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
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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 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
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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 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/)
No information available.
Summary of Clinical Use Click here for help
Bromhexine is a component of expectorant cough medicines. It is not approved by the FDA or EMA, but is authorised for clinical use in many other countries. In the UK it is used only in veterinary medicine. Clinical trials in patients with COVID-19 are underway in a number of countries including Iran (trial 46969), Russia, Slovenia, China and Mexico.
Clinical Trials
Clinical Trial ID Title Type Source Comment References
NCT04355026 Use of Bromhexine and Hydroxychloroquine for Treatment of COVID-19 Pneumonia Phase 4 Interventional General and Teaching Hospital Celje
NCT04424134 BromhexIne And Spironolactone For CoronаVirUs Infection Requiring HospiTalization Phase 3 Interventional Lomonosov Moscow State University Medical Research and Educational Center
NCT04405999 Prevention of Infection and Incidence of COVID-19 in Medical Personnel Assisting Patients With New Coronavirus Disease Phase 4 Interventional Federal State Budgetary Institution, V. A. Almazov Federal North-West Medical Research Centre, of the Ministry of Health