PHENELZINE SULFATE

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

Structure Search

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)

HIDE SMILES / InChI

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

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Monoamine oxidase A 48 Target ID: CHEMBL1951 Sources: http://www.drugbank.ca/drugs/DB00780	Inhibitor 7728
Monoamine oxidase B 66 Target ID: CHEMBL2039 Sources: http://www.drugbank.ca/drugs/DB00780	Inhibitor 7728
Monoamine oxidase B 66 Target ID: CHEMBL2993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11591508	Inhibitor 7728	76.3 nM [IC50]
Monoamine oxidase A 48 Target ID: CHEMBL3358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11591508	Inhibitor 7728	30.0 nM [IC50]
Cytochrome P450 2C19 49 Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16669850	Inhibitor 7728
Cytochrome P450 3A 21 Target ID: CHEMBL2364675 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16669850	Inhibitor 7728

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 215 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf	Primary		Approved 8043	Nardil Approved Use Nardil is used for: Treating depression in patients who do not respond well to other medicines. Launch Date -2.70345601E11

C_max

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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf	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

T_1/2

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 DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf	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 Dose: 750 mg Route: oral Route: single Dose: 750 mg Sources: https://pubmed.ncbi.nlm.nih.gov/14489944	unhealthy, 20 n = 1 Health Status: unhealthy Condition: Depression Age Group: 20 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14489944	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: https://pubmed.ncbi.nlm.nih.gov/14489944
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: https://pubmed.ncbi.nlm.nih.gov/17823790 Page: p.1007	unhealthy, 23 n = 1 Health Status: unhealthy Condition: Depression Age Group: 23 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/17823790 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: https://pubmed.ncbi.nlm.nih.gov/17823790 Page: p.1007
225 mg single, oral Overdose Dose: 225 mg Route: oral Route: single Dose: 225 mg Sources: https://pubmed.ncbi.nlm.nih.gov/6391305 Page: p.1137/99	unhealthy, 26 n = 1 Health Status: unhealthy Condition: Depression Age Group: 26 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/6391305 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: https://pubmed.ncbi.nlm.nih.gov/6391305 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Depression Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf Page: p.1	Disc. AE: Suicidal ideation... AEs leading to discontinuation/dose reduction: Suicidal ideation Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf 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: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf Page: p.6	unhealthy Health Status: unhealthy Condition: Depression Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf Page: p.6	Disc. AE: Crisis hypertensive... AEs leading to discontinuation/dose reduction: Crisis hypertensive Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf Page: p.6

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1467	inhibitor 1604	inhibitor 1702	inhibitor 1475

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 818 CYP1A2 1383 CYP2C19 1325 CYP3A 191 CYP3A5 70 CYP3A7 7 CYP2A6 627 CYP2E1 790 P-gp 1330 BSEP 376 OATP1B1 733 OATP1B3 657

Drug as perpetrator

Target	Modality	Activity
CYP2A6 659	inhibitor 3045 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEwODkifX0%3D	no [IC50 >10 uM]
CYP2E1 871	inhibitor 3045 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEwODkifX0%3D	no [IC50 >10 uM]
P-gp 1514	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/16997908/	no
BSEP 377	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/22961681/	unlikely [IC50 >897.2 uM]
CYP2C8 865	inhibitor 3045 Sources: https://go.drugbank.com/drugs/DB00780\| https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=biology&ligandId=7266	yes [Ki 1.2 uM]
CYP1A2 1532	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/16669850/\| https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2C19 1392	inhibitor 3045 Sources: https://go.drugbank.com/drugs/DB00780\| https://pubmed.ncbi.nlm.nih.gov/16669850/, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2C9 1648	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/16669850/\| https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2D6 1738	inhibitor 3045 Sources: https://go.drugbank.com/drugs/DB00780\| https://pubmed.ncbi.nlm.nih.gov/16669850/, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP3A 271	inhibitor 3045 Sources: https://go.drugbank.com/drugs/DB00780\| https://pubmed.ncbi.nlm.nih.gov/16669850/	yes
CYP3A4 1772	inhibitor 3045 Sources: https://go.drugbank.com/drugs/DB00780\| https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP3A5 122	inhibitor 3045 Sources: https://go.drugbank.com/drugs/DB00780 \| https://pubmed.ncbi.nlm.nih.gov/16669850/	yes
CYP3A7 21	inhibitor 3045 Sources: https://go.drugbank.com/drugs/DB00780 \| https://pubmed.ncbi.nlm.nih.gov/16669850/	yes
OATP1B1 748	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
OATP1B3 666	inhibitor 3045 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1507	inhibitor 1489 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMTA4OSJ9fQ%3D%3D

