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Showing metabocard for Tranylcypromine (HMDB0014890)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:46 UTC
HMDB IDHMDB0014890
Secondary Accession Numbers
  • HMDB14890
Metabolite Identification
Common NameTranylcypromine
DescriptionTranylcypromine, also known as parnate or parnic acid, belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group. Tranylcypromine is a very strong basic compound (based on its pKa). Tranylcypromine is a potentially toxic compound. Within neurons, MAO appears to regulate the levels of monoamines released upon synaptic firing. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. In overdosage, some patients exhibit insomnia, restlessness and anxiety, progressing in severe cases to agitation, mental confusion and incoherence. Rare cases have been reported of hypertensive crisis, serotonin syndrome, myoclonus, hyperpyrexia, psychosis, and delirium, some of which progressed to coma. When hypotension requires treatment, the standard measures for managing circulatory shock should be initiated.
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014890 (Tranylcypromine)

752
  Mrv0541 02231214582D          

 10 11  0  0  1  0            999 V2000
    3.4916    1.5453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    1.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
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3D MOL for HMDB0014890 (Tranylcypromine)

HMDB0014890
     RDKit          3D
Tranylcypromine
 21 22  0  0  0  0  0  0  0  0999 V2000
    3.3096    0.1633   -0.8783 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9705    0.5879   -0.5141 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7235    0.6785    0.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0675   -0.4141    0.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883   -0.3030    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1439   -1.4514    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5314   -1.4143    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1540   -0.1920   -0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4397    0.9859   -0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    0.8929   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9722    0.7605   -0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4693   -0.8485   -0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5946    1.4310   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885    1.5093    1.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4946    0.2841    1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811   -1.4325    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021   -2.4442    0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1022   -2.3401    0.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2497   -0.2035   -0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9349    1.9412   -0.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4621    1.8090   -0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4  2  1  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  6
  3 14  1  0
  3 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
M  END
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3D SDF for HMDB0014890 (Tranylcypromine)

752
  Mrv0541 02231214582D          

 10 11  0  0  1  0            999 V2000
    3.4916    1.5453    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    0.4183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    1.1327    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.9520    1.1327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.4067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.8192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -1.6443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -2.0568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  3  1  1  1  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  2  0  0  0  0
  8 10  2  0  0  0  0
  9 10  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014890

> <DATABASE_NAME>
hmdb

> <SMILES>
N[C@@H]1CC1C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/t8?,9-/m1/s1

> <INCHI_KEY>
AELCINSCMGFISI-YGPZHTELSA-N

> <FORMULA>
C9H11N

> <MOLECULAR_WEIGHT>
133.1903

> <EXACT_MASS>
133.089149357

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
15.334201185763868

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R)-2-phenylcyclopropan-1-amine

> <ALOGPS_LOGP>
1.50

> <JCHEM_LOGP>
1.338882470333333

> <ALOGPS_LOGS>
-1.95

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.622454981560159

> <JCHEM_POLAR_SURFACE_AREA>
26.02

> <JCHEM_REFRACTIVITY>
41.696600000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.49e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
tranylcypromine sulfate

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0014890 (Tranylcypromine)

HMDB0014890
     RDKit          3D
Tranylcypromine
 21 22  0  0  0  0  0  0  0  0999 V2000
    3.3096    0.1633   -0.8783 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9705    0.5879   -0.5141 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.7235    0.6785    0.9545 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0675   -0.4141    0.0800 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3883   -0.3030    0.0332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1439   -1.4514    0.1168 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5314   -1.4143    0.0784 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1540   -0.1920   -0.0466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4397    0.9859   -0.1339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    0.8929   -0.0908 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9722    0.7605   -0.3288 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4693   -0.8485   -0.6186 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5946    1.4310   -1.1357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0885    1.5093    1.3156 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4946    0.2841    1.6678 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4811   -1.4325    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7021   -2.4442    0.2167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1022   -2.3401    0.1467 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2497   -0.2035   -0.0732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9349    1.9412   -0.2318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4621    1.8090   -0.1574 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  4  2  1  0
 10  5  1  0
  1 11  1  0
  1 12  1  0
  2 13  1  6
  3 14  1  0
  3 15  1  0
  4 16  1  0
  6 17  1  0
  7 18  1  0
  8 19  1  0
  9 20  1  0
 10 21  1  0
M  END
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PDB for HMDB0014890 (Tranylcypromine)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 752                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       6.518   2.885   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0       4.414   0.781   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.184   2.114   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.644   2.114   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.414  -0.759   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.748  -1.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.080  -1.529   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748  -3.069   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.080  -3.069   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -3.839   0.000  0.00  0.00           C+0
CONECT    1    3                                                            
CONECT    2    3    4    5                                                  
CONECT    3    1    2    4                                                  
CONECT    4    2    3                                                       
CONECT    5    2    6    7                                                  
CONECT    6    5    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   10                                                       
CONECT   10    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END
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3D PDB for HMDB0014890 (Tranylcypromine)

COMPND    HMDB0014890
HETATM    1  N1  UNL     1       3.310   0.163  -0.878  1.00  0.00           N  
HETATM    2  C1  UNL     1       1.971   0.588  -0.514  1.00  0.00           C  
HETATM    3  C2  UNL     1       1.724   0.679   0.955  1.00  0.00           C  
HETATM    4  C3  UNL     1       1.067  -0.414   0.080  1.00  0.00           C  
HETATM    5  C4  UNL     1      -0.388  -0.303   0.033  1.00  0.00           C  
HETATM    6  C5  UNL     1      -1.144  -1.451   0.117  1.00  0.00           C  
HETATM    7  C6  UNL     1      -2.531  -1.414   0.078  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.154  -0.192  -0.047  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.440   0.986  -0.134  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.063   0.893  -0.091  1.00  0.00           C  
HETATM   11  H1  UNL     1       3.972   0.760  -0.329  1.00  0.00           H  
HETATM   12  H2  UNL     1       3.469  -0.849  -0.619  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.595   1.431  -1.136  1.00  0.00           H  
HETATM   14  H4  UNL     1       1.088   1.509   1.316  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.495   0.284   1.668  1.00  0.00           H  
HETATM   16  H6  UNL     1       1.481  -1.432   0.182  1.00  0.00           H  
HETATM   17  H7  UNL     1      -0.702  -2.444   0.217  1.00  0.00           H  
HETATM   18  H8  UNL     1      -3.102  -2.340   0.147  1.00  0.00           H  
HETATM   19  H9  UNL     1      -4.250  -0.203  -0.073  1.00  0.00           H  
HETATM   20  H10 UNL     1      -2.935   1.941  -0.232  1.00  0.00           H  
HETATM   21  H11 UNL     1      -0.462   1.809  -0.157  1.00  0.00           H  
CONECT    1    2   11   12
CONECT    2    3    4   13
CONECT    3    4   14   15
CONECT    4    5   16
CONECT    5    6    6   10
CONECT    6    7   17
CONECT    7    8    8   18
CONECT    8    9   19
CONECT    9   10   10   20
CONECT   10   21
END
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SMILES for HMDB0014890 (Tranylcypromine)

N[C@@H]1CC1C1=CC=CC=C1
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INCHI for HMDB0014890 (Tranylcypromine)

InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/t8?,9-/m1/s1
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View in JSmolView NMR AssignmentsView Stereo Labels
Synonyms
ValueSource
ParnateKegg
Parnic acidGenerator
Allphar brand OF tranylcypromine sulfateHMDB
GlaxoSmithKline brand OF tranylcypromine sulfateHMDB
Goldshield brand OF tranylcypromine sulfateHMDB
JatrosomHMDB
Link brand OF tranylcypromine sulfateHMDB
SmithKline brand OF tranylcypromine sulfateHMDB
Sulfate, tranylcypromineHMDB
TransamineHMDB
Tranylcypromine sulfateHMDB
Esparma brand OF tranylcypromine sulfateHMDB
trans 2 PhenylcyclopropylamineHMDB
trans-2-PhenylcyclopropylamineHMDB
Chemical FormulaC9H11N
Average Molecular Weight133.1903
Monoisotopic Molecular Weight133.089149357
IUPAC Name(1R)-2-phenylcyclopropan-1-amine
Traditional Nametranylcypromine sulfate
CAS Registry Number155-09-9
SMILES
N[C@@H]1CC1C1=CC=CC=C1
InChI Identifier
InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/t8?,9-/m1/s1
InChI KeyAELCINSCMGFISI-YGPZHTELSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as aralkylamines. These are alkylamines in which the alkyl group is substituted at one carbon atom by an aromatic hydrocarbyl group.
KingdomOrganic compounds
Super ClassOrganic nitrogen compounds
ClassOrganonitrogen compounds
Sub ClassAmines
Direct ParentAralkylamines
Alternative Parents
Substituents
  • Aralkylamine
  • Benzenoid
  • Monocyclic benzene moiety
  • Organopnictogen compound
  • Hydrocarbon derivative
  • Primary amine
  • Primary aliphatic amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
ProcessNot Available
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point79 - 80 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.49 g/LNot Available
LogP1.4Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+CBM127.630932474
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
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 DB00752 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00752 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 IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID390008
KEGG Compound IDC07155
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTranylcypromine
METLIN IDNot Available
PubChem Compound441233
PDB IDNot Available
ChEBI IDNot Available
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 References
  1. Nolen WA: [Classical monoamine oxidase inhibitor: not registered for, but still a place in the treatment of depression]. Ned Tijdschr Geneeskd. 2003 Oct 4;147(40):1940-3. [PubMed:14574774 ]
  2. Frieling H, Bleich S: Tranylcypromine: new perspectives on an "old" drug. Eur Arch Psychiatry Clin Neurosci. 2006 Aug;256(5):268-73. [PubMed:16927039 ]

Enzymes

Enzyme Details
1. Amine oxidase [flavin-containing] B
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. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  2. Volz HP, Gleiter CH: Monoamine oxidase inhibitors. A perspective on their use in the elderly. Drugs Aging. 1998 Nov;13(5):341-55. [PubMed:9829163 ]
  3. Shioda K, Nisijima K, Yoshino T, Kato S: Mirtazapine abolishes hyperthermia in an animal model of serotonin syndrome. Neurosci Lett. 2010 Oct 4;482(3):216-9. doi: 10.1016/j.neulet.2010.07.039. Epub 2010 Jul 23. [PubMed:20655983 ]
  4. Gatch MB, Taylor CM, Flores E, Selvig M, Forster MJ: Effects of monoamine oxidase inhibitors on cocaine discrimination in rats. Behav Pharmacol. 2006 Mar;17(2):151-9. [PubMed:16495723 ]
  5. Lang W, Masucci JA, Caldwell GW, Hageman W, Hall J, Jones WJ, Rafferty BM: Liquid chromatographic and tandem mass spectrometric assay for evaluation of in vivo inhibition of rat brain monoamine oxidases (MAO) A and B following a single dose of MAO inhibitors: application of biomarkers in drug discovery. Anal Biochem. 2004 Oct 1;333(1):79-87. [PubMed:15351283 ]
  6. Shioda K, Nisijima K, Yoshino T, Kato S: Extracellular serotonin, dopamine and glutamate levels are elevated in the hypothalamus in a serotonin syndrome animal model induced by tranylcypromine and fluoxetine. Prog Neuropsychopharmacol Biol Psychiatry. 2004 Jul;28(4):633-40. [PubMed:15276688 ]
  7. Salsali M, Holt A, Baker GB: Inhibitory effects of the monoamine oxidase inhibitor tranylcypromine on the cytochrome P450 enzymes CYP2C19, CYP2C9, and CYP2D6. Cell Mol Neurobiol. 2004 Feb;24(1):63-76. [PubMed:15049511 ]
  8. Nolen WA: [Classical monoamine oxidase inhibitor: not registered for, but still a place in the treatment of depression]. Ned Tijdschr Geneeskd. 2003 Oct 4;147(40):1940-3. [PubMed:14574774 ]
  9. Cohen C, Curet O, Perrault G, Sanger DJ: Reduction of oral ethanol self-administration in rats by monoamine oxidase inhibitors. Pharmacol Biochem Behav. 1999 Nov;64(3):535-9. [PubMed:10548268 ]
  10. Wiest SA, Steinberg MI: 3H[2-(2-benzofuranyl)-2-imidazoline] (BFI) binding in human platelets: modulation by tranylcypromine. Naunyn Schmiedebergs Arch Pharmacol. 1999 Aug;360(2):209-16. [PubMed:10494892 ]
  11. Loscher W, Lehmann H, Teschendorf HJ, Traut M, Gross G: Inhibition of monoamine oxidase type A, but not type B, is an effective means of inducing anticonvulsant activity in the kindling model of epilepsy. J Pharmacol Exp Ther. 1999 Mar;288(3):984-92. [PubMed:10027835 ]
  12. Todd KG, Baker GB: GABA-elevating effects of the antidepressant/antipanic drug phenelzine in brain: effects of pretreatment with tranylcypromine, (-)-deprenyl and clorgyline. J Affect Disord. 1995 Dec 13;35(3):125-9. [PubMed:8749840 ]
  13. Finberg JP, Youdim MB: Pharmacological properties of the anti-Parkinson drug rasagiline; modification of endogenous brain amines, reserpine reversal, serotonergic and dopaminergic behaviours. Neuropharmacology. 2002 Dec;43(7):1110-8. [PubMed:12504917 ]
Enzyme Details
2. Amine oxidase [flavin-containing] A
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. Volz HP, Gleiter CH: Monoamine oxidase inhibitors. A perspective on their use in the elderly. Drugs Aging. 1998 Nov;13(5):341-55. [PubMed:9829163 ]
  3. Shioda K, Nisijima K, Yoshino T, Kato S: Mirtazapine abolishes hyperthermia in an animal model of serotonin syndrome. Neurosci Lett. 2010 Oct 4;482(3):216-9. doi: 10.1016/j.neulet.2010.07.039. Epub 2010 Jul 23. [PubMed:20655983 ]
  4. Gatch MB, Taylor CM, Flores E, Selvig M, Forster MJ: Effects of monoamine oxidase inhibitors on cocaine discrimination in rats. Behav Pharmacol. 2006 Mar;17(2):151-9. [PubMed:16495723 ]
  5. Lang W, Masucci JA, Caldwell GW, Hageman W, Hall J, Jones WJ, Rafferty BM: Liquid chromatographic and tandem mass spectrometric assay for evaluation of in vivo inhibition of rat brain monoamine oxidases (MAO) A and B following a single dose of MAO inhibitors: application of biomarkers in drug discovery. Anal Biochem. 2004 Oct 1;333(1):79-87. [PubMed:15351283 ]
