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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:40:52 UTC
HMDB IDHMDB0015054
Secondary Accession Numbers
  • HMDB15054
Metabolite Identification
Common NameAlmotriptan
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.
Structure
Data?1582753252
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 Weight335.464
Monoisotopic Molecular Weight335.166747749
IUPAC Namedimethyl(2-{5-[(pyrrolidine-1-sulfonyl)methyl]-1H-indol-3-yl}ethyl)amine
Traditional Namealmotriptan
CAS Registry Number181183-52-8
SMILES
CN(C)CCC1=CNC2=C1C=C(CS(=O)(=O)N1CCCC1)C=C2
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.12 g/LNot Available
LogP1.6Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM175.830932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.12 g/LALOGPS
logP10(2.04) g/LALOGPS
logP10(1.52) g/LChemAxon
logS10(-3.4) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+178.36431661259
DarkChem[M-H]-177.2731661259

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
AlmotriptanCN(C)CCC1=CNC2=C1C=C(CS(=O)(=O)N1CCCC1)C=C24613.7Standard polar33892256
AlmotriptanCN(C)CCC1=CNC2=C1C=C(CS(=O)(=O)N1CCCC1)C=C23041.8Standard non polar33892256
AlmotriptanCN(C)CCC1=CNC2=C1C=C(CS(=O)(=O)N1CCCC1)C=C23047.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Almotriptan,1TMS,isomer #1CN(C)CCC1=CN([Si](C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C122939.2Semi standard non polar33892256
Almotriptan,1TMS,isomer #1CN(C)CCC1=CN([Si](C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C122923.9Standard non polar33892256
Almotriptan,1TMS,isomer #1CN(C)CCC1=CN([Si](C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C124011.5Standard polar33892256
Almotriptan,1TBDMS,isomer #1CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C123136.4Semi standard non polar33892256
Almotriptan,1TBDMS,isomer #1CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C123209.6Standard non polar33892256
Almotriptan,1TBDMS,isomer #1CN(C)CCC1=CN([Si](C)(C)C(C)(C)C)C2=CC=C(CS(=O)(=O)N3CCCC3)C=C124021.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Almotriptan GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9120000000-8636aefe6f44933ba51b2017-11-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Almotriptan GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almotriptan 10V, Positive-QTOFsplash10-000i-2169000000-911884b25f81ab3a71842016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almotriptan 20V, Positive-QTOFsplash10-00di-8691000000-449e57d16a963ed1b74e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almotriptan 40V, Positive-QTOFsplash10-00dl-9510000000-6004be92a59ee97c688d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almotriptan 10V, Negative-QTOFsplash10-001i-1926000000-1904ba0b8d011df20b742016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almotriptan 20V, Negative-QTOFsplash10-001i-3931000000-ce8a83db474ffb7c17202016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almotriptan 40V, Negative-QTOFsplash10-03di-9210000000-cd68178eac1c4d05f3f42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almotriptan 10V, Positive-QTOFsplash10-000i-0019000000-946584fd7a8aeaa099632021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almotriptan 20V, Positive-QTOFsplash10-0006-1695000000-9e83c6cf357b6d2f2b992021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almotriptan 40V, Positive-QTOFsplash10-0ab9-9410000000-4ebc2e87bfec77e89c932021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almotriptan 10V, Negative-QTOFsplash10-001i-0903000000-b62a8e072289815a1db02021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almotriptan 20V, Negative-QTOFsplash10-001i-2529000000-c131caf01f261a061ede2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Almotriptan 40V, Negative-QTOFsplash10-03di-3792000000-25e1db8e7ba47860dbf02021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00918 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00918 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00918
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID110198
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkAlmotriptan
METLIN IDNot Available
PubChem Compound123606
PDB IDNot Available
ChEBI ID520985
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
Molecular weight:
59681.27
References
  1. McEnroe JD, Fleishaker JC: Clinical pharmacokinetics of almotriptan, a serotonin 5-HT(1B/1D) receptor agonist for the treatment of migraine. Clin Pharmacokinet. 2005;44(3):237-46. [PubMed:15762767 ]
  2. Gras J, Llenas J, Jansat JM, Jauregui J, Cabarrocas X, Palacios JM: Almotriptan, a new anti-migraine agent: a review. CNS Drug Rev. 2002 Fall;8(3):217-34. [PubMed:12353056 ]
  3. Salva M, Jansat JM, Martinez-Tobed A, Palacios JM: Identification of the human liver enzymes involved in the metabolism of the antimigraine agent almotriptan. Drug Metab Dispos. 2003 Apr;31(4):404-11. [PubMed:12642466 ]
General function:
Involved in flavin-containing monooxygenase activity
Specific function:
Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an important role in the metabolism of trimethylamine (TMA), via the production of TMA N-oxide (TMAO). Is also able to perform S-oxidation when acting on sulfide compounds.
