U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C8H12N2
Molecular Weight 136.1946
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PHENELZINE

SMILES

c1ccc(cc1)CCNN

InChI

InChIKey=RMUCZJUITONUFY-UHFFFAOYSA-N
InChI=1S/C8H12N2/c9-10-7-6-8-4-2-1-3-5-8/h1-5,10H,6-7,9H2

HIDE SMILES / InChI

Description
Curator's Comment:: Description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf

Phenelzine is an irreversible non-selective inhibitor of monoamine oxidase. Although the exact mechanism of action has not been determined, it appears that the irreversible, nonselective inhibition of MAO by phenelzine relieves depressive symptoms by causing an increase in the levels of serotonin, norepinephrine, and dopamine in the neuron. Phenelzine is used for the treatment of major depressive disorder. Has also been used with some success in the management of bulimia nervosa.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Nardil

Approved Use

Nardil is used for: Treating depression in patients who do not respond well to other medicines.

Launch Date

-2.70345601E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
10.14 ng/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENELZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
19.8 ng/mL
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENELZINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
384.2 ng × h/mL
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENELZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9.75 h
15 mg single, oral
dose: 15 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENELZINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
11.6 h
30 mg single, oral
dose: 30 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
PHENELZINE plasma
Homo sapiens
population: UNKNOWN
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Disc. AE: Weakness, Lethargy...
AEs leading to
discontinuation/dose reduction:
Weakness
Lethargy
Dizziness
Gait abnormal NOS
Restlessness
Grand mal seizure
Hyperreflexia
Coma
Depression central nervous system
Sources:
2760 mg single, oral
Overdose
Dose: 2760 mg
Route: oral
Route: single
Dose: 2760 mg
Co-administed with::
olanzapine, p.o(50 mg; single)
Sources: Page: p.1007
unhealthy, 23
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 23
Sex: F
Population Size: 1
Sources: Page: p.1007
Disc. AE: Depressed level of consciousness, Seizures...
AEs leading to
discontinuation/dose reduction:
Depressed level of consciousness
Seizures
Tachycardia
Acute myocarditis (grade 5)
Sources: Page: p.1007
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Disc. AE: Muscular tone excessive, Hyperthermia...
AEs leading to
discontinuation/dose reduction:
Muscular tone excessive
Hyperthermia (severe)
Coma
Cardiovascular collapse
Acute renal failure
Hemolysis
Rhabdomyolysis
Disseminated intravascular coagulation
Sources: Page: p.1137/99
90 mg 1 times / day multiple, oral
Recommended
Dose: 90 mg, 1 times / day
Route: oral
Route: multiple
Dose: 90 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Depression
Sources: Page: p.1
Disc. AE: Suicidal ideation...
AEs leading to
discontinuation/dose reduction:
Suicidal ideation
Sources: Page: p.1
90 mg 1 times / day multiple, oral
Recommended
Dose: 90 mg, 1 times / day
Route: oral
Route: multiple
Dose: 90 mg, 1 times / day
Sources: Page: p.6
unhealthy
Health Status: unhealthy
Condition: Depression
Sources: Page: p.6
Disc. AE: Crisis hypertensive...
AEs leading to
discontinuation/dose reduction:
Crisis hypertensive
Sources: Page: p.6
AEs

