U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C14H20Br2N2
Molecular Weight 376.13
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BROMHEXINE

SMILES

CN(CC1=C(N)C(Br)=CC(Br)=C1)C2CCCCC2

InChI

InChIKey=OJGDCBLYJGHCIH-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C14H20Br2N2
Molecular Weight 376.13
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: http://www.drugsupdate.com/generic/view/745/Bromhexine | https://www.old.health.gov.il/units/pharmacy/trufot/alonim/5329.pdf | https://docetp.mpa.se/LMF/Bisolvon%20oral%20solution%20in%20sachet%20ENG%20PAR.pdf

Bromhexine is used for conditions where there are a lot of thick mucus in the airways. Bromhexine acts on the mucus at the formative stages in the glands, within the mucus-secreting cells. Bromhexine disrupts the structure of acid mucopolysaccharide fibres in mucoid sputum and produces a less viscous mucus, which is easier to expectorate. In addition, bromhexine has antioxidant properties. Occasional, mild side effects include: a feeling of fullness in the stomach (bloatedness), diarrhea, dizziness, headache, indigestion, nausea, sweating and skin rashes. Bromhexine may increase the concentration of concurrently administered antibiotics in bronchial secretions. No clinically relevant interactions with other medications have been reported.

Originator

Sources: DOI: 10.1002/jlac.19636620119
Curator's Comment: BE 625022

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Bisolvon

Approved Use

Secretolytic therapy in acute and chronic bronchopulmonary diseases associated with abnormal mucus secretion and impaired mucus transport.
PubMed

PubMed

TitleDatePubMed
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.
2001 Apr
Efficacy and safety of Ascoril in the management of cough--National Study Group report.
2001 Feb
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Changing paradigms in the diagnosis and management of bronchiectasis.
2002
Stevens-Johnson syndrome presumably induced by bromhexine. A case report.
2002 Apr
[Use of mucoregulating drugs in combined therapy of exudative otitis media].
2003
In vitro inhibition of human neutrophil histotoxicity by ambroxol: evidence for a multistep mechanism.
2003 Oct
Synchronous germinomas in the pineal and suprasellar region.
2005 Apr
Randomized trial of a fixed combination (KanJang) of herbal extracts containing Adhatoda vasica, Echinacea purpurea and Eleutherococcus senticosus in patients with upper respiratory tract infections.
2005 Aug
Effect of bromhexine hydrochloride therapy for alcoholic chronic pancreatitis.
2005 Dec
A case of a GH-producing pituitary adenoma associated with a unilateral headache with autonomic signs.
2005 Jun
[A case of hepatocellular carcinoma complicating cardiac cirrhosis caused by constrictive pericarditis].
2005 Jun
Kinetics of bromhexine-mediated down-regulation of focal adhesive molecules of uterus and trophectoderm affecting conception in the rat.
2006 Jun
[Abdominal tuberculosis in CT imaging].
2007
Mediastinal extension of a complicated pancreatic pseudocyst; a case report and literature review.
2007 Apr 25
Current status of herbal drugs in India: an overview.
2007 Jul
Amiodarone inhibits tocopherol-mediated human lipoprotein peroxidation.
2007 Jul 15
Design and evaluation of deformable talc agglomerates prepared by crystallo-co-agglomeration technique for generating heterogeneous matrix.
2007 Jul 27
Simultaneous determination of salbutamol sulphate, bromhexine hydrochloride and etofylline in pharmaceutical formulations with the use of four rapid derivative spectrophotometric methods.
2007 Jul 30
Hemorrhage into pancreatic pseudocyst.
2007 May-Jun
Pulmonary Paragonimus westermani with false-positive fluorodeoxyglucose positron emission tomography mimicking primary lung cancer.
2007 Nov
Pharmacokinetic interaction between cefaclor and bromhexine in healthy Chinese volunteers.
2007 Oct
Voltammetric behaviour of bromhexine and its determination in pharmaceuticals.
2007 Oct 31
Protective effect of Adhatoda vascia Nees against radiation-induced damage at cellular, biochemical and chromosomal levels in Swiss albino mice.
2007 Sep
Successful resection of dermatomyositis associated with thymic carcinoma: report of a case.
2008
Subjective pulsatile tinnitus associated with extensive pneumatization of temporal bone.
2008 Jan
Recent developments in the treatment of alcoholic chronic pancreatitis.
2008 Jun
Malignant medulloepithelioma of optic nerve head.
2008 Jun
Posterior impingement syndromes of the ankle.
2008 Jun
The role of (124)I-PET in diagnosis and treatment of thyroid carcinoma.
2008 Mar
A simple micellar electrokinetic capillary chromatographic method for the quantitative analysis of organic expectorants.
2008 Sep
Pharyngolaryngeal sarcoidosis: report of 12 cases.
2008 Sep
Evaluation of a combined strategy directed towards health-care professionals and patients with chronic obstructive pulmonary disease (COPD): information and health education feedback for improving clinical monitoring and quality-of-life.
2009 Dec 1
Feline herpesvirus infection. ABCD guidelines on prevention and management.
2009 Jul
Acidic and basic solutions dissolve protein plugs made of lithostathine complicating choledochal cyst/pancreaticobiliary maljunction.
2009 Jul
[Acute mediastinitis--optimum diagnostic and therapeutic measures].
2009 May
Solitary fibrous tumor of the lung: three rare cases of intraparenchymal nodules.
2009 May
Molecularly imprinted solid-phase extraction for the selective determination of bromhexine in human serum and urine with high performance liquid chromatography.
2009 Nov 15
Ambroxol - Resurgence of an old molecule as an anti-inflammatory agent in chronic obstructive airway diseases.
2010 Apr
Quantification of the major metabolites of bromhexine in human plasma using RRLC-MS/MS and its application to pharmacokinetics.
2010 Apr 6
Anatomical suitability for endovascular AAA repair may affect outcomes following rupture.
2010 Aug
[Codeine and cutaneous drug reactions: Absence of cross-allergy with tramadol and fentanyl].
2010 May
Patents