  6. Shioda K, Nisijima K, Yoshino T, Kato S: Extracellular serotonin, dopamine and glutamate levels are elevated in the hypothalamus in a serotonin syndrome animal model induced by tranylcypromine and fluoxetine. Prog Neuropsychopharmacol Biol Psychiatry. 2004 Jul;28(4):633-40. [PubMed:15276688 ]
  7. Salsali M, Holt A, Baker GB: Inhibitory effects of the monoamine oxidase inhibitor tranylcypromine on the cytochrome P450 enzymes CYP2C19, CYP2C9, and CYP2D6. Cell Mol Neurobiol. 2004 Feb;24(1):63-76. [PubMed:15049511 ]
  8. Nolen WA: [Classical monoamine oxidase inhibitor: not registered for, but still a place in the treatment of depression]. Ned Tijdschr Geneeskd. 2003 Oct 4;147(40):1940-3. [PubMed:14574774 ]
  9. Cohen C, Curet O, Perrault G, Sanger DJ: Reduction of oral ethanol self-administration in rats by monoamine oxidase inhibitors. Pharmacol Biochem Behav. 1999 Nov;64(3):535-9. [PubMed:10548268 ]
  10. Wiest SA, Steinberg MI: 3H[2-(2-benzofuranyl)-2-imidazoline] (BFI) binding in human platelets: modulation by tranylcypromine. Naunyn Schmiedebergs Arch Pharmacol. 1999 Aug;360(2):209-16. [PubMed:10494892 ]
  11. Loscher W, Lehmann H, Teschendorf HJ, Traut M, Gross G: Inhibition of monoamine oxidase type A, but not type B, is an effective means of inducing anticonvulsant activity in the kindling model of epilepsy. J Pharmacol Exp Ther. 1999 Mar;288(3):984-92. [PubMed:10027835 ]
  12. Todd KG, Baker GB: GABA-elevating effects of the antidepressant/antipanic drug phenelzine in brain: effects of pretreatment with tranylcypromine, (-)-deprenyl and clorgyline. J Affect Disord. 1995 Dec 13;35(3):125-9. [PubMed:8749840 ]
  13. Finberg JP, Youdim MB: Pharmacological properties of the anti-Parkinson drug rasagiline; modification of endogenous brain amines, reserpine reversal, serotonergic and dopaminergic behaviours. Neuropharmacology. 2002 Dec;43(7):1110-8. [PubMed:12504917 ]
Enzyme Details
3. Cytochrome P450 3A4
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 ]
Enzyme Details
4. Cytochrome P450 2C9
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. Salsali M, Holt A, Baker GB: Inhibitory effects of the monoamine oxidase inhibitor tranylcypromine on the cytochrome P450 enzymes CYP2C19, CYP2C9, and CYP2D6. Cell Mol Neurobiol. 2004 Feb;24(1):63-76. [PubMed:15049511 ]
  2. 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 ]
Enzyme Details
5. Cytochrome P450 2C19
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. Stadel R, Yang J, Nalwalk JW, Phillips JG, Hough LB: High-affinity binding of [3H]cimetidine to a heme-containing protein in rat brain. Drug Metab Dispos. 2008 Mar;36(3):614-21. Epub 2007 Dec 19. [PubMed:18094038 ]
  2. Salsali M, Holt A, Baker GB: Inhibitory effects of the monoamine oxidase inhibitor tranylcypromine on the cytochrome P450 enzymes CYP2C19, CYP2C9, and CYP2D6. Cell Mol Neurobiol. 2004 Feb;24(1):63-76. [PubMed:15049511 ]
  3. 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 ]
Enzyme Details
6. Cytochrome P450 2E1
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. 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 ]
Enzyme Details
7. Cytochrome P450 2D6
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. Salsali M, Holt A, Baker GB: Inhibitory effects of the monoamine oxidase inhibitor tranylcypromine on the cytochrome P450 enzymes CYP2C19, CYP2C9, and CYP2D6. Cell Mol Neurobiol. 2004 Feb;24(1):63-76. [PubMed:15049511 ]
  2. 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 ]
Enzyme Details
8. Cytochrome P450 1A2
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 ]
Enzyme Details
9. Cytochrome P450 2A6
General function:
Involved in monooxygenase activity
Specific function:
Exhibits a high coumarin 7-hydroxylase activity. Can act in the hydroxylation of the anti-cancer drugs cyclophosphamide and ifosphamide. Competent in the metabolic activation of aflatoxin B1. Constitutes the major nicotine C-oxidase. Acts as a 1,4-cineole 2-exo-monooxygenase. Possesses low phenacetin O-deethylation activity.
Gene Name:
CYP2A6
Uniprot ID:
P11509
Molecular weight:
56517.005
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 ]