TRANYLCYPROMINE SULFATE

Details

Stereochemistry	RACEMIC
Molecular Formula	2C9H11N.H2O4S
Molecular Weight	364.459
Optical Activity	( + / - )
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.N[C@H]1C[C@@H]1C2=CC=CC=C2.N[C@H]3C[C@@H]3C4=CC=CC=C4

InChI

InChIKey=BKPRVQDIOGQWTG-KAVFMPKWSA-N

InChI=1S/2C9H11N.H2O4S/c2*10-9-6-8(9)7-4-2-1-3-5-7;1-5(2,3)4/h2*1-5,8-9H,6,10H2;(H2,1,2,3,4)/t2*8-,9+;/m11./s1

HIDE SMILES / InChI

Molecular Formula	C9H11N
Molecular Weight	133.1903
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	( + / - )

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16927039 | https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/012342s063lbl.pdf | https://www.drugbank.ca/drugs/DB00752

Tranylcypromine is a non-hydrazine monoamine oxidase inhibitor with a rapid onset of activity. Tranylcypromine has being marketed under original trade name Parnate, indicated for the treatment of major depressive episode without melancholia. Tranylcypromine irreversibly and nonselectively inhibits monoamine oxidase (MAO). Within neurons, MAO appears to regulate the levels of monoamines released upon synaptic firing. Since depression is associated with low levels of monoamines, the inhibition of MAO serves to ease depressive symptoms, as this results in an increase in the concentrations of these amines within the CNS.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Monoamine oxidase A 52 Target ID: CHEMBL1951 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/012342s063lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/2248058	Inhibitor 8504	23.6 µM [IC50]
Monoamine oxidase B 75 Target ID: CHEMBL2039 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/012342s063lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/2248058	Inhibitor 8504	4.02 µM [IC50]
Lysine-specific histone demethylase 1 7 Target ID: CHEMBL6136 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25759518	Inhibitor 8504	5.8 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive episode without melancholia 3 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/012342s063lbl.pdf https://www.drugs.com/pro/tranylcypromine.html	Primary		Approved 8583	PARNATE Approved Use INDICATIONS For the treatment of Major Depressive Episode Without Melancholia. PARNATE should be used in adult patients who can be closely supervised. It should rarely be the first antidepressant drug given. Rather, the drug is suited for patients who have failed to respond to the drugs more commonly administered for depression. The effectiveness of PARNATE has been established in adult outpatients, most of whom had a depressive illness which would correspond to a diagnosis of Major Depressive Episode Without Melancholia. As described in the American Psychiatric Association’s Diagnostic and Statistical Manual, third edition (DSM III), Major Depressive Episode implies a prominent and relatively persistent (nearly every day for at least 2 weeks) depressed or dysphoric mood that usually interferes with daily functioning and includes at least 4 of the following 8 symptoms: change in appetite, change in sleep, psychomotor agitation or retardation, loss of interest in usual activities or decrease in sexual drive, increased fatigability, feelings of guilt or worthlessness, slowed thinking or impaired concentration, and suicidal ideation or attempts. The effectiveness of PARNATE in patients who meet the criteria for Major Depressive Episode with Melancholia (endogenous features) has not been established. Launch Date 1961

