Sumatriptan (CHEM002244)

Record Information
Version1.0
Creation Date2009-07-21 20:27:23 UTC
Update Date2026-05-14 16:45:35 UTC
Accession NumberCHEM002244
Identification
Common NameSumatriptan
ClassSmall Molecule
Description
Oftentimes, serotonin levels in the brain become extremely erratic before the onset of a migraine. In an attempt to stabilize this, sumatriptan is administered to help aid in leveling the serotonin levels in the brain. Sumatriptan is structurally similar to serotonin, and is a 5-HT (5-HT1D) agonist, which is one of the receptors that serotonin binds to. The specific receptor subtype it activates is present in the cranial and basilar arteries. Activation of these receptors causes vasoconstriction of those dilated arteries. Sumatriptan is also shown to decrease the activity of the trigeminal nerve. Sumatriptan is a triptan drug including a sulfonamide group structurally similar to serotonin, and is a 5-HT (5-HT1D) agonist, which is one of the receptors that serotonin binds to. Oftentimes, serotonin levels in the brain become extremely erratic before the onset of a migraine. In an attempt to stabilize this, sumatriptan is administered to help aid in leveling the serotonin levels in the brain. A serotonin agonist that acts selectively at 5HT1 receptors. It is used in the treatment of migraines. Sumatriptan (Imitrex, Imigran, Imigran Recovery) is a triptan drug including a sulfonamide group which was originally developed by Glaxo for the treatment of migraine headaches.
Contaminant Sources
  • FooDB Chemicals
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Drug
  • Food Toxin
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Selective Serotonin Agonist
  • Serotonin 5-HT1 Receptor Agonist
  • Serotonin Agonist
  • Serotonin Antagonist
  • Serotonin Receptor Agonist
  • Synthetic Compound
  • Vasoconstrictor Agent
Chemical Structure
MOLSDF3D SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulfonamideChEBI
1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulfonamideChEBI
3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulfonamideChEBI
3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulfonamideChEBI
ImigranChEBI
ImitrexChEBI
SumatranChEBI
SumatriptanumChEBI
SumaxChEBI
(3-[2-(Dimethylamino)ethyl]-1H-indol-5-yl)-N-methylmethanesulphonamideGenerator
1-[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]-N-methyl-methanesulphonamideGenerator
3-(2-(Dimethylamino)ethyl)-N-methyl-1H-indole-5-methanesulphonamideGenerator
3-[2-(Dimethylamino)ethyl]-N-methylindole-5-methanesulphonamideGenerator
Imigran recoveryHMDB
Glaxo wellcome brand OF sumatriptanHMDB
Sumatriptan GSK brandHMDB
GSK Brand OF sumatriptanHMDB
Sumatriptan succinateHMDB
Succinate, sumatriptanHMDB
Chemical FormulaC14H21N3O2S
Average Molecular Mass295.400 g/mol
Monoisotopic Mass295.135 g/mol
CAS Registry Number103628-46-2
IUPAC Name1-{3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}-N-methylmethanesulfonamide
Traditional Namesumatriptan
SMILESCNS(=O)(=O)CC1=CC2=C(NC=C2CCN(C)C)C=C1
InChI IdentifierInChI=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
InChI KeyKQKPFRSPSRPDEB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as tryptamines and derivatives. Tryptamines and derivatives are compounds containing the tryptamine backbone, which is structurally characterized by an indole ring substituted at the 3-position by an ethanamine.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassTryptamines and derivatives
Direct ParentTryptamines and derivatives
Alternative Parents
Substituents
  • Tryptamine
  • 3-alkylindole
  • Indole
  • Aralkylamine
  • Substituted pyrrole
  • Organic sulfonic acid amide
  • Benzenoid
  • Organosulfonic acid amide
  • Pyrrole
  • Organic sulfonic acid or derivatives
  • Heteroaromatic compound
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Organic nitrogen compound
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue Locations
  • Brain
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point169-171°C
Boiling PointNot Available
Solubility21.4 mg/ml
Predicted Properties
PropertyValueSource
Water Solubility0.13 g/LALOGPS
logP1.17ALOGPS
logP0.74ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)11.24ChemAxon
