103628-48-4

Basic information

• Product Name: Sumatriptan succinate
• Synonyms: 3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide, Succinate, Imigran, Imitrex,;Butanedioic acid, compd. with 3-2-(dimethylamino)ethyl-N-methyl-1H-indole-5-methanesulfonamide (1:1);SUMATRIPTANSUCCINATE(1:1);1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamide succinate;Sumatriptan succinate;SuMatriptan Succinate, EP;Sumatriptan Succinate (200 mg);SuMitrex
• CAS NO: 103628-48-4
• Molecular Formula: C₄H₆O₄*C₁₄H₂₁N₃O₂S
• Molecular Weight: 413.48848
• EINECS: 1308068-626-2
• Product Categories: Indoles and derivatives;Inhibitors;Intermediates & Fine Chemicals;Pharmaceuticals;Sumatriptan;Serotonin receptor;OPTIMINE
• Mol File: 103628-48-4.mol

Chemical Properties

• Melting Point: 165-166°C
• Boiling Point: 497.7 °C at 760 mmHg
• Flash Point: 254.8 °C
• Appearance: white to off-white/
• Density: 1.243 g/cm³
• Vapor Pressure: 1.24E-17mmHg at 25°C
• Storage Temp.: Store at +4°C
• Solubility: H2O: >20mg/mL
• Merck: 14,8997
• CAS DataBase Reference: Sumatriptan succinate(CAS DataBase Reference)
• NIST Chemistry Reference: Sumatriptan succinate(103628-48-4)
• EPA Substance Registry System: Sumatriptan succinate(103628-48-4)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37/38-41
• Safety Statements: 26-36-39
• RIDADR: 3077
• WGK Germany: 3
• RTECS: EJ9940000
• Hazardous Substances Data: 103628-48-4(Hazardous Substances Data)

Usage

References

https://en.wikipedia.org/wiki/Sumatriptan http://www.medicinenet.com/sumatriptan_succinate-injection/article.htm http://bodyandhealth.canada.com/drug/getdrug/teva-sumatriptan-df http://www.webmd.com/drugs/2/drug-7741/sumatriptan-oral/details

Originator

Glaxo (United Kingdom)

World Health Organization (WHO)

Suprofen, a nonsteroidal anti-inflammatory agent, was introduced in 1983 for use as an analgesic for the symptomatic relief of mild to moderate pain and for primary dysmenorrhoea. By 1986 it had become evident that its use was occasionally associated with flank pain sometimes accompanied by evidence of decreased renal function. The Arthritis Advisory Committee of the United States Food and Drug Administration met in December 1986 to review the situation and decided against withdrawing suprofen from the market. However, in May 1987 the Committee for Proprietary Medicinal Products of the European Community recommended that all marketing authorizations should be suspended. The manufacturer subsequently decided to suspend sale worldwide on the grounds that sales had diminished to the point where the product was no longer economically viable.

Biological Activity

Selective 5-HT 1 receptor agonist (K i values are 17, 27 and 100 nM at 5-HT 1D , 5-HT 1B and 5-HT 1A receptors respectively). Antimigraine agent.

Biochem/physiol Actions

Sumatriptan succinate is a 5-HT1 serotonin receptor agonist.

InChI:InChI=1/C14H21N3O2S.C4H6O4/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3;5-3(6)1-2-4(7)8/h4-5,8-9,15-16H,6-7,10H2,1-3H3;1-2H2,(H,5,6)(H,7,8)/p-2

Synthetic route

sumatripan (103628-46-2) → sumatriptan succinate (103628-48-4)

Conditions	Yield
With succinic acid In acetone at 25 - 35℃; for 1 - 2h; Heating / reflux;
With succinic acid In dichloromethane at 25 - 35℃; for 1 - 1.5h; Heating / reflux;
With succinic acid In ethyl acetate at 25 - 35℃; for 1 - 2h; Heating / reflux;

succinic acid (110-15-6) + sumatripan (103628-46-2) → sumatriptan succinate (103628-48-4)