Sample Use Guides

8 to 16 mg three times daily
Route of Administration: Oral
In Vitro Use Guide
Bromhexine is shown to be scavengers of both superoxide and hydroxyl radicals. The dismutation of superoxide was accelerated 3-fold by bromhexine over the rate of spontaneous dismutation. The reaction constant of hydroxyl radicals with bromhexine was determined by competition kinetics to be 1.58 +/- 0.15 x 10(10) M-1S-1.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:20:48 GMT 2023
Edited
by admin
on Fri Dec 15 15:20:48 GMT 2023
Record UNII
Q1J152VB1P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BROMHEXINE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
BROMHEXINE [MI]
Common Name English
BROMHEXINE [MART.]
Common Name English
bromhexine [INN]
Common Name English
Bromhexine [WHO-DD]
Common Name English
BENZENEMETHANAMINE, 2-AMINO-3,5-DIBROMO-N-CYCLOHEXYL-N-METHYL-
Systematic Name English
FLUIBRON
Brand Name English
Classification Tree Code System Code
WHO-ATC R05CB02
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
LIVERTOX 122
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
WHO-VATC QR05CB02
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
FDA ORPHAN DRUG 34789
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL253376
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
DRUG BANK
DB09019
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
FDA UNII
Q1J152VB1P
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
SMS_ID
100000088676
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
NCI_THESAURUS
C172826
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
MERCK INDEX
m2668
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
402
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
CAS
3572-43-8
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
ECHA (EC/EINECS)
222-684-1
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
CHEBI
77032
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
EPA CompTox
DTXSID6022686
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
MESH
D001964
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
WIKIPEDIA
BROMHEXINE
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
EVMPD
SUB05914MIG
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
PUBCHEM
2442
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
RXCUI
1753
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY RxNorm
DAILYMED
Q1J152VB1P
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
INN
2584
Created by admin on Fri Dec 15 15:20:48 GMT 2023 , Edited by admin on Fri Dec 15 15:20:48 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
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 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.
IC50
BINDER->LIGAND
SALT/SOLVATE -> PARENT
Related Record Type Details
METABOLITE ACTIVE -> PARENT
When bromhexine is administered orally, the systemic exposure to ambroxol is much lower (;8-fold; Liu et al., 2010), but since the true molecular action of these agents is not entirely known, it cannot be ascertained whether bromhexine or ambroxol, or both, contribute to activity. Ambroxol has also been associated with a reduction in throat pain, which has triggered investigation into the activity of it and bromhexine at sodium channels (such as NaV1.8 and the tetrodotoxin sensitive channel; Leffler et al., 2010).
MAJOR
PLASMA
METABOLITE -> PARENT
MINOR
PLASMA
METABOLITE -> PARENT
MAJOR
PLASMA
METABOLITE -> PARENT
MINOR
PLASMA
Related Record Type Details
ACTIVE MOIETY