bromodiphenhydramine   Click here for help

GtoPdb Ligand ID: 7132

Synonyms: Ambodryl®
Approved drug
bromodiphenhydramine is an approved drug
Compound class: Synthetic organic
Comment: Bromazine (bromodiphenhydramine) is an antihistamine. This drug also has antimicrobial action but is known to cause drowsiness. The only information regarding approval for clinical use of this drug on the US FDA website is in a drug combination with codeine. Other national approval agencies may have granted marketing authorisation.
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 6
Topological polar surface area 12.47
Molecular weight 333.07
XLogP 3.96
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 CN(CCOC(c1ccc(cc1)Br)c1ccccc1)C
Isomeric SMILES CN(CCOC(c1ccc(cc1)Br)c1ccccc1)C
InChI InChI=1S/C17H20BrNO/c1-19(2)12-13-20-17(14-6-4-3-5-7-14)15-8-10-16(18)11-9-15/h3-11,17H,12-13H2,1-2H3
InChI Key NUNIWXHYABYXKF-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-[(4-bromophenyl)(phenyl)methoxy]ethyl}dimethylamine
International Nonproprietary Names Click here for help
INN number INN
336 bromazine
Synonyms Click here for help
Ambodryl®
Database Links Click here for help
CAS Registry No. 118-23-0
ChEMBL Ligand CHEMBL1201245
DrugBank Ligand DB01237
DrugCentral Ligand 404
GtoPdb PubChem SID 178103708
PubChem CID 2444
Search Google for chemical match using the InChIKey NUNIWXHYABYXKF-UHFFFAOYSA-N
Search Google for chemicals with the same backbone NUNIWXHYABYXKF
Search PubMed clinical trials bromazine
Search PubMed titles bromazine
Search PubMed titles/abstracts bromazine
UniChem Compound Search for chemical match using the InChIKey NUNIWXHYABYXKF-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey NUNIWXHYABYXKF-UHFFFAOYSA-N
Wikipedia Bromazine