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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.

CNS Activity

Originator

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

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Modulator
828
Modulator
828
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
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
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
Congenital chylothorax associated with isolated congenital hypoplastic superior caval vein: a case report.
2005 Dec
Gastrointestinal stromal tumor in a child and review of the literature.
2005 Nov
[Imaging of metabolic bone diseases].
2006
Cost-effectiveness of routine mediastinoscopy in computed tomography- and positron emission tomography-screened patients with stage I lung cancer.
2006 Apr
Colovesical fistula complicating diverticular disease: one-stage resection.
2006 Jan-Feb
Progress and regression within primary Sjögren's syndrome.
2006 Jan-Feb
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
Development and validation of chemometrics-assisted spectrophotometric and liquid chromatographic methods for the simultaneous determination of two multicomponent mixtures containing bronchodilator drugs.
2007 Feb 19
Hemorrhage into pancreatic pseudocyst.
2007 May-Jun
Pulmonary Paragonimus westermani with false-positive fluorodeoxyglucose positron emission tomography mimicking primary lung cancer.
2007 Nov
The role for S-carboxymethylcysteine (carbocisteine) in the management of chronic obstructive pulmonary disease.
2008
Oromandibular dystonia and persistent psychiatric symptoms in extra-pontine myelinolysis.
2008 Apr
Chemiluminescence determination of bromhexine hydrochloride with morin as chemiluminescent reagent.
2008 Jan-Feb
Three case reports of laparoscopic management of granulosa cell tumor with intraoperative rupture and subsequent upstaging.
2008 Jul-Aug
Perinatal tumours: the contribution of radiology to management.
2008 Jun
The role of (124)I-PET in diagnosis and treatment of thyroid carcinoma.
2008 Mar
Simultaneous UV Spectrophotometric Estimation of Ambroxol Hydrochloride and Levocetirizine Dihydrochloride.
2008 Mar-Apr
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.
2009 Dec 2
Simultaneous determination of salbutamol sulphate and bromhexine hydrochloride in tablets by reverse phase liquid chromatography.
2009 Jan
Activity of some mucolytics against bacterial adherence to mammalian cells.
2009 Jul
Sensitive spectrophotometric method for quantitation of guaifenesin and dropropizine in their dosage forms.
2010
Ambroxol - Resurgence of an old molecule as an anti-inflammatory agent in chronic obstructive airway diseases.
2010 Apr
Superior mesenteric artery aneurysm: importance of sonography as the primary imaging technique for detection.
2010 Oct
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 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
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WHO-VATC QR05CB02
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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
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PRIMARY
DRUG BANK
DB09019
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PRIMARY
FDA UNII
Q1J152VB1P
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PRIMARY
SMS_ID
100000088676
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PRIMARY
NCI_THESAURUS
C172826
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PRIMARY
MERCK INDEX
m2668
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PRIMARY Merck Index
DRUG CENTRAL
402
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PRIMARY
CAS
3572-43-8
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PRIMARY
ECHA (EC/EINECS)
222-684-1
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PRIMARY
CHEBI
77032
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PRIMARY
EPA CompTox
DTXSID6022686
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PRIMARY
MESH
D001964
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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
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PRIMARY
PUBCHEM
2442
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PRIMARY
RXCUI
1753
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PRIMARY RxNorm
DAILYMED
Q1J152VB1P
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PRIMARY
INN
2584
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PRIMARY
Related Record Type Details
TRANSMEMBRANE PROTEASE SERINE 2
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
PLASMA PROTEIN FRACTION (HUMAN)
BINDER->LIGAND
Structure of BROMHEXINE HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of AMBROXOL
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
Structure of AMBROXOL, CIS-
METABOLITE -> PARENT
MINOR
PLASMA
Structure of 3-HYDROXYDEMETHYLBROMHEXINE, TRANS-
METABOLITE -> PARENT
MAJOR
PLASMA
Structure of 3-HYDROXYDEMETHYLBROMHEXINE, CIS-
METABOLITE -> PARENT
MINOR
PLASMA
Related Record Type Details
Structure of BROMHEXINE
ACTIVE MOIETY
NIH
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