Phenelzine

Identification

Summary

Phenelzine is a monoamine oxidase inhibitor used to treat atypical, nonendogenous, or neurotic depression.

Brand Names
Nardil
Generic Name
Phenelzine
DrugBank Accession Number
DB00780
Background

Phenelzine, with the formula β-phenylethylhydrazine, is a monoamine oxidase inhibiting antidepressant that is effective in the treatment of panic disorder and social anxiety disorder.3 It was developed by Parke Davis and originally FDA approved on June 9th, 1961. It is currently approved under prescription by the name of Nardil.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 136.1943
Monoisotopic: 136.100048394
Chemical Formula
C8H12N2
Synonyms
  • Fenelzina
  • Phenelzin
  • Phénelzine
  • Phenelzine
  • Phenelzinum
External IDs
  • W 1544

Pharmacology

Indication

Phenelzine is indicated for the treatment of nonendogenous, neurotic or atypical depression for patients that do not tolerate other forms of therapy.12

Atypical depression has a high prevalence rate, starts in early life, tends to last longer, is more likely to occur in people with bipolar disorder, has a high comorbidity with anxiety disorder and carries more risk of suicidal behavior. It is important to specify the atypical feature to predict the clinical course of depression and hence generate the best treatment and service. The featuring symptoms of the atypical feature include mood reactivity, two or more of this symptoms: 1) increased appetite, 2) increased sleep, 3) leaden paralysis and 4) interpersonal rejection sensitivity and should not have melancholic or catatonic features of depression.4

Neurotic depression is a depression of an emotionally unstable person. It is a secondary condition to major personality disorder, neuroses and drug use disorders. Likewise, a primary depression with a family history of depression spectrum disease would fit in this category.5

A nonendogenous depression is characterized by a disturbance in mood and general outlook. The physical symptoms tend to be less severe and it often occurs in response to stressful life events that keep occurring over a large period of time generating a continuous stress in the daily living.6

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Treatment ofExogenous depression••••••••••••
Treatment ofNeurotic depression••••••••••••
Treatment ofAtypical depressive disorder••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

The elimination of monoamine oxidase by phenelzine results in the elevation of brain amines such as 2-phenylethylamine which is a metabolite of phenelzine. These amines have then marked effects on the uptake and release of catecholamines and serotonin in nerve endings.7 Phenelzine is shown to elevate brain levels of the gamma-aminobutyric acid (GABA) and alanine (ALA) as well as to inhibit the activity of the transaminases that normally metabolize these amino acids. In preclinical studies, it has been shown to be neuroprotective in cerebral ischemia.3

Mechanism of action

The basic mechanism of action of phenelzine acts as an inhibitor and substrate of monoamine oxidase which subsequently causes an elevation in brain levels of catecholamines and serotonin. It also presents a similar structure to amphetamine which explains the effect on the uptake and release of dopamine, noradrenaline, and serotonin. Phenelzine has been reported to inhibit tyrosine aminotransferase, aromatic amino acid decarboxylase, and dopamine B-hydroxylase.7

TargetActionsOrganism
AAmine oxidase [flavin-containing] A
antagonist
Humans
AAmine oxidase [flavin-containing] B
antagonist
Humans
UMembrane primary amine oxidase
inhibitor
Humans
U4-aminobutyrate aminotransferase, mitochondrial
inhibitor
Humans
UAlanine aminotransferase 1
inhibitor
Humans
UAlanine aminotransferase 2
inhibitor
Humans
UGlutamic acid decarboxylase
inhibitor
Humans
Absorption

Phenelzine is rapidly absorbed from the gastrointestinal tract. The decay of the drug action is not dependent on the pharmacokinetic parameters but on the rate of protein synthesis which restores the functional levels of monoamine oxidase.13 The mean Cmax is 19.8 ng/ml and it occurs after 43 minutes of dose administration.Label

Volume of distribution

The volume of distribution of phenelzine is hard to determine as drugs from this kind penetrate the CNS very well into the tissue where their activity is desired.10

Protein binding

Unchanged phenelzine presents a high protein binding which reduced its bioavailability.11

