Identification
- Summary
Bromhexine is a mucolytic drug used to decrease the viscosity of mucus in the airway, enhancing mucus clearance.
- Generic Name
- Bromhexine
- DrugBank Accession Number
- DB09019
- Background
Bromhexine is mucolytic agent used for a variety of respiratory conditions associated with increased mucus secretion. It is derived from the Adhatoda vasica plant and aids in the clearance of excess mucus, improving breathing and reducing cough. It was introduced into the market in 1963, and is widely available as an over-the-counter drug in many countries.1 Recently, bromhexine and its metabolite ambroxol have garnered interest for the potential prevention and treatment of COVID-19 due to their interactions with cell receptors in the lungs.5,6
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Bromhexine (DB09019)
- Weight
- Average: 376.13
Monoisotopic: 373.999323944 - Chemical Formula
- C14H20Br2N2
- Synonyms
- 3,5-dibromo-N(alpha)-cyclohexyl-N(alpha)-methyltoluene-alpha-2-diamine
- Bromexina
- Bromhexina
- Bromhexine
- Bromhexinum
- N-cyclohexyl-N-methyl-(2-amino-3,5-dibrombenzyl)amine
- External IDs
- NA 274
Pharmacology
- Indication
Bromohexine is used alone or with other ingredients such as diphenhydramine, dextromethorphan, and guaifenesin to reduce mucus viscosity and clear mucus in conditions associated with mucus hypersecretion, including the common cold, influenza, respiratory tract infections, or other conditions.16,15,13
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination for symptomatic treatment of Bronchiectasis Combination Product in combination with: Albuterol (DB01001) •••••••••••• ••••• Used in combination for symptomatic treatment of Common cold Combination Product in combination with: Dextromethorphan (DB00514), Diphenhydramine (DB01075), Phenylpropanolamine (DB00397) ••• ••• •••••• Used in combination for therapy Common cold Combination Product in combination with: Guaifenesin (DB00874), Brompheniramine (DB00835), Phenylephrine (DB00388) •••••••••••• •••••••• •••••• ••••••• •••••• Used in combination for symptomatic treatment of Cough caused by common cold Combination Product in combination with: Dextromethorphan (DB00514), Guaifenesin (DB00874) •••••••••••• •••••••• •••••• Used in combination for symptomatic treatment of Coughing Combination Product in combination with: Diphenhydramine (DB01075), Dextromethorphan (DB00514), Phenylpropanolamine (DB00397) ••• ••• •••••• - Associated Therapies
- Contraindications & Blackbox Warnings
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Bromhexine thins airway secretions, improving breathing and discomfort associated with thick mucus in airways associated with a variety of respiratory conditions.1,11,13
- Mechanism of action
Inflammation of the airways, increased mucus secretion, and altered mucociliary clearance are the hallmarks of various diseases of the respiratory tract. Mucus clearance is necessary for lung health; bromhexine aids in mucus clearance by reducing the viscosity of mucus and activating the ciliary epithelium13, allowing secretions to be expelled from the respiratory tract.1
Recent have studies have demonstrated that bromhexine inhibits the transmembrane serine protease 2 receptor (TMPRSS2) in humans. Activation of TMPRSS2 plays an important role in viral respiratory diseases such as influenza A and Middle East Respiratory Syndrome (MERS). Inhibition of receptor activation and viral entry by bromhexine may be effective in preventing or treating various respiratory illnesses, including COVID-19.5,9 In vitro studies have suggested the action of ambroxol (a metabolite of bromhexine) on the angiogensin-converting enzyme receptor 2 (ACE2), prevents entry of the viral envelope-anchored spike glycoprotein of SARS-Cov-2 into alveolar cells or increases the secretion of surfactant, preventing viral entry.10,6
Target Actions Organism UTransmembrane protease serine 2 Not Available Humans UAngiotensin-converting enzyme 2 binderHumans - Absorption
