tranylcypromine   Click here for help

GtoPdb Ligand ID: 5281

Synonyms: Parnate® | tranylcypromine sulphate
Approved drug
tranylcypromine is an approved drug (FDA (1961))
Compound class: Synthetic organic
Comment: The approved drug tranylcypromine is a racemic mixture of two enantiomers. The structure shown here does not specify stereochemistry and represents the mixture. The two enantiomers are represented by CID 19493 and CID 26070.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species

IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: tranylcypromine

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 26.02
Molecular weight 133.09
XLogP 1.36
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES NC1CC1c1ccccc1
Isomeric SMILES NC1CC1c1ccccc1
InChI InChI=1S/C9H11N/c10-9-6-8(9)7-4-2-1-3-5-7/h1-5,8-9H,6,10H2
InChI Key AELCINSCMGFISI-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Used in the treatment of major depressive episodes without melancholia.
The more recent observation that tranylcypromine inhibits the demethylase activity of lysine demethylase 1A (LSD1; KDM1A) has lead to its evaluation as an antinoplastic agent in acute myelogenous leukemia and myelodysplastic syndromes as an adjunct to chemotherapy with tretinoin. Development has reached Phase 1/2 for these conditions (see NCT02261779 as an example).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Irreversible and non-selective monoamine oxidase inhibitor. Inhibition of monoamine oxidase leads to increased monoamine levels in the CNS, resulting in relief of depressive symptoms.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT02261779 Phase I/II Trial of ATRA and TCP in Patients With Relapsed or Refractory AML and no Intensive Treatment is Possible Phase 1/Phase 2 Interventional Martin-Luther-Universität Halle-Wittenberg
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com