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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-03-02 21:33:50 UTC
HMDB IDHMDB15302
Secondary Accession NumbersNone
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
Thumb
Synonyms
ValueSource
MoclobemidaChEBI
MoclobemidumChEBI
4-Chlor-N-(2-morpholinoethyl)benzamidHMDB
4-chloro-N-(2-(4-Morpholinyl)ethyl)benzamideHMDB
4-chloro-N-(2-Morpholin-4-yl-ethyl)-benzamideHMDB
MoclaimeHMDB
MoclamideHMDB
MoclamineHMDB
MoclobemidHMDB
P-chloro-N-(2-Morpholinoethyl)benzamideHMDB
1a Brand OF moclobemideMeSH
ArimaMeSH
AurorixMeSH
Chem mart moclobemideMeSH
DBL MoclobemideMeSH
Faulding brand OF moclobemideMeSH
GenRX moclobemideMeSH
Hoffmann-la roche brand OF moclobemideMeSH
Kendrick brand OF moclobemideMeSH
ManerixMeSH
Moclobemid purenMeSH
Moclobemide alpharma brandMeSH
Moclobemide BC brandMeSH
Moclobemide bull brandMeSH
Moclobemide hexal brandMeSH
Moclobemide stadapharm brandMeSH
Moclobemide CT-arzneimittel brandMeSH
Moclobemide ratiopharm brandMeSH
NovoMoclobemideMeSH
Nu moclobemideMeSH
NuMoclobemideMeSH
Betapharm brand OF moclobemideMeSH
Ratiopharm brand OF moclobemideMeSH
Alphapharm brand OF moclobemideMeSH
apo MoclobemideMeSH
apo-MoclobemideMeSH
Azupharma brand OF moclobemideMeSH
Bull brand OF moclobemideMeSH
FerakenMeSH
MoclobamideMeSH
Moclobemid ratiopharmMeSH
Moclobemid-1a pharmaMeSH
Moclobemide healthsense brandMeSH
Moclobemide kendrick brandMeSH
Moclobemide novopharm brandMeSH
Moclobemide temmler brandMeSH
Moclobemide, genrxMeSH
MocloduraMeSH
MoclonormMeSH
novo MoclobemideMeSH
novo-MoclobemideMeSH
Novopharm brand OF moclobemideMeSH
Nu-moclobemideMeSH
Nu-pharm brand OF moclobemideMeSH
PMS-MoclobemideMeSH
Stadapharm brand OF moclobemideMeSH
Terry white chemists brand OF moclobemideMeSH
CT-Arzneimittel brand OF moclobemideMeSH
Esparma brand OF moclobemideMeSH
AZU, moclobemidMeSH
BC Brand OF moclobemideMeSH
DeprenormMeSH
Healthsense moclobemideMeSH
Hexal brand OF moclobemideMeSH
Hoffmann la roche brand OF moclobemideMeSH
MoclixMeSH
Moclobemid 1a pharmaMeSH
Moclobemid azuMeSH
Moclobemid stadaMeSH
Moclobemid-purenMeSH
Moclobemid-ratiopharmMeSH
Moclobemid1a pharmaMeSH
Moclobemide 1a brandMeSH
Moclobemide azupharma brandMeSH
Moclobemide faulding brandMeSH
Moclobemide nu-pharm brandMeSH
Moclobemide betapharm brandMeSH
Moclobemide esparma brandMeSH
Moclobemide, chem martMeSH
Moclobemide, healthsenseMeSH
Pharmascience brand OF moclobemideMeSH
Stada, moclobemidMeSH
Temmler brand OF moclobemideMeSH
Terry white chemists moclobemideMeSH
CT Arzneimittel brand OF moclobemideMeSH
Alpharma brand OF moclobemideMeSH
Apotex brand OF moclobemideMeSH
AurorexMeSH
Chem mart brand OF moclobemideMeSH
Healthsense brand OF moclobemideMeSH
Merck dura brand OF moclobemideMeSH
Moclobemid von CTMeSH
Moclobemide alphapharm brandMeSH
Moclobemide apotex brandMeSH
Moclobemide pharmascience brandMeSH
Moclobemide roche brandMeSH
Moclobemide, DBLMeSH
MoclobetaMeSH
Nu pharm brand OF moclobemideMeSH
PMS MoclobemideMeSH
RimocMeSH
Roche brand OF moclobemideMeSH
Von CT, moclobemidMeSH
Chemical FormulaC13H17ClN2O2
Average Molecular Weight268.739
Monoisotopic Molecular Weight268.097855505
IUPAC Name4-chloro-N-[2-(morpholin-4-yl)ethyl]benzamide
Traditional Namearima
CAS Registry Number71320-77-9
SMILES
ClC1=CC=C(C=C1)C(=O)NCCN1CCOCC1
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
DescriptionThis compound belongs to the class of chemical entities known as 4-halobenzoic acids and derivatives. These are benzoic acids or derivatives carrying a halogen atom at the 4-position of the benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct Parent4-halobenzoic acids and derivatives
Alternative Parents
Substituents
  • 4-halobenzoic acid or derivatives
  • Benzamide
  • Benzoyl
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Morpholine
  • Oxazinane
  • Amino acid or derivatives
  • Carboxamide group
  • Secondary carboxylic acid amide
  • Tertiary amine
  • Tertiary aliphatic amine
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Azacycle
  • Hydrocarbon derivative
  • Organic nitrogen compound
  • Amine
  • Organic oxide
  • Organic oxygen compound
  • Organooxygen compound
  • Organopnictogen compound
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antidepressive Agents
  • Monoamine Oxidase Inhibitors
Application
  • Pharmaceutical
Cellular locations
  • Cytoplasm
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.12e+00 g/LNot Available
LogP1.5Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.12 mg/mLALOGPS
logP1.56ALOGPS
logP1.45ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)14.73ChemAxon
pKa (Strongest Basic)6.02ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area41.57 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.93 m3·mol-1ChemAxon
Polarizability28.28 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-3436435ae42cfbae36f0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0090000000-ebaa843d45c4c64c1d3dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00lr-0970000000-ab2fbe8b1feae9ff3141View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-e3243f45e1029a4c0e71View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-927950435244f3ac04e4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-6fe640038cbc911e2baeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-26e37ce9ba0b814b7409View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0090000000-07e0ca3dba489a2810ecView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00lr-0980000000-70103607e1e68c966be9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-ac7d3f04849dde0da3d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001r-0900000000-6634fb6b07312ce02ee6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-c43f4a856e6d225766efView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-1231bd387729155af4abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-a885de4ee2be84e3748dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-0950000000-2942178c074461702181View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0019-2900000000-bf1e7c693c96e9a69966View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-0udi-2900000000-c3230d46878446405991View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01171 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01171 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-4 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01171
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4087
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMoclobemide
NuGOwiki LinkHMDB15302
Metagene LinkHMDB15302
METLIN IDNot Available
PubChem Compound4235
PDB IDNot Available
ChEBI ID239099
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 ]