After oral administration, bromhexine demonstrates linear pharmacokinetics when given in doses of 8-32 mg. Bromhexine is readily absorbed in the gastrointestinal tract at a rapid rate. This drug undergoes extensive first-pass effect in the range of 75-80%.3,13 The bioavailability is therefore reduced to approximately 22-27%.13
- Volume of distribution
After intravenous administration in a pharmacokinetic study, bromhexine was found to be widely distributed. Bromhexine is known to cross the blood-brain barrier; small concentrations may cross the placenta. The average volume of distribution of bromhexine was 1209 ± 206 L (19 L/kg). Lung tissue concentrations of bromhexine two hours after a dose were 1.5 to 3.2 times higher in bronchial tissues than plasma concentrations. Pulmonary parynchema concentrations were 3.4 to 5.9 times higher when compared to plasma concentrations.13
- Protein binding
Bromhexine is approximately 95% bound to plasma proteins.13
- Metabolism
Bromhexine is almost completely metabolized to a variety of hydroxylated metabolites in addition to dibromanthranilic acid. Ambroxol is a known metabolite of bromhexine.13 In one study of human plasma, (E)-4-hydroxydemethylbromhexine (E-4-HDMB) and (E)-3-hydroxydemethylbromhexine (E-3-HDMB) were quantified as major metabolites of ambroxol, and (Z)-4-hydroxydemethylbromhexine and (Z)-3-hydroxydemethylbromhexine were quantified as minor metabolites.4
- Route of elimination
After a dose of bromhexine was administered during a pharmacokinetic study, approximately 97% of the radiolabeled dose was detected in the urine; under 1% was detected as the parent drug.13
- Half-life
Following single oral doses ranging from 8 and 32 mg, the terminal half-life of bromhexine has been measured between 6.6 and 31.4 hours.13
- Clearance
The clearance of bromhexine ranges from 843-1073 mL/min, within the range of the hepatic circulation.13
- Adverse Effects
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The oral LD50 of bromhexine in rats is 6 g/kg.14 The observed symptoms of accidental overdose with bromhexine are consistent with the known adverse effects of bromhexine, including headache, nausea, and vomiting, among other symptoms. Provide symptomatic treatment and contact poison control services if an overdose is confirmed or suspected.13
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Bromhexine hydrochloride YC2ZOM3Z8V 611-75-6 UCDKONUHZNTQPY-UHFFFAOYSA-N - International/Other Brands
- Amiorel (Boehringer Ingelheim) / Bisolmed (Boehringer Ingelheim) / Bisolvon (Boehringer Ingelheim) / Bisolvon Chesty (Boehringer Ingelheim) / Fluibron
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image AXCEL BROMHEXINE (CHILDREN) SYRUP Syrup Oral KOTRA PHARMA (M) SDN. BHD. 2020-09-08 Not applicable Malaysia 
AXCEL BROMHEXINE TABLET Tablet Oral KOTRA PHARMA (M) SDN. BHD. 2020-09-08 Not applicable Malaysia AXINE SYRUP 4MG/5ML Syrup Oral ROYCE PHARMA MANUFACTURING SDN. BHD. 2020-09-08 Not applicable Malaysia AXINE TABLET 8MG Tablet Oral ROYCE PHARMA MANUFACTURING SDN. BHD. 2020-09-08 Not applicable Malaysia BEACOLYTIC ELIXIR 4MG/5ML Elixir Oral DUOPHARMA MANUFACTURING (BANGI) SDN BHD 2020-09-08 Not applicable Malaysia - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image ATHEN JARABE Bromhexine hydrochloride (0.08 g) + Guaifenesin (2 g) Syrup Oral COLOMPACK S.A. 2014-04-02 2016-05-06 Colombia 
AXIV TOSTHERAPY® NIÑOS Bromhexine hydrochloride (0.04 g) + Guaifenesin (2 g) Syrup Oral Laboratorios Incobra S.A. 2021-08-28 Not applicable Colombia BREMIEL® JARABE ADULTOS Bromhexine hydrochloride (0.08 g) + Guaifenesin (2 g) Syrup Oral COASPHARMA S.A.S. 2011-08-23 Not applicable Colombia BREMIEL®JARABE PEDIATRICO Bromhexine hydrochloride (0.04 g) + Guaifenesin (1 g) Syrup Oral LABORATORIOS LEGRAND S.A. 2011-08-09 2018-10-11 Colombia BREMONEX JARABE Bromhexine hydrochloride (80 mg) + Guaifenesin (2 g) Syrup Oral FABRIFARMA S.A 2006-11-10 2016-02-03 Colombia
Categories
- ATC Codes
- R05CB02 — Bromhexine
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Phenylmethylamines
