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Details

Stereochemistry RACEMIC
Molecular Formula C9H11N
Molecular Weight 133.1903
Optical Activity ( + / - )
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRANYLCYPROMINE

SMILES

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

InChI

InChIKey=AELCINSCMGFISI-DTWKUNHWSA-N
InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2/t8-,9+/m0/s1

HIDE SMILES / InChI

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 TargetPharmacologyConditionPotency
23.6 µM [IC50]
4.02 µM [IC50]
5.8 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
PARNATE

Cmax

ValueDoseCo-administeredAnalytePopulation
112 ng/mL
20 mg 2 times / day steady-state, oral
TRANYLCYPROMINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
373 ng × h/mL
20 mg 2 times / day steady-state, oral
TRANYLCYPROMINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2.45 h
20 mg 2 times / day steady-state, oral
TRANYLCYPROMINE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

PubMed

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).