Gene Name:
FMO3
Uniprot ID:
P31513
Molecular weight:
60032.975
References
  1. Salva M, Jansat JM, Martinez-Tobed A, Palacios JM: Identification of the human liver enzymes involved in the metabolism of the antimigraine agent almotriptan. Drug Metab Dispos. 2003 Apr;31(4):404-11. [PubMed:12642466 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. Salva M, Jansat JM, Martinez-Tobed A, Palacios JM: Identification of the human liver enzymes involved in the metabolism of the antimigraine agent almotriptan. Drug Metab Dispos. 2003 Apr;31(4):404-11. [PubMed:12642466 ]
  3. McEnroe JD, Fleishaker JC: Clinical pharmacokinetics of almotriptan, a serotonin 5-HT(1B/1D) receptor agonist for the treatment of migraine. Clin Pharmacokinet. 2005;44(3):237-46. [PubMed:15762767 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular weight:
55944.565
References
  1. Salva M, Jansat JM, Martinez-Tobed A, Palacios JM: Identification of the human liver enzymes involved in the metabolism of the antimigraine agent almotriptan. Drug Metab Dispos. 2003 Apr;31(4):404-11. [PubMed:12642466 ]
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
References
  1. Salva M, Jansat JM, Martinez-Tobed A, Palacios JM: Identification of the human liver enzymes involved in the metabolism of the antimigraine agent almotriptan. Drug Metab Dispos. 2003 Apr;31(4):404-11. [PubMed:12642466 ]
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
  2. McEnroe JD, Fleishaker JC: Clinical pharmacokinetics of almotriptan, a serotonin 5-HT(1B/1D) receptor agonist for the treatment of migraine. Clin Pharmacokinet. 2005;44(3):237-46. [PubMed:15762767 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. Salva M, Jansat JM, Martinez-Tobed A, Palacios JM: Identification of the human liver enzymes involved in the metabolism of the antimigraine agent almotriptan. Drug Metab Dispos. 2003 Apr;31(4):404-11. [PubMed:12642466 ]
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme responsible for the metabolism the anti-cancer drug paclitaxel (taxol).
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular weight:
55824.275
References
  1. Salva M, Jansat JM, Martinez-Tobed A, Palacios JM: Identification of the human liver enzymes involved in the metabolism of the antimigraine agent almotriptan. Drug Metab Dispos. 2003 Apr;31(4):404-11. [PubMed:12642466 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1B
Uniprot ID:
P28222
Molecular weight:
43567.5
References
  1. Napier C, Stewart M, Melrose H, Hopkins B, McHarg A, Wallis R: Characterisation of the 5-HT receptor binding profile of eletriptan and kinetics of [3H]eletriptan binding at human 5-HT1B and 5-HT1D receptors. Eur J Pharmacol. 1999 Mar 5;368(2-3):259-68. [PubMed:10193663 ]
  2. Fleishaker JC, Sisson TA, Carel BJ, Azie NE: Pharmacokinetic interaction between verapamil and almotriptan in healthy volunteers. Clin Pharmacol Ther. 2000 May;67(5):498-503. [PubMed:10824628 ]
  3. van den Broek RW, MaassenVanDenBrink A, de Vries R, Bogers AJ, Stegmann AP, Avezaat CJ, Saxena PR: Pharmacological analysis of contractile effects of eletriptan and sumatriptan on human isolated blood vessels. Eur J Pharmacol. 2000 Oct 27;407(1-2):165-73. [PubMed:11050304 ]
  4. Knyihar-Csillik E, Tajti J, Csillik AE, Chadaide Z, Mihaly A, Vecsei L: Effects of eletriptan on the peptidergic innervation of the cerebral dura mater and trigeminal ganglion, and on the expression of c-fos and c-jun in the trigeminal complex of the rat in an experimental migraine model. Eur J Neurosci. 2000 Nov;12(11):3991-4002. [PubMed:11069595 ]
  5. Bou J, Domenech T, Puig J, Heredia A, Gras J, Fernandez-Forner D, Beleta J, Palacios JM: Pharmacological characterization of almotriptan: an indolic 5-HT receptor agonist for the treatment of migraine. Eur J Pharmacol. 2000 Dec 20;410(1):33-41. [PubMed:11134654 ]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This is one of the several different receptors for 5- hydroxytryptamine (serotonin), a biogenic hormone that functions as a neurotransmitter, a hormone, and a mitogen. The activity of this receptor is mediated by G proteins that inhibit adenylate cyclase activity
Gene Name:
HTR1D
Uniprot ID:
P28221
Molecular weight:
41906.4
References
  1. Napier C, Stewart M, Melrose H, Hopkins B, McHarg A, Wallis R: Characterisation of the 5-HT receptor binding profile of eletriptan and kinetics of [3H]eletriptan binding at human 5-HT1B and 5-HT1D receptors. Eur J Pharmacol. 1999 Mar 5;368(2-3):259-68. [PubMed:10193663 ]
  2. Bou J, Domenech T, Puig J, Heredia A, Gras J, Fernandez-Forner D, Beleta J, Palacios JM: Pharmacological characterization of almotriptan: an indolic 5-HT receptor agonist for the treatment of migraine. Eur J Pharmacol. 2000 Dec 20;410(1):33-41. [PubMed:11134654 ]
  3. Gras J, Llupia J, Llenas J, Palacios JM: Safety profile of almotriptan, a new antimigraine agent. Effects on central nervous system, renal function and respiratory dynamics. Arzneimittelforschung. 2001 Sep;51(9):726-32. [PubMed:11642004 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]