- Direct Parent
- Phenylmethylamines
- Alternative Parents
- Benzylamines / 2-bromoanilines / Cyclohexylamines / Bromobenzenes / Aralkylamines / Aryl bromides / Trialkylamines / Primary amines / Organopnictogen compounds / Organobromides show 1 more
- Substituents
- 2-bromoaniline / Amine / Aniline or substituted anilines / Aralkylamine / Aromatic homomonocyclic compound / Aryl bromide / Aryl halide / Benzylamine / Bromobenzene / Cyclohexylamine show 11 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- organobromine compound, tertiary amino compound, substituted aniline (CHEBI:77032)
- Affected organisms
- Rat
- Mouse
Chemical Identifiers
- UNII
- Q1J152VB1P
- CAS number
- 3572-43-8
- InChI Key
- OJGDCBLYJGHCIH-UHFFFAOYSA-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
- IUPAC Name
- 2,4-dibromo-6-{[cyclohexyl(methyl)amino]methyl}aniline
- SMILES
- CN(CC1=CC(Br)=CC(Br)=C1N)C1CCCCC1
References
- Synthesis Reference
童元峰杨庆云张嵩张对良. (2015). Production method of bromhexine hydrochloride(Worldwide CN2013103399540A ).https://patents.google.com/patent/CN103396323A/en
- General References
- Zanasi A, Mazzolini M, Kantar A: A reappraisal of the mucoactive activity and clinical efficacy of bromhexine. Multidiscip Respir Med. 2017 Mar 20;12:7. doi: 10.1186/s40248-017-0088-1. eCollection 2017. [Article]
- Ansarin K, Tolouian R, Ardalan M, Taghizadieh A, Varshochi M, Teimouri S, Vaezi T, Valizadeh H, Saleh P, Safiri S, Chapman KR: Effect of bromhexine on clinical outcomes and mortality in COVID-19 patients: A randomized clinical trial. Bioimpacts. 2020;10(4):209-215. doi: 10.34172/bi.2020.27. Epub 2020 Jul 19. [Article]
- Bechgaard E, Nielsen A: Bioavailability of bromhexine tablets and preliminary pharmacokinetics in humans. Biopharm Drug Dispos. 1982 Oct-Dec;3(4):337-44. doi: 10.1002/bdd.2510030407. [Article]
- Liu J, Chen X, Hu Y, Cheng G, Zhong D: Quantification of the major metabolites of bromhexine in human plasma using RRLC-MS/MS and its application to pharmacokinetics. J Pharm Biomed Anal. 2010 Apr 6;51(5):1134-41. doi: 10.1016/j.jpba.2009.11.024. Epub 2009 Dec 1. [Article]
- Habtemariam S, Nabavi SF, Ghavami S, Cismaru CA, Berindan-Neagoe I, Nabavi SM: Possible use of the mucolytic drug, bromhexine hydrochloride, as a prophylactic agent against SARS-CoV-2 infection based on its action on the Transmembrane Serine Protease 2. Pharmacol Res. 2020 Jul;157:104853. doi: 10.1016/j.phrs.2020.104853. Epub 2020 Apr 30. [Article]
- Alkotaji M: Azithromycin and ambroxol as potential pharmacotherapy for SARS-CoV-2. Int J Antimicrob Agents. 2020 Dec;56(6):106192. doi: 10.1016/j.ijantimicag.2020.106192. Epub 2020 Oct 10. [Article]
- Gupta PR: Ambroxol - Resurgence of an old molecule as an anti-inflammatory agent in chronic obstructive airway diseases. Lung India. 2010 Apr;27(2):46-8. doi: 10.4103/0970-2113.63603. [Article]
- Jauch R, Bozler G, Hammer R, Koss FW, Karlsson M, Vitek E, Haring I, Beschke K, Hadamovsky S, Maass D, Wollmann R: [Ambroxol, studies of biotransformation in man and determination in biological samples (author's transl)]. Arzneimittelforschung. 1978;28(5a):904-11. [Article]
- Maggio R, Corsini GU: Repurposing the mucolytic cough suppressant and TMPRSS2 protease inhibitor bromhexine for the prevention and management of SARS-CoV-2 infection. Pharmacol Res. 2020 Jul;157:104837. doi: 10.1016/j.phrs.2020.104837. Epub 2020 Apr 22. [Article]
- Olaleye OA, Kaur M, Onyenaka CC: Ambroxol Hydrochloride Inhibits the Interaction between Severe Acute Respiratory Syndrome Coronavirus 2 Spike Protein's Receptor Binding Domain and Recombinant Human ACE2. bioRxiv. 2020 Sep 14. doi: 10.1101/2020.09.13.295691. [Article]
- NPRA Product Information: Salmodil (salbutamol sulfate/bromhexine hydrochloride) oral syrup [Link]
- NPRA Product Information: Rexom Unizet (diphenhydramine hydrochloride/bromhexine hydrochloride/ammonium chloride) oral syrup [Link]
- AUSTRALIAN PRODUCT INFORMATION – BISOLVON® CHESTY (BROMHEXINE HYDROCHLORIDE) for oral use [Link]
- Fischer Scientific MSDS: Bromhexine hydrochloride [Link]
