Details
Stereochemistry | ACHIRAL |
Molecular Formula | C8H12N2.H2O4S |
Molecular Weight | 234.2742 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
c1ccc(cc1)CCNN.OS(=O)(=O)O
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 | 136.1946 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | H2O4S |
Molecular Weight | 98.0796 |
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 |
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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 |
---|---|---|
Abuse of monoamine oxidase inhibitors. | 1992 |
|
Depression after cyproheptadine: MAO treatment. | 1992 Jun 1 |
|
Possible interaction between an MAOI and "ecstasy". | 1992 Mar |
|
Phenelzine-induced sexual dysfunction treated with sildenafil. | 1999 Apr-Jun |
|
[Clinical case of the month. Mental confusion due to the administration of tramadol in a patient treated with MOAI]. | 1999 Dec |
|
Treatment of social phobia with antidepressants. | 2001 |
|
Current status of psychotherapeutic interventions for social phobia. | 2001 |
|
Social phobia: etiology, neurobiology, and treatment. | 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 |
|
[The safety of herbal medicines in the psychiatric practice]. | 2001 Aug |
|
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 |
|
Effect of chronic phenelzine treatment on REM sleep: report of three patients. | 2001 Nov |
|
Synthesis of N-propargylphenelzine and analogues as neuroprotective agents. | 2001 Oct 22 |
|
Influence of different antidepressant drugs on the effect of chronic variable stress on restraint-induced dopamine release in frontal cortex. | 2001 Sep |
|
Panax ginseng: a systematic review of adverse effects and drug interactions. | 2002 |
|
Effects of psychotropic drugs on seizure threshold. | 2002 |
|
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 |
|
Effects of the antidepressant/antipanic drug phenelzine and its putative metabolite phenylethylidenehydrazine on extracellular gamma-aminobutyric acid levels in the striatum. | 2002 Jan 1 |
|
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 |
|
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 |
|
Effect of antidepressants on GABA(B) receptor function and subunit expression in rat hippocampus. | 2004 Oct 15 |
|
Modafinil augmentation of phenelzine for residual fatigue in dysthymia. | 2004 Sep |
|
Sleep and psychiatry. | 2005 |
|
Herb-drug interactions: a literature review. | 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 |
|
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 |
|
Pharmacotherapy of social anxiety disorder: what does the evidence tell us? | 2006 |
|
Monoamine oxidase inhibitors allow locomotor and rewarding responses to nicotine. | 2006 Aug |
|
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 |
|
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 |
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
Sat Jun 26 03:44:55 UTC 2021
by
admin
on
Sat Jun 26 03:44:55 UTC 2021
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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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-
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C667
Created by
admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
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Code System | Code | Type | Description | ||
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M8605
Created by
admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
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PRIMARY | Merck Index | ||
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2681D7P965
Created by
admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
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PRIMARY | |||
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8124
Created by
admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
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PRIMARY | RxNorm | ||
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205-856-0
Created by
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PRIMARY | |||
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CHEMBL1089
Created by
admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
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PRIMARY | |||
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156-51-4
Created by
admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
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PRIMARY | |||
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1517006
Created by
admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
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PRIMARY | USP-RS | ||
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DBSALT000954
Created by
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PRIMARY | |||
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156-51-4
Created by
admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
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PRIMARY | |||
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SUB03740MIG
Created by
admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
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PRIMARY | |||
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C47668
Created by
admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
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PRIMARY | |||
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61100
Created by
admin on Sat Jun 26 03:44:55 UTC 2021 , Edited by admin on Sat Jun 26 03:44:55 UTC 2021
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PRIMARY |
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PARENT -> SALT/SOLVATE |
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ACTIVE MOIETY |