Identification

Name
Ambroxol
Accession Number
DB06742
Type
Small Molecule
Groups
Investigational
Description

Ambroxol is a secretolytic agent used in the treatment of respiratory diseases associated with viscid or excessive mucus. It is the active ingredient of Mucosolvan, Lasolvan or Mucoangin. The substance is a mucoactive drug with several properties including secretolytic and secretomotoric actions that restore the physiological clearance mechanisms of the respiratory tract which play an important role in the body’s natural defence mechanisms. It stimulates synthesis and release of surfactant by type II pneumocytes. Surfactants acts as an anti-glue factor by reducing the adhesion of mucus to the bronchial wall, in improving its transport and in providing protection against infection and irritating agents.

Structure
Thumb
Synonyms
  • Ambroxolum
  • Bisolvon metabolite vIII
  • Bromhexine metabolite vIII
  • Bromhexine-metabolite vIII
  • Cyclohexanol, 4-((2-amino-3,5-dibromobenzyl)amino)- (E)-
  • N-(2-Amino-3,4-dibromociclohexil)-trans-4-aminociclohexanol
  • N-(2-Amino-3,4-dibromocyclohexyl)-trans-4-aminocyclohexanol
  • trans-4-((2-Amino-3,5-dibromobencil)amino)ciclohexanol
  • trans-4-((2-Amino-3,5-dibromobenzyl)amine)cyclohexanol
  • trans-4-((2-Amino-3,5-dibromobenzyl)amino)cyclohexanol
External IDs
NA-872
Product Ingredients
IngredientUNIICASInChI Key
Ambroxol hydrochlorideCC995ZMV9023828-92-4QNVKOSLOVOTXKF-PFWPSKEQSA-N
International/Other Brands
Ambrolex (GlaxoSmithKline Inc.) / Ambrox (Square) / Tabcin
Categories
UNII
200168S0CL
CAS number
18683-91-5
Weight
Average: 378.108
Monoisotopic: 375.978589
Chemical Formula
C13H18Br2N2O
InChI Key
JBDGDEWWOUBZPM-XYPYZODXSA-N
InChI
InChI=1S/C13H18Br2N2O/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/t10-,11-
IUPAC Name
(1r,4r)-4-{[(2-amino-3,5-dibromophenyl)methyl]amino}cyclohexan-1-ol
SMILES
NC1=C(Br)C=C(Br)C=C1CN[C@H]1CC[C@H](O)CC1

Pharmacology

Indication

Ambroxol is indicated as “secretolytic therapy in bronchopulmonary diseases associated with abnormal mucus secretion and impaired mucus transport. It promotes mucus clearance, facilitates expectoration and eases productive cough, allowing patients to breathe freely and deeply.

Pharmacodynamics
Not Available
Mechanism of action

Ambroxol is a mucolytic agent. Excessive Nitric oxide (NO) is associated with inflammatory and some other disturbances of airways function. NO enhances the activation of soluble guanylate cyclase and cGMP accumulation. Ambroxol has been shown to inhibit the NO-dependent activation of soluble guanylate cyclase. It is also possible that the inhibition of NO-dependent activation of soluble guanylate cyclase can suppress the excessive mucus secretion, therefore it lowers the phlegm viscosity and improves the mucociliary transport of bronchial secretions.

Absorption

Rapid and almost complete.

Volume of distribution
Not Available
Protein binding

Approximately 90%

Metabolism
Not Available
Route of elimination
Not Available
Half life

7-12 hours

Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Ambroxol.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Ambroxol.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Ambroxol.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Ambroxol.
5-androstenedioneThe metabolism of Ambroxol can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Ambroxol can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Ambroxol.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Ambroxol.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Ambroxol.
AbirateroneThe metabolism of Ambroxol can be decreased when combined with Abiraterone.
Food Interactions
Not Available

References

Synthesis Reference

Kack, J., Koss, F.W., Schraven, E. and Beisenherz, G.; US. Patent 3,536,713; October 27, 1970; assigned to Boehringer lngelheim G.m.b.H.

General References
Not Available
External Links
PubChem Compound
2132
PubChem Substance
347827790
ChemSpider
10276826
BindingDB
50395322
ChEBI
135590
ChEMBL
CHEMBL153479
Wikipedia
Ambroxol
ATC Codes
R05CB06 — Ambroxol
MSDS
Download (47.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentHealthy Volunteers1
1, 2CompletedHealth Services ResearchIn the Present Study, we Investigated the Effects of Oral Ambroxol on Tear Film and Ocular Surface1
1, 2SuspendedTreatmentType I Gaucher Disease1
2Active Not RecruitingPreventionParkinson's Disease (PD)1
2Not Yet RecruitingBasic ScienceCoughing1
2RecruitingTreatmentParkinson's Disease Dementia (PDD)1
3CompletedTreatmentPharyngitis3

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)233-234.5Kack, J., Koss, F.W., Schraven, E. and Beisenherz, G.; US. Patent 3,536,713; October 27, 1970; assigned to Boehringer lngelheim G.m.b.H.
Predicted Properties
PropertyValueSource
Water Solubility0.0185 mg/mLALOGPS
logP3.72ALOGPS
logP2.65ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)15.26ChemAxon
pKa (Strongest Basic)9.01ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area58.28 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity81.94 m3·mol-1ChemAxon
Polarizability32.8 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenylmethylamines
Direct Parent
Phenylmethylamines
Alternative Parents
Benzylamines / 2-bromoanilines / Cyclohexylamines / Cyclohexanols / Bromobenzenes / Aralkylamines / Aryl bromides / Cyclic alcohols and derivatives / Dialkylamines / Primary amines
show 3 more
Substituents
Benzylamine / Aniline or substituted anilines / 2-bromoaniline / Phenylmethylamine / Bromobenzene / Aralkylamine / Cyclohexanol / Cyclohexylamine / Halobenzene / Aryl bromide
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on September 01, 2010 13:05 / Updated on November 02, 2018 08:40