Almotriptan (CHEM002302)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (2)XML
Record Information
Version1.0
Creation Date2009-07-21 20:27:58 UTC
Update Date2016-11-09 01:08:44 UTC
Accession NumberCHEM002302
Identification
Common NameAlmotriptan
ClassSmall Molecule
DescriptionAlmotriptan is a triptan drug for the treatment of migraine headaches. Almotriptan is in a class of medications called selective serotonin receptor agonists. It works by narrowing blood vessels in the brain, stopping pain signals from being sent to the brain, and stopping the release of certain natural substances that cause pain, nausea, and other symptoms of migraine. Almotriptan does not prevent migraine attacks.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
  • ToxCast & Tox21 Chemicals
Contaminant Type
  • Amide
  • Amine
  • Anti-Inflammatory Agent
  • Anti-Migraine Agent
  • Drug
  • Metabolite
  • Organic Compound
  • Selective Serotonin Agonist
  • Serotonin Agonist
  • Serotonin Antagonist
  • Serotonin Receptor Agonist
  • Synthetic Compound
  • Vasoconstrictor Agent
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
1-(((3-(2-(Dimethylamino)ethyl)indol-5-yl)methyl)sulfonyl)pyrrolidineChEBI
1-(((3-(2-(Dimethylamino)ethyl)indol-5-yl)methyl)sulphonyl)pyrrolidineGenerator
AlmogranHMDB
Almotriptan malateHMDB
AxertHMDB
Chemical FormulaC17H25N3O2S
Average Molecular Mass335.464 g/mol
Monoisotopic Mass335.167 g/mol
CAS Registry Number181183-52-8
IUPAC Namedimethyl(2-{5-[(pyrrolidine-1-sulfonyl)methyl]-1H-indol-3-yl}ethyl)amine
Traditional Namealmotriptan
SMILESCN(C)CCC1=CNC2=C1C=C(CS(=O)(=O)N1CCCC1)C=C2
InChI IdentifierInChI=1S/C17H25N3O2S/c1-19(2)10-7-15-12-18-17-6-5-14(11-16(15)17)13-23(21,22)20-8-3-4-9-20/h5-6,11-12,18H,3-4,7-10,13H2,1-2H3
InChI KeyWKEMJKQOLOHJLZ-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
  • Pyrrolidine
  • Organic sulfonic acid or derivatives
  • Heteroaromatic compound
  • Organosulfonic acid or derivatives
  • 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
  • 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
Solubility1.21e-01 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP2.04ALOGPS
logP1.52ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)17.14ChemAxon
pKa (Strongest Basic)9.55ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area56.41 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity94.52 m³·mol⁻¹ChemAxon
Polarizability37.01 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-9120000000-8636aefe6f44933ba51bSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-2169000000-911884b25f81ab3a7184Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-8691000000-449e57d16a963ed1b74eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9510000000-6004be92a59ee97c688dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-1926000000-1904ba0b8d011df20b74Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-3931000000-ce8a83db474ffb7c1720Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-9210000000-cd68178eac1c4d05f3f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0019000000-946584fd7a8aeaa09963Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-1695000000-9e83c6cf357b6d2f2b99Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ab9-9410000000-4ebc2e87bfec77e89c93Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0903000000-b62a8e072289815a1db0Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-2529000000-c131caf01f261a061edeSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-3792000000-25e1db8e7ba47860dbf0Spectrum
Toxicity Profile
Route of ExposureOral
Mechanism of ToxicityAlmotriptan binds with high affinity to human 5-HT1B and 5-HT1D receptors leading to cranial blood vessel constriction.
MetabolismHepatic. Route of Elimination: Almotriptan is eliminated primarily by renal excretion (about 75% of the oral dose), with approximately 40% of an administered dose excreted unchanged in urine. Approximately 13% of the administered dose is excreted via feces, both unchanged and metabolized. Half Life: 3-4 hours
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesAlmotriptan is indicated for the acute treatment of migraine with or without aura in adults. [Wikipedia]
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNausea, drowsiness, dizziness, diarrhea, headache, sweating, or dry mouth may occur.
TreatmentGastrointestinal decontamination (i.e., gastric lavage followed by activated charcoal) should be considered in patients suspected of an overdose with Almotriptan. Clinical and electrocardiographic monitoring should be continued for at least 20 hours, even if clinical symptoms are not observed. (2)
Concentrations
Not Available
DrugBank IDDB00918
HMDB IDHMDB0015054
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkAlmotriptan
Chemspider ID110198
ChEBI ID520985
PubChem Compound ID123606
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Ramasubramanian Sridharan, Vandanapu Purushotham, Kori Algooram, Nitin Pradhan, “Crystalline forms of almotriptan and processes for their preparation.” U.S. Patent US20070112055, issued May 17, 2007.

MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=17870541