Sourcing

Vendor/Aggregator	ID	URL
3B Scientific (Wuhan) Corp	3B3-036093	http://www.3bsc.com/index/pro_info.php?id=58125
AA Blocks	AA00I926	https://www.aablocks.com/goods/Goods/detail?id=AA00I926
AHH Chemical co.,ltd	MT-20901	http://www.ahhchemical.com/product/MT-20901.html
AK Scientific, Inc. (AKSCI)	4752AE	http://www.aksci.com/item_detail.php?cat=4752AE
Alfa Chemistry	51-71-8	https://www.alfa-chemistry.com/phenelzine-cas-51-71-8-item-168473.htm
Alichem	250001552	http://www.alichem.com/en/products/51-71-8.html
Ambinter	Amb1117029	http://www.ambinter.com/reference/1117029
Angel Pharmatech	AG199778	http://www.angelpharmatech.com/51-71-8.html
Angene	AGN-PC-0JK6MF	http://www.angenechemical.com/productshow/AGN-PC-0JK6MF.html
Aurora Fine Chemicals LLC	A00.215.116	http://online.aurorafinechemicals.com/info?ID=A00.215.116
BLD Pharm	BD44517	http://www.bldpharm.com/products/51-71-8.html
CSNpharm	CSN16899	https://www.csnpharm.com/products/phenelzine.html
Capot Chemical	16246	http://www.capotchem.com/en/16246.htm
Capot Chemical	PubChem16246	http://www.capotchem.com/en/16246.htm
Chem Scene	CS-4532	http://www.chemscene.com/51-71-8.html
ChemMol	49417192	http://www.chemmol.com/chemmol/49417192.html
Debye Scientific	DB-052010	http://www.debyesci.com/cas_51-71-8.html
Finetech	FT-0631225	http://www.finetechnology-ind.com/prod/detail/pub/51-71-8.html
Hairui	HR100277	http://www.hairuichem.com/en/product/51-71-8.html
Lab Network	LN00126164	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00126164
Matrix Scientific	20638	https://www.matrixscientific.com/020638.html
MedChem Express	HY-B1018	https://www.medchemexpress.com/Phenelzine.html
MuseChem	I003863	https://www.musechem.com/product/I003863.html
OChem	4816	http://www.ocheminc.com/index.php?act=psearch&pid=047P825
Sigma-Aldrich	CDS021446_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/cds021446?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S017495	http://www.sinfoobiotech.com/product/1020893
Smolecule	S568415	https://www.smolecule.com/products/s568415
THE BioTek	bt-315150	https://www.thebiotek.com/product/others/bt-315150
abcr GmbH	AB200546	http://www.abcr.com/shop/en/AB200546
iChemical	EBD46347	http://www.ichemical.com/products/51-71-8.html?utm_source=PubChem&utm_medium=website&utm_campaign=product%20catalogs
mcule	MCULE-2911295500	https://mcule.com/MCULE-2911295500/