Metabolism

For the metabolic studies, it is assumed that phenelzine is acetylated. Some of the metabolites of phenelzine are phenylacetic acid, 2-phenylethylamine and 4-hydroxyphenylacetic acid as major metabolites and N-acetyl-phenelzine as a minor metabolite.7

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Route of elimination

The elimination of the administered dose is mainly composed of the phenelzine metabolites, phenylacetic acid and parahydroxyphenylacetic acid that constitute 79% of the dose found in the urine in the first 96 hours.8

Half-life

After administration phenelzine presents a very short half-life of 11.6 hours in humans.13

Clearance

Not Available

Adverse Effects
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Toxicity

Phenelzine, as must of the monoamine oxidase inhibitors, can cause transient, mild and asymptomatic aminotransferase elevations. It has also been reported to be associated with cases of liver injury after 1-3 months of treatment.9

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Phenelzine is combined with 1,2-Benzodiazepine.
AbacavirPhenelzine may decrease the excretion rate of Abacavir which could result in a higher serum level.
AbaloparatidePhenelzine may increase the orthostatic hypotensive activities of Abaloparatide.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Phenelzine is combined with Abciximab.
AcarbosePhenelzine may increase the hypoglycemic activities of Acarbose.
Food Interactions
  • Avoid alcohol.
  • Avoid St. John's Wort. Administering phenelzine with St. John's Wort may increase the risk of serotonin syndrome.
  • Avoid tyramine-containing foods and supplements. Tyramine-containing foods and beverages can cause a sudden elevation in blood pressure or a hypertensive crisis. Foods that contain tyramine include aged cheese, ripe bananas, red wine, some alcoholic beverages (beer), cured food, pickled food, and fava beans.
  • Limit caffeine intake. Excess caffeine intake can also cause a hypertensive crisis.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Phenelzine sulfate2681D7P965156-51-4RXBKMJIPNDOHFR-UHFFFAOYSA-N
International/Other Brands
Margyl (DIM) / Nardelzine (Pfizer)
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
NardilTablet, film coated15 mg/1OralParke-Davis Div of Pfizer Inc1961-06-09Not applicableUS flag
NardilTablet15 mgOralSearchlight Pharma Inc1981-12-31Not applicableCanada flag
Nardil Phenelzine SulfateTablet, film coated15 mg/1OralFarmea1961-06-09Not applicableUS flag
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Greenstone Brand Phenelzine SulfateTablet15 mg/1OralFarmea1961-06-09Not applicableUS flag
Phenelzine SulfateTablet15 mg/1OralGolden State Medical Supply, Inc.2010-12-142015-02-28US flag
Phenelzine SulfateTablet15 mg/1OralNovel Laboratories, Inc.2011-02-14Not applicableUS flag
Phenelzine SulfateTablet, film coated15 mg/1OralGreenstone LLC2011-03-23Not applicableUS flag
Phenelzine SulfateTablet15 mg/1OralLupin Pharmaceuticals2010-12-14Not applicableUS flag

Categories

ATC Codes
N06AF03 — Phenelzine
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Not Available
Direct Parent
Benzene and substituted derivatives
Alternative Parents
Alkylhydrazines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Alkylhydrazine / Aromatic homomonocyclic compound / Hydrazine derivative / Hydrocarbon derivative / Monocyclic benzene moiety / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
primary amine (CHEBI:8060) / a small molecule (CPD-13895)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
O408N561GF
CAS number
51-71-8
InChI Key
RMUCZJUITONUFY-UHFFFAOYSA-N
InChI
InChI=1S/C8H12N2/c9-10-7-6-8-4-2-1-3-5-8/h1-5,10H,6-7,9H2
IUPAC Name
(2-phenylethyl)hydrazine
SMILES
NNCCC1=CC=CC=C1

