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

Similar Structures

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

Airway secretion clearance therapy

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.

Drug	Interaction
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Abametapir	The serum concentration of Ambroxol can be increased when it is combined with Abametapir.
Amiodarone	The metabolism of Ambroxol can be decreased when combined with Amiodarone.
Amprenavir	The metabolism of Ambroxol can be decreased when combined with Amprenavir.
Apalutamide	The metabolism of Ambroxol can be increased when combined with Apalutamide.
Aprepitant	The metabolism of Ambroxol can be decreased when combined with Aprepitant.
Atazanavir	The metabolism of Ambroxol can be decreased when combined with Atazanavir.
Avanafil	The serum concentration of Avanafil can be increased when it is combined with Ambroxol.
Berotralstat	The metabolism of Ambroxol can be decreased when combined with Berotralstat.
Boceprevir	The metabolism of Ambroxol can be decreased when combined with Boceprevir.
Carbamazepine	The metabolism of Ambroxol can be increased when combined with Carbamazepine.

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Food Interactions

Not Available

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Ambroxol hydrochloride	CC995ZMV90	23828-92-4	QNVKOSLOVOTXKF-PFWPSKEQSA-N

International/Other Brands

Ambrolex (GlaxoSmithKline Inc.) / Ambrox (Square) / Tabcin

Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
AMCOSOL SYRUP 30MG/5ML	Syrup		Oral	PRIME PHARMACEUTICAL SDN. BHD.	2020-09-08	Not applicable
AMCOSOL TABLET 30MG	Tablet		Oral	PRIME PHARMACEUTICAL SDN. BHD.	2020-09-08	Not applicable
AMSOLVAN ORAL SOLUTION 30mg/5ml	Solution		Oral	XEPA-SOUL PATTINSON (MALAYSIA) SDN BHD	2020-09-08	Not applicable
AMTUSS (Syrup )	Syrup	30 mg/5ml	Oral	MEDISPEC (M) SDN.BHD	2020-09-08	Not applicable
AMTUSS 30 MG TABLET	Tablet	30 mg	Oral	MEDISPEC (M) SDN.BHD	2020-09-08	Not applicable
AMXOL SYRUP 30MG/5ML	Syrup	30 mg/5ml	Oral	MEDISPEC (M) SDN.BHD	2020-09-08	Not applicable
AMXOL TABLETS 30MG	Tablet	30 mg	Oral	MEDISPEC (M) SDN.BHD	2020-09-08	Not applicable
AXOL LIQUID 3MG/ML	Liquid		Oral	Y.S.P. INDUSTRIES (M) SDN BHD	2020-09-08	Not applicable
BOOTS AMBROXOL 30 MG	Tablet	30 mg		บริษัท ไบโอแลป จำกัด จำกัด	2000-12-14	Not applicable
Hovid Desolvon-30 Tablet	Tablet		Oral	Hovid Berhad	2020-09-08	Not applicable

Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
BRONSINEX JARABE	Ambroxol hydrochloride (300 mg) + Clenbuterol (0.2 mg)	Syrup	Oral	GONHER FARMACEUTICA LTDA	2009-06-04	Not applicable
MUCOSOLVAN COMPOSITUM JARABE PEDIATRICO. 7.5 MG / 0.005MG / 5ML.	Ambroxol hydrochloride (0.15 g) + Clenbuterol hydrochloride (0.1 mg)	Syrup	Oral	PHARMETIQUE S.A.	2006-11-10	2018-02-20
Mucospas - Saft	Ambroxol hydrochloride (7.5 mg/5ml) + Clenbuterol hydrochloride (0.005 mg/5ml)	Solution	Oral	Opella Healthcare Austria Gmb H	1987-03-12	Not applicable
Mucospas - Tabletten	Ambroxol hydrochloride (30 mg) + Clenbuterol hydrochloride (0.02 mg)	Tablet	Oral	Opella Healthcare Austria Gmb H	1987-03-12	Not applicable
MUXOL ® JARABE NIÑOS	Ambroxol hydrochloride (0.3 g) + Salbutamol sulfate (0.04 g)	Syrup	Oral	C.I. FARMACAPSULAS S.A.S - PLANTA NO. 2	2007-10-13	Not applicable
RESPHIR® JARABE	Ambroxol hydrochloride (300 mg) + Salbutamol sulfate (40 mg)	Syrup	Oral	COLOMPACK S.A.	2007-10-25	Not applicable
TOS-XOL ® JARABE	Ambroxol hydrochloride (0.3 g) + Salbutamol sulfate (0.04 g)	Syrup	Oral	LABORATORIOS LEGRAND S.A.	2011-07-22	2018-08-30
TRIATUSIC® JARABE	Ambroxol hydrochloride (250 mg) + Dextromethorphan hydrobromide (300 mg) + Theophylline (1300 mg)	Syrup	Oral	GONHER FARMACEUTICA LTDA PLANTA DE PRODUCCIÓN II	2009-05-13	Not applicable