- FDA Thailand: BIMED (bromhexine, brompheniramine, guaifenesin, phenylephrine) oral tablets [Link]
- BPOM: Dextromethorphan [Link]
- External Links
- KEGG Drug
- D07542
- PubChem Compound
- 2442
- PubChem Substance
- 310264976
- ChemSpider
- 2348
- BindingDB
- 50239965
- 1753
- ChEBI
- 77032
- ChEMBL
- CHEMBL253376
- ZINC
- ZINC000000608220
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Bromhexine
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Prevention Coronavirus Disease 2019 (COVID‑19) / Increased Risk of SARS-CoV-2 Infection 1 4 Completed Treatment Coronavirus Disease 2019 (COVID‑19) / Treatment Efficacy 1 4 Unknown Status Treatment Coronavirus Disease 2019 (COVID‑19) 1 3 Completed Treatment Abnormal Mucus Secretions / Respiratory Tract Diseases 1 3 Not Yet Recruiting Treatment Coronavirus Disease 2019 (COVID‑19) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral Granule 8 MG Injection Intramuscular; Intravenous Injection, solution 4 MG/2ML Solution Respiratory (inhalation) 0.200 g Suppository Rectal 16 mg Suppository Rectal 8 mg Tablet, soluble Oral 8 MG Solution Oral 2 mg/ml Solution Oral Solution Oral 8 MG/5ML Tablet Oral 8 mg/1 Solution Respiratory (inhalation) 0.2 g Solution Oral 0.160 g Tablet Oral 8 mg Syrup Oral 200 ml Syrup Oral 100 ml Tablet, sugar coated Oral 8 mg/1 Solution Oral 8 MG/10ML Tablet Oral 12 MG Solution Oral 12 MG/ML Solution Oral 8 MG/ML Powder Not applicable 1000 g/1000g Tablet Oral Cream Oral; Vaginal Syrup Oral 50 mg Syrup Oral 0.16 g Syrup Oral 0.08 g Capsule Oral 8.782 mg Solution Oral 0.0800 g Powder Elixir Oral 8 MG/5ML Solution Oral 12 mg/15ml Elixir Oral 12 mg/15mL Solution Oral Solution Oral 80 mg Tablet Oral Tablet Capsule, liquid filled Oral 8 mg Elixir Oral Tablet Oral 8.00 mg Syrup Oral Elixir Oral Capsule, liquid filled Oral 800000 mg Syrup Oral 8000000 mg Solution Oral 160 mg Syrup Oral Injection Intramuscular; Intravenous 4 mg/2ml Syrup Oral 80 mg Solution Oral 0.08 g Solution Oral 0.16 g Solution Oral 160.000 mg Syrup Oral 160 mg Capsule Oral 8.000 mg Suspension Oral Syrup Oral 8 mg/10ml Syrup Oral 40 mg Elixir Oral 4 mg/5ml Solution Oral 80.000 mg Tablet, film coated Oral Solution Tablet, sugar coated Oral Capsule Capsule Oral 8 mg Solution Oral 4 mg/5ml Solution 4 mg/5ml Syrup Elixir Oral 4 mg/5ml Syrup Oral 4 mg/5ml Solution 2 mg/1ml Syrup Oral 8 mg/5ml Tablet, film coated - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 232-235 https://www.chemicalbook.com/ChemicalProductProperty_EN_CB3249453.htm boiling point (°C) 413.8 https://www.guidechem.com/dictionary/en/3572-43-8.html water solubility <1 mg/mL https://www.scbt.com/p/bromhexine-hydrochloride-611-75-6https://www.scbt.com/p/bromhexine-hydrochloride-611-75-6 logP 5.14 https://www.guidechem.com/dictionary/en/3572-43-8.html pKa 8.69 https://www.chemicalbook.com/ChemicalProductProperty_EN_CB92617054.htm - Predicted Properties
Property Value Source Water Solubility 0.00362 mg/mL ALOGPS logP 4.08 ALOGPS logP 4.42 Chemaxon logS -5 ALOGPS pKa (Strongest Acidic) 19.89 Chemaxon pKa (Strongest Basic) 9.23 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 29.26 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 85.56 m3·mol-1 Chemaxon Polarizability 32.98 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 157.35127 predictedDeepCCS 1.0 (2019) [M+H]+ 159.70927 predictedDeepCCS 1.0 (2019) [M+Na]+ 165.80244 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Plasma membrane-anchored serine protease that participates in proteolytic cascades of relevance for the normal physiologic function of the prostate (PubMed:25122198). Androgen-induced TMPRSS2 activates several substrates that include pro-hepatocyte growth factor/HGF, the protease activated receptor-2/F2RL1 or matriptase/ST14 leading to extracellular matrix disruption and metastasis of prostate cancer cells (PubMed:15537383, PubMed:26018085, PubMed:25122198). In addition, activates trigeminal neurons and contribute to both spontaneous pain and mechanical allodynia (By similarity).
