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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2020-02-26 21:41:21 UTC
HMDB IDHMDB0015302
Secondary Accession Numbers
  • HMDB15302
Metabolite Identification
Common NameMoclobemide
DescriptionMoclobemide is only found in individuals that have used or taken this drug. It is a reversible monoamine oxidase inhibitor (MAOI) selective for isoform A (RIMA) used to treat major depressive disorder.The mechanism of action of moclobemide involves the selective, reversible inhibition of MAO-A. This inhibition leads to a decrease in the metabolism and destruction of monoamines in the neurotransmitters. This results in an increase in the monoamines, relieving depressive symptoms.
Structure
Data?1582753281
SynonymsNot Available
Chemical FormulaC13H17ClN2O2
Average Molecular Weight268.739
Monoisotopic Molecular Weight268.097855505
IUPAC NameNot Available
Traditional NameNot Available
CAS Registry Number71320-77-9
SMILESNot Available
InChI Identifier
InChI=1S/C13H17ClN2O2/c14-12-3-1-11(2-4-12)13(17)15-5-6-16-7-9-18-10-8-16/h1-4H,5-10H2,(H,15,17)
InChI KeyYHXISWVBGDMDLQ-UHFFFAOYSA-N
Chemical Taxonomy
ClassificationNot classified
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.12 g/LNot Available
LogP1.5Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM162.530932474
Predicted Molecular PropertiesNot Available
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+158.44330932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MoclobemideClC1=CC=C(C=C1)C(=O)NCCN1CCOCC13025.8Standard polar33892256
MoclobemideClC1=CC=C(C=C1)C(=O)NCCN1CCOCC12217.0Standard non polar33892256
MoclobemideClC1=CC=C(C=C1)C(=O)NCCN1CCOCC12256.7Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Moclobemide,1TMS,isomer #1C[Si](C)(C)N(CCN1CCOCC1)C(=O)C1=CC=C(Cl)C=C12262.2Semi standard non polar33892256
Moclobemide,1TMS,isomer #1C[Si](C)(C)N(CCN1CCOCC1)C(=O)C1=CC=C(Cl)C=C12216.0Standard non polar33892256
Moclobemide,1TMS,isomer #1C[Si](C)(C)N(CCN1CCOCC1)C(=O)C1=CC=C(Cl)C=C13093.4Standard polar33892256
Moclobemide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCN1CCOCC1)C(=O)C1=CC=C(Cl)C=C12506.9Semi standard non polar33892256
Moclobemide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCN1CCOCC1)C(=O)C1=CC=C(Cl)C=C12427.0Standard non polar33892256
Moclobemide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)N(CCN1CCOCC1)C(=O)C1=CC=C(Cl)C=C13172.9Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Moclobemide GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fmr-7930000000-f5021f0bbc3af0c7125e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Moclobemide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-2900000000-c3230d468784464059912014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-3436435ae42cfbae36f02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-014i-0090000000-ebaa843d45c4c64c1d3d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-00lr-0970000000-ab2fbe8b1feae9ff31412017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-e3243f45e1029a4c0e712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-927950435244f3ac04e42017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-6fe640038cbc911e2bae2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-26e37ce9ba0b814b74092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-014i-0090000000-07e0ca3dba489a2810ec2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-00lr-0980000000-70103607e1e68c966be92017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-ac7d3f04849dde0da3d22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-001r-0900000000-6634fb6b07312ce02ee62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-c43f4a856e6d225766ef2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-000i-0900000000-1231bd387729155af4ab2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide LC-ESI-ITFT , positive-QTOFsplash10-001i-0900000000-a885de4ee2be84e3748d2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide , positive-QTOFsplash10-00lr-0950000000-2942178c0744617021812017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide , positive-QTOFsplash10-0019-2900000000-bf1e7c693c96e9a699662017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide 30V, Positive-QTOFsplash10-00lr-0980000000-8285f9b18fe84bc8a89e2021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide 75V, Positive-QTOFsplash10-000i-0900000000-c758091b215c9b205bf92021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Moclobemide 30V, Positive-QTOFsplash10-00lr-0970000000-774856bf69fc87f3c69d2021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moclobemide 10V, Positive-QTOFsplash10-014i-0590000000-abe04a26339f19caa3d52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moclobemide 20V, Positive-QTOFsplash10-01q9-0910000000-f57d5ee7c11ceba003002016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moclobemide 40V, Positive-QTOFsplash10-08g3-9700000000-e573e8a9813088fd720e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moclobemide 10V, Negative-QTOFsplash10-014i-0190000000-f48d994ed4df3ae5c60a2016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moclobemide 20V, Negative-QTOFsplash10-014i-3890000000-a3699392c661a9c95f772016-08-04Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Moclobemide 40V, Negative-QTOFsplash10-03dl-9800000000-aaddfd0cc344b9fa04462016-08-04Wishart 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 DB01171 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01171 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
External LinksNot 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. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
Molecular weight:
58762.475
References
  1. Fisar Z, Hroudova J, Raboch J: Inhibition of monoamine oxidase activity by antidepressants and mood stabilizers. Neuro Endocrinol Lett. 2010;31(5):645-56. [PubMed:21200377 ]
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Berlin I, Zimmer R, Thiede HM, Payan C, Hergueta T, Robin L, Puech AJ: Comparison of the monoamine oxidase inhibiting properties of two reversible and selective monoamine oxidase-A inhibitors moclobemide and toloxatone, and assessment of their effect on psychometric performance in healthy subjects. Br J Clin Pharmacol. 1990 Dec;30(6):805-16. [PubMed:1705137 ]
  3. Fulton B, Benfield P: Moclobemide. An update of its pharmacological properties and therapeutic use. Drugs. 1996 Sep;52(3):450-74. [PubMed:8875133 ]
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. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
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 ]
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. 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 ]
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 ]
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. 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 ]