Identification

Name
Ambroxol
Accession Number
DB06742
Type
Small Molecule
Groups
Approved, 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[[email protected]]1CC[[email protected]](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.

Structured Indications
Not Available
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
DrugInteractionDrug group
AmiodaroneThe metabolism of Ambroxol can be decreased when combined with Amiodarone.Approved, Investigational
AprepitantThe serum concentration of Ambroxol can be increased when it is combined with Aprepitant.Approved, Investigational
AtazanavirThe metabolism of Ambroxol can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Ambroxol can be decreased when combined with Atomoxetine.Approved
AtorvastatinThe risk or severity of adverse effects can be increased when Ambroxol is combined with Atorvastatin.Approved
BoceprevirThe metabolism of Ambroxol can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Ambroxol can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Ambroxol can be decreased when it is combined with Bosentan.Approved, Investigational
BromocriptineThe risk or severity of adverse effects can be increased when Bromocriptine is combined with Ambroxol.Approved, Investigational
CabergolineThe risk or severity of adverse effects can be increased when Cabergoline is combined with Ambroxol.Approved
CarbamazepineThe metabolism of Ambroxol can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Ambroxol can be increased when it is combined with Ceritinib.Approved
CerivastatinThe serum concentration of Cerivastatin can be increased when it is combined with Ambroxol.Withdrawn
ClarithromycinThe metabolism of Ambroxol can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Ambroxol can be decreased when combined with Clemastine.Approved
ClotrimazoleThe metabolism of Ambroxol can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Ambroxol can be decreased when combined with Cobicistat.Approved
ConivaptanThe serum concentration of Ambroxol can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Ambroxol can be decreased when combined with Crizotinib.Approved
CyclosporineThe metabolism of Ambroxol can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Ambroxol can be decreased when it is combined with Dabrafenib.Approved
DarunavirThe metabolism of Ambroxol can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Ambroxol can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Ambroxol can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Ambroxol can be decreased when combined with Delavirdine.Approved
DihydroergocornineThe risk or severity of adverse effects can be increased when Dihydroergocornine is combined with Ambroxol.Approved
DihydroergocristineThe risk or severity of adverse effects can be increased when Dihydroergocristine is combined with Ambroxol.Experimental
DihydroergocryptineThe risk or severity of adverse effects can be increased when Dihydroergocryptine is combined with Ambroxol.Experimental
DihydroergotamineThe metabolism of Ambroxol can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Ambroxol can be decreased when combined with Diltiazem.Approved
DoxycyclineThe metabolism of Ambroxol can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Ambroxol can be decreased when combined with Dronedarone.Approved
EnzalutamideThe serum concentration of Ambroxol can be decreased when it is combined with Enzalutamide.Approved
ErgonovineThe risk or severity of adverse effects can be increased when Ergonovine is combined with Ambroxol.Approved
ErgotamineThe risk or severity of adverse effects can be increased when Ergotamine is combined with Ambroxol.Approved
ErythromycinThe metabolism of Ambroxol can be decreased when combined with Erythromycin.Approved, Vet Approved
FluconazoleThe metabolism of Ambroxol can be decreased when combined with Fluconazole.Approved
FluvastatinThe serum concentration of Fluvastatin can be increased when it is combined with Ambroxol.Approved
FluvoxamineThe metabolism of Ambroxol can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Ambroxol can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Ambroxol can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Ambroxol can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Ambroxol can be increased when it is combined with Fusidic Acid.Approved
IdelalisibThe serum concentration of Ambroxol can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Ambroxol can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Ambroxol can be decreased when combined with Indinavir.Approved
IsavuconazoniumThe metabolism of Ambroxol can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Ambroxol can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Ambroxol can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Ambroxol can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Ambroxol can be decreased when combined with Ketoconazole.Approved, Investigational
LisurideThe risk or severity of adverse effects can be increased when Lisuride is combined with Ambroxol.Approved, Investigational
LopinavirThe metabolism of Ambroxol can be decreased when combined with Lopinavir.Approved
