Identification
NameAmbroxol
Accession NumberDB06742
TypeSmall Molecule
GroupsApproved
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 KeyDetails
Ambroxol hydrochlorideCC995ZMV90 23828-92-4QNVKOSLOVOTXKF-PFWPSKEQSA-NDetails
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AmbrolexGlaxoSmithKline Inc.
AmbroxSquare
TabcinNot Available
Brand mixturesNot Available
Categories
UNII200168S0CL
CAS number18683-91-5
WeightAverage: 378.108
Monoisotopic: 375.978589
Chemical FormulaC13H18Br2N2O
InChI KeyJBDGDEWWOUBZPM-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
PharmacodynamicsNot 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.

Related Articles
Absorption

Rapid and almost complete.

Volume of distributionNot Available
Protein binding

Approximately 90%

MetabolismNot Available
Route of eliminationNot Available
Half life

7-12 hours

ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot 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
BexaroteneThe serum concentration of Ambroxol can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Ambroxol can be decreased when combined with Boceprevir.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
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
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
DexamethasoneThe serum concentration of Ambroxol can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
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
EfavirenzThe serum concentration of Ambroxol can be decreased when it is combined with Efavirenz.Approved, Investigational
EnzalutamideThe serum concentration of Ambroxol can be decreased when it is combined with Enzalutamide.Approved
ErythromycinThe metabolism of Ambroxol can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Ambroxol can be decreased when it is combined with Eslicarbazepine acetate.Approved
EtravirineThe serum concentration of Ambroxol can be decreased when it is combined with Etravirine.Approved
FluconazoleThe metabolism of Ambroxol can be decreased when combined with Fluconazole.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
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
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
ModafinilThe serum concentration of Ambroxol can be decreased when it is combined with Modafinil.Approved, Investigational
NafcillinThe serum concentration of Ambroxol can be decreased when it is combined with Nafcillin.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
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
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
PosaconazoleThe metabolism of Ambroxol can be decreased when combined with Posaconazole.Approved, Investigational, Vet 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
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
St. John's WortThe serum concentration of Ambroxol can be decreased when it is combined with St. John's Wort.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.Withdrawn
TelithromycinThe metabolism of Ambroxol can be decreased when combined with Telithromycin.Approved
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
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 InteractionsNot 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 ReferencesNot Available
External Links
ATC CodesR05CB06 — Ambroxol
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (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
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
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 featuresNot Available
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
Direct ParentPhenylmethylamines
Alternative ParentsBenzylamines / 2-bromoanilines / Cyclohexylamines / Cyclohexanols / Bromobenzenes / Aralkylamines / Aryl bromides / Cyclic alcohols and derivatives / Dialkylamines / Primary amines
SubstituentsBenzylamine / Aniline or substituted anilines / 2-bromoaniline / Phenylmethylamine / Bromobenzene / Aralkylamine / Cyclohexanol / Cyclohexylamine / Halobenzene / Aryl bromide
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinhibitor
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
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 September 01, 2017 11:30