PHENELZINE SULFATE

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

Structure Search

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)

HIDE SMILES / InChI

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

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

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 49 Target ID: CHEMBL1951 Sources: http://www.drugbank.ca/drugs/DB00780	Inhibitor 8297
Monoamine oxidase B 72 Target ID: CHEMBL2039 Sources: http://www.drugbank.ca/drugs/DB00780	Inhibitor 8297
Monoamine oxidase B 72 Target ID: CHEMBL2993 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11591508	Inhibitor 8297	76.3 nM [IC50]
Monoamine oxidase A 49 Target ID: CHEMBL3358 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11591508	Inhibitor 8297	30.0 nM [IC50]
Cytochrome P450 2C19 51 Target ID: CHEMBL3622 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16669850	Inhibitor 8297
Cytochrome P450 3A 22 Target ID: CHEMBL2364675 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16669850	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Depression 235 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2007/011909s038lbl.pdf	Primary		Approved 8429	Nardil Approved Use Nardil is used for: Treating depression in patients who do not respond well to other medicines. Launch Date 1961

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 1587	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP2C8 911 CYP1A2 1524 CYP2C19 1478 CYP3A 214 CYP3A5 73 CYP3A7 7 CYP2A6 707 CYP2E1 882 P-gp 1461 BSEP 402 OATP1B1 788 OATP1B3 706