LovastatinThe metabolism of Ambroxol can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Ambroxol can be increased when it is combined with Luliconazole.Approved
LumacaftorThe metabolism of Ambroxol can be increased when combined with Lumacaftor.Approved
Lysergic Acid DiethylamideThe risk or severity of adverse effects can be increased when Lysergic Acid Diethylamide is combined with Ambroxol.Illicit, Investigational, Withdrawn
MetergolineThe risk or severity of adverse effects can be increased when Metergoline is combined with Ambroxol.Experimental
MethylergometrineThe risk or severity of adverse effects can be increased when Methylergometrine is combined with Ambroxol.Approved
MethysergideThe risk or severity of adverse effects can be increased when Methysergide is combined with Ambroxol.Approved
MevastatinThe serum concentration of Mevastatin can be increased when it is combined with Ambroxol.Experimental
MifepristoneThe serum concentration of Ambroxol can be increased when it is combined with Mifepristone.Approved, Investigational
MitotaneThe serum concentration of Ambroxol can be decreased when it is combined with Mitotane.Approved
NefazodoneThe metabolism of Ambroxol can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Ambroxol can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Ambroxol can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Ambroxol can be increased when combined with Nevirapine.Approved
NicergolineThe risk or severity of adverse effects can be increased when Nicergoline is combined with Ambroxol.Approved, Investigational
NilotinibThe metabolism of Ambroxol can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Ambroxol can be decreased when combined with Olaparib.Approved
OsimertinibThe serum concentration of Ambroxol can be increased when it is combined with Osimertinib.Approved
PalbociclibThe serum concentration of Ambroxol can be increased when it is combined with Palbociclib.Approved
PentobarbitalThe metabolism of Ambroxol can be increased when combined with Pentobarbital.Approved, Vet Approved
PergolideThe risk or severity of adverse effects can be increased when Pergolide is combined with Ambroxol.Approved, Investigational, Vet Approved, Withdrawn
PhenobarbitalThe metabolism of Ambroxol can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Ambroxol can be increased when combined with Phenytoin.Approved, Vet Approved
PitavastatinThe serum concentration of Pitavastatin can be increased when it is combined with Ambroxol.Approved
PosaconazoleThe metabolism of Ambroxol can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Pravastatin can be increased when it is combined with Ambroxol.Approved
PrimidoneThe metabolism of Ambroxol can be increased when combined with Primidone.Approved, Vet Approved
RanolazineThe metabolism of Ambroxol can be decreased when combined with Ranolazine.Approved, Investigational
RifabutinThe metabolism of Ambroxol can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Ambroxol can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Ambroxol can be increased when combined with Rifapentine.Approved
RitonavirThe metabolism of Ambroxol can be decreased when combined with Ritonavir.Approved, Investigational
RosuvastatinThe serum concentration of Rosuvastatin can be increased when it is combined with Ambroxol.Approved
SaquinavirThe metabolism of Ambroxol can be decreased when combined with Saquinavir.Approved, Investigational
SildenafilThe metabolism of Ambroxol can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Ambroxol can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Ambroxol can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Simvastatin can be increased when it is combined with Ambroxol.Approved
St. John's WortThe serum concentration of Ambroxol can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Ambroxol can be increased when it is combined with Stiripentol.Approved
SulfisoxazoleThe metabolism of Ambroxol can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
TelaprevirThe metabolism of Ambroxol can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Ambroxol can be decreased when combined with Telithromycin.Approved
TergurideThe risk or severity of adverse effects can be increased when Terguride is combined with Ambroxol.Experimental
TiclopidineThe metabolism of Ambroxol can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Ambroxol can be decreased when it is combined with Tocilizumab.Approved
UbidecarenoneThe serum concentration of Ubidecarenone can be increased when it is combined with Ambroxol.Approved, Experimental
VenlafaxineThe metabolism of Ambroxol can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Ambroxol can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Ambroxol can be decreased when combined with Voriconazole.Approved, Investigational
ZiprasidoneThe metabolism of Ambroxol can be decreased when combined with Ziprasidone.Approved
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
2Not Yet RecruitingPreventionParkinson's Disease (PD)1
2RecruitingTreatmentParkinson's Disease Dementia (PDD)1
3CompletedTreatmentPharyngitis2

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
Inhibitor
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 09, 2017 03:55