bretylium   Click here for help

GtoPdb Ligand ID: 7130

Synonyms: ASL-603 | bretylium tosylate | Bretylol®
Approved drug
bretylium is an approved drug
Compound class: Synthetic organic
Comment: Bretylium is a substrate for the noradrenaline transporter so it accumulates inside nerve terminals which have this transporter. This accumulation underlies its inhibitory action on the sympathetic nervous system. Bretylium tosylate is no longer available in the US.
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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 0
Hydrogen bond donors 0
Rotatable bonds 3
Topological polar surface area 0
Molecular weight 242.05
XLogP 2.8
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 CC[N+](Cc1ccccc1Br)(C)C
Isomeric SMILES CC[N+](Cc1ccccc1Br)(C)C
InChI InChI=1S/C11H17BrN/c1-4-13(2,3)9-10-7-5-6-8-11(10)12/h5-8H,4,9H2,1-3H3/q+1
InChI Key AAQOQKQBGPPFNS-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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes
IUPAC Name Click here for help
[(2-bromophenyl)methyl](ethyl)dimethylazanium
International Nonproprietary Names Click here for help
INN number INN
927 bretylium tosilate
Synonyms Click here for help
ASL-603 | bretylium tosylate | Bretylol®
Database Links Click here for help
CAS Registry No. 61-75-6
ChEMBL Ligand CHEMBL1199080
DrugBank Ligand DB01158
DrugCentral Ligand 394
GtoPdb PubChem SID 178103706
PubChem CID 2431
Search Google for chemical match using the InChIKey AAQOQKQBGPPFNS-UHFFFAOYSA-N
Search Google for chemicals with the same backbone AAQOQKQBGPPFNS
Search PubMed clinical trials bretylium tosilate
Search PubMed titles bretylium tosilate
Search PubMed titles/abstracts bretylium tosilate
UniChem Compound Search for chemical match using the InChIKey AAQOQKQBGPPFNS-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey AAQOQKQBGPPFNS-UHFFFAOYSA-N
Wikipedia Bretylium