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

External Links

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

Phase	Status	Purpose	Conditions	Count
4	Recruiting	Treatment	Community Acquired Pneumonia (CAP) / Coronavirus Disease 2019 (COVID‑19) / Critically Ill Patients / Nosocomial Pneumonia / Severe Pneumonia	1
3	Completed	Treatment	Abnormal Mucus Secretions / Respiratory Tract Diseases	1
3	Completed	Treatment	Pharyngitis	4
2	Active Not Recruiting	Treatment	Parkinsons Disease With Dementia (PDD)	1
2	Completed	Basic Science	Cough	1
2	Completed	Prevention	Parkinson's Disease (PD)	1
2	Completed	Treatment	Gaucher Disease, Type 1	1
2	Completed	Treatment	Pain / Pharyngitis	1
2	Recruiting	Treatment	Dementia With Lewy Body Disease	1
2	Recruiting	Treatment	GBA Gene Mutation / Parkinson's Disease (PD)	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

Form	Route	Strength
Injection, solution	Parenteral	15 mg/2ml
Solution	Oral
Tablet	Oral
Solution
Capsule	Oral
Tablet, soluble	Oral
Solution	Oral	7.5 MG/ML
Solution	Oral	15 MG/ML
Syrup	Oral	300 mg
Solution	Oral	0.3 g
Solution	Oral	15 MG/5ML
Tablet, for solution; tablet, for suspension	Oral	30 MG
Tablet, effervescent	Oral	60 MG
Syrup	Oral	600 g
Solution	Oral; Respiratory (inhalation)	7.5 mg/ml
Solution	Oral	3 mg/ml
Elixir	Oral	30 MG/5ML
Syrup	Oral	0.6 g
Syrup	Oral	600 mg
Tablet	Oral	60 MG
Syrup	Oral	0.3 g
Granule, for suspension	Oral
Spray		7.5 MG/ML
Tablet, extended release	Oral
Solution	Oral	0.6 g
Syrup	Oral
Solution / drops; suspension / drops		7.5 MG/ML
Granule, for solution	Oral	30 mg
Granule, for solution	Oral	65 mg
Granule, for suspension	Oral	30 MG
Solution	Oral	0.75 %
Solution	Respiratory (inhalation)	15 MG/2ML
Spray		15 MG/2ML
Suppository	Rectal	30 mg
Tablet, effervescent	Oral	30 MG
Granule	Oral
Tablet
Solution	Respiratory (inhalation)	7.5 MG/ML
Syrup	Oral	3 MG/ML
Syrup	Oral	30 MG/10ML
Tablet		31 MG
Spray	Oral
Lozenge	Oral
Lozenge	Oral	20 MG
Tablet	Oral	30 mg
Liquid	Oral
Solution	Intravenous	15 mg/2ml
Granule, for solution	Oral
Solution	Respiratory (inhalation)
Spray
Suppository	Rectal
Syrup	Oral	200 ML
Tablet, chewable	Oral
Tablet, coated	Oral
Tablet, effervescent	Oral
Tablet	Oral	20 mg
Pastille	Oral
Capsule	Oral	75 mg
Capsule, delayed release	Oral	75 mg
Syrup	Oral
Tablet, film coated	Oral	60 MG
Granule	Oral	2 g
Solution	Respiratory (inhalation)	15 MG
Liquid	Oral	30 mg/5mL
Pastille	Oral	15 MG
Solution	Respiratory (inhalation)	0.75 g
Solution	Oral	30 MG/2ML
Capsule, extended release	Oral
Tablet, chewable	Oral	15 mg
Tablet	Oral
Solution / drops; suspension / drops
Syrup	Oral	150 ml
Solution	Oral
Solution	Oral	300 mg
Solution	Oral	7.5 mg
Granule, for solution	Oral	15 MG
Granule, for solution	Oral	60 MG
Spray	Respiratory (inhalation)	15 MG/2ML
Spray	Respiratory (inhalation)	30 MG/4ML
Syrup	Oral	15 mg/mL
Solution	Intramuscular; Intravenous
Elixir	Oral	15 mg/5ml
Solution	Intravenous	1 G/50ML
Suspension	Oral	300 mg
Syrup	Oral	0.3 g
Granule, effervescent
Solution	Oral	6 MG/ML
Tablet	Transmucosal
Syrup	Oral	15 mg/5mL
Syrup	Oral	30 mg/5mL
Capsule, extended release	Oral	75 mg
Lozenge	Oral	15 mg
Tablet		30 mg
Tablet, coated	Oral	30 mg
Solution	Oral	30 mg/5ml

Prices

Not Available

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	233-234.5	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.

Predicted Properties

Property	Value	Source
Water Solubility	0.0185 mg/mL	ALOGPS
logP	3.72	ALOGPS
logP	2.65	Chemaxon
logS	-4.3	ALOGPS
pKa (Strongest Acidic)	15.26	Chemaxon
pKa (Strongest Basic)	9.01	Chemaxon
Physiological Charge	1	Chemaxon
Hydrogen Acceptor Count	3	Chemaxon
Hydrogen Donor Count	3	Chemaxon
Polar Surface Area	58.28 Å²	Chemaxon
Rotatable Bond Count	3	Chemaxon
Refractivity	81.94 m³·mol^-1	Chemaxon
Polarizability	32.8 Å³	Chemaxon
Number of Rings	2	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	Yes	Chemaxon
Ghose Filter	Yes	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	No	Chemaxon

Predicted ADMET Features

Not Available

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Enzymes

Details1. Cytochrome P450 3A4

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

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 February 03, 2023 08:15

Ambroxol

Identification

Structure for Ambroxol (DB06742)

Pharmacology

Interactions

Products

Categories

Chemical Identifiers

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Enzymes

References