levomepromazine   Click here for help

GtoPdb Ligand ID: 7603

Synonyms: Levoprome® | methotrimeprazine | Nosinan® | Nozinan® | RP-7044 | SK&F-5116
Approved drug
levomepromazine is an approved drug
Compound class: Synthetic organic
Comment: Marketed formulations contain either levomepromazine hydrochloride or levomepromazine maleate.
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levomepromazine is commercially available from our sponsors

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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 2
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 41.01
Molecular weight 328.16
XLogP 4.51
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES COc1ccc2c(c1)N(CC(CN(C)C)C)c1c(S2)cccc1
Isomeric SMILES COc1ccc2c(c1)N(C[C@@H](CN(C)C)C)c1c(S2)cccc1
InChI InChI=1S/C19H24N2OS/c1-14(12-20(2)3)13-21-16-7-5-6-8-18(16)23-19-10-9-15(22-4)11-17(19)21/h5-11,14H,12-13H2,1-4H3/t14-/m1/s1
InChI Key VRQVVMDWGGWHTJ-CQSZACIVSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Used extensively in palliative care to treat intractable nausea or vomiting and to alleviate severe end-stage delirium and/or agitation. May also be used to treat psychosis (schizophrenia, and manic phases of bipolar disorder) and nausea and insomnia at low dose. There is no information regarding approval of ths drug on either the US FDA or EMA websites. Individual national approval agencies may have granted marketing authorisation for this drug (eg UK in 2009).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The major clinical benefits of levomepromazine arise from its antagonism of D2-like dopamine receptor in the CNS and from its antihistamine activity. However, in addition, levomepromazine interacts with a wide spectrum of other receptors including adrenergic, muscarinic acetylcholine and serotonin receptors.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)