C_max

Value	Dose	Co-administered	Analyte	Population
112 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3757407	20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		TRANYLCYPROMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
373 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3757407	20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		TRANYLCYPROMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.45 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/3757407	20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		TRANYLCYPROMINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
500 mg single, oral Overdose Dose: 500 mg Route: oral Route: single Dose: 500 mg Sources: https://pubmed.ncbi.nlm.nih.gov/5014984	unhealthy, 27 Health Status: unhealthy Age Group: 27 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/5014984	Disc. AE: Restlessness, Drowsiness... AEs leading to discontinuation/dose reduction: Restlessness Drowsiness Sweating Muscle contractions involuntary Cyanosed Cyanosis Dyspnea Spasms Acute renal failure Hyperpyrexia Sources: https://pubmed.ncbi.nlm.nih.gov/5014984
250 mg single, oral Overdose Dose: 250 mg Route: oral Route: single Dose: 250 mg Sources: https://pubmed.ncbi.nlm.nih.gov/7263132	unhealthy, 35 Health Status: unhealthy Age Group: 35 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/7263132	Disc. AE: Headache, Obtundation... AEs leading to discontinuation/dose reduction: Headache (severe) Obtundation Hypertension Electrocardiogram T wave peaked Sources: https://pubmed.ncbi.nlm.nih.gov/7263132
600 mg single, oral Overdose Dose: 600 mg Route: oral Route: single Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/4939226	unhealthy, 42 Health Status: unhealthy Age Group: 42 Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/4939226	Disc. AE: Sweating, Nystagmus... AEs leading to discontinuation/dose reduction: Sweating Nystagmus Generalised spasm Tachycardia Sources: https://pubmed.ncbi.nlm.nih.gov/4939226
30 mg 2 times / day multiple, oral Highest studied dose Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33495312	unhealthy, 47–82 Health Status: unhealthy Age Group: 47–82 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/33495312	DLT: Asthenia, Weakness of limbs... Dose limiting toxicities: Asthenia (grade 2, 33.3%) Weakness of limbs (grade 2, 33.3%) Nausea (grade 2, 33.3%) Vomiting (grade 2, 33.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/33495312
20 mg 2 times / day multiple, oral MTD Dose: 20 mg, 2 times / day Route: oral Route: multiple Dose: 20 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/33495312	unhealthy, 47–82 Health Status: unhealthy Age Group: 47–82 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/33495312	DLT: Dizziness... Dose limiting toxicities: Dizziness (grade 2, 16.7%) Sources: https://pubmed.ncbi.nlm.nih.gov/33495312
4000 mg single, oral Overdose Dose: 4000 mg Route: oral Route: single Dose: 4000 mg Sources: https://pubmed.ncbi.nlm.nih.gov/9316000 https://pubmed.ncbi.nlm.nih.gov/23791433	unknown Health Status: unknown Sources: https://pubmed.ncbi.nlm.nih.gov/9316000 https://pubmed.ncbi.nlm.nih.gov/23791433	Disc. AE: Hyperthermia, Delirium... AEs leading to discontinuation/dose reduction: Hyperthermia Delirium Thrombocytopenia Sources: https://pubmed.ncbi.nlm.nih.gov/9316000 https://pubmed.ncbi.nlm.nih.gov/23791433
30 mg 2 times / day multiple, oral Recommended Dose: 30 mg, 2 times / day Route: oral Route: multiple Dose: 30 mg, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/012342s064lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/012342s064lbl.pdf	Disc. AE: Suicidal tendency, Suicidal behavior... AEs leading to discontinuation/dose reduction: Suicidal tendency Suicidal behavior Hypertensive crisis Serotonin syndrome Mania Hypomania Hypotension Hepatotoxicity Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2018/012342s064lbl.pdf

AEs

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252	inhibitor 2438	inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2C19 2057 CYP2E1 1060 CYP2B6 926 CYP2C8 1057 OATP1B1 1079 OATP1B3 961 OATP2B1 157 BSEP 550

Drug as perpetrator

Target	Modality	Activity
CYP2D6 2546	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00752	no [IC50 112 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00752	no [IC50 >10 uM]
BSEP 554	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw2MDIwIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExNzkifX0%3D	no [IC50 >1000 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00752	weak [IC50 >10 uM]
OATP2B1 162	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/	weak
CYP2A6 911	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00752	yes [IC50 0.42 uM]
CYP2C8 1117	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/15601807/, https://pubmed.ncbi.nlm.nih.gov/26721703/	yes [IC50 12.1 uM]
CYP2B6 1160	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw0NzI5IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDExNzkifX0%3D, https://pubmed.ncbi.nlm.nih.gov/17101742/	yes [IC50 6.9 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00752	yes [Ki 32 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://go.drugbank.com/drugs/DB00752	yes [Ki 56 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000155099, https://pubmed.ncbi.nlm.nih.gov/11996015/	yes
OATP1B1 1095	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes
OATP1B3 970	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/22541068/, https://pubmed.ncbi.nlm.nih.gov/23571415/	yes