AEs

AESignificanceDosePopulation
Coma Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Depression central nervous system Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Dizziness Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Gait abnormal NOS Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Grand mal seizure Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Hyperreflexia Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Lethargy Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Restlessness Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Weakness Disc. AE
750 mg single, oral
Overdose
Dose: 750 mg
Route: oral
Route: single
Dose: 750 mg
Sources:
unhealthy, 20
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 20
Sex: F
Population Size: 1
Sources:
Depressed level of consciousness Disc. AE
2760 mg single, oral
Overdose
Dose: 2760 mg
Route: oral
Route: single
Dose: 2760 mg
Co-administed with::
olanzapine, p.o(50 mg; single)
Sources: Page: p.1007
unhealthy, 23
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 23
Sex: F
Population Size: 1
Sources: Page: p.1007
Seizures Disc. AE
2760 mg single, oral
Overdose
Dose: 2760 mg
Route: oral
Route: single
Dose: 2760 mg
Co-administed with::
olanzapine, p.o(50 mg; single)
Sources: Page: p.1007
unhealthy, 23
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 23
Sex: F
Population Size: 1
Sources: Page: p.1007
Tachycardia Disc. AE
2760 mg single, oral
Overdose
Dose: 2760 mg
Route: oral
Route: single
Dose: 2760 mg
Co-administed with::
olanzapine, p.o(50 mg; single)
Sources: Page: p.1007
unhealthy, 23
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 23
Sex: F
Population Size: 1
Sources: Page: p.1007
Acute myocarditis grade 5
Disc. AE
2760 mg single, oral
Overdose
Dose: 2760 mg
Route: oral
Route: single
Dose: 2760 mg
Co-administed with::
olanzapine, p.o(50 mg; single)
Sources: Page: p.1007
unhealthy, 23
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 23
Sex: F
Population Size: 1
Sources: Page: p.1007
Acute renal failure Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Cardiovascular collapse Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Coma Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Disseminated intravascular coagulation Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Hemolysis Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Muscular tone excessive Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Rhabdomyolysis Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Hyperthermia severe
Disc. AE
225 mg single, oral
Overdose
Dose: 225 mg
Route: oral
Route: single
Dose: 225 mg
Sources: Page: p.1137/99
unhealthy, 26
n = 1
Health Status: unhealthy
Condition: Depression
Age Group: 26
Sex: F
Population Size: 1
Sources: Page: p.1137/99
Suicidal ideation Disc. AE
90 mg 1 times / day multiple, oral
Recommended
Dose: 90 mg, 1 times / day
Route: oral
Route: multiple
Dose: 90 mg, 1 times / day
Sources: Page: p.1
unhealthy
Health Status: unhealthy
Condition: Depression
Sources: Page: p.1
Crisis hypertensive Disc. AE
90 mg 1 times / day multiple, oral
Recommended
Dose: 90 mg, 1 times / day
Route: oral
Route: multiple
Dose: 90 mg, 1 times / day
Sources: Page: p.6
unhealthy
Health Status: unhealthy
Condition: Depression
Sources: Page: p.6
Overview

Overview

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
no [IC50 >10 uM]
no [IC50 >10 uM]
no
unlikely [IC50 >897.2 uM]
yes [Ki 1.2 uM]
yes
yes
yes
yes
yes
yes
yes
yes
yes
yes
Tox targets
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Phenelzine associated peripheral neuropathy--clinical and electrophysiologic findings.
1991 Jun
Abuse of monoamine oxidase inhibitors.
1992
Depression after cyproheptadine: MAO treatment.
1992 Jun 1
Antioxidant effect of phenelzine on MPP+-induced cell viability loss in differentiated PC12 cells.
2003 Dec
A quantitative neuromotor predictor of antidepressant non-response in patients with major depression.
2003 Nov
Panax ginseng.
2003 Oct 15
[Classical monoamine oxidase inhibitor: not registered for, but still a place in the treatment of depression].
2003 Oct 4
Phenylethylidenehydrazine, a novel GABA-transaminase inhibitor, reduces epileptiform activity in rat hippocampal slices.
2004
Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro.
2004 Dec
[Neurobiology and pharmacotherapy of social phobia].
2004 Jul-Aug
Hypericum perforatum L (St John's wort) preferentially increases extracellular dopamine levels in the rat prefrontal cortex.
2004 Jun
Efficacy of quality criteria to identify potentially harmful information: a cross-sectional survey of complementary and alternative medicine web sites.
2004 Jun 29
Coadministration of phenelzine and methylphenidate for treatment-resistant depression.
2004 Mar
Efficacy and tolerability of tranylcypromine versus phenelzine: a double-blind study in antidepressant-refractory depressed inpatients.
2004 Nov
Effect of antidepressants on GABA(B) receptor function and subunit expression in rat hippocampus.
2004 Oct 15
Monoamine oxidase inhibitors, their structural analogues, and neuroprotection.
2004 Sep
Modafinil augmentation of phenelzine for residual fatigue in dysthymia.
2004 Sep
Sleep and psychiatry.
2005
Neuroendocrine predictors of the evolution of depression.
2005
Herb-drug interactions: a literature review.
2005
Validity of sudden gains in acute phase treatment of depression.
2005 Feb
Brainstem levels of transcription factor AP-2 in rat are changed after treatment with phenelzine, but not with citalopram.
2005 Jan 21
A microarray study of MPP+-treated PC12 Cells: Mechanisms of toxicity (MOT) analysis using bioinformatics tools.
2005 Jul 15
Inhibition of monoamine oxidase-A activity in rat brain by synthetic hydrazines: structure-activity relationship (SAR).
2005 Jun
Remission rates with 3 consecutive antidepressant trials: effectiveness for depressed outpatients.
2005 Jun
Chronic treatment with the monoamine oxidase inhibitor phenelzine increases hypothalamic-pituitary-adrenocortical activity in male C57BL/6 mice: relevance to atypical depression.
2005 Mar
Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.
2005 Oct
A selective test for antidepressant treatments using rats bred for stress-induced reduction of motor activity in the swim test.
2005 Oct
Traumatic stress: effects on the brain.
2006
Pharmacotherapy of social anxiety disorder: what does the evidence tell us?
2006
Antidepressants reverse corticosterone-mediated decrease in brain-derived neurotrophic factor expression: differential regulation of specific exons by antidepressants and corticosterone.
2006
Use of antidepressant medications in relation to the incidence of breast cancer.
2006 Apr 10
Monoamine oxidase inhibitors allow locomotor and rewarding responses to nicotine.
2006 Aug
Serotonin syndrome from the interaction of cyclobenzaprine with other serotoninergic drugs.
2006 Dec
Rapid identification of P-glycoprotein substrates and inhibitors.
2006 Dec
The effect of antidepressants on glucose homeostasis and insulin sensitivity: synthesis and mechanisms.
2006 Jan
Effects of monoamine oxidase inhibitors on cocaine discrimination in rats.
2006 Mar
Quetiapine for insomnia associated with refractory depression exacerbated by phenelzine.
2006 Mar
An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid.
2006 May
Transdermal selegiline: the new generation of monoamine oxidase inhibitors.
2006 May
Leading the way: advances in the diagnosis, treatment, and management of neuropsychiatric illnesses.
2006 May
Tamoxifen protect against hydroxyl radical generation induced by phenelzine in rat striatum.
2006 May 1
13C magnetic resonance spectroscopy studies of alterations in glutamate neurotransmission.
2006 May 15
Increased nicotine self-administration following prenatal exposure in female rats.
2006 Nov
Modeling anxiety-like states: pharmacological characterization of the chick separation stress paradigm.
2006 Nov
Aldehyde load in ischemia-reperfusion brain injury: neuroprotection by neutralization of reactive aldehydes with phenelzine.
2006 Nov 29
Sustained effects of phenelzine and tranylcypromine on orthostatic challenge in antidepressant-refractory depression.
2006 Oct
Antidepressants and inflammatory bowel disease: a systematic review.
2006 Sep 20
Antidepressant therapy in tinnitus.
2007 Apr
Successful use of phenelzine in treatment-resistant panic disorder.
2007 Feb
Patents