References

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. [Article]
  2. Sowa BN, Holt A, Todd KG, Baker GB: Monoamine oxidase inhibitors, their structural analogues, and neuroprotection. Indian J Exp Biol. 2004 Sep;42(9):851-7. [Article]
  3. Todd KG, Baker GB: Neurochemical effects of the monoamine oxidase inhibitor phenelzine on brain GABA and alanine: A comparison with vigabatrin. J Pharm Pharm Sci. 2008 May 16;11(2):14s-21s. [Article]
  4. Singh T, Williams K: Atypical depression. Psychiatry (Edgmont). 2006 Apr;3(4):33-9. [Article]
  5. Winokur G, Black DW, Nasrallah A: Neurotic depression: a diagnosis based on preexisting characteristics. Eur Arch Psychiatry Neurol Sci. 1987;236(6):343-8. [Article]
  6. Benjaminsen S: Primary non-endogenous depression and features attributed to reactive depression. J Affect Disord. 1981 Sep;3(3):245-59. [Article]
  7. Baker GB, Coutts RT, McKenna KF, Sherry-McKenna RL: Insights into the mechanisms of action of the MAO inhibitors phenelzine and tranylcypromine: a review. J Psychiatry Neurosci. 1992 Nov;17(5):206-14. [Article]
  8. Robinson DS, Cooper TB, Jindal SP, Corcella J, Lutz T: Metabolism and pharmacokinetics of phenelzine: lack of evidence for acetylation pathway in humans. J Clin Psychopharmacol. 1985 Dec;5(6):333-7. [Article]
  9. Friedrich ME, Akimova E, Huf W, Konstantinidis A, Papageorgiou K, Winkler D, Toto S, Greil W, Grohmann R, Kasper S: Drug-Induced Liver Injury during Antidepressant Treatment: Results of AMSP, a Drug Surveillance Program. Int J Neuropsychopharmacol. 2016 Apr 20;19(4). pii: pyv126. doi: 10.1093/ijnp/pyv126. Print 2016 Apr. [Article]
  10. Preskon S., Feighner J., Stanga C. and Ross R. (2004). Antidepressants: Past, Present and Future. Springer-Verlag.
  11. Owens D. (2010). Companion to psychiatric studies (8th ed.). Elsevier.
  12. Nardil monograph [Link]
  13. New Zealand report [Link]
Human Metabolome Database
HMDB0014918
KEGG Drug
D08349
KEGG Compound
C07430
PubChem Compound
3675
PubChem Substance
46507348
ChemSpider
3547
BindingDB
50105417
RxNav
8123
ChEBI
8060
ChEMBL
CHEMBL1089
ZINC
ZINC000019166991
Therapeutic Targets Database
DAP000578
PharmGKB
PA450903
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Phenelzine
FDA label
Download (38.9 KB)
MSDS
Download (25 KB)

