Ambroxol

Identification

Name
Ambroxol
Accession Number
DB06742
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.

Type
Small Molecule
Groups
Approved, Investigational
Structure
Thumb
Weight
Average: 378.108
Monoisotopic: 375.978589
Chemical Formula
C13H18Br2N2O
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

Pharmacology

Indication

Ambroxol is indicated for secretolytic therapy in bronchoplmonary diseaes with abnormal mucus secretion and transport. It allows the mucus to be more easily cleared and ease a patient's breathing.

Associated Therapies
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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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
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Ambroxol can be increased when it is combined with Abametapir.
CenobamateThe serum concentration of Ambroxol can be decreased when it is combined with Cenobamate.
HaloperidolThe serum concentration of Haloperidol can be increased when it is combined with Ambroxol.
MetreleptinThe metabolism of Ambroxol can be increased when combined with Metreleptin.
PitolisantThe serum concentration of Ambroxol can be decreased when it is combined with Pitolisant.
RitonavirThe serum concentration of Ambroxol can be increased when it is combined with Ritonavir.
SatralizumabThe serum concentration of Ambroxol can be decreased when it is combined with Satralizumab.
TucatinibThe metabolism of Tucatinib can be decreased when combined with Ambroxol.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

Products

Product Ingredients
IngredientUNIICASInChI Key
Ambroxol hydrochlorideCC995ZMV9023828-92-4QNVKOSLOVOTXKF-PFWPSKEQSA-N
International/Other Brands
Ambrolex (GlaxoSmithKline Inc.) / Ambrox (Square) / Tabcin

Categories

ATC Codes
R03CC63 — Clenbuterol and ambroxolR05CB06 — Ambroxol
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
2-bromoaniline / Alcohol / Amine / Aniline or substituted anilines / Aralkylamine / Aromatic homomonocyclic compound / Aryl bromide / Aryl halide / Benzylamine / Bromobenzene
show 17 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
Not Available

Chemical Identifiers

UNII
200168S0CL
CAS number
18683-91-5
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

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
PubChem Compound
2132
PubChem Substance
347827790
ChemSpider
10276826
BindingDB
50395322
RxNav
625
ChEBI
135590
ChEMBL
CHEMBL153479
ZINC
ZINC000100070274
Wikipedia
Ambroxol
MSDS
Download (47.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentPharyngitis4
3RecruitingTreatmentAbnormal Mucus Secretions / Respiratory Tract Diseases1
2CompletedBasic ScienceCoughing1
2CompletedPreventionAllergic Sensitization / Asthma1
2CompletedPreventionParkinson's Disease (PD)1
2CompletedTreatmentHypersensitivity, Food1
2CompletedTreatmentPain / Pharyngitis1
2Not Yet RecruitingTreatmentMelanoma1
2RecruitingTreatmentGaucher Disease, Type 1 / Gaucher's Disease Type 11
2RecruitingTreatmentHead and Neck Mucosal Melanomas1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SyrupOral15 mg/5mL
Solution7.5 mg/ml
CapsuleOral75 mg
Tablet, solubleOral30 mg
SolutionOral7.5 MG/ML
Tablet30 MG
SolutionOral15 MG/ML
SyrupOral
SyrupOral300 mg
SolutionOral0.15 g
SyrupOral600 mg
SolutionOral0.3 g
SolutionOral15 MG/5ML
Capsule, extended releaseOral75 MG
Tablet, for solution; tablet, for suspensionOral30 MG
Tablet, effervescentOral60 MG
SolutionOral30 MG/5ML
Tablet, solubleOral60 mg
SolutionRespiratory (inhalation)7.5 mg/mL
Injection, solutionParenteral15 MG/2ML
Tablet60 MG
SolutionOral3 MG/ML
SyrupOral30 MG/5ML
Syrup
Tablet
SolutionOral
SolutionOral0.6 g
Elixir
Tablet, coatedOral30 mg
Capsule, extended release75 MG
Granule, for solutionOral65 mg
Granule, for suspensionOral30 MG
SolutionOral0.75 %
Spray15 MG/2ML
SuppositoryRectal30 mg
Syrup15 MG/5ML
Syrup150 ml
Spray7.5 MG/ML
Syrup3 MG/ML
Syrup30 MG/10ML
TabletOral20 mg
SprayOral17.86 mg/ml
LozengeOral20 MG
Injection, solution15 mg/2mL
Liquid
Capsule, extended release
Granule, for solutionOral15 MG
Granule, for solutionOral30 MG
Granule, for solutionOral60 MG
Solution / dropsOral30 mg/5mL
Suppository15 MG
Suppository30 MG
Suppository60 MG
Syrup200 ML
Syrup30 MG/5ML
Tablet15 MG
Tablet, chewableOral15 MG
Tablet, coated60 MG
Solution15 mg/5ml
Solution7.5 mg/1ml
SyrupOral0.15 g
Tablet, film coatedOral60 MG
SolutionRespiratory (inhalation)15 MG
PastilleOral15 MG
Pastille15 mg
SolutionRespiratory (inhalation)0.75 g
SolutionOral30 MG/2ML
Solution / drops; suspension / drops
SolutionOral300 mg
SolutionOral7.5 mg
SprayRespiratory (inhalation)15 MG/2ML
SprayRespiratory (inhalation)30 MG/4ML
SyrupOral15 mg/mL
TabletOral30 MG
Solution2 ml
Lozenge15 mg
SyrupOral250 mg
SyrupOral0.3 g
SyrupOral0.6 g
Tablet, effervescentOral30 MG
SolutionOral6 MG/ML
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

Enzymes

Kind
Protein
Organism
Humans
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. Ishiguro N, Senda C, Kishimoto W, Sakai K, Funae Y, Igarashi T: Identification of CYP3A4 as the predominant isoform responsible for the metabolism of ambroxol in human liver microsomes. Xenobiotica. 2000 Jan;30(1):71-80. [PubMed:10659952]

Drug created on September 01, 2010 13:05 / Updated on July 02, 2020 07:24

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