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
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.

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Associated Therapies
Contraindications & Blackbox Warnings
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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
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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.
AbemaciclibThe risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Ambroxol.
AbirateroneThe risk or severity of methemoglobinemia can be increased when Abiraterone is combined with Ambroxol.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Ambroxol.
AcetazolamideThe risk or severity of methemoglobinemia can be increased when Acetazolamide is combined with Ambroxol.
Food Interactions
Not Available

Products

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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 )Syrup30 mg/5mlOralMEDISPEC (M) SDN.BHD2020-09-08Not applicableMalaysia flag
AMTUSS 30 MG TABLETTablet30 mgOralMEDISPEC (M) SDN.BHD2020-09-08Not applicableMalaysia flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
BRONSINEX JARABEAmbroxol hydrochloride (300 mg) + Clenbuterol (0.2 mg)SyrupOralGONHER FARMACEUTICA LTDA2009-06-04Not applicableColombia flag
MUCOSOLVAN COMPOSITUM JARABE ADULTOSAmbroxol hydrochloride (300 mg) + Clenbuterol (0.2 mg)SyrupOralPHARMETIQUE S.A.2006-11-102021-04-01Colombia flag
MUCOSOLVAN COMPOSITUM JARABE PEDIATRICO. 7.5 MG / 0.005MG / 5ML.Ambroxol hydrochloride (0.15 g) + Clenbuterol hydrochloride (0.1 mg)SyrupOralPHARMETIQUE S.A.2006-11-102018-02-20Colombia flag
Mucospas - SaftAmbroxol hydrochloride (7.5 mg/5ml) + Clenbuterol hydrochloride (0.005 mg/5ml)SolutionOralOpella Healthcare Austria Gmb H1987-03-12Not applicableAustria flag
Mucospas - TablettenAmbroxol hydrochloride (30 mg) + Clenbuterol hydrochloride (0.02 mg)TabletOralOpella Healthcare Austria Gmb H1987-03-12Not applicableAustria flag

Categories

ATC Codes
R02AD05 — AmbroxolR03CC63 — 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

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Solution7.5 mg/ml
Tablet, solubleOral30 mg
SolutionOral7.5 MG/ML
SolutionOral15 MG/ML
Tablet, effervescentOral
SolutionOral; Respiratory (inhalation)7.5 mg/ml
SolutionOral0.3 g
SyrupOral600 mg
SolutionOral15 MG/5ML
Tablet, for solution; tablet, for suspensionOral30 MG
Tablet, effervescentOral60 MG
SyrupOral600 g
Tablet, solubleOral60 mg
SolutionOral3 mg/ml
ElixirOral30 MG/5ML
SolutionRespiratory (inhalation)7.5 mg/mL
SyrupOral0.6 g
SyrupOral60000000 mg
SyrupOral300 mg
Injection, solutionParenteral15 MG/2ML
TabletOral60 MG
SyrupOral0.3 g
Granule, for suspensionOral
Tablet, extended releaseOral
SprayOral
Solution300.000 mg
SolutionOral0.6 g
SolutionOral300.0000 mg
SolutionIntramuscular15.000 mg
SuspensionOral
Suspension
TabletOral30.000 mg
TabletOral
TabletOral
SyrupOral
Solution / drops; suspension / drops7.5 MG/ML
Granule, for solutionOral65 mg
Granule, for suspensionOral30 MG
SolutionOral0.75 %
SolutionRespiratory (inhalation)15 MG/2ML
Spray15 MG/2ML
SuppositoryRectal30 mg
GranuleOral
Spray
SuppositoryRectal
Tablet
SyrupOral3 MG/ML
SyrupOral30 MG/10ML
CapsuleOral
Tablet31 MG
TabletOral20 mg
Granule, for solutionOral
TabletBuccal20.000 mg
SprayOral17.86 mg/ml
LozengeOral20 MG
TabletOral30 mg
LiquidOral
Capsule, extended releaseOral
SolutionIntravenous15 mg/2ml
Granule, for solutionOral15 MG
Granule, for solutionOral30 MG
Granule, for solutionOral60 MG
SolutionParenteral15.00 mg
SolutionRespiratory (inhalation)
Spray7.5 MG/ML
SuppositoryRectal15 MG
SuppositoryRectal60 MG
SyrupOral200 ML
Tablet, chewableOral15 MG
Tablet, coatedOral60 MG
CapsuleOral75 mg
Capsule, delayed releaseOral75 mg
SyrupOral
Tablet, film coatedOral60 MG
GranuleOral2 g
SolutionRespiratory (inhalation)15 MG
LiquidOral30 mg/5mL
PastilleOral15 MG
Solution7.5 mg/1ml
SolutionRespiratory (inhalation)0.75 g
SolutionOral30 MG/2ML
SolutionOral0.750 g
Solution / drops; suspension / drops
SolutionOral10 MG
SyrupOral150 ml
SolutionOral300.00 mg
SolutionOral
SolutionOral300 mg
SolutionOral300.000 mg
SolutionOral7.5 mg
SprayRespiratory (inhalation)15 MG/2ML
SprayRespiratory (inhalation)30 MG/4ML
SyrupOral15 mg/mL
SolutionIntramuscular; Intravenous
ElixirOral15 mg/5ml
LozengeOral
SolutionIntravenous1 G/50ML
SuspensionOral300 mg
SolutionOral0.3000 g
Syrup
SyrupOral0.15 g
SolutionOral750.000 mg
CapsuleOral30.000 mg
SuspensionOral0.2700 g
SolutionOral
SolutionOral0.300 g
Granule, effervescent
Tablet, effervescentOral30 MG
SolutionOral6 MG/ML
SprayOral2.5 MG
TabletTransmucosal
TabletTransmucosal20 MG
SprayOral15 MG/2ML
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-MSsplash10-02ta-8029000000-8223c803de340f8e8fe9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-004i-0029000000-0d55218ce7d65b7096d8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-004j-1697000000-8b0734e20916cf9d08c9
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0009000000-135b59221d032f784217
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-076r-3098000000-c24ddfc154ebfb78b69c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-01qa-9352000000-86c766d6ca5bc2e8eaba
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9101000000-1ad2659ed4ee6fd1d89e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-164.98965
predicted
DeepCCS 1.0 (2019)
[M+H]+167.34764
predicted
DeepCCS 1.0 (2019)
[M+Na]+173.4408
predicted
DeepCCS 1.0 (2019)

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 at September 01, 2010 19:05 / Updated at March 03, 2024 02:32