Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H12N2.H2O4S |
Molecular Weight | 234.273 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.NNCCC1=CC=CC=C1
InChI
InChIKey=RXBKMJIPNDOHFR-UHFFFAOYSA-N
InChI=1S/C8H12N2.H2O4S/c9-10-7-6-8-4-2-1-3-5-8;1-5(2,3)4/h1-5,10H,6-7,9H2;(H2,1,2,3,4)
Molecular Formula | C8H12N2 |
Molecular Weight | 136.1943 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | H2O4S |
Molecular Weight | 98.078 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB00780Curator's Comment: Description was created based on several sources, including
https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00780
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1951 Sources: http://www.drugbank.ca/drugs/DB00780 |
|||
Target ID: CHEMBL2039 Sources: http://www.drugbank.ca/drugs/DB00780 |
|||
Target ID: CHEMBL2993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11591508 |
76.3 nM [IC50] | ||
Target ID: CHEMBL3358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11591508 |
30.0 nM [IC50] | ||
Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16669850 |
|||
Target ID: CHEMBL2364675 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16669850 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Nardil Approved UseNardil is used for:
Treating depression in patients who do not respond well to other medicines. Launch Date-2.70345601E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.14 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27085800 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
384.2 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27085800 |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.75 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27085800 |
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
Dose | Population | Adverse events |
---|---|---|
750 mg single, oral Overdose |
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 Sources: Lethargy Dizziness Gait abnormal NOS Restlessness Grand mal seizure Hyperreflexia Coma Depression central nervous system |
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 Sources: Page: p.1007Seizures Tachycardia Acute myocarditis (grade 5) |
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 Sources: Page: p.1137/99Hyperthermia (severe) Coma Cardiovascular collapse Acute renal failure Hemolysis Rhabdomyolysis Disseminated intravascular coagulation |
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
AE | Significance | Dose | Population |
---|---|---|---|
Coma | Disc. AE | 750 mg single, oral Overdose |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical 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
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
PubMed
Title | Date | PubMed |
---|---|---|
The antidepressants fluoxetine, idazoxan and phenelzine alter corticotropin-releasing hormone and tyrosine hydroxylase mRNA levels in rat brain: therapeutic implications. | 1992 Feb 14 |
|
Possible interaction between an MAOI and "ecstasy". | 1992 Mar |
|
Interactions between herbal medicines and prescribed drugs: a systematic review. | 2001 |
|
Treatment of social phobia with antidepressants. | 2001 |
|
Animal models for the study of antidepressant activity. | 2001 Apr |
|
Application of capillary electrophoresis with laser-induced fluorescence detection to the determination of biogenic amines and amino acids in brain microdialysate and homogenate samples. | 2001 Apr 20 |
|
[Liver angiosarcoma in humans: epidemiologic considerations]. | 2001 Jan-Feb |
|
The role of dopamine-metabolizing enzymes in the regulation of renal sodium excretion in the rat. | 2001 Jul |
|
Common effects of chronically administered antipanic drugs on brainstem GABA(A) receptor subunit gene expression. | 2001 Jul |
|
Sleep and sleep electroencephalogram in depressed patients treated with phenelzine. | 2001 Mar |
|
Inhibition of MAO-A fails to alter cocaine-induced increases in extracellular dopamine and norepinephrine in rat nucleus accumbens. | 2001 Mar 5 |
|
The management of panic disorder. | 2002 |
|
Panax ginseng: a systematic review of adverse effects and drug interactions. | 2002 |
|
Effects of psychotropic drugs on seizure threshold. | 2002 |
|
Remission in major depressive disorder: a comparison of pharmacotherapy, psychotherapy, and control conditions. | 2002 Aug |
|
Effects of antidepressants in rats trained to discriminate centrally administered isoproterenol. | 2002 Aug |
|
Antidepressants reduce phosphoinositide-specific phospholipase C (PI-PLC) activity and the mRNA and protein expression of selective PLC beta 1 isozyme in rat brain. | 2002 Dec |
|
Selective mutism: a review of the concept and treatment. | 2002 Dec |
|
Endogenous and endobiotic induced reactive oxygen species formation by isolated hepatocytes. | 2002 Jan 1 |
|
The effects of tricyclic antidepressants on breast cancer risk. | 2002 Jan 7 |
|
Clonidine potentiates the effects of tranylcypromine, phenelzine and two analogues in the forced swimming test in mice. | 2002 May |
|
World Federation of Societies of Biological Psychiatry (WFSBP) guidelines for the pharmacological treatment of anxiety, obsessive-compulsive and posttraumatic stress disorders. | 2002 Oct |
|
Different effects of phenelzine treatment on EEG topography in waking and sleep in depressed patients. | 2002 Sep |
|
Differential blockade of neuronal voltage-gated Na(+) and K(+) channels by antidepressant drugs. | 2002 Sep 27 |
|
Pharmacological treatment of social anxiety disorder: a meta-analysis. | 2003 |
|
Phenelzine efficacy in refractory social anxiety disorder: a case series. | 2003 |
|
Phenelzine treatment increases transcription factor AP-2 levels in rat brain. | 2003 Aug 28 |
|
Prior exposure to the elevated plus-maze sensitizes mice to the acute behavioral effects of fluoxetine and phenelzine. | 2003 Jan 17 |
|
Comparing depression treatments. | 2003 Jun |
|
Rapid tryptophan depletion reverses phenelzine-induced suppression of REM sleep. | 2003 Mar |
|
Selectively bred Wistar-Kyoto rats: an animal model of depression and hyper-responsiveness to antidepressants. | 2003 Nov |
|
Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro. | 2004 Dec |
|
[Neurobiology and pharmacotherapy of social phobia]. | 2004 Jul-Aug |
|
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 |
|
Monoamine oxidase inhibitors, their structural analogues, and neuroprotection. | 2004 Sep |
|
Contribution of sleep research to the development of new antidepressants. | 2005 |
|
Neuroendocrine predictors of the evolution of depression. | 2005 |
|
Social anxiety disorder : current treatment recommendations. | 2005 |
|
Screening antidepressants in the chick separation-stress paradigm. | 2005 Aug |
|
Brainstem levels of transcription factor AP-2 in rat are changed after treatment with phenelzine, but not with citalopram. | 2005 Jan 21 |
|
Shy-Drager syndrome: multisystem atrophy with comorbid depression. | 2005 Jan-Feb |
|
A microarray study of MPP+-treated PC12 Cells: Mechanisms of toxicity (MOT) analysis using bioinformatics tools. | 2005 Jul 15 |
|
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 |
|
Pharmacotherapy of social anxiety disorder: what does the evidence tell us? | 2006 |
|
Monoamine oxidase inhibitors allow locomotor and rewarding responses to nicotine. | 2006 Aug |
|
Transdermal selegiline: the new generation of monoamine oxidase inhibitors. | 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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16669850
20 uM of Phenelzine inactivated all human liver microsomal CYP (CYP1A2, CYP2C9, CYP2C19, CYP2D6 and CYP3A) but were most potent toward CYP3A and CYP2C19
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:34:24 UTC 2023
by
admin
on
Wed Jul 05 22:34:24 UTC 2023
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Record UNII |
2681D7P965
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C667
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M8605
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PRIMARY | Merck Index | ||
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2681D7P965
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8124
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205-856-0
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CHEMBL1089
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DTXSID3021144
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DBSALT000954
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156-51-4
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1517006
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SUB03740MIG
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C47668
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100000092820
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170957
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61100
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2681D7P965
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |