and the combined filtrates were evaporatedunder reduced pressure. The residue was partitioned between ethyl acetateand water. The organic phase was separated, washed with water, brine, dried(Na2SO4), and evaporated under reduced pressure to afford a oil product.Column chromatography of this product using silica gel and elution withmethylene chloride/absolute ethanol/ammonia afforded the appropriate (R)-5-(2-phenylsulfonylethyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole. The salt eletriptan hydrobromide may be produced by reaction of the (R)-5-(2-phenylsulfonylethyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole withhydrobromic acid. |
| Brand name | Relpax (Pfizer). |
| Therapeutic Function | Serotonin agonist |
| Biological Activity | Orally active, selective 5-HT 1B/1D receptor agonist. Produces a dose-dependent reduction in carotid artery blood flow in vivo . Displays antimigraine activity. |
| storage | room temperature (desiccate) |
Eletriptan hydrobromide Preparation Products And Raw materials
| Raw materials | Phosphine-->Hydrochloric acid-->Hydrogen bromide-->Triethylamine-->Phenyl vinyl sulfone-->Palladium hydroxide-->2-Methylindole-->Palladium (II) Acetate-->1-Pyrrolidinecarboxylic acid, 2-[(5-bromo-1H-indol-3-yl)carbonyl]-, phenyl ester, (2R)--->(R)-pyrrolidine-1,2-dicarboxylic acid 1-phenyl ester-->(R)-5-(2-phenylsulphonylethenyl)-3-(N-methylpyrrolidine-2-yl-methyl)-1H-indole hydrobromide-->Eletriptan Hydrobromide Monohydrate-->3-[((2R)-1-METHYLPYRROLIDIN-2-YL)METHYL]-5-[(E)-2-(PHENYLSULFONYL)VINYL]INDOLE-->(R)-N-Acetyl-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole-->(R)-1-acetyl-5-[2-(phenylsulfonyl)ethyenyl]-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole-->(R)-5-BROMO-3-[(1-METHYL-2-PYRROLIDINYL)METHYL]-1H-INDOLE-->Eletriptan-->(R)-5-Bromo-3-((1-methylpyrrolidin-2-yl)methyl)-1H-indole |