- Specific Function
- Scavenger receptor activity
- Gene Name
- TMPRSS2
- Uniprot ID
- O15393
- Uniprot Name
- Transmembrane protease serine 2
- Molecular Weight
- 53858.845 Da
References
- Habtemariam S, Nabavi SF, Ghavami S, Cismaru CA, Berindan-Neagoe I, Nabavi SM: Possible use of the mucolytic drug, bromhexine hydrochloride, as a prophylactic agent against SARS-CoV-2 infection based on its action on the Transmembrane Serine Protease 2. Pharmacol Res. 2020 Jul;157:104853. doi: 10.1016/j.phrs.2020.104853. Epub 2020 Apr 30. [Article]
- Maggio R, Corsini GU: Repurposing the mucolytic cough suppressant and TMPRSS2 protease inhibitor bromhexine for the prevention and management of SARS-CoV-2 infection. Pharmacol Res. 2020 Jul;157:104837. doi: 10.1016/j.phrs.2020.104837. Epub 2020 Apr 22. [Article]
- Depfenhart M, de Villiers D, Lemperle G, Meyer M, Di Somma S: Potential new treatment strategies for COVID-19: is there a role for bromhexine as add-on therapy? Intern Emerg Med. 2020 Aug;15(5):801-812. doi: 10.1007/s11739-020-02383-3. Epub 2020 May 26. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- Curator comments
- Ambroxol is a major metabolite of bromhexine.
- General Function
- Zinc ion binding
- Specific Function
- Carboxypeptidase which converts angiotensin I to angiotensin 1-9, a peptide of unknown function, and angiotensin II to angiotensin 1-7, a vasodilator. Also able to hydrolyze apelin-13 and dynorphin...
- Gene Name
- ACE2
- Uniprot ID
- Q9BYF1
- Uniprot Name
- Angiotensin-converting enzyme 2
- Molecular Weight
- 92462.4 Da
References
- Olaleye OA, Kaur M, Onyenaka CC: Ambroxol Hydrochloride Inhibits the Interaction between Severe Acute Respiratory Syndrome Coronavirus 2 Spike Protein's Receptor Binding Domain and Recombinant Human ACE2. bioRxiv. 2020 Sep 14. doi: 10.1101/2020.09.13.295691. [Article]
- Alkotaji M: Azithromycin and ambroxol as potential pharmacotherapy for SARS-CoV-2. Int J Antimicrob Agents. 2020 Dec;56(6):106192. doi: 10.1016/j.ijantimicag.2020.106192. Epub 2020 Oct 10. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Zinc ion binding
- Specific Function
- Carboxypeptidase which converts angiotensin I to angiotensin 1-9, a peptide of unknown function, and angiotensin II to angiotensin 1-7, a vasodilator. Also able to hydrolyze apelin-13 and dynorphin...
- Gene Name
- ACE2
- Uniprot ID
- Q9BYF1
- Uniprot Name
- Angiotensin-converting enzyme 2
- Molecular Weight
- 92462.4 Da
References
- Olaleye OA, Kaur M, Onyenaka CC: Ambroxol Hydrochloride Inhibits the Interaction between Severe Acute Respiratory Syndrome Coronavirus 2 Spike Protein's Receptor Binding Domain and Recombinant Human ACE2. bioRxiv. 2020 Sep 14. doi: 10.1101/2020.09.13.295691. [Article]
Drug created at June 24, 2014 16:22 / Updated at December 02, 2023 07:01