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

• ChemBase ID: 551
• Molecular Formular: C14H21N3O2S
• Molecular Mass: 295.40044
• Monoisotopic Mass: 295.13544793
• SMILES: S(=O)(=O)(NC)Cc1cc2c(CCN(C)C)c[nH]c2cc1
• Canonical SMILES: CNS(=O)(=O)Cc1ccc2c(c1)c(CCN(C)C)c[nH]2
• InChI: InChI=1S/C14H21N3O2S/c1-15-20(18,19)10-11-4-5-14-13(8-11)12(9-16-14)6-7-17(2)3/h4-5,8-9,15-16H,6-7,10H2,1-3H3
• InChIKey: KQKPFRSPSRPDEB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide
• IUPAC Traditional name: sumatriptan
• Brand Name: Imigran; Sumatran; Sumax; Imitrex; Imitrex Oral; Imitrex, Imigran ,Treximet
• Synonyms: Sumatriptan Succinate; Sumatriptanum [INN-Latin]; NP101; sumatriptan; triptan; Sumatriptan; SUMATRIPTAN SUCCINATE

Database IDs

• CAS Number: 103628-48-4; 103628-46-2
• PubChem SID: 160964014; 46506520
• PubChem CID: 5358
• CHEBI ID: 10650
• ATC CODE: N02CC01
• CHEMBL: 128
• Chemspider ID: 5165
• DrugBank ID: DB00669
• IUPHAR ligand ID: 54
• KEGG ID: D00451
• Unique Ingredient Identifier: 8R78F6L9VO
• Wikipedia Title: Sumatriptan

CALCULATED PROPERTIES

JChem

• 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: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.17
• LOG S: -3.37
• Solubility (Water): 1.27e-01 g/l

PROPERTIES

Physical Property

• Solubility: 21.4 mg/ml
• Hydrophobicity(logP): 0.8

Pharmacology Properties

• Admin Routes: tablet, subcutaneous injection, nasal spray
• Bioavailability: 15% (oral)/ 96% (s.c)
• Excretion: 60% urine; 40% feces
• Half Life: 2.5 hours
• Metabolism: MAO
• Protein Bound: 14%-21%
• Legal Status: Rx-only (US)
• Pregnancy Category: C
• US Licence: Sumatriptan

Product Information

• Purity: 98%

DETAILS

DrugBank - DB00669

• Drug Groups: approved; investigational
• Description: A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of migraine disorders. A transdermal patch version of sumatriptan is currently in phase I trials in the U.S. under the code name NP101 (NuPathe).
• Indication: For the treatment of migraine attacks with or without aura.
• Pharmacology: Sumatriptan, an antimigraine drug, is a selective agonist of vascular serotonin ((5-hydroxytryptamine; 5-HT) type 1-like receptors, likely the 5-HT_1D and 5-HT_1B subtypes. It has no significant affinity (as measured using standard radioligand binding assays) or pharmacological activity at 5-HT2, 5-HT3 receptor subtypes or at alpha1-, alpha2-, or beta-adrenergic; dopamine1; dopamine2; muscarinic; or benzodiazepine receptors.
• Toxicity: Symptoms of overdose include convulsions, tremor, paralysis, inactivity, ptosis, erythema of the extremities, abnormal respiration, cyanosis, ataxia, mydriasis, salivation, and lacrimation.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. In vitro studies with human microsomes suggest that sumatriptan is metabolized by monoamine oxidase (MAO), predominantly the A isoenzyme.
• Absorption: Approximately 15%
• Half Life: 2.5 hours
• Protein Binding: 14%-21%
• Elimination: Only 3% of the dose is excreted in the urine as unchanged sumatriptan; 42% of the dose is excreted as the major metabolite, the indole acetic acid analogue of sumatriptan.
• Distribution: * 2.7 L/kg [subcutaneous dosing]
• Clearance: * 1200 mL/min [Following a 6-mg SC injection]
• References: Nikai T, Basbaum AI, Ahn AH: Profound reduction of somatic and visceral pain in mice by intrathecal administration of the anti-migraine drug, sumatriptan. Pain. 2008 Oct 31;139(3):533-40. Epub 2008 Aug 23. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• Nikai T, Basbaum AI, Ahn AH: Profound reduction of somatic and visceral pain in mice by intrathecal administration of the anti-migraine drug, sumatriptan. Pain. 2008 Oct 31;139(3):533-40. Epub 2008 Aug 23. Pubmed