Drug as perpetrator

Target	Modality	Activity
CYP2A6 739	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEwODkifX0%3D	no [IC50 >10 uM]
CYP2E1 970	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDEwODkifX0%3D	no [IC50 >10 uM]
P-gp 1650	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16997908/	no
BSEP 403	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/22961681/	unlikely [IC50 >897.2 uM]
CYP2C8 965	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00780\| https://www.guidetopharmacology.org/GRAC/LigandDisplayForward?tab=biology&ligandId=7266	yes [Ki 1.2 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16669850/\| https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2C19 1553	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00780\| https://pubmed.ncbi.nlm.nih.gov/16669850/, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2C9 1819	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/16669850/\| https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP2D6 1891	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00780\| https://pubmed.ncbi.nlm.nih.gov/16669850/, https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP3A 298	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00780\| https://pubmed.ncbi.nlm.nih.gov/16669850/	yes
CYP3A4 1925	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00780\| https://pubmed.ncbi.nlm.nih.gov/22931300/	yes
CYP3A5 130	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00780 \| https://pubmed.ncbi.nlm.nih.gov/16669850/	yes
CYP3A7 22	inhibitor 3277 Sources: https://go.drugbank.com/drugs/DB00780 \| https://pubmed.ncbi.nlm.nih.gov/16669850/	yes
OATP1B1 803	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
OATP1B3 715	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/23571415/	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 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
Phenelzine associated peripheral neuropathy--clinical and electrophysiologic findings.	1991 Jun	1659356
Abuse of monoamine oxidase inhibitors.	1992	1449122
The antidepressants fluoxetine, idazoxan and phenelzine alter corticotropin-releasing hormone and tyrosine hydroxylase mRNA levels in rat brain: therapeutic implications.	1992 Feb 14	1351783
Depression after cyproheptadine: MAO treatment.	1992 Jun 1	1525285
The management of panic disorder.	2002	12562114
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
Pharmacological treatment of social anxiety disorder: a meta-analysis.	2003	12900950
Phenelzine efficacy in refractory social anxiety disorder: a case series.	2003	12888407
Phenelzine treatment increases transcription factor AP-2 levels in rat brain.	2003 Aug 28	12943557
Antioxidant effect of phenelzine on MPP+-induced cell viability loss in differentiated PC12 cells.	2003 Dec	14649725
Comparing depression treatments.	2003 Jun	12777284
Rapid tryptophan depletion reverses phenelzine-induced suppression of REM sleep.	2003 Mar	12603782
A quantitative neuromotor predictor of antidepressant non-response in patients with major depression.	2003 Nov	14607390
Selectively bred Wistar-Kyoto rats: an animal model of depression and hyper-responsiveness to antidepressants.	2003 Nov	14593430
Panax ginseng.	2003 Oct 15	14596440
[Classical monoamine oxidase inhibitor: not registered for, but still a place in the treatment of depression].	2003 Oct 4	14574774
Hypericum perforatum L (St John's wort) preferentially increases extracellular dopamine levels in the rat prefrontal cortex.	2004 Jun	15148244
Efficacy of quality criteria to identify potentially harmful information: a cross-sectional survey of complementary and alternative medicine web sites.	2004 Jun 29	15249270
Coadministration of phenelzine and methylphenidate for treatment-resistant depression.	2004 Mar	14970373
Efficacy and tolerability of tranylcypromine versus phenelzine: a double-blind study in antidepressant-refractory depressed inpatients.	2004 Nov	15554763
Modafinil augmentation of phenelzine for residual fatigue in dysthymia.	2004 Sep	15337670
Sleep and psychiatry.	2005	16416705
Neuroendocrine predictors of the evolution of depression.	2005	16156385
Herb-drug interactions: a literature review.	2005	15916450
Social anxiety disorder : current treatment recommendations.	2005	15907150
Screening antidepressants in the chick separation-stress paradigm.	2005 Aug	15778882
Validity of sudden gains in acute phase treatment of depression.	2005 Feb	15709845
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
A microarray study of MPP+-treated PC12 Cells: Mechanisms of toxicity (MOT) analysis using bioinformatics tools.	2005 Jul 15	16026605
Inhibition of monoamine oxidase-A activity in rat brain by synthetic hydrazines: structure-activity relationship (SAR).	2005 Jun	16119198
Traumatic stress: effects on the brain.	2006	17290802
Pharmacotherapy of social anxiety disorder: what does the evidence tell us?	2006	17092192
Antidepressants reverse corticosterone-mediated decrease in brain-derived neurotrophic factor expression: differential regulation of specific exons by antidepressants and corticosterone.	2006	16500030
Use of antidepressant medications in relation to the incidence of breast cancer.	2006 Apr 10	16523201
Serotonin syndrome from the interaction of cyclobenzaprine with other serotoninergic drugs.	2006 Dec	17122225
Rapid identification of P-glycoprotein substrates and inhibitors.	2006 Dec	16997908
Effects of monoamine oxidase inhibitors on cocaine discrimination in rats.	2006 Mar	16495723
Quetiapine for insomnia associated with refractory depression exacerbated by phenelzine.	2006 Mar	16478812
An evaluation of potential mechanism-based inactivation of human drug metabolizing cytochromes P450 by monoamine oxidase inhibitors, including isoniazid.	2006 May	16669850
Transdermal selegiline: the new generation of monoamine oxidase inhibitors.	2006 May	16641841
Leading the way: advances in the diagnosis, treatment, and management of neuropsychiatric illnesses.	2006 May	16641838
Tamoxifen protect against hydroxyl radical generation induced by phenelzine in rat striatum.	2006 May 1	16500014
Increased nicotine self-administration following prenatal exposure in female rats.	2006 Nov	17196243
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 `Fri Dec 15 15:02:20 GMT 2023` Edited by `admin` on `Fri Dec 15 15:02:20 GMT 2023`
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

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

Systematic Name

English

Phenelzine sulfate [WHO-DD]

Common Name

English

PHENELZINE ACID SULFATE [MI]

Common Name

English

PHENELZINE SULFATE [ORANGE BOOK]

Common Name

English

NSC-170957

Code

English

PHENELZINE SULFATE [USP MONOGRAPH]

Common Name

English

PHENELZINE SULFATE [USP-RS]

Common Name

English

PHENELZINE SULFATE [MART.]

Common Name

English

Phenethylhydrazine sulfate (1:1)

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C667