Details
Stereochemistry | ACHIRAL |
Molecular Formula | C13H18Br2N2O.ClH |
Molecular Weight | 414.564 |
Optical Activity | NONE |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NC1=C(CN[C@H]2CC[C@H](O)CC2)C=C(Br)C=C1Br
InChI
InChIKey=QNVKOSLOVOTXKF-PFWPSKEQSA-N
InChI=1S/C13H18Br2N2O.ClH/c14-9-5-8(13(16)12(15)6-9)7-17-10-1-3-11(18)4-2-10;/h5-6,10-11,17-18H,1-4,7,16H2;1H/t10-,11-;
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/18680446Curator's Comment: Description was created based on several sources, including
http://adisinsight.springer.com/drugs/800035262 | https://www.ncbi.nlm.nih.gov/pubmed/23158495 | https://www.ncbi.nlm.nih.gov/pubmed/18482096 | https://www.ncbi.nlm.nih.gov/pubmed/19578116 | http://zywiebio.com/drug-development/therapeutic-areas-of-interest/gaucher-disease/
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18680446
Curator's Comment: Description was created based on several sources, including
http://adisinsight.springer.com/drugs/800035262 | https://www.ncbi.nlm.nih.gov/pubmed/23158495 | https://www.ncbi.nlm.nih.gov/pubmed/18482096 | https://www.ncbi.nlm.nih.gov/pubmed/19578116 | http://zywiebio.com/drug-development/therapeutic-areas-of-interest/gaucher-disease/
Ambroxol, a substituted benzylamine, is an active
metabolite of bromhexine, which is itself
a synthetic derivative of vasicine, the active principle extracted from the plant species Adhatoda vasica. Ambroxol is an expectorant exerting mucokinetic properties, mucociliary activity, stimulation of surfactant production, anti-inflammatory and antioxidative actions and the local anaesthetic effect. Ambroxol was discovered at and has been manufactured by Dr. Karl Thomae GmbH, a division of Boehringer Ingelheim. The ambroxol patent is expired and the drug is available as a generic product from many different companies. Ambroxol was originally developed by Boehringer Ingelheim as a OTC therapy for respiratory disorders related to excessive mucus. Ambroxol's indication is secretolytic therapy in acute and chronic bronchopulmonary diseases associated with abnormal mucus secretion and impaired mucus transport. Boehringer Ingelheim markets the product under various brand names such as Mucosolvan® and Lasolvan®. Ambroxol was identified and found to be a pH-dependent, mixed-type inhibitor of glucocerebrosidase (GCase). Its inhibitory activity was maximal at neutral pH, found in the endoplasmic reticulum, and undetectable at the acidic pH of lysosomes. The pH dependence of Ambroxol to bind and stabilize the enzyme was confirmed. Ambroxol increases both the lysosomal fraction and the enzymatic activity of several mutant GCase variants. This profile of Ambroxol would allow to bind and stabilize GCase in the endoplasmic reticulum (thus preventing its degradation within endoplasmic reticulum), but without affecting GCase in the lysosomes (thus allowing it to degrade glucosylceramide). Indeed, studies showed that Ambroxol treatment significantly increased N370S and F213I mutant GCase activity and protein levels in fibroblasts originally obtained from Gaucher patients. Gaucher's disease is caused by the deficiency of glucocerebrosidase; ambroxol is a chaperone that acts by binding to and stabilising glucocerebrosidase. Zywie (formerly ExSAR Corporation) and Belrose Pharma are developing ambroxol hydrochloride (BEL 0218) for the treatment of type III Gaucher's disease.
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CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2179 |
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Target ID: GO:0043129 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | MUCOSOLVAN Approved UseMUCOSOLVAN (ambroxol hydrochloride) is indicated for secretolytic therapy in acute and chronic bronchopulmonary diseases associated with abnormal mucus secretion and impaired mucus transport. |
PubMed
Title | Date | PubMed |
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The effect of a single oral administration of ambroxol on the ultrastructure of the epithelium of terminal bronchioles in rabbits. | 2001 |
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[Lipoid pneumonia following attempted suicide by intravenous injection of lamp oil]. | 2001 Nov 15 |
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Pharmacoeconomic analysis of prescriptions in Italian pediatric general practice. | 2002 |
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Efficacy and tolerability of ambroxol hydrochloride lozenges in sore throat. Randomised, double-blind, placebo-controlled trials regarding the local anaesthetic properties. | 2002 |
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Local anaesthetic properties of ambroxol hydrochloride lozenges in view of sore throat. Clinical proof of concept. | 2002 |
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Pulmonary alveolar proteinosis successfully treated with ambroxol. | 2002 Dec |
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Effect of ambroxol on ion transport -- a model study. | 2002 Jun |
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[Mucolytics in acute and chronic respiratory tract disorders. II. Uses for treatment and antioxidant properties]. | 2002 Mar |
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[Ambroxol in etiotropic chemotherapy of pulmonary tuberculosis]. | 2002 May |
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Ambroxol inhibits peroxynitrite-induced damage of alpha1-antiproteinase and free radical production in activated phagocytic cells. | 2002 Sep |
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Inhibition of tetrodotoxin (TTX)-resistant and TTX-sensitive neuronal Na(+) channels by the secretolytic ambroxol. | 2002 Sep |
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Current perspectives on the prevention and management of chronic lung disease in preterm infants. | 2003 |
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Depressant effects of ambroxol and erdosteine on cytokine synthesis, granule enzyme release, and free radical production in rat alveolar macrophages activated by lipopolysaccharide. | 2003 Apr |
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Quantitative determination of ambroxol in tablets by derivative UV spectrophotometric method and HPLC. | 2003 Apr 1 |
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Inhibition of bleomycin-induced cell death in rat alveolar macrophages and human lung epithelial cells by ambroxol. | 2003 Oct 1 |
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Effect of twelve-months therapy with oral ambroxol in preventing exacerbations in patients with COPD. Double-blind, randomized, multicenter, placebo-controlled study (the AMETHIST Trial). | 2004 |
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Ambroxol reduces LPS toxicity mediated by induction of alkaline phosphatases in rat lung. | 2004 Aug |
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[Protective effects of ambroxol on lung injury during cardiacpulmonary bypass in patients undergoing valve replacement]. | 2004 Dec |