Clinical Trials

Clinical Trials

Pharmacoeconomics

Manufacturers
  • Parke davis div warner lambert co
Packagers
  • Farmea
  • Kaiser Foundation Hospital
  • Murfreesboro Pharmaceutical Nursing Supply
  • Pfizer Inc.
  • Professional Co.
  • Warner Lambert Company LLC
Dosage Forms
FormRouteStrength
Tablet, film coatedOral
TabletOral15 mg
Tablet, film coatedOral15 mg/1
TabletOral15 mg/1
Prices
Unit descriptionCostUnit
Phenelzine sulfate powder51.0USD g
Nardil 15 mg tablet0.95USD tablet
Nardil 15 mg Tablet0.39USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)157-161ºC'MSDS' for phenelzine sulfate (solid form)
boiling point (°C)74 °C at 1.00E-01 mm HgUS Environmental Protection Agency (liquid form)
water solubility29.1 g/L'MSDS' for phenelzine sulfate (solid form)
pKa6.5-8Zaragoza F. Lead Optimization for Medicinal Chemists. (2012)
Predicted Properties
PropertyValueSource
Water Solubility11.1 mg/mLALOGPS
logP1.2ALOGPS
logP1.2Chemaxon
logS-1.1ALOGPS
pKa (Strongest Basic)5.55Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area38.05 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity54.26 m3·mol-1Chemaxon
Polarizability15.8 Å3Chemaxon
Number of Rings1Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9926
Blood Brain Barrier+0.9405
Caco-2 permeable+0.6863
P-glycoprotein substrateNon-substrate0.6728
P-glycoprotein inhibitor INon-inhibitor0.9439
P-glycoprotein inhibitor IINon-inhibitor0.9767
Renal organic cation transporterNon-inhibitor0.6026
CYP450 2C9 substrateNon-substrate0.9166
CYP450 2D6 substrateNon-substrate0.5788
CYP450 3A4 substrateNon-substrate0.8056
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.8945
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8995
CYP450 3A4 inhibitorInhibitor0.7961
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7748
Ames testAMES toxic0.6836
CarcinogenicityCarcinogens 0.699
BiodegradationNot ready biodegradable0.8301
Rat acute toxicity2.6507 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7405
hERG inhibition (predictor II)Non-inhibitor0.8735
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-0007-9200000000-b2c57d1368223a96c523
GC-MS Spectrum - EI-BGC-MSsplash10-0a4l-9800000000-fec970db2245559d8531
Mass Spectrum (Electron Ionization)MSsplash10-0002-9000000000-833e467e14c48ae4f6b3
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-01t9-0592000000-92a48c620c961fdb430f
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4i-0900000000-cf09dbe619ab21f16ce0
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0900000000-f13c26b0751fc2e77dce
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0k9i-0900000000-3b17159bf4712101228a
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00kf-9800000000-e851e2d869bb0d8c567e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pb9-1900000000-ef6988e8a71bfbfff818
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0006-9000000000-efe2daca378a1c1d8bff
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00ou-9100000000-9a6d7dff97276097ccc7
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-132.0253663
predicted
DarkChem Lite v0.1.0
[M-H]-132.1347663
predicted
DarkChem Lite v0.1.0
[M-H]-124.77582
predicted
DeepCCS 1.0 (2019)
[M+H]+132.1413663
predicted
DarkChem Lite v0.1.0
[M+H]+132.1191663
predicted
DarkChem Lite v0.1.0
[M+H]+127.78832
predicted
DeepCCS 1.0 (2019)
[M+Na]+132.0779663
predicted
DarkChem Lite v0.1.0
[M+Na]+132.0092663
predicted
DarkChem Lite v0.1.0
[M+Na]+136.51532
predicted
DeepCCS 1.0 (2019)