PubMed

Title	Date	PubMed
Abuse of monoamine oxidase inhibitors.	1992	1449122
Depression after cyproheptadine: MAO treatment.	1992 Jun 1	1525285
Possible interaction between an MAOI and "ecstasy".	1992 Mar	1346952
Phenelzine-induced sexual dysfunction treated with sildenafil.	1999 Apr-Jun	10327382
[Clinical case of the month. Mental confusion due to the administration of tramadol in a patient treated with MOAI].	1999 Dec	10686795
Treatment of social phobia with antidepressants.	2001	11206033
Current status of psychotherapeutic interventions for social phobia.	2001	11206032
Social phobia: etiology, neurobiology, and treatment.	2001	11206031
Animal models for the study of antidepressant activity.	2001 Apr	11275519
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	11358224
[The safety of herbal medicines in the psychiatric practice].	2001 Aug	11547487
Sleep and sleep electroencephalogram in depressed patients treated with phenelzine.	2001 Mar	11231834
Inhibition of MAO-A fails to alter cocaine-induced increases in extracellular dopamine and norepinephrine in rat nucleus accumbens.	2001 Mar 5	11245920
Effect of chronic phenelzine treatment on REM sleep: report of three patients.	2001 Nov	11682276
Synthesis of N-propargylphenelzine and analogues as neuroprotective agents.	2001 Oct 22	11591508
Influence of different antidepressant drugs on the effect of chronic variable stress on restraint-induced dopamine release in frontal cortex.	2001 Sep	11522466
Panax ginseng: a systematic review of adverse effects and drug interactions.	2002	12020172
Effects of psychotropic drugs on seizure threshold.	2002	11888352
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	12527476
Selective mutism: a review of the concept and treatment.	2002 Dec	12516908
Endogenous and endobiotic induced reactive oxygen species formation by isolated hepatocytes.	2002 Jan 1	11755311
Effects of the antidepressant/antipanic drug phenelzine and its putative metabolite phenylethylidenehydrazine on extracellular gamma-aminobutyric acid levels in the striatum.	2002 Jan 1	11754874
Clonidine potentiates the effects of tranylcypromine, phenelzine and two analogues in the forced swimming test in mice.	2002 May	12066447
World Federation of Societies of Biological Psychiatry (WFSBP) guidelines for the pharmacological treatment of anxiety, obsessive-compulsive and posttraumatic stress disorders.	2002 Oct	12516310
Selectively bred Wistar-Kyoto rats: an animal model of depression and hyper-responsiveness to antidepressants.	2003 Nov	14593430
Mechanism-based inactivation of human cytochrome P4502C8 by drugs in vitro.	2004 Dec	15304522
Effect of antidepressants on GABA(B) receptor function and subunit expression in rat hippocampus.	2004 Oct 15	15451391
Modafinil augmentation of phenelzine for residual fatigue in dysthymia.	2004 Sep	15337670
Sleep and psychiatry.	2005	16416705
Herb-drug interactions: a literature review.	2005	15916450
Screening antidepressants in the chick separation-stress paradigm.	2005 Aug	15778882
Brainstem levels of transcription factor AP-2 in rat are changed after treatment with phenelzine, but not with citalopram.	2005 Jan 21	15663788
Shy-Drager syndrome: multisystem atrophy with comorbid depression.	2005 Jan-Feb	15765825
Chronic treatment with the monoamine oxidase inhibitor phenelzine increases hypothalamic-pituitary-adrenocortical activity in male C57BL/6 mice: relevance to atypical depression.	2005 Mar	15564336
Cytochrome p450 enzymes mechanism based inhibitors: common sub-structures and reactivity.	2005 Oct	16248836
Pharmacotherapy of social anxiety disorder: what does the evidence tell us?	2006	17092192
Monoamine oxidase inhibitors allow locomotor and rewarding responses to nicotine.	2006 Aug	16395299
Rapid identification of P-glycoprotein substrates and inhibitors.	2006 Dec	16997908
The effect of antidepressants on glucose homeostasis and insulin sensitivity: synthesis and mechanisms.	2006 Jan	16370964
Effects of monoamine oxidase inhibitors on cocaine discrimination in rats.	2006 Mar	16495723
Modeling anxiety-like states: pharmacological characterization of the chick separation stress paradigm.	2006 Nov	17021390
Aldehyde load in ischemia-reperfusion brain injury: neuroprotection by neutralization of reactive aldehydes with phenelzine.	2006 Nov 29	17026969
Sustained effects of phenelzine and tranylcypromine on orthostatic challenge in antidepressant-refractory depression.	2006 Oct	16974207
Antidepressants and inflammatory bowel disease: a systematic review.	2006 Sep 20	16984660
Antidepressant therapy in tinnitus.	2007 Apr	16973315
Successful use of phenelzine in treatment-resistant panic disorder.	2007 Feb	17335337

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Sat Jun 26 03:44:55 UTC 2021` Edited by `admin` on `Sat Jun 26 03:44:55 UTC 2021`
Record UNII	2681D7P965
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PHENELZINE SULFATE

Common Name

English

PHENETHYLHYDRAZINE SULPHATE (1:1)

Systematic Name

English

PHENELZINE SULFATE [VANDF]

Common Name

English

PHENELZINE SULPHATE

Common Name

English

HYDRAZINE, (2-PHENYLETHYL)-, SULPHATE (1:1)

Systematic Name

English

PHENELZINE SULFATE [IARC]

Common Name

English

NARDIL

Brand Name

English

PHENELZINE SULFATE [WHO-DD]

Common Name

English

HYDRAZINE, (2-PHENYLETHYL)-, SULFATE (1:1)

Systematic Name

English

PHENELZINE ACID SULFATE [MI]

Common Name

English

PHENELZINE SULFATE [ORANGE BOOK]

Common Name

English

NSC-170957

Code

English

PHENELZINE SULFATE [USP-RS]

Common Name

English

PHENELZINE SULFATE [USP]

Common Name

English

PHENELZINE SULFATE [MART.]

Common Name

English

PHENETHYLHYDRAZINE SULFATE (1:1)

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C667