Ambroxol

Identification

Summary

Ambroxol is a medication indicated for airway secretion clearance therapy.

Generic Name
Ambroxol
DrugBank Accession Number
DB06742
Background

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
  • Ambroxol
  • 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 disease with abnormal mucus secretion and transport. It allows the mucus to be more easily cleared and ease a patient's breathing.

Pharmacology
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Associated Therapies
Contraindications & Blackbox Warnings
Contraindications
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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
Adverseeffects
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Toxicity

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.
AbirateroneThe metabolism of Ambroxol can be decreased when combined with Abiraterone.
AmiodaroneThe metabolism of Ambroxol can be decreased when combined with Amiodarone.
AmprenavirThe metabolism of Ambroxol can be decreased when combined with Amprenavir.
ApalutamideThe metabolism of Ambroxol can be increased when combined with Apalutamide.
AprepitantThe metabolism of Ambroxol can be decreased when combined with Aprepitant.
AtazanavirThe metabolism of Ambroxol can be decreased when combined with Atazanavir.
BerotralstatThe metabolism of Ambroxol can be decreased when combined with Berotralstat.
BoceprevirThe metabolism of Ambroxol can be decreased when combined with Boceprevir.
CarbamazepineThe metabolism of Ambroxol can be increased when combined with Carbamazepine.
Interactions
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Food Interactions
Not Available

Products

Products2
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dosage, form, labeller, route of administration, and marketing period.
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Product Ingredients
IngredientUNIICASInChI Key
Ambroxol hydrochlorideCC995ZMV9023828-92-4QNVKOSLOVOTXKF-PFWPSKEQSA-N
International/Other Brands
Ambrolex (GlaxoSmithKline Inc.) / Ambrox (Square) / Tabcin
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
AMCOSOL SYRUP 30MG/5MLSyrupOralPRIME PHARMACEUTICAL SDN. BHD.2020-09-08Not applicableMalaysia flag
AMCOSOL TABLET 30MGTabletOralPRIME PHARMACEUTICAL SDN. BHD.2020-09-08Not applicableMalaysia flag
AMSOLVAN ORAL SOLUTION 30mg/5mlSolutionOralXEPA-SOUL PATTINSON (MALAYSIA) SDN BHD2020-09-08Not applicableMalaysia flag
AMTUSS (Syrup )SyrupOralMEDISPEC (M) SDN.BHD2020-09-08Not applicableMalaysia flag
AMTUSS 30 MG TABLETTabletOralMEDISPEC (M) SDN.BHD2020-09-08Not applicableMalaysia flag
AMXOL SYRUP 30MG/5MLSyrupOralMEDISPEC (M) SDN.BHD2020-09-08Not applicableMalaysia flag
AMXOL TABLETS 30MGTabletOralMEDISPEC (M) SDN.BHD2020-09-08Not applicableMalaysia flag
AXOL LIQUID 3MG/MLLiquidOralY.S.P. INDUSTRIES (M) SDN BHD2020-09-08Not applicableMalaysia flag
BOOTS AMBROXOL 30 MGTablet30 mgบริษัท ไบโอแลป จำกัด จำกัด2000-12-14Not applicableThailand flag
Hovid Desolvon-30 TabletTabletOralHovid Berhad2020-09-08Not applicableMalaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
AMBROXOL 150 MG / 100 ML + CLENBUTEROL 0.1 MG / 100 ML SOLUCIÓN ORAL NIÑOSAmbroxol hydrochloride (0.15 g) + Clenbuterol (0.0001 g)SolutionOralCOASPHARMA S.A.S. PLANTA PALOQUEMAO2006-11-102021-10-01Colombia flag
AMBROXOL 300 MG/100 ML + CLENBUTEROL 0.2 MG/100 MLSOLUCIÓN ORAL ADULTOSAmbroxol hydrochloride (0.3 g) + Clenbuterol (0.0002 g)SolutionOralCOASPHARMA S.A.S.2006-11-102021-10-01Colombia flag
BRONSINEX JARABEAmbroxol hydrochloride (300 mg) + Clenbuterol (0.2 mg)SyrupOralGONHER FARMACEUTICA LTDA2009-06-04Not applicableColombia flag
MUCOSOLVAN COMPOSITUM JARABE PEDIATRICO. 7.5 MG / 0.005MG / 5ML.Ambroxol hydrochloride (0.15 g) + Clenbuterol hydrochloride (0.1 mg)SyrupOralPHARMETIQUE S.A2006-11-102018-02-20Colombia flag
RESPHIR® JARABEAmbroxol hydrochloride (300 mg) + Salbutamol sulfate (40 mg)SyrupOralCOLOMPACK S.A.2007-10-25Not applicableColombia flag
TOS-XOL ® JARABEAmbroxol hydrochloride (0.3 g) + Salbutamol sulfate (0.04 g)SyrupOralLABORATORIOS LEGRAND S.A.2011-07-222018-08-30Colombia flag
TRIATUSIC® JARABEAmbroxol hydrochloride (250 mg) + Dextromethorphan hydrobromide (300 mg) + Theophylline (1300 mg)SyrupOralGONHER FARMACEUTICA LTDA PLANTA DE PRODUCCIÓN II2009-05-13Not applicableColombia flag
TUSIMED JARABEAmbroxol hydrochloride (0.3 g) + Clenbuterol (0.0002 g)SyrupOralBIOCHEM FARMACEUTICA DE COLOMBIAS.A.2006-11-102016-03-23Colombia flag
TUSSFREL ADULTOSAmbroxol hydrochloride (0.6 g) + Salbutamol sulfate (0.08 g)SyrupOralBIOQUIMICO PHARMAS.A.2010-03-012021-10-01Colombia flag

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
Affected organisms
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[C@H]1CC[C@H](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
3CompletedTreatmentAbnormal Mucus Secretions / Respiratory Tract Diseases1
3CompletedTreatmentPharyngitis4
2CompletedBasic ScienceCough1
2CompletedPreventionParkinson's Disease (PD)1
2CompletedTreatmentPain / Pharyngitis1
2RecruitingTreatmentDementia With Lewy Body Disease1
2RecruitingTreatmentGaucher Disease, Type 11
2RecruitingTreatmentParkinsons Disease With Dementia (PDD)1
1CompletedTreatmentHealthy Subjects (HS)6
1, 2CompletedHealth Services ResearchIn the Present Study, we Investigated the Effects of Oral Ambroxol on Tear Film and Ocular Surface1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionOral7.5 mg
Injection, solutionParenteral
SolutionOral
TabletOral
Solution
CapsuleOral
Tablet, solubleOral
SolutionOral7.5 MG/ML
SolutionOral15 MG/ML
SolutionOral0.3 g
SolutionOral15 MG/5ML
Tablet, for solution; tablet, for suspensionOral30 MG
Tablet, effervescentOral60 MG
SyrupOral600 g
SolutionOral; Respiratory (inhalation)
SolutionRespiratory (inhalation)7.5 mg/mL
SyrupOral0.6 g
SyrupOral600 mg
SyrupOral300 mg
Injection, solutionParenteral15 MG/2ML
TabletOral60 MG
TabletOral30 mg
SolutionOral3 MG/ML
SyrupOral0.3 g
Granule, for suspensionOral
Spray7.5 MG/ML
Tablet, extended releaseOral
SolutionOral0.6 g
SyrupOral
Granule, for solutionOral30 mg
Granule, for solutionOral65 mg
Granule, for suspensionOral30 MG
SolutionOral0.75 %
SolutionRespiratory (inhalation)15 MG/2ML
Spray15 MG/2ML
SuppositoryRectal30 mg
GranuleOral
Tablet
SyrupOral3 MG/ML
SyrupOral30 MG/10ML
SprayOral
LozengeOral
LozengeOral20 MG
LiquidOral
SolutionIntravenous
Granule, for solutionOral
SolutionRespiratory (inhalation)
Spray
SuppositoryRectal
SyrupOral200 ML
Tablet, chewableOral
Tablet, coatedOral
Tablet, effervescentOral
TabletOral20 mg
PastilleOral
SyrupOral
Tablet, film coatedOral60 MG
GranuleOral2 g
SolutionRespiratory (inhalation)15 MG
PastilleOral15 MG
SolutionRespiratory (inhalation)0.75 g
SolutionOral30 MG/2ML
Capsule, extended releaseOral
Tablet, chewableOral15 mg
SolutionOral
TabletOral
Solution / drops; suspension / drops
SolutionOral300 mg
Granule, for solutionOral15 MG
Granule, for solutionOral60 MG
SprayRespiratory (inhalation)15 MG/2ML
SprayRespiratory (inhalation)30 MG/4ML
SyrupOral15 mg/mL
SolutionIntramuscular; Intravenous
Elixir
SuspensionOral300 mg
Granule, effervescent
Tablet, effervescentOral30 MG
SolutionOral6 MG/ML
TabletTransmucosal
SyrupOral15 mg/5mL
SyrupOral30 mg/5mL
Capsule, extended releaseOral75 mg
LozengeOral15 mg
Tablet30 mg
Tablet, coatedOral30 mg
SolutionOral30 mg/5ml
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. [Article]

Drug created on September 01, 2010 19:05 / Updated on August 07, 2021 00:37