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Details

Stereochemistry ACHIRAL
Molecular Formula C14H20Br2N2.ClH
Molecular Weight 412.591
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BROMHEXINE HYDROCHLORIDE

SMILES

Cl.CN(CC1=CC(Br)=CC(Br)=C1N)C2CCCCC2

InChI

InChIKey=UCDKONUHZNTQPY-UHFFFAOYSA-N
InChI=1S/C14H20Br2N2.ClH/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;1H

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
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.

CNS Activity

Originator

Keck, J.
2
Sources: DOI: 10.1002/jlac.19636620119
Curator's Comment: BE 625022

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
846
Modulator
846
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8583
Bisolvon

Approved Use

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

Cmax

ValueDoseCo-administeredAnalytePopulation
89 nM
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/6897618/
32 mg single, oral
dose: 32 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMHEXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
24.6 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20031363/
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMHEXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
3.11 ng/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20031363/
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMBROXOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
140 nM × h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/6897618/
32 mg single, oral
dose: 32 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMHEXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FED
94.2 ng × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20031363/
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMHEXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
39.3 nmol × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20031363/
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMBROXOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.6 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20031363/
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BROMHEXINE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
8.4 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/20031363/
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
AMBROXOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
5%
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/32458206/
BROMHEXINE plasma
Homo sapiens
Doses

Doses

DosePopulationAdverse events​
32 mg 3 times / day steady-state, oral
Studied dose
Dose: 32 mg, 3 times / day
Route: oral
Route: steady-state
Dose: 32 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32881359/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/32881359/
Other AEs: Hepatic injury, Insomnia...
Other AEs:
Hepatic injury (grade 1, 3 patients)
Insomnia (1 pt)
Gingivitis (2 patients)
Sources:
https://pubmed.ncbi.nlm.nih.gov/32881359/
8 mg 4 times / day steady-state, oral
Studied dose
Dose: 8 mg, 4 times / day
Route: oral
Route: steady-state
Dose: 8 mg, 4 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/33722999/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/33722999/
Sources:
https://pubmed.ncbi.nlm.nih.gov/33722999/
AEs

AEs

AESignificanceDosePopulation
Insomnia 1 pt
32 mg 3 times / day steady-state, oral
Studied dose
Dose: 32 mg, 3 times / day
Route: oral
Route: steady-state
Dose: 32 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32881359/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/32881359/
Gingivitis 2 patients
32 mg 3 times / day steady-state, oral
Studied dose
Dose: 32 mg, 3 times / day
Route: oral
Route: steady-state
Dose: 32 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32881359/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/32881359/
Hepatic injury grade 1, 3 patients
32 mg 3 times / day steady-state, oral
Studied dose
Dose: 32 mg, 3 times / day
Route: oral
Route: steady-state
Dose: 32 mg, 3 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/32881359/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/32881359/
PubMed

PubMed

TitleDatePubMed
Tuberculosis should not be ignored in patients with peripheral gangrene.
2010-12
[Juvenile Gougerot Sjögren syndrome: report of 3 cases].
2010-11
Superior mesenteric artery aneurysm: importance of sonography as the primary imaging technique for detection.
2010-10
Contaminations of herbal products determined by NMR fingerprint.
2010-09
Anatomical suitability for endovascular AAA repair may affect outcomes following rupture.
2010-08
Analyses and localization of pectin-like carbohydrates in cell wall and mucilage of the green alga Netrium digitus.
2010-07
[Codeine and cutaneous drug reactions: Absence of cross-allergy with tramadol and fentanyl].
2010-05
Quantification of the major metabolites of bromhexine in human plasma using RRLC-MS/MS and its application to pharmacokinetics.
2010-04-06
Ambroxol - Resurgence of an old molecule as an anti-inflammatory agent in chronic obstructive airway diseases.
2010-04
Effect of drug content and agglomerate size on tabletability and drug release characteristics of bromhexine hydrochloridetalc agglomerates prepared by crystallo-co-agglomeration.
2010-03
Differential modulation of IgE-dependent activation of human basophils by ambroxol and related secretolytic analogues.
2010-01-16
Sensitive spectrophotometric method for quantitation of guaifenesin and dropropizine in their dosage forms.
2010
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.
2009-12-02
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.
2009-12-01
Molecularly imprinted solid-phase extraction for the selective determination of bromhexine in human serum and urine with high performance liquid chromatography.
2009-11-15
Feline calicivirus infection. ABCD guidelines on prevention and management.
2009-07
Feline herpesvirus infection. ABCD guidelines on prevention and management.
2009-07
Acidic and basic solutions dissolve protein plugs made of lithostathine complicating choledochal cyst/pancreaticobiliary maljunction.
2009-07
Activity of some mucolytics against bacterial adherence to mammalian cells.
2009-07
[Pharmacological treatment of acute cough].
2009-05-14
[Acute mediastinitis--optimum diagnostic and therapeutic measures].
2009-05
Solitary fibrous tumor of the lung: three rare cases of intraparenchymal nodules.
2009-05
Foetus-in-fetu: an unusual cause of abdominal mass in the newborn.
2009-04-04
[Traumatic perforation of the duodenum--a case review].
2009-02
Simultaneous determination of salbutamol sulphate and bromhexine hydrochloride in tablets by reverse phase liquid chromatography.
2009-01
The effect of retroperitoneal fat tissue thickness on testicular venous drainage.
2009
Pancreatic cancer metastasis to the rectum detected on colonoscopy.
2009
Bioequivalence study of bromhexine by liquid chromatography-electrospray ionization-mass spectrometry after oral administration of bromhexine hydrochloride tablets.
2008-12-01
Challenges of utilizing immunostains to facilitate the diagnosis and management of metastatic adenocarcinoma.
2008-12
Huge ascending aortic pseudoaneurysm caused by a penetrating atherosclerotic ulcer.
2008-11
A simple micellar electrokinetic capillary chromatographic method for the quantitative analysis of organic expectorants.
2008-09
Pharyngolaryngeal sarcoidosis: report of 12 cases.
2008-09
Unsuspected breast carcinoma presenting as orbital complication of rhinosinusitis.
2008-08
Recent developments in the treatment of alcoholic chronic pancreatitis.
2008-06
Malignant medulloepithelioma of optic nerve head.
2008-06
Posterior impingement syndromes of the ankle.
2008-06
Perinatal tumours: the contribution of radiology to management.
2008-06
Mediastinal pancreatic pseudocyst with isolated thoracic symptoms: a case report.
2008-05-27
Oromandibular dystonia and persistent psychiatric symptoms in extra-pontine myelinolysis.
2008-04
Three case reports of laparoscopic management of granulosa cell tumor with intraoperative rupture and subsequent upstaging.
2008-02-03
Chemiluminescence determination of bromhexine hydrochloride with morin as chemiluminescent reagent.
2008-01-05
The role for S-carboxymethylcysteine (carbocisteine) in the management of chronic obstructive pulmonary disease.
2008
[The history of antitussive and expectorants].
2008
Successful resection of dermatomyositis associated with thymic carcinoma: report of a case.
2008
Pulmonary Paragonimus westermani with false-positive fluorodeoxyglucose positron emission tomography mimicking primary lung cancer.
2007-11
Voltammetric behaviour of bromhexine and its determination in pharmaceuticals.
2007-10-31
Current status of herbal drugs in India: an overview.
2007-07
Development and evaluation of oral controlled release chlorpheniramine-ion exchange resinate suspension.
2007-05-05
Simultaneous UV Spectrophotometric Estimation of Ambroxol Hydrochloride and Levocetirizine Dihydrochloride.
2006-12-13
Role of mucolytics in the management of COPD.
2006
Patents