PubMed

Title	Date	PubMed
On the formation and nature of the imidazoline I2 binding site on human monoamine oxidase-B.	2010-12	20832472
Ziprasidone, monoamine oxidase inhibitors, and the serotonin syndrome.	2010-08	20631570
An overview of curcumin in neurological disorders.	2010-03	20838516
TCP-FA4: a derivative of tranylcypromine showing improved blood-brain permeability.	2009-12-01	19679106
Inhibition of monoamine oxidases desensitizes 5-HT1A autoreceptors and allows nicotine to induce a neurochemical and behavioral sensitization.	2009-01-28	19176807
Effects of bisphenol-A and other endocrine disruptors compared with abnormalities of schizophrenia: an endocrine-disruption theory of schizophrenia.	2009-01	18245062
Safety of high-intensity treatment with the irreversible monoamine oxidase inhibitor tranylcypromine in patients with treatment-resistant depression.	2008-11	19067263
NF-Y substitutes H2A-H2B on active cell-cycle promoters: recruitment of CoREST-KDM1 and fine-tuning of H3 methylations.	2008-11	18940868
Synthesis and studies on antidepressant and anticonvulsant activities of some 3-(2-thienyl)pyrazoline derivatives.	2008-11	18816586
Repeated unpredictable stress and antidepressants differentially regulate expression of the bcl-2 family of apoptotic genes in rat cortical, hippocampal, and limbic brain structures.	2008-06	17700647
Withdrawal from high-dose tranylcypromine.	2008-03	18344110
Pharmacological management of panic disorder.	2008-02	18728820
Rasagiline in treatment of Parkinson's disease.	2008-02	18728823
Cellular and molecular mechanisms in the long-term action of antidepressants.	2008	19170396
A possible role for the endocannabinoid system in the neurobiology of depression.	2007-11-19	18021439
Not all monoamine oxidase inhibitors are created equal.	2007-11	17979910
The guinea pig forced swim test as a new behavioral despair model to characterize potential antidepressants.	2007-11	17646967
Receptor mediation of exaggerated responses to serotonin-enhancing drugs in serotonin transporter (SERT)-deficient mice.	2007-10	17765930
Involvement of alpha1-adrenergic receptors in tranylcypromine enhancement of nicotine self-administration in rat.	2007-09	17486319
Effect on [11C]DASB binding after tranylcypromine-induced increase in serotonin concentration: positron emission tomography studies in monkeys and rats.	2007-06	17372973
Tranylcypromine enhancement of nicotine self-administration.	2007-05	17412372
Venlafaxine in the treatment of panic disorder.	2007-02	19300538
Honokiol up-regulates prostacyclin synthease protein expression and inhibits endothelial cell apoptosis.	2007-01-05	17109844
CYP3A4 mediated in vitro metabolism of vinflunine in human liver microsomes.	2007-01	17184591
New findings from the Bipolar Collaborative Network: clinical implications for therapeutics.	2006-12	17162830
Sustained effects of phenelzine and tranylcypromine on orthostatic challenge in antidepressant-refractory depression.	2006-10	16974207
Monoamine oxidase inhibitors allow locomotor and rewarding responses to nicotine.	2006-08	16395299
Tyramine pressor sensitivity during treatment with the selegiline transdermal system 6 mg/24 h in healthy subjects.	2006-08	16855078
Combination rapid transcranial magnetic stimulation in treatment refractory depression.	2006-03	19412449
Isatin interaction with glyceraldehyde-3-phosphate dehydrogenase, a putative target of neuroprotective drugs: partial agonism with deprenyl.	2006	17447420
Cyp2a6 is a principal enzyme involved in hydroxylation of 1,7-dimethylxanthine, a main caffeine metabolite, in humans.	2005-09	15980104
An extensive new literature concerning low-dose effects of bisphenol A shows the need for a new risk assessment.	2005-08	16079060
Potential of [11C]DASB for measuring endogenous serotonin with PET: binding studies.	2005-02	15721758
Effect of antidepressants on GABA(B) receptor function and subunit expression in rat hippocampus.	2004-10-15	15451391
Evaluation of the effect of chronic antidepressant treatment on neurokinin-1 receptor expression in the rat brain.	2004-06	15111024
Zinc treatment induces cortical brain-derived neurotrophic factor gene expression.	2004-05-10	15145706
Purification and characterization of recombinant human prostacyclin synthase.	2004-04	15115769
Current perspectives in the management of treatment-resistant depression.	2004-03	22034070
Utility of microtiter plate assays for human cytochrome P450 inhibition studies in drug discovery: application of simple method for detecting quasi-irreversible and irreversible inhibitors.	2004-02	15499170
Treatment of seasonal affective disorders.	2003-12	22033639
Differential regulation of brain derived neurotrophic factor transcripts by antidepressant treatments in the adult rat brain.	2003-09	12907316
Noradrenergic and serotonergic blockade inhibits BDNF mRNA activation following exercise and antidepressant.	2003-04	12759116
Regulation of GAP-43 expression by chronic desipramine treatment in rat cultured hippocampal cells.	2003-03-15	12644358
Effects of stress and tranylcypromine on amphetamine-induced locomotor activity and GABA(B) receptor function in rat brain.	2003-01-17	12495786
[Protease inhibitors as an anesthetic component in ENT surgery].	2002-12-05	12462777
The N-demethylation of the doxepin isomers is mainly catalyzed by the polymorphic CYP2C19.	2002-07	12180536
Successful treatment of recurrent brief depression with reboxetine -- a single case analysis.	2002-03	11951149
Synthesis and antidepressant activities of some 3,5-diphenyl-2-pyrazolines.	2001-06	11525844
Role of ETB and B2 receptors in the ex vivo platelet inhibitory properties of endothelin and bradykinin in the mouse.	2001-02	11181435
Regulation of GFRalpha-1 and GFRalpha-2 mRNAs in rat brain by electroconvulsive seizure.	2001-01	11071708