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In vitro and in vivo antioxidant activity of ambroxol. | 2004 Dec |
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Oral ambroxol supplement in pregnant women induces fetal lung maturation. | 2004 Dec |
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Bioequivalence assessment of ambroxol tablet after a single oral dose administration to healthy male volunteers. | 2004 Jan |
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Inhibition of inflammatory responses by ambroxol, a mucolytic agent, in a murine model of acute lung injury induced by lipopolysaccharide. | 2004 Jan |
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Pivotal role of superoxide anion and beneficial effect of antioxidant molecules in murine steatohepatitis. | 2004 May |
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Cell-specific modulation of surfactant proteins by ambroxol treatment. | 2005 Feb 15 |
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Effect of ambroxol, spirulina and vitamin-E in naphthalene induced cataract in female rats. | 2005 Jan |
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[Prophylactic effect of ambroxol on acute hydrochloric acid aspiration - induced lung injury]. | 2005 Jun |
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The effect of taste masking agents on in situ gelling pectin formulations for oral sustained delivery of paracetamol and ambroxol. | 2005 Jun 13 |
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Nondestructive determination of the ambroxol content in tablets by Raman spectroscopy. | 2005 Jun 15 |
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Adsorptive stripping voltammetric determination of ambroxol. | 2005 Mar |
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[Treatment of sore throat pain with ambroxol-containing lozenges. Results of a pharmacy supported patient questionnaire]. | 2005 Nov |
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Determination of roxithromycin in rat lung tissue by liquid chromatography-mass spectrometry. | 2005 Sep 15 |
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Effects of cigarette smoke on degranulation and NO production by mast cells and epithelial cells. | 2005 Sep 19 |
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Differences in tidal breathing between infants with chronic lung diseases and healthy controls. | 2005 Sep 8 |
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[Ambroxol]. | 2006 |
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Systematic review of clinical data with BNO-101 (Sinupret) in the treatment of sinusitis. | 2006 Apr |
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[Efficacy of intravenous or atomizing ambroxol for prevention of respiratory distress syndrome in preterm infants]. | 2006 Aug |
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D-MEKK1, the Drosophila orthologue of mammalian MEKK4/MTK1, and Hemipterous/D-MKK7 mediate the activation of D-JNK by cadmium and arsenite in Schneider cells. | 2006 Feb 1 |
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Determination of ambroxol hydrochloride, methylparaben and benzoic acid in pharmaceutical preparations based on sequential injection technique coupled with monolithic column. | 2006 Feb 13 |
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[Influence of ambroxol on paraquat-induced lung tissue injury and change of pulmonary surfactant-associated protein A in the experimental rats]. | 2006 Jun |
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Ambroxol for the prevention of acute upper respiratory disease. | 2006 Jun |
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[Atomization inhalation of ambroxol as an auxiliary therapy for severe pneumonia in neonates]. | 2006 Jun |
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Comparison of the effects of four Na+ channel analgesics on TTX-resistant Na+ currents in rat sensory neurons and recombinant Nav1.2 channels. | 2006 Mar 13 |
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[Ambroxol-induced immune hemolytic anemia]. | 2006 Oct |
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Safety and usage pattern of an over-the-counter ambroxol cough syrup: a community pharmacy-based cohort study. | 2006 Sep |
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Simultaneous determination and pharmacokinetic study of roxithromycin and ambroxol hydrochloride in human plasma by LC-MS/MS. | 2007 Jul |
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Determination of ambroxol in human plasma by high performance liquid chromatography-electrospray ionization mass spectrometry (HPLC-MS/ESI). | 2007 Jun 15 |
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[Determination of ambroxol and clenbuterol in human plasma by LC-MS/MS method]. | 2007 Mar |
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Parenteral ambroxol treatment causes xanthine and calcium oxalate stones in rats. | 2007 May |
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Solid-state chemistry of ambroxol theophylline-7-acetate. | 2007 May |
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Action of neltenexine on anion secretion in human airway epithelia. | 2007 May 18 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/ambroxol.html
Adults: daily dose of 30 mg (one Ambroxol tablet ) to 120 mg (4 Ambroxol tablets) taken in 2 to 3 divided doses
Children up to 2 years: half a teaspoonful Ambroxol syrup twice daily
Children 2 - 5 years: half a teaspoonful Ambroxol syrup 3 times daily
Children over 5 years: One teaspoonful Ambroxol syrup 2-3 times daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26560688
Ambroxol exerted a biphasic response in surfactant secretion, with a significant increase at low concentrations (1 - 10 uM) and an inhibition at high concentrations (≥ 0.1 mM), which is beyond reported plasma Ambroxol concentrations in blood
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EU-Orphan Drug |
EU/3/18/2017
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NCI_THESAURUS |
C74536
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SUB00427MIG
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DBSALT000563
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758224
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438399
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DTXSID2045442
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m1650
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23828-92-4
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CC995ZMV90
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C78113
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100000090754
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CHEMBL153479
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245-899-2
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CC995ZMV90
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ACTIVE MOIETY
SUBSTANCE RECORD