Moclobemide (T3D3004)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-07-21 20:28:31 UTC
Update Date2014-12-24 20:25:55 UTC
Accession NumberT3D3004
Identification
Common NameMoclobemide
ClassSmall Molecule
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.
Compound Type
  • Amide
  • Amine
  • Antidepressant
  • Antidepressive Agent
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Monoamine Oxidase Inhibitor
  • Organic Compound
  • Organochloride
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
4-Chlor-N-(2-morpholinoethyl)benzamid
4-Chloro-N-(2-(4-morpholinyl)ethyl)benzamide
4-Chloro-N-(2-morpholin-4-yl-ethyl)-benzamide
Aurorix
Manerix
Moclaime
Moclamide
Moclamine
Moclobemid
Moclobemida
Moclobemidum
p-Chloro-N-(2-morpholinoethyl)benzamide
Chemical FormulaC13H17ClN2O2
Average Molecular Mass268.739 g/mol
Monoisotopic Mass268.098 g/mol
CAS Registry Number71320-77-9
IUPAC Name4-chloro-N-[2-(morpholin-4-yl)ethyl]benzamide
Traditional Namearima
SMILESClC1=CC=C(C=C1)C(=O)NCCN1CCOCC1
InChI IdentifierInChI=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 KeyInChIKey=YHXISWVBGDMDLQ-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and 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
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
Solubility1.12e+00 g/L
LogP1.5
Predicted Properties
PropertyValueSource
Water Solubility1.12 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity71.93 m³·mol⁻¹ChemAxon
Polarizability28.28 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0fmr-7930000000-f5021f0bbc3af0c7125e2017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-3436435ae42cfbae36f02017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0090000000-ebaa843d45c4c64c1d3d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00lr-0970000000-ab2fbe8b1feae9ff31412017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-e3243f45e1029a4c0e712017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-927950435244f3ac04e42017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-6fe640038cbc911e2bae2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-26e37ce9ba0b814b74092017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-014i-0090000000-07e0ca3dba489a2810ec2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-00lr-0980000000-70103607e1e68c966be92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-ac7d3f04849dde0da3d22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001r-0900000000-6634fb6b07312ce02ee62017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-c43f4a856e6d225766ef2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-000i-0900000000-1231bd387729155af4ab2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITFT , positivesplash10-001i-0900000000-a885de4ee2be84e3748d2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-00lr-0950000000-2942178c0744617021812017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0019-2900000000-bf1e7c693c96e9a699662017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00lr-0980000000-8285f9b18fe84bc8a89e2021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 75V, Positivesplash10-000i-0900000000-c758091b215c9b205bf92021-09-20View Spectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-00lr-0970000000-774856bf69fc87f3c69d2021-09-20View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0590000000-abe04a26339f19caa3d52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q9-0910000000-f57d5ee7c11ceba003002016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-08g3-9700000000-e573e8a9813088fd720e2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0190000000-f48d994ed4df3ae5c60a2016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-3890000000-a3699392c661a9c95f772016-08-04View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03dl-9800000000-aaddfd0cc344b9fa04462016-08-04View Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-2900000000-c3230d468784464059912014-09-20View Spectrum
Toxicity Profile
Route of ExposureWell absorbed from the gastrointestinal tract (> 95%). The presence of food reduces the rate but not the extent of absorption. Hepatic first pass metabolism reduces bioavailability to 45-70% following administration of a single dose, but increases to 80% with multiple dosing as a result of saturation of the first pass effect. Peak plasma concentrations are reached within 1 - 2 hours following oral administration.
Mechanism of ToxicityThe 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.
MetabolismMoclobemide is almost completely metabolized in the liver by Cytochrome P450 2C19 and 2D6. Half Life: 1-2 hours (4 hours in cirrhotic patients); metabolites are renally excreted
Toxicity ValuesLD50: 730mg/kg (Mouse) (1) LD50: 1300mg/kg (Rat) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of depression.
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB01171
HMDB IDHMDB15302
PubChem Compound ID4235
ChEMBL IDCHEMBL86304
ChemSpider ID4087
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI ID239099
BioCyc IDNot Available
CTD IDNot Available
Stitch IDMoclobemide
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkMoclobemide
References
Synthesis ReferenceNot Available
MSDST3D3004.pdf
General References
  1. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
  2. Drugs.com [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Amine oxidase [flavin-containing] A
General Function:
Serotonin binding
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 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]