BROMHEXINE

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 Search

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

Description
Sources: https://www.hpra.ie/img/uploaded/swedocuments/2173773.PA0007_025_002.aa7cc0c2-c2ff-4b55-80c9-8e666ce5f551.000001Product%20Leaflet%20Approved.160429.pdf
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

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
mucopolysaccharide metabolic process 2 Target ID: GO:1903510 Sources: http://www.drugsupdate.com/generic/view/745/Bromhexine	Modulator 828
response to oxidative stress 20 Target ID: GO:0006979 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8831801	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bronchopulmonary diseases 2 Sources: http://www.hsa.gov.sg/content/dam/HSA/HPRG/Western_Medicine/Overview_Framework_Policies/Reclassified_Medicines/Updates/Patient_Information_Leaflets/PIL_Bromhexine_29-6-2011.pdf	Palliative		Approved 8429	Bisolvon Approved Use Secretolytic therapy in acute and chronic bronchopulmonary diseases associated with abnormal mucus secretion and impaired mucus transport.

PubMed

Title	Date	PubMed
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.	2001 Apr	11340978
Solubilization of bromhexine hydrochloride in aqueous lecithin dispersions. Physicochemical characterization of interactions between drug and carrier.	2001 Sep	11593995
Changing paradigms in the diagnosis and management of bronchiectasis.	2002	14720036
Stevens-Johnson syndrome presumably induced by bromhexine. A case report.	2002 Apr	11965223
[Treatment of patients with acute pneumonia].	2003 Apr-Jun	12889364
Metabolism of bromhexine in pig hepatocyte cultures.	2004 Aug	15305850
Mediastinal pancreatic pseudocyst caused by obstruction of the pancreatic duct was eliminated by bromhexine hydrochloride.	2004 Nov	15609697
Synchronous germinomas in the pineal and suprasellar region.	2005 Apr	15876601
Simultaneous spectrophotometric determination of salbutamol and bromhexine in tablets.	2005 Mar	15784245
Cost-effectiveness of routine mediastinoscopy in computed tomography- and positron emission tomography-screened patients with stage I lung cancer.	2006 Apr	16580440
Kinetics of bromhexine-mediated down-regulation of focal adhesive molecules of uterus and trophectoderm affecting conception in the rat.	2006 Jun	16730500
Congenital aorto-azygous fistula treated with coil embolization: case report and review of the literature.	2006 Sep-Oct	16755348
Diurnal variation of prescribing pattern of primary care doctors in Bahrain.	2007 Feb	17286720
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	17046190
Amiodarone inhibits tocopherol-mediated human lipoprotein peroxidation.	2007 Jul 15	17531203
Simultaneous determination of salbutamol sulphate, bromhexine hydrochloride and etofylline in pharmaceutical formulations with the use of four rapid derivative spectrophotometric methods.	2007 Jul 30	17658320
Acute cholecystitis due to strangulation of a floating gallbladder by the lesser omentum.	2007 May-Jun	16897276
Pulmonary Paragonimus westermani with false-positive fluorodeoxyglucose positron emission tomography mimicking primary lung cancer.	2007 Nov	18049856
Pharmacokinetic interaction between cefaclor and bromhexine in healthy Chinese volunteers.	2007 Oct	18007084
Protective effect of Adhatoda vascia Nees against radiation-induced damage at cellular, biochemical and chromosomal levels in Swiss albino mice.	2007 Sep	17965765
[The history of antitussive and expectorants].	2008	18956357
Challenges of utilizing immunostains to facilitate the diagnosis and management of metastatic adenocarcinoma.	2008 Dec	19110917
Development and evaluation of oral controlled release chlorpheniramine-ion exchange resinate suspension.	2008 Jul-Aug	20046790
Posterior impingement syndromes of the ankle.	2008 Jun	18509795
Perinatal tumours: the contribution of radiology to management.	2008 Jun	18470458
Simultaneous UV Spectrophotometric Estimation of Ambroxol Hydrochloride and Levocetirizine Dihydrochloride.	2008 Mar-Apr	20046721
Mediastinal pancreatic pseudocyst with isolated thoracic symptoms: a case report.	2008 May 27	18505589
The effect of retroperitoneal fat tissue thickness on testicular venous drainage.	2009	19641367
[Traumatic perforation of the duodenum--a case review].	2009 Feb	19413259
Acidic and basic solutions dissolve protein plugs made of lithostathine complicating choledochal cyst/pancreaticobiliary maljunction.	2009 Jul	18989781
Solitary fibrous tumor of the lung: three rare cases of intraparenchymal nodules.	2009 May	19308764
Sensitive spectrophotometric method for quantitation of guaifenesin and dropropizine in their dosage forms.	2010	20671996
Ambroxol - Resurgence of an old molecule as an anti-inflammatory agent in chronic obstructive airway diseases.	2010 Apr	20616932
Quantification of the major metabolites of bromhexine in human plasma using RRLC-MS/MS and its application to pharmacokinetics.	2010 Apr 6	20031363
Anatomical suitability for endovascular AAA repair may affect outcomes following rupture.	2010 Aug	20434374
Tuberculosis should not be ignored in patients with peripheral gangrene.	2010 Dec	20843626
Analyses and localization of pectin-like carbohydrates in cell wall and mucilage of the green alga Netrium digitus.	2010 Jul	19340523
Effect of drug content and agglomerate size on tabletability and drug release characteristics of bromhexine hydrochloridetalc agglomerates prepared by crystallo-co-agglomeration.	2010 Mar	20228039
[Codeine and cutaneous drug reactions: Absence of cross-allergy with tramadol and fentanyl].	2010 May	20470933
[Juvenile Gougerot Sjögren syndrome: report of 3 cases].	2010 Nov	20850283
Superior mesenteric artery aneurysm: importance of sonography as the primary imaging technique for detection.	2010 Oct	20876907
Contaminations of herbal products determined by NMR fingerprint.	2010 Sep	20803376

Patents

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.

Name

Type

Language

BROMHEXINE

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