Targets

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insights and accelerate drug research.
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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
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...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
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. [Article]
  2. Chiche F, Le Guillou M, Chetrite G, Lasnier F, Dugail I, Carpene C, Moldes M, Feve B: Antidepressant phenelzine alters differentiation of cultured human and mouse preadipocytes. Mol Pharmacol. 2009 May;75(5):1052-61. doi: 10.1124/mol.108.052563. Epub 2009 Feb 6. [Article]
  3. Chenu F, El Mansari M, Blier P: Long-term administration of monoamine oxidase inhibitors alters the firing rate and pattern of dopamine neurons in the ventral tegmental area. Int J Neuropsychopharmacol. 2009 May;12(4):475-85. doi: 10.1017/S1461145708009218. Epub 2008 Aug 13. [Article]
  4. Wooters TE, Bardo MT: The monoamine oxidase inhibitor phenelzine enhances the discriminative stimulus effect of nicotine in rats. Behav Pharmacol. 2007 Nov;18(7):601-8. [Article]
  5. Volz HP, Gleiter CH: Monoamine oxidase inhibitors. A perspective on their use in the elderly. Drugs Aging. 1998 Nov;13(5):341-55. [Article]
  6. 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. [Article]
  7. Pickar D, Murphy DL, Cohen RM, Campbell IC, Lipper S: Selective and nonselective monoamine oxidase inhibitors: behavioral disturbances during their administration to depressed patients. Arch Gen Psychiatry. 1982 May;39(5):535-40. [Article]
  8. MacKenzie EM, Grant SL, Baker GB, Wood PL: Phenelzine causes an increase in brain ornithine that is prevented by prior monoamine oxidase inhibition. Neurochem Res. 2008 Mar;33(3):430-6. Epub 2007 Aug 31. [Article]
  9. McIntyre RS, Soczynska JK, Konarski JZ, Kennedy SH: The effect of antidepressants on glucose homeostasis and insulin sensitivity: synthesis and mechanisms. Expert Opin Drug Saf. 2006 Jan;5(1):157-68. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Antagonist
General Function
Primary amine oxidase 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...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  2. Chiche F, Le Guillou M, Chetrite G, Lasnier F, Dugail I, Carpene C, Moldes M, Feve B: Antidepressant phenelzine alters differentiation of cultured human and mouse preadipocytes. Mol Pharmacol. 2009 May;75(5):1052-61. doi: 10.1124/mol.108.052563. Epub 2009 Feb 6. [Article]
  3. Chenu F, El Mansari M, Blier P: Long-term administration of monoamine oxidase inhibitors alters the firing rate and pattern of dopamine neurons in the ventral tegmental area. Int J Neuropsychopharmacol. 2009 May;12(4):475-85. doi: 10.1017/S1461145708009218. Epub 2008 Aug 13. [Article]
  4. Wooters TE, Bardo MT: The monoamine oxidase inhibitor phenelzine enhances the discriminative stimulus effect of nicotine in rats. Behav Pharmacol. 2007 Nov;18(7):601-8. [Article]
  5. Volz HP, Gleiter CH: Monoamine oxidase inhibitors. A perspective on their use in the elderly. Drugs Aging. 1998 Nov;13(5):341-55. [Article]
  6. 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. [Article]
  7. Pickar D, Murphy DL, Cohen RM, Campbell IC, Lipper S: Selective and nonselective monoamine oxidase inhibitors: behavioral disturbances during their administration to depressed patients. Arch Gen Psychiatry. 1982 May;39(5):535-40. [Article]
  8. McIntyre RS, Soczynska JK, Konarski JZ, Kennedy SH: The effect of antidepressants on glucose homeostasis and insulin sensitivity: synthesis and mechanisms. Expert Opin Drug Saf. 2006 Jan;5(1):157-68. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Tryptamine:oxygen oxidoreductase (deaminating) activity
Specific Function
Cell adhesion protein that participates in lymphocyte extravasation and recirculation by mediating the binding of lymphocytes to peripheral lymph node vascular endothelial cells in an L-selectin-in...
Gene Name
AOC3
Uniprot ID
Q16853
Uniprot Name
Membrane primary amine oxidase
Molecular Weight
84621.27 Da
References
  1. Tipnis UR, Tao M, Boor PJ: Purification and characterization of semicarbazide-sensitive amine oxidase from porcine aorta. Cell Mol Biol (Noisy-le-grand). 1992 Aug-Sep;38(5-6):575-84. [Article]
  2. Kumar D, Trent MB, Boor PJ: Allylamine and beta-aminopropionitrile induced aortic medial necrosis: mechanisms of synergism. Toxicology. 1998 Feb 6;125(2-3):107-15. [Article]
  3. Chiche F, Le Guillou M, Chetrite G, Lasnier F, Dugail I, Carpene C, Moldes M, Feve B: Antidepressant phenelzine alters differentiation of cultured human and mouse preadipocytes. Mol Pharmacol. 2009 May;75(5):1052-61. doi: 10.1124/mol.108.052563. Epub 2009 Feb 6. [Article]
  4. Biasi D, Caramaschi P, Pacor ML, Carletto A, Melchiori S, Manzo T, Bambara LM: [Multiple osseous avascular necrosis in a patient with systemic lupus erythematosus with antiphospholipid antibody positivity]. Recenti Prog Med. 1995 Nov;86(11):449-50. [Article]
  5. MacKenzie EM, Grant SL, Baker GB, Wood PL: Phenelzine causes an increase in brain ornithine that is prevented by prior monoamine oxidase inhibition. Neurochem Res. 2008 Mar;33(3):430-6. Epub 2007 Aug 31. [Article]
  6. Lizcano JM, Fernandez de Arriba A, Tipton KF, Unzeta M: Inhibition of bovine lung semicarbazide-sensitive amine oxidase (SSAO) by some hydrazine derivatives. Biochem Pharmacol. 1996 Jul 26;52(2):187-95. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Succinate-semialdehyde dehydrogenase binding
Specific Function
Catalyzes the conversion of gamma-aminobutyrate and L-beta-aminoisobutyrate to succinate semialdehyde and methylmalonate semialdehyde, respectively. Can also convert delta-aminovalerate and beta-al...
Gene Name
ABAT
Uniprot ID
P80404
Uniprot Name
4-aminobutyrate aminotransferase, mitochondrial
Molecular Weight
56438.405 Da
References
  1. MacKenzie EM, Grant SL, Baker GB, Wood PL: Phenelzine causes an increase in brain ornithine that is prevented by prior monoamine oxidase inhibition. Neurochem Res. 2008 Mar;33(3):430-6. Epub 2007 Aug 31. [Article]
  2. Tanay VA, Parent MB, Wong JT, Paslawski T, Martin IL, Baker GB: Effects of the antidepressant/antipanic drug phenelzine on alanine and alanine transaminase in rat brain. Cell Mol Neurobiol. 2001 Aug;21(4):325-39. [Article]
