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103628-46-2 molecular structure
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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 and InChIs

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

Cite this record

CBID:551 http://www.chembase.cn/molecule-551.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
103628-46-2
103628-48-4
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

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
A&J Pharmtech
AJA-O40223 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 11.244988  H Acceptors
H Donor LogD (pH = 5.5) -2.4983597 
LogD (pH = 7.4) -1.2358891  Log P 0.7419289 
Molar Refractivity 82.0842 cm3 Polarizability 33.330933 Å3
Polar Surface Area 65.2 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P 1.17  LOG S -3.37 
Solubility (Water) 1.27e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
21.4 mg/ml expand Show data source
Hydrophobicity(logP)
0.8 expand Show data source
Admin Routes
tablet, subcutaneous injection, nasal spray expand Show data source
Bioavailability
15% (oral)/ 96% (s.c) expand Show data source
Excretion
60% urine; 40% feces expand Show data source
Half Life
2.5 hours expand Show data source
Metabolism
MAO expand Show data source
Protein Bound
14%-21% expand Show data source
Legal Status
Rx-only (US) expand Show data source
Pregnancy Category
C expand Show data source
US Licence
Sumatriptan expand Show data source
Purity
98% expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB00669 external link
Item Information
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-HT1D and 5-HT1B 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

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • 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
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PATENTS

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