Patents

Sample Use Guides

In Vivo Use Guide

The usual effective dosage is 30 mg per day, usually given in divided doses. If there are no signs of improvement after a reasonable period (up to 2 weeks), then the dosage may be increased in 10 mg per day increments at intervals of 1 to 3 weeks; the dosage range may be extended to a maximum of 60 mg per day from the usual 30 mg per day.

Route of Administration: Oral

In Vitro Use Guide

Studies were conducted in vitro in the presence of 2×10(-5) M tranylcypromine, which inhibited the MAO activity of both the extrasynaptosomal mitochondria and the mitochondria contained within the nerve endings (intrasynaptosomal mitochondria).

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:30:02 GMT 2025` Edited by `admin` on `Mon Mar 31 21:30:02 GMT 2025`
Record UNII	7ZAT6ES870
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

PARNATE

Preferred Name

English

TRANYLCYPROMINE SULFATE

Official Name

English

TRANYLCYPROMINE SULFATE [MI]

Common Name

English

CYCLOPROPYLAMINE, 2-PHENYL-, SULFATE, TRANS-(±)-, (2:1)

Common Name

English

(±)-TRANS-2-PHENYLCYCLOPROPYLAMINE SULFATE (2:1)

Systematic Name

English

TRANYLCYPROMINE SULFATE [VANDF]

Common Name

English

TRANYLCYPROMINE SULPHATE

Common Name

English

CYCLOPROPYLAMINE, 2-PHENYL-, SULPHATE, TRANS-(±)-, (2:1)

Common Name

English

NSC-757342

Code

English

TRANYLCYPROMINE SULFATE [ORANGE BOOK]

Common Name

English

TRANYLCYPROMINE SULFATE [MART.]

Common Name

English

TRANYLCYPROMINE SULFATE [USP-RS]

Common Name

English

Tranylcypromine sulfate [WHO-DD]

Common Name

English

CYCLOPROPANAMINE, 2-PHENYL-, TRANS-(±)-, SULFATE (2:1)

Systematic Name

English

TRANYLCYPROMINE SULFATE [USP MONOGRAPH]

Common Name

English

CYCLOPROPANAMINE, 2-PHENYL-, TRANS-(±)-, SULPHATE (2:1)

Systematic Name

English

TRANYLCYPROMINE SULFATE [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C667