  3. McKenna KF, McManus DJ, Baker GB, Coutts RT: Chronic administration of the antidepressant phenelzine and its N-acetyl analogue: effects on GABAergic function. J Neural Transm Suppl. 1994;41:115-22. [Article]
  4. McManus DJ, Baker GB, Martin IL, Greenshaw AJ, McKenna KF: Effects of the antidepressant/antipanic drug phenelzine on GABA concentrations and GABA-transaminase activity in rat brain. Biochem Pharmacol. 1992 Jun 9;43(11):2486-9. [Article]
  5. 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. [Article]
  6. Todd KG, Baker GB: Neurochemical effects of the monoamine oxidase inhibitor phenelzine on brain GABA and alanine: A comparison with vigabatrin. J Pharm Pharm Sci. 2008 May 16;11(2):14s-21s. [Article]
  7. McKenna KF, Baker GB, Coutts RT: N2-acetylphenelzine: effects on rat brain GABA, alanine and biogenic amines. Naunyn Schmiedebergs Arch Pharmacol. 1991 May;343(5):478-82. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes the reversible transamination between alanine and 2-oxoglutarate to form pyruvate and glutamate. Participates in cellular nitrogen metabolism and also in liver gluconeogenesis starting wi...
Gene Name
GPT
Uniprot ID
P24298
Uniprot Name
Alanine aminotransferase 1
Molecular Weight
54636.415 Da
References
  1. Todd KG, Baker GB: Neurochemical effects of the monoamine oxidase inhibitor phenelzine on brain GABA and alanine: A comparison with vigabatrin. J Pharm Pharm Sci. 2008 May 16;11(2):14s-21s. [Article]
  2. Tanay VA, Parent MB, Wong JT, Paslawski T, Martin IL, Baker GB: Effects of the antidepressant/antipanic drug phenelzine on alanine and alanine transaminase in rat brain. Cell Mol Neurobiol. 2001 Aug;21(4):325-39. [Article]
  3. McKenna KF, Baker GB, Coutts RT: N2-acetylphenelzine: effects on rat brain GABA, alanine and biogenic amines. Naunyn Schmiedebergs Arch Pharmacol. 1991 May;343(5):478-82. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Pyridoxal phosphate binding
Specific Function
Catalyzes the reversible transamination between alanine and 2-oxoglutarate to form pyruvate and glutamate.
Gene Name
GPT2
Uniprot ID
Q8TD30
Uniprot Name
Alanine aminotransferase 2
Molecular Weight
57903.11 Da
References
  1. Todd KG, Baker GB: Neurochemical effects of the monoamine oxidase inhibitor phenelzine on brain GABA and alanine: A comparison with vigabatrin. J Pharm Pharm Sci. 2008 May 16;11(2):14s-21s. [Article]
  2. Tanay VA, Parent MB, Wong JT, Paslawski T, Martin IL, Baker GB: Effects of the antidepressant/antipanic drug phenelzine on alanine and alanine transaminase in rat brain. Cell Mol Neurobiol. 2001 Aug;21(4):325-39. [Article]
  3. McKenna KF, Baker GB, Coutts RT: N2-acetylphenelzine: effects on rat brain GABA, alanine and biogenic amines. Naunyn Schmiedebergs Arch Pharmacol. 1991 May;343(5):478-82. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Pyridoxal phosphate binding
Specific Function
Not Available
Gene Name
GAD65
Uniprot ID
Q9UGI5
Uniprot Name
Glutamic acid decarboxylase
Molecular Weight
47343.69 Da
References
  1. McKenna KF, McManus DJ, Baker GB, Coutts RT: Chronic administration of the antidepressant phenelzine and its N-acetyl analogue: effects on GABAergic function. J Neural Transm Suppl. 1994;41:115-22. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
Current data on this enzyme inhibition is limited to one in vitro study.
General Function
Steroid hydroxylase 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 im...
Gene Name
CYP2C19
Uniprot ID
P33261
Uniprot Name
Cytochrome P450 2C19
Molecular Weight
55930.545 Da
References
  1. Polasek TM, Elliot DJ, Somogyi AA, Gillam EM, Lewis BC, Miners JO: An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid. Br J Clin Pharmacol. 2006 May;61(5):570-84. doi: 10.1111/j.1365-2125.2006.02627.x. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
Curator comments
The inhibition of CYP2C8 by phenelzine is supported by in vitro data. Clinical significance is unknown.
General Function
Steroid hydroxylase 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 un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Polasek TM, Elliot DJ, Lewis BC, Miners JO: Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro. J Pharmacol Exp Ther. 2004 Dec;311(3):996-1007. doi: 10.1124/jpet.104.071803. Epub 2004 Aug 10. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase 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 react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Gillman PK: Advances pertaining to the pharmacology and interactions of irreversible nonselective monoamine oxidase inhibitors. J Clin Psychopharmacol. 2011 Feb;31(1):66-74. doi: 10.1097/JCP.0b013e31820469ea. [Article]
  2. Polasek TM, Elliot DJ, Lewis BC, Miners JO: Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro. J Pharmacol Exp Ther. 2004 Dec;311(3):996-1007. doi: 10.1124/jpet.104.071803. Epub 2004 Aug 10. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
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 un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Polasek TM, Elliot DJ, Somogyi AA, Gillam EM, Lewis BC, Miners JO: An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid. Br J Clin Pharmacol. 2006 May;61(5):570-84. doi: 10.1111/j.1365-2125.2006.02627.x. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Oxygen binding
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 un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Polasek TM, Elliot DJ, Somogyi AA, Gillam EM, Lewis BC, Miners JO: An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid. Br J Clin Pharmacol. 2006 May;61(5):570-84. doi: 10.1111/j.1365-2125.2006.02627.x. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Steroid hydroxylase 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...
Gene Name
CYP2D6
Uniprot ID
P10635
Uniprot Name
Cytochrome P450 2D6
Molecular Weight
55768.94 Da
References
  1. Polasek TM, Elliot DJ, Somogyi AA, Gillam EM, Lewis BC, Miners JO: An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid. Br J Clin Pharmacol. 2006 May;61(5):570-84. doi: 10.1111/j.1365-2125.2006.02627.x. [Article]
Kind
Protein group
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vitamin d3 25-hydroxylase 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 react...

