Zolmitriptan (CHEM002167)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2009-07-21 20:26:34 UTC
Update Date2026-03-27 01:32:06 UTC
Accession NumberCHEM002167
Identification
Common NameZolmitriptan
ClassSmall Molecule
DescriptionZolmitriptan is only found in individuals that have used or taken this drug. It is a synthetic tryptamine derivative and appears as a white powder that is readily soluble in water. Zolmitriptan binds with high affinity to human 5-HT1B and 5-HT1D receptors leading to cranial blood vessel constriction. Current theories proposed to explain the etiology of migraine headache suggest that symptoms are due to local cranial vasodilatation and/or to the release of sensory neuropeptides (vasoactive intestinal peptide, substance P and calcitonin gene-related peptide) through nerve endings in the trigeminal system. The therapeutic activity of zolmitriptan for the treatment of migraine headache can most likely be attributed to the agonist effects at the 5HT1B/1D receptors on intracranial blood vessels (including the arterio-venous anastomoses) and sensory nerves of the trigeminal system which result in cranial vessel constriction and inhibition of pro-inflammatory neuropeptide release.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amine
  • Anti-Inflammatory Agent
  • Anti-Migraine Agent
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Organic Compound
  • Selective Serotonin Agonist
  • Serotonin 5-HT1 Receptor Agonist
  • Serotonin Agonist
  • Serotonin Antagonist
  • Serotonin Receptor Agonist
  • Synthetic Compound
  • Vasoconstrictor Agent
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
311c90ChEBI
4-[[3-(2-Dimethylaminoethyl)-1H-indol-5-yl]methyl]oxazolidin-2-oneChEBI
ZiptonChEBI
ZolmitriptanumChEBI
ZomigChEBI
ZomigoroChEBI
ZominatChEBI
ZMTHMDB
Ferrer brand OF zolmitriptanHMDB
AscoTopHMDB
Zeneca brand OF zolmitriptanHMDB
4-((3-(2-(Dimethylamino)ethyl)-1H-indol-5-yl)methyl)-2-oxazolidinoneHMDB
AstraZeneca brand OF zolmitriptanHMDB
FlezolHMDB
Astra brand OF zolmitriptanHMDB
Chemical FormulaC16H21N3O2
Average Molecular Mass287.357 g/mol
Monoisotopic Mass287.163 g/mol
CAS Registry Number139264-17-8
IUPAC Name(4S)-4-({3-[2-(dimethylamino)ethyl]-1H-indol-5-yl}methyl)-1,3-oxazolidin-2-one
Traditional Namezomig
SMILESCN(C)CCC1=CNC2=CC=C(C[C@H]3COC(=O)N3)C=C12
InChI IdentifierInChI=1S/C16H21N3O2/c1-19(2)6-5-12-9-17-15-4-3-11(8-14(12)15)7-13-10-21-16(20)18-13/h3-4,8-9,13,17H,5-7,10H2,1-2H3,(H,18,20)/t13-/m0/s1
InChI KeyULSDMUVEXKOYBU-ZDUSSCGKSA-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
  • Oxazolidinone
  • Substituted pyrrole
  • Benzenoid
  • Oxazolidine
  • Pyrrole
  • Heteroaromatic compound
  • Carbamic acid ester
  • Carbonic acid derivative
  • Tertiary amine
  • Tertiary aliphatic amine
  • Oxacycle
  • Azacycle
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility1.90e-01 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.19 g/LALOGPS
logP2.25ALOGPS
logP2.04ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)13ChemAxon
pKa (Strongest Basic)9.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.36 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity82.44 m³·mol⁻¹ChemAxon
Polarizability31.65 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9140000000-8d3d0029a006c9f3ba49Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-1390000000-5eb2470575d7a40b35ddSpectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-000i-0390000000-d91f1c70da42e9043a7bSpectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a5l-4970000000-d6feef1af8c3d273bbe4Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-000i-0090000000-c74574aba82b34fbcfc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0090000000-2eab59f442a95263f917Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000l-1290000000-4b3bf33424e3bd5259dcSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00du-2910000000-46170261887fb6bb2a86Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-2090000000-33a4ce8acdaace7f51cbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9060000000-dc863874d2aa1113bab8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-ee342e011f9a483f3bedSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2090000000-59447660b4ff1ee0d5a8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9170000000-ae1576ef07f3ffa1d131Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9320000000-d3b22cc0b99199c251b7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-85a896e022373a149d53Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-000l-0090000000-78d6b93aa92bfd05a777Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-5970000000-3b90408e256cd6d8ae19Spectrum
Toxicity Profile
Route of ExposureTopical(nasal); Oral. Mean absolute oral bioavailability is approximately 40%. Food has no affect on the rate and extent of absorption.
Mechanism of ToxicityZolmitriptan binds with high affinity to human 5-HT1B and 5-HT1D receptors leading to cranial blood vessel constriction. Current theories proposed to explain the etiology of migraine headache suggest that symptoms are due to local cranial vasodilatation and/or to the release of sensory neuropeptides (vasoactive intestinal peptide, substance P and calcitonin gene-related peptide) through nerve endings in the trigeminal system. The therapeutic activity of zolmitriptan for the treatment of migraine headache can most likely be attributed to the agonist effects at the 5HT1B/1D receptors on intracranial blood vessels (including the arterio-venous anastomoses) and sensory nerves of the trigeminal system which result in cranial vessel constriction and inhibition of pro-inflammatory neuropeptide release.
MetabolismHepatic. There have been three metabolites identified: indole acetic acid, N -oxide, and N-desmethyl metabolites. However, the N-desmethyl is the only active metabolite. Half Life: The mean elimination half-life of zolmitriptan and of the active N-desmethyl metabolite is 3 hours.
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed in the acute treatment of migraine attacks with or without aura and cluster headaches.
Minimum Risk LevelNot Available
Health EffectsSerious cardiac events, including myocardial infarction migth occur. [Wikipedia]
SymptomsNot Available
TreatmentThere is no specific antidote to zolmitriptan. In cases of severe intoxication, intensive care procedures are recommended, including establishing and maintaining a patent airway, ensuring adequate oxygenation and ventilation, and monitoring and support of the cardiovascular system. (4)
Concentrations
Not Available
DrugBank IDDB00315
HMDB IDHMDB0014460
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkZolmitriptan
Chemspider ID54844
ChEBI ID10124
PubChem Compound ID60857
Kegg Compound IDC07218
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Islam Aminul, Bhar Chandan, Katam Sahadev, “Process for preparing optically pure zolmitriptan.” U.S. Patent US20050245585, issued November 03, 2005.

MSDSNot Available
General References
1. Martin GR: Pre-clinical pharmacology of zolmitriptan (Zomig; formerly 311C90), a centrally and peripherally acting 5HT1B/1D agonist for migraine. Cephalalgia. 1997 Oct;17 Suppl 18:4-14.
2. Pascual J: [Mechanism of action of zolmitriptan]. Neurologia. 1998 Oct;13 Suppl 2:9-15.