buclizine   Click here for help

GtoPdb Ligand ID: 7134

Synonyms: UCB-4445
Approved drug
buclizine is an approved drug
Compound class: Synthetic organic
Comment: Buclizine is a piperazine derivative antihistamine and anticholinergic drug, with antiemetic properties.
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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 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 6
Topological polar surface area 6.48
Molecular weight 432.23
XLogP 7.14
No. Lipinski's rules broken 1

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 Clc1ccc(cc1)C(c1ccccc1)N1CCN(CC1)Cc1ccc(cc1)C(C)(C)C
Isomeric SMILES Clc1ccc(cc1)C(c1ccccc1)N1CCN(CC1)Cc1ccc(cc1)C(C)(C)C
InChI InChI=1S/C28H33ClN2/c1-28(2,3)25-13-9-22(10-14-25)21-30-17-19-31(20-18-30)27(23-7-5-4-6-8-23)24-11-15-26(29)16-12-24/h4-16,27H,17-21H2,1-3H3
InChI Key MOYGZHXDRJNJEP-UHFFFAOYSA-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
Mainly used for its antiemetic and antivertigo actions. There is no information regarding approval for clinical use of this drug on the US FDA website. Other national approval agencies may have granted marketing authorisation. The Electronic Medicines Compendium (eMC) lists buclizine only as an active ingredient in a multi-component anti-migraine treatment (Migraleve&re;) alongside paracetamol and codeine.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Buclizine has various and complex actions likely involving inhibition of muscarinic cholinergic and histaminic synapses within the chemotrigger zone (CTZ) of the medulla, and this controls vomiting.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com