Components:
References
  1. Polasek TM, Elliot DJ, Somogyi AA, Gillam EM, Lewis BC, Miners JO: An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid. Br J Clin Pharmacol. 2006 May;61(5):570-84. doi: 10.1111/j.1365-2125.2006.02627.x. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
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...
Gene Name
MAOA
Uniprot ID
P21397
Uniprot Name
Amine oxidase [flavin-containing] A
Molecular Weight
59681.27 Da
References
  1. MacKenzie EM, Grant SL, Baker GB, Wood PL: Phenelzine causes an increase in brain ornithine that is prevented by prior monoamine oxidase inhibition. Neurochem Res. 2008 Mar;33(3):430-6. Epub 2007 Aug 31. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Primary amine oxidase 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...
Gene Name
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. MacKenzie EM, Grant SL, Baker GB, Wood PL: Phenelzine causes an increase in brain ornithine that is prevented by prior monoamine oxidase inhibition. Neurochem Res. 2008 Mar;33(3):430-6. Epub 2007 Aug 31. [Article]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase 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 ...
Gene Name
CYP2E1
Uniprot ID
P05181
Uniprot Name
Cytochrome P450 2E1
Molecular Weight
56848.42 Da
References
  1. Runge-Morris M, Feng Y, Zangar RC, Novak RF: Effects of hydrazine, phenelzine, and hydralazine treatment on rat hepatic and renal drug-metabolizing enzyme expression. Drug Metab Dispos. 1996 Jul;24(7):734-7. [Article]

Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:59