GtoPdb is requesting financial support from commercial users. Please see our sustainability page for more information.

bromhexine   Click here for help

GtoPdb Ligand ID: 11218

Synonyms: Bisolvon® | NA-274 | NA274
Approved drug
bromhexine is an approved drug
Compound class: Synthetic organic
Comment: Bromhexine is a widely used mucolytic (expectorant) drug. In response to the SARS-CoV-2 pandemic of 2019/20 it was investigated as an add-on treatment for patients with COVID-19 [1]. In addition to its mucolytic activity, bromhexine may also inhibit the human protease TMPRSS2 that is exploited by certain coronaviruses for spike (S) protein priming, thus reducing the viruses' infection mechanism [2].
2D Structure
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 3
Topological polar surface area 29.26
Molecular weight 374
XLogP 4.38
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
Click here for help

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/)

✖
Canonical SMILES Brc1cc(CN(C2CCCCC2)C)c(c(c1)Br)N
Isomeric SMILES Brc1cc(CN(C2CCCCC2)C)c(c(c1)Br)N
InChI InChI=1S/C14H20Br2N2/c1-18(12-5-3-2-4-6-12)9-10-7-11(15)8-13(16)14(10)17/h7-8,12H,2-6,9,17H2,1H3
InChI Key OJGDCBLYJGHCIH-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.
Is prodrug? Yes
Active form ambroxol
IUPAC Name Click here for help
2,4-dibromo-6-[[cyclohexyl(methyl)amino]methyl]aniline
International Nonproprietary Names Click here for help
INN number INN
2584 bromhexine
Synonyms Click here for help
Bisolvon® | NA-274 | NA274
Database Links Click here for help
CAS Registry No. 3572-43-8 (source: ChemIDplus)
ChEMBL Ligand CHEMBL253376
DrugBank Ligand DB09019
DrugCentral Ligand 402
GtoPdb PubChem SID 434122278
PubChem CID 2442
Search Google for chemical match using the InChIKey OJGDCBLYJGHCIH-UHFFFAOYSA-N
Search Google for chemicals with the same backbone OJGDCBLYJGHCIH
Search PubMed clinical trials bromhexine
Search PubMed titles bromhexine
Search PubMed titles/abstracts bromhexine
UniChem Compound Search for chemical match using the InChIKey OJGDCBLYJGHCIH-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey OJGDCBLYJGHCIH-UHFFFAOYSA-N