Conditions	Yield
Stage #1: succinic acid; sumatripan In water; acetonitrile for 0.25 - 0.5h; Heating / reflux; Stage #2: In cyclohexane at 25 - 35℃; for 1 - 2h;
In acetone for 2h; Purification / work up; Heating / reflux;
In dichloromethane for 4h; Purification / work up; Heating / reflux;

sumatriptan succinate (103628-48-4) → sumatripan (103628-46-2)

Conditions	Yield
With sodium hydrogencarbonate In water

Upstream product

• 110-15-6 succinic acid 
• 103628-46-2 sumatripan 

Downstream Products

• 103628-46-2 sumatripan 

Relevant articles and documents

Isotope-Edited Infrared Spectroscopy for Efficient Discrimination between Pharmaceutical Salts and Cocrystals

Isotope-edited infrared spectroscopy using carboxylic acids selectively labeled with 13C is proposed herein for the efficient discrimination of pharmaceutical salts and cocrystals, whereby proton-transfer probe vibrations are highlighted by isotope shifts. This new technique can accurately discriminate even a confusing salt from a cocrystal for the traditional method, highlighting the diagnostic peaks. In addition, the established technique also provided the OH in-plane bending vibrations corresponding to intermolecular hydrogen bonding at the carbonyl oxygens of the cocrystals. The technique will accelerate the discrimination, which is a critical process in cocrystal development.

PROCESS FOR PREPARING 3-(2-(DIMETHYLAMINO)ETHYL)-N- METHYL-1H-INDOLE-5-METHANESULFONAMIDE AND PRODUCT THEREOF

The present invention relates to an improved process for the preparation of 3-(2- (dimethylamino) ethyl)-N-methyl- 1 H-indole-5-methanesulfonamide (sumatriptan) acid addition salt and the base having enhanced yield and purity. Further the present invention also provides a novel crystalline sumatriptan base.

SUMATRIPTAN CRYSTALLINE FORMS, PHARMACEUTICAL COMPOSITIONS AND METHODS

The invention provides novel soluble sumatriptan crystalline forms that include polymorphs, salts, co-crystals and related solvates useful as pharmaceuticals. The invention also provides pharmaceutical compositions comprising, and processes for making, these sumatriptan crystalline forms. Methods of using such compositions for the treatment or prevention of migraine headaches and related neurological disorders are also provided.

Amorphous form of 3-[2-(dimethylamino) ethyl]-N-methyl-1H-indole-5-methane sulfonamide succinate (sumatriptan succinate)

The present invention relates to an amorphous form of Sumatriptan succinate of Formula (1). The present invention also relates to process for the preparation of an amorphous form of Sumatriptan succinate. The process for the preparation of an amorphous form of Sumatriptan succinate comprises refluxing an aqueous mixture of Sumatriptan or its succinate salt in alcoholic solvents such as methanol or nitrile solvents such as acetonitrile followed by evaporation of the solvent from the filtrate. The resulting residue is triturated with water immiscible aromatic or aliphatic hydrocarbon solvents such as cyclohexane to afford an amorphous form of Sumatriptan succinate.

NOVEL CRYSTALLINE FORMS OF SUMATRIPTAN SUCCINATE

The present invention relates to novel crystalline forms of sumatriptan succinate, to processes for their preparation and to pharmaceutical compositions containing them.

A NOVEL PROCESS FOR PREPARATION OF INDOLE DERIVATIVES

A novel process of preparation of a compound of 3-(2-Dimethylamino)-N-methyl-lH-indole-5-methane sulfonamide, which comprises of a reaction 4-hydrazino-N-methyl benzene methane sulfonamide with 4-dimethyl amino butyraldehyde diethyl acetal in a chlorinated solvent in the presence of ethyl poly phosphate and conversion of the crude product to a product of 3-(2-Dimethylamino)-N-methyl-lH-indole-5-methane sulfonamide succinate of extra high purity and colour.

3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide and the Succinate Thereof

A process for the preparation of highly pure Sumatriptan is described. A process for the preparation of novel crystalline Form I and crystalline Form II of Sumatriptan succinate is described. Sumatriptan is used for alleviating the pain of migraine headaches.