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
Structure for Ambroxol (DB06742)
- 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.
Learn More- 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.
Drug Interaction Unlock Additional DataAbametapir The serum concentration of Ambroxol can be increased when it is combined with Abametapir. Cenobamate The serum concentration of Ambroxol can be decreased when it is combined with Cenobamate. Haloperidol The serum concentration of Haloperidol can be increased when it is combined with Ambroxol. Metreleptin The metabolism of Ambroxol can be increased when combined with Metreleptin. Pitolisant The serum concentration of Ambroxol can be decreased when it is combined with Pitolisant. Ritonavir The serum concentration of Ambroxol can be increased when it is combined with Ritonavir. Satralizumab The serum concentration of Ambroxol can be decreased when it is combined with Satralizumab. Tucatinib The metabolism of Tucatinib can be decreased when combined with Ambroxol. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- 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
Categories
- ATC Codes
- R03CC63 — Clenbuterol and ambroxol
- R03CC — Selective beta-2-adrenoreceptor agonists
- R03C — ADRENERGICS FOR SYSTEMIC USE
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- Drug Categories
- Adrenergics for Systemic Use
- Amines
- Aniline Compounds
- Cough and Cold Preparations
- Cyclohexanes
- Cyclohexylamines
- Cycloparaffins
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Drugs for Obstructive Airway Diseases
- Expectorants
- Respiratory System Agents
- Selective Beta 2-adrenergic Agonists
- 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
- External Links
- PubChem Compound
- 2132
- PubChem Substance
- 347827790
- ChemSpider
- 10276826
- BindingDB
- 50395322
- 625
- ChEBI
- 135590
- ChEMBL
- CHEMBL153479
- ZINC
- ZINC000100070274
- Wikipedia
- Ambroxol
- MSDS
- Download (47.4 KB)
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Pharyngitis 4 3 Recruiting Treatment Abnormal Mucus Secretions / Respiratory Tract Diseases 1 2 Completed Basic Science Coughing 1 2 Completed Prevention Allergic Sensitization / Asthma 1 2 Completed Prevention Parkinson's Disease (PD) 1 2 Completed Treatment Hypersensitivity, Food 1 2 Completed Treatment Pain / Pharyngitis 1 2 Not Yet Recruiting Treatment Melanoma 1 2 Recruiting Treatment Gaucher Disease, Type 1 / Gaucher's Disease Type 1 1 2 Recruiting Treatment Head and Neck Mucosal Melanomas 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Syrup Oral 15 mg/5mL Solution 7.5 mg/ml Capsule Oral 75 mg Tablet, soluble Oral 30 mg Solution Oral 7.5 MG/ML Tablet 30 MG Solution Oral 15 MG/ML Syrup Oral Syrup Oral 300 mg Solution Oral 0.15 g Syrup Oral 600 mg Solution Oral 0.3 g Solution Oral 15 MG/5ML Capsule, extended release Oral 75 MG Tablet, for solution; tablet, for suspension Oral 30 MG Tablet, effervescent Oral 60 MG Solution Oral 30 MG/5ML Tablet, soluble Oral 60 mg Solution Respiratory (inhalation) 7.5 mg/mL Injection, solution Parenteral 15 MG/2ML Tablet 60 MG Solution Oral 3 MG/ML Syrup Oral 30 MG/5ML Syrup Tablet Solution Oral Solution Oral 0.6 g Elixir Tablet, coated Oral 30 mg Capsule, extended release 75 MG Granule, for solution Oral 65 mg Granule, for suspension Oral 30 MG Solution Oral 0.75 % Spray 15 MG/2ML Suppository Rectal 30 mg Syrup 15 MG/5ML Syrup 150 ml Spray 7.5 MG/ML Syrup 3 MG/ML Syrup 30 MG/10ML Tablet Oral 20 mg Spray Oral 17.86 mg/ml Lozenge Oral 20 MG Injection, solution 15 mg/2mL Liquid Capsule, extended release Granule, for solution Oral 15 MG Granule, for solution Oral 30 MG Granule, for solution Oral 60 MG Solution / drops Oral 30 mg/5mL Suppository 15 MG Suppository 30 MG Suppository 60 MG Syrup 200 ML Syrup 30 MG/5ML Tablet 15 MG Tablet, chewable Oral 15 MG Tablet, coated 60 MG Solution 15 mg/5ml Solution 7.5 mg/1ml Syrup Oral 0.15 g Tablet, film coated Oral 60 MG Solution Respiratory (inhalation) 15 MG Pastille Oral 15 MG Pastille 15 mg Solution Respiratory (inhalation) 0.75 g Solution Oral 30 MG/2ML Solution / drops; suspension / drops Solution Oral 300 mg Solution Oral 7.5 mg Spray Respiratory (inhalation) 15 MG/2ML Spray Respiratory (inhalation) 30 MG/4ML Syrup Oral 15 mg/mL Tablet Oral 30 MG Solution 2 ml Lozenge 15 mg Syrup Oral 250 mg Syrup Oral 0.3 g Syrup Oral 0.6 g Tablet, effervescent Oral 30 MG Solution Oral 6 MG/ML - 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
- 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. [PubMed:10659952]
Drug created on September 01, 2010 13:05 / Updated on July 02, 2020 07:24
Are you a
new drug developer?
