1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide; butanedioic acid

• ChemBase ID: 72677
• Molecular Formular: C18H27N3O6S
• Molecular Mass: 413.48848
• Monoisotopic Mass: 413.1620566
• SMILES: c1(ccc2c(c1)c(c[nH]2)CCN(C)C)CS(=O)(=O)NC.OC(=O)CCC(=O)O
• Canonical SMILES: OC(=O)CCC(=O)O.CNS(=O)(=O)Cc1ccc2c(c1)c(CCN(C)C)c[nH]2
• InChI: InChI=1S/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)
• InChIKey: PORMUFZNYQJOEI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide; butanedioic acid
• IUPAC Traditional name: succinic acid; sumatriptan
• Synonyms: 3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide,butanedioate(1:1); 3-[2-(Dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide succinate; GR-43175; Sumatriptan succinate; Imigran; mitrex; Imitrex; Suminat; Sumitrex; Sumatriptan succinate

Database IDs

• CAS Number: 103628-48-4
• MDL Number: MFCD00902856
• PubChem SID: 162037598
• PubChem CID: 59772

CALCULATED PROPERTIES

• Acid pKa: 11.244988
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -2.4983597
• LogD (pH = 7.4): -1.2358891
• Log P: 0.7419289
• Molar Refractivity: 82.0842 cm^3
• Polarizability: 33.330933 Å^3
• Polar Surface Area: 65.2 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >20 mg/mL; Water
• Apperance: White Solid; white to off-white solid
• Melting Point: 165-166°C

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 41
• Safety Statements: 26-39
• GHS Pictograms: GHS05
• GHS Signal Word: Danger
• GHS Hazard statements: H318
• GHS Precautionary statements: P280-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Pharmacology Properties

• Target: 5-HT receptor

Product Information

• Purity: ≥98% (HPLC); 95+%
• Salt Data: Succinate
• Empirical Formula (Hill Notation): C14H21N3O2S · C4H6O4

DETAILS

Selleck Chemicals - S1432

Research Area: Neurological Disease
Biological Activity:
Sumatriptan succinate(mitrex, Imigran) is a triptan sulfa drug containing a sulfonamide group for the treatment of migraine headaches. Sumatriptan is structurally similar to serotonin (5HT), and is a 5-HT (types 5-HT1D and 5-HT1B) agonist. The specific receptor subtypes it activates are present on the cranial arteries and veins. Acting as an agonist at these receptors, Sumatriptan reduces the vascular inflammation associated with migraine. [1]

Sigma Aldrich - S1198

Biochem/physiol Actions
Sumatriptan succinate is a 5-HT1 serotonin receptor agonist.

Toronto Research Chemicals - S810000

A serotonin 5HT1-receptor agonist.

REFERENCES

• http://www.rxlist.com/imitrex-drug.htm
• Humphrey, P.P.A., et al.: Brit. J. Pharmacol., 94, 1123 (1988)
• Doenicke, A., et al.: Lancet 1, 1309 (1988)