TRANYLCYPROMINE HYDROCHLORIDE

Details

Stereochemistry	RACEMIC
Molecular Formula	C9H11N.ClH
Molecular Weight	169.651
Optical Activity	( + / - )
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure of TRANYLCYPROMINE HYDROCHLORIDE

SMILES

Cl.N[C@H]1C[C@@H]1C2=CC=CC=C2

InChI

InChIKey=ZPEFMSTTZXJOTM-RJUBDTSPSA-N

InChI=1S/C9H11N.ClH/c10-9-6-8(9)7-4-2-1-3-5-7;/h1-5,8-9H,6,10H2;1H/t8-,9+;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C9H11N
Molecular Weight	133.1903
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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 49	Inhibitor 8,297	23.6 µM [IC50]
Monoamine oxidase B 72	Inhibitor 8,297	4.02 µM [IC50]
Lysine-specific histone demethylase 1 7	Inhibitor 8,297	5.8 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Major depressive episode without melancholia 3	Primary		Approved 8,429	PARNATE

C_max

Value	Dose	Co-administered	Analyte	Population
112 ng/mL	20 mg 2 times / day steady-state, oral		TRANYLCYPROMINE plasma	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
373 ng × h/mL	20 mg 2 times / day steady-state, oral		TRANYLCYPROMINE plasma	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.45 h	20 mg 2 times / day steady-state, oral		TRANYLCYPROMINE plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
500 mg single, oral Overdose	unhealthy, 27 n = 1	Disc. AE: Drowsiness, Restlessness...
250 mg single, oral Overdose	unhealthy, 35 n = 1	Disc. AE: Headache, Obtundation...
600 mg single, oral Overdose	unhealthy, 42 n = 1	Disc. AE: Sweating, Nystagmus...
30 mg 2 times / day multiple, oral Highest studied dose	unhealthy, 47–82 n = 3	DLT: Asthenia, Weakness of limbs...
20 mg 2 times / day multiple, oral MTD	unhealthy, 47–82 n = 6	DLT: Dizziness...

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AEs

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AE	Significance	Dose	Population
Acute renal failure	Disc. AE	500 mg single, oral Overdose	unhealthy, 27 n = 1
Cyanosed	Disc. AE	500 mg single, oral Overdose	unhealthy, 27 n = 1
Cyanosis	Disc. AE	500 mg single, oral Overdose	unhealthy, 27 n = 1
Drowsiness	Disc. AE	500 mg single, oral Overdose	unhealthy, 27 n = 1
Dyspnea	Disc. AE	500 mg single, oral Overdose	unhealthy, 27 n = 1

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Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1,587	inhibitor 1,767	inhibitor 1,852

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2A6 707 CYP2C19 1,478 CYP2E1 882 CYP2B6 810 CYP2C8 911 OATP1B1 788 OATP1B3 706 OATP2B1 123 BSEP 402

Drug as perpetrator

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Target	Modality	Activity
CYP2D6 1,891	inhibitor 3,277	no [IC50 112 uM]
CYP3A4 1,925	inhibitor 3,277	no [IC50 >10 uM]
BSEP 403	inhibitor 3,277	no [IC50 >1000 uM]
CYP1A2 1,692	inhibitor 3,277	weak [IC50 >10 uM]
OATP2B1 126	inhibitor 3,277	weak

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PubMed

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Title	Date	PubMed
Successful treatment of recurrent brief depression with reboxetine -- a single case analysis.	2002 Mar	11951149
Regulation of corticotropin-releasing factor neuronal systems and hypothalamic-pituitary-adrenal axis activity by stress and chronic antidepressant treatment.	2002 Mar	11861819
Nitric oxide and prostacyclin play a role in the regulation of microvascular protein and hydraulic permeability in cat skeletal muscle.	2003 Apr	12700590
Treatment of seasonal affective disorders.	2003 Dec	22033639
Successful suppression of cataplectic attacks with tramadol.	2003 Sep 23	14504345

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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
Record UNII	7H4CZX4FYH
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

TRANYLCYPROMINE HYDROCHLORIDE

Common Name

English

CYCLOPROPANAMINE, 2-PHENYL-, HYDROCHLORIDE (1:1), (1R,2S)-REL-

Systematic Name

English

TRANYLCYPROMINE HYDROCHLORIDE [MI]

Common Name

English

SKF-385 HYDROCHLORIDE

Common Name

English

CYCLOPROPYLAMINE, 2-PHENYL-, HYDROCHLORIDE, TRANS-(±)-

Common Name

English

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Code System

Code

Type

Description

PUBCHEM

6419961

PRIMARY

MERCK INDEX

m11004

PRIMARY

EPA CompTox

DTXSID6047781

PRIMARY

CAS

1986-47-6

PRIMARY

FDA UNII

7H4CZX4FYH

PRIMARY

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Related Record

Type

Details


					3E3V44J4Z9

TRANYLCYPROMINE

PARENT -> SALT/SOLVATE

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Related Record

Type

Details


					3E3V44J4Z9

TRANYLCYPROMINE

ACTIVE MOIETY

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SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

PubMed

Patents

Sample Use Guides

C_max

T_1/2

Drug as perpetrator