Contact us to learn more about our customized products and solutions.
![]({"CS-Molecular-Health-1.jpg":"/assets/ads/CS-Molecular-Health-1-19e76f023997d5ac198da2cb9976457f7b9ba733f0ea8a780fe21191c759e8fa.jpg","Drug-Dev-2.jpg":"/assets/ads/Drug-Dev-2-7c3039d93245f493c23278efbf759e4f933848a676262d579087d5cc516af179.jpg","Drug-Search-3.jpg":"/assets/ads/Drug-Search-3-7346c33d2133f62b46cbfbbe2b666e78f955c6847e242692c6081fec37c4d10d.jpg","PM-3.jpg":"/assets/ads/PM-3-13494ac4c996d71619127a11f685681418d4280832dec162c0b2c9c8bc2eda50.jpg","OD-Webinar-1.jpg":"/assets/ads/OD-Webinar-1-f9357f6d57fef5e411aa1c0439ef46c86d9151214434659d096eeed6407b799b.jpg","DDI-3.jpg":"/assets/ads/DDI-3-12808cf864d540ad43757b10b08fc52ae93e793b0c6e81345555187b2840ad09.jpg","EMR-2.jpg":"/assets/ads/EMR-2-adacf8de3f42cb06d6676d06fce611c29781db6ad30776cd18b72a7d8e69f0c8.jpg","Covid.jpg":"/assets/ads/Covid-eed8f17668b0308db62ce3c656f5e2f562376e9185ae08dda5ce6ed9ab0bbd1f.jpg","CS-Molecular-Health-2.jpg":"/assets/ads/CS-Molecular-Health-2-22f41f94b3f87e44a1dcaa8f6c03dc411ab69558efd4f3148ff9bb6adaa956dc.jpg","PM-5.jpg":"/assets/ads/PM-5-d0dc031e0fa0d0097d912eff07b7e80b27b867264dd5b055e379a57bfa2a8723.jpg","DDI-4.jpg":"/assets/ads/DDI-4-313b9c374b937fd78bb2ade652b9b030abb9e6cb90efd35833f793e384e8185b.jpg","Discover-1.jpg":"/assets/ads/Discover-1-b48ae6a3872eeb442f4c22a9a1d867428c83a917ec78a8c3ff4e02f84c5d4fef.jpg","Discover-2.jpg":"/assets/ads/Discover-2-6e7759998ee0fdc234cd84eea962f2480f0c7dafadabd785924918420decb102.jpg","Repurpose-1.jpg":"/assets/ads/Repurpose-1-265fbec40f0eac18d51d3ec4f558c10cb623d834ea75e0296259e458b72ee6d4.jpg","Repurpose-2.jpg":"/assets/ads/Repurpose-2-d12bd1d18b92d36eab60e71e6fd59acf04ef60a53783570e11eef397a0e0f4f5.jpg","PM-6.jpg":"/assets/ads/PM-6-3ae66e41f7ae1e851a0910be89141cf2533509b46df6379464efc885d5ee2f07.jpg","Drug-Search-4.jpg":"/assets/ads/Drug-Search-4-2a9102bd41f16e8c40c9d8044d1dcb6f206ff80107cc269aa83d02ea683bc829.jpg","DDI-5.jpg":"/assets/ads/DDI-5-fa1c287946f4044094c723161577cb5ac631f9cd1217446e510dc79ace6cb94e.jpg","TH-1.jpg":"/assets/ads/TH-1-55a9077bb39e8c38a68c67b555b8091d21a9d41b1c21c7daed3fe53e6f9f3c97.jpg","TH-2.jpg":"/assets/ads/TH-2-1d488747fa4af00ab970a48dba0b228b054d166aa22c1760a310e2b72dd22589.jpg"})
Stay in the know!
As part of our commitment to providing the most up-to-date drug information, we will be releasing #DrugBankUpdates with our newly added curated drug pages.
#DrugBankUpdates