pKa (Strongest Basic)9.54ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area65.2 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.08 m³·mol⁻¹ChemAxon
Polarizability32.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Toxicity Profile
Route of ExposureSubcutaneous, Oral, Nasal, Transdermal
Mechanism of ToxicityThe 5-HT1B and 5-HT1D receptors function as autoreceptors, which inhibit the firing of serotonin neurons and a reduction in the synthesis and release of serotonin upon activation. After sumatriptan binds to these receptors, adenylate cyclase activity is inhibited via regulatory G proteins, incrases intracellular calcium, and affects other intracellular events. This results in vasoconstriction and inhibtion of sensory nociceptive (trigeminal) nerve firing and vasoactive neuropeptide release. Sumatriptan stimulates 5-HT receptors of the 1D subtype, most likely presynaptic receptors, resulting in selective vasoconstriction of inflamed and dilated cranial blood vessels in the carotid circulation. Sumatriptan also blocks the release of vasoactive neuropeptides from perivascular trigeminal axons in the dura mater during migraine and may inhibit the release of inflammatory mediators from the trigeminal nerve.
MetabolismHepatic. In vitro studies with human microsomes suggest that sumatriptan is metabolized by monoamine oxidase (MAO), predominantly the A isoenzyme. Route of 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. Half Life: 2.5 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of migraine attacks with or without aura.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsSymptoms of overdose include convulsions, tremor, paralysis, inactivity, ptosis, erythema of the extremities, abnormal respiration, cyanosis, ataxia, mydriasis, salivation, and lacrimation.
TreatmentNot Available
Concentrations
Not Available
External Links
DrugBank IDDB00669
HMDB IDHMDB0005037
FooDB IDFDB023604
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN ID2612
PDB IDNot Available
Wikipedia LinkSumatriptan
Chemspider ID5165
ChEBI ID10650
PubChem Compound ID5358
Kegg Compound IDC07319
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Rajeev Mathur, T. Kumar, Sunilendu Roy, Rajiv Malik, “Taste masked sumatriptan tablets and processes for their preparation.” U.S. Patent US20060233875, issued October 19, 2006.

MSDSLink
General References
1. Torner Montoya, Miguel. Process for the synthesis of 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide [sumatriptan]. Span. (1994), 6 pp. CODEN: SPXXAD ES 2059236 A1 19941101 CAN 122:265245 AN 1995:520544
2. Torner Montoya, Miguel. Process for the synthesis of 3-[2-(dimethylamino)ethyl]-N-methyl-1H-indole-5-methanesulfonamide [sumatriptan]. Span. (1994), 6 pp. CODEN: SPXXAD ES 2059236 A1 19941101 CAN 122:265245 AN 1995:520544
3. Pascual J, del Arco C, Romon T, del Olmo E, Castro E, Pazos A: Autoradiographic distribution of [3H]sumatriptan-binding sites in post-mortem human brain. Cephalalgia. 1996 Aug;16(5):317-22.
4. Castro ME, Pascual J, Romon T, del Arco C, del Olmo E, Pazos A: Differential distribution of [3H]sumatriptan binding sites (5-HT1B, 5-HT1D and 5-HT1F receptors) in human brain: focus on brainstem and spinal cord. Neuropharmacology. 1997 Apr-May;36(4-5):535-42.
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8. https://www.ncbi.nlm.nih.gov/pubmed/?term=12856385
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=12917936
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=15652399
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=16120224
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=16142613
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=17557349
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=18442019
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=19619527
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=19825906
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=22106962
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=22150557
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=22272067
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=22302025
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=22336849
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=22336867
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=22336868
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=22435741