Sample Use Guides

Initial dose: The usual starting dose of NARDIL is one tablet (15 mg) three times a day. Early phase treatment: Dosage should be increased to at least 60 mg per day at a fairly rapid pace consistent with patient tolerance. It may be necessary to increase dosage up to 90 mg per day to obtain sufficient MAO inhibition. Many patients do not show a clinical response until treatment at 60 mg has been continued for at least 4 weeks.
Route of Administration: Oral
20 uM of Phenelzine inactivated all human liver microsomal CYP (CYP1A2, CYP2C9, CYP2C19, CYP2D6 and CYP3A) but were most potent toward CYP3A and CYP2C19
Name Type Language
PHENELZINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
PHENETHYLHYDRAZINE
Systematic Name English
HYDRAZINE, (2-PHENYLETHYL)-
Systematic Name English
PHENELZINE [VANDF]
Common Name English
PHENELZINE [WHO-DD]
Common Name English
PHENELZINE [MI]
Common Name English
PHENELZINE [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C667
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
NDF-RT N0000000184
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
WHO-VATC QN06AF03
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
NCI_THESAURUS C265
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
WHO-ATC N06AF03
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
LIVERTOX 768
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
NDF-RT N0000175744
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
Code System Code Type Description
HSDB
8127
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
EPA CompTox
51-71-8
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
RXCUI
8123
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY RxNorm
NCI_THESAURUS
C61888
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
MESH
D010624
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
DRUG BANK
DB00780
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
DRUG CENTRAL
2123
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
CAS
51-71-8
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
INN
919
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
IUPHAR
7266
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
LACTMED
Phenelzine
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-117-9
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
ChEMBL
CHEMBL1089
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
FDA UNII
O408N561GF
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
WIKIPEDIA
PHENELZINE
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
MERCK INDEX
M8605
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY Merck Index
EVMPD
SUB09757MIG
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY
PUBCHEM
3675
Created by admin on Sat Jun 26 04:01:49 UTC 2021 , Edited by admin on Sat Jun 26 04:01:49 UTC 2021
PRIMARY