lofepramine   Click here for help

GtoPdb Ligand ID: 7551

Synonyms: Gamanil ® | Lomont ® | WHR-2908A
Approved drug
lofepramine is an approved drug
Compound class: Synthetic organic
Comment: Marketed formulations may contain lofepramine hydrochloride (PubChem CID 33611).
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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

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View more information in the IUPHAR Pharmacology Education Project: lofepramine

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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 3
Hydrogen bond donors 0
Rotatable bonds 7
Topological polar surface area 23.55
Molecular weight 418.18
XLogP 6.01
No. Lipinski's rules broken 1
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 CN(CC(=O)c1ccc(cc1)Cl)CCCN1c2ccccc2CCc2c1cccc2
Isomeric SMILES CN(CC(=O)c1ccc(cc1)Cl)CCCN1c2ccccc2CCc2c1cccc2
InChI InChI=1S/C26H27ClN2O/c1-28(19-26(30)22-13-15-23(27)16-14-22)17-6-18-29-24-9-4-2-7-20(24)11-12-21-8-3-5-10-25(21)29/h2-5,7-10,13-16H,6,11-12,17-19H2,1H3
InChI Key SAPNXPWPAUFAJU-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Used to treat major depressive disorder. However, there is no information regarding approval for clinical use of this drug on the US FDA or European Medicines Agency (EMA) websites. Individual national approval agencies may have granted marketing authorisation. For example, in 2002 the UK approved this drug for the treatment of symptoms of depressive illness and although some brands have been discontinued, the generic drug is still in use.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Lofepramine acts as a norepinephrine and serotonin reuptake inhibitor [2], with little anticholinergic activity at muscarinic receptors [1]. Lofepramine is extensively metabolized to the active metabolite, desipramine, which also acts as a norepinephrine reuptake inhibitor (with low efficacy serotonin transporter inhibition).
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)