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
SMILES
CN(CC1=CC(Br)=CC(Br)=C1N)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
| 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 |
DescriptionCurator'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
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 |
|---|---|---|---|
Target ID: GO:1903510 |
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Target ID: GO:0006979 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | Bisolvon Approved UseSecretolytic therapy in acute and chronic bronchopulmonary diseases associated with abnormal
mucus secretion and impaired mucus transport. |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
5% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/32458206/ |
BROMHEXINE plasma | Homo sapiens |
Doses
| Dose | Population | Adverse 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: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Other AEs: Hepatic injury, Insomnia... Other AEs: Hepatic injury (grade 1, 3 patients) Sources: Insomnia (1 pt) Gingivitis (2 patients) |
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: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| 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: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| 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: |
unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
Sample Use Guides
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
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| Record UNII |
Q1J152VB1P
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| Record Status |
Validated (UNII)
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Official Name | English | ||
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WHO-ATC |
R05CB02
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LIVERTOX |
122
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WHO-VATC |
QR05CB02
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FDA ORPHAN DRUG |
34789
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CHEMBL253376
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C172826
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m2668
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402
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BROMHEXINE
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SUB05914MIG
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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.
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SALT/SOLVATE -> PARENT |
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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).
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ACTIVE MOIETY |