Patents

BE625022
2
JP2001226264A
5
JPS6344521A
2

Sample Use Guides

In Vivo Use Guide
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 Mon Mar 31 17:47:53 GMT 2025
Edited
by admin
on Mon Mar 31 17:47:53 GMT 2025
Record UNII
YC2ZOM3Z8V
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BISOLVON
Preferred Name English
BROMHEXINE HYDROCHLORIDE
EP   MART.   MI   USAN   WHO-DD  
USAN  
Official Name English
BENZENEMETHANAMINE, 2-AMINO-3,5-DIBROMO-N-CYCLOHEXYL-N-METHYL-, MONOHYDROCHLORIDE
Common Name English
BROMEHEXINE HYDROCHLORIDE
Common Name English
NA-274
Code English
N-CYCLOHEXYL-N-METHYL-(2-AMINO-3,5-DIBROMOBENZYL)AMMONIUM CHLORIDE
Systematic Name English
BROMHEXINE HYDROCHLORIDE [USAN]
Common Name English
BROMHEXINE HYDROCHLORIDE [JAN]
Common Name English
Bromhexine hydrochloride [WHO-DD]
Common Name English
NA 274
Code English
BROMHEXINE HYDROCHLORIDE [MI]
Common Name English
BROMHEXINE HYDROCHLORIDE [EP MONOGRAPH]
Common Name English
3,5-DIBROMO-N(SUP .ALPHA.)-CYCLOHEXYL-N(SUP .ALPHA.)-METHYLTOLUENE-.ALPHA.,2-DIAMINE MONOHYDROCHLORIDE
Systematic Name English
BROMHEXINE HCL
Common Name English
NSC-758383
Code English
BROMHEXINE HYDROCHLORIDE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C74536
Created by admin on Mon Mar 31 17:47:53 GMT 2025 , Edited by admin on Mon Mar 31 17:47:53 GMT 2025
Code System Code Type Description
SMS_ID
100000091917
Created by admin on Mon Mar 31 17:47:53 GMT 2025 , Edited by admin on Mon Mar 31 17:47:53 GMT 2025
PRIMARY
NCI_THESAURUS
C142968
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PRIMARY
NSC
758383
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PRIMARY
EVMPD
SUB00875MIG
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PRIMARY
DAILYMED
YC2ZOM3Z8V
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PRIMARY
DRUG BANK
DBSALT001092
Created by admin on Mon Mar 31 17:47:53 GMT 2025 , Edited by admin on Mon Mar 31 17:47:53 GMT 2025
PRIMARY
PUBCHEM
5702220
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PRIMARY
ECHA (EC/EINECS)
210-280-8
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PRIMARY
RXCUI
1601
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PRIMARY RxNorm
CHEBI
31303
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PRIMARY
EPA CompTox
DTXSID0045886
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PRIMARY
FDA UNII
YC2ZOM3Z8V
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PRIMARY
ChEMBL
CHEMBL253376
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PRIMARY
CAS
611-75-6
Created by admin on Mon Mar 31 17:47:53 GMT 2025 , Edited by admin on Mon Mar 31 17:47:53 GMT 2025
PRIMARY
MERCK INDEX
m2668
Created by admin on Mon Mar 31 17:47:53 GMT 2025 , Edited by admin on Mon Mar 31 17:47:53 GMT 2025
PRIMARY Merck Index
Related Record Type Details
Structure of BROMHEXINE
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of BROMHEXINE
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