Ambroxol

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Pharmaceutical drug

title: "Ambroxol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["expectorants", "anilines", "bromobenzene-derivatives", "secondary-amines", "secondary-alcohols", "human-drug-metabolites"] description: "Pharmaceutical drug" topic_path: "general/expectorants" source: "https://en.wikipedia.org/wiki/Ambroxol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Pharmaceutical drug ::

::data[format=table title="Infobox drug"]

FieldValue
Verifiedfieldschanged
verifiedrevid464186402
IUPAC_nametrans-4-(2-Amino-3,5-dibromobenzylamino)-cyclohexanol
imageAmbroxol structural formulae.png
image_classskin-invert-image
image2Ambroxol ball-and-stick.png
image_class2bg-transparent
Drugs.com
ATC_prefixR05
ATC_suffixCB06
ATC_supplemental
legal_statusotc
routes_of_administrationoral, inhaled, intramuscular, intravenous
CAS_number_Ref
CAS_number18683-91-5
PubChem2132
DrugBank_Ref
ChemSpiderID_Ref
ChemSpiderID10276826
UNII_Ref
UNII200168S0CL
KEGG_Ref
KEGGD07442
ChEMBL_Ref
ChEMBL153479
C13
H18
Br2
N2
O1
smilesC1CC(CCC1NCC2=C(C(=CC(=C2)Br)Br)N)O
StdInChI_Ref
StdInChI1S/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-
StdInChIKey_Ref
StdInChIKeyJBDGDEWWOUBZPM-XYPYZODXSA-N
::

| Verifiedfields = changed | verifiedrevid = 464186402 | IUPAC_name = trans-4-(2-Amino-3,5-dibromobenzylamino)-cyclohexanol | image = Ambroxol structural formulae.png | image_class = skin-invert-image | alt = | image2 = Ambroxol ball-and-stick.png | image_class2 = bg-transparent | alt2 = | Drugs.com = | pregnancy_category = | ATC_prefix = R05 | ATC_suffix = CB06 | ATC_supplemental = | legal_status = otc | routes_of_administration = oral, inhaled, intramuscular, intravenous | bioavailability = | metabolism = | excretion = | CAS_number_Ref = | CAS_number = 18683-91-5 | PubChem = 2132 | DrugBank_Ref = | ChemSpiderID_Ref = | ChemSpiderID = 10276826 | UNII_Ref = | UNII = 200168S0CL | KEGG_Ref = | KEGG = D07442 | ChEMBL_Ref = | ChEMBL = 153479 | C = 13 | H = 18 | Br = 2 | N = 2 | O = 1 | smiles = C1CC(CCC1NCC2=C(C(=CC(=C2)Br)Br)N)O | StdInChI_Ref = | StdInChI = 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- | StdInChIKey_Ref = | StdInChIKey = JBDGDEWWOUBZPM-XYPYZODXSA-N

Ambroxol is a drug that breaks up phlegm, used in the treatment of respiratory diseases associated with viscid or excessive mucus. Ambroxol is often administered as an active ingredient in cough syrup.

It was patented in 1966 and came into medical use in 1979.

Medical uses

Ambroxol is indicated as "secretolytic therapy in bronchopulmonary diseases associated with abnormal mucus secretion and impaired mucus transport. It promotes mucus clearance, facilitates expectoration and eases productive cough, allowing patients to breathe freely and deeply".

::figure[src="https://upload.wikimedia.org/wikipedia/commons/6/66/Antbron_15mg_by_Towa_Pharmaceutical.jpg" caption="Ambroxol [[hydrochloride]] tablets in Japan"] ::

There are many different formulations developed since the first marketing authorisation in 1978. Ambroxol is available as syrup, tablets, pastilles, dry powder sachets, inhalation solution, drops and ampules as well as effervescent tablets.

Ambroxol also provides pain relief in acute sore throat. Pain in sore throat is the hallmark of acute pharyngitis. Sore throat is usually caused by a viral infection. The infection is self limited and the patient recovers normally after a few days. What is most bothering for the patient is the continuous pain in the throat maximized when the patient is swallowing. The main goal of treatment is thus to reduce pain. The main property of ambroxol for treating sore throat is the local anaesthetic effect, described first in the late 1970s, but explained and confirmed in more recent work.

High-dose ambroxol, delivered via intravenous injection, reduces the mortality rate in paraquat poisoning by 31%.

Side effects

Studies and observations to date have not uncovered specific contraindications of ambroxol; however, caution is suggested for patients with gastric ulceration, and usage during the first trimester of pregnancy is not recommended.

Mechanism of action

The substance acts on mucous membranes, restoring the physiological clearance mechanisms of the respiratory tract (which play an important role in the body's natural defence mechanisms) through several mechanisms, including breaking up phlegm, stimulating mucus production, and stimulating synthesis and release of surfactant by type II pneumocytes. Surfactant 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.

Ambroxol is a potent inhibitor of the neuronal Na+ channels, explaining its anaesthetic effect. This property led to the development of a lozenge containing 20 mg of ambroxol. Many state-of-the-art clinical studies have demonstrated the efficacy of ambroxol in relieving pain in acute sore throat, with a rapid onset of action, with its effect lasting at least three hours.

Ambroxol is also anti-inflammatory, reducing redness in a sore throat. It reduces the release of inflammatory cytokines and histamines in cell cultures. It also acts as an antioxidant, scavenging free radicals and hypochloric acid generated by neutrophils. These two effects explain its effect in treating acute lung injury caused by paraquat.

Ambroxol has recently been shown to increase activity of the lysosomal enzyme glucocerebrosidase. Because of this it may be a useful therapeutic agent for both Gaucher disease and Parkinson's disease. It was also recently shown that ambroxol triggers exocytosis of lysosomes by releasing calcium from acidic cellular calcium stores. This occurs by diffusion of ambroxol into lysosomes and lysosomal pH neutralization. This mechanism is most likely responsible for the mucolytic effects of the drug, but may also explain the reported activity in Gaucher and Parkinson's disease.

Both ambroxol and its parent drug bromhexine have been shown to induce autophagy in several cell types, and ambroxol was shown to potentiate rifampicin therapy in a model of tuberculosis through host directed effects. Ambroxol also enhances lung levels of a wide range of antibiotics.

Brand names

Ambroxol is the active ingredient of Muciclar (Italy), Mucosolvan, Mucobrox (Spain), Bisolvon (Switzerland), Cloxan (Mexico), Mucol, Lasolvan, Mucoangin, Surbronc, Brontex (Lithuania), Ambro (Kazakhstan), Ambolar, Inhalex, Mucolite (India), Fluibrox (Greece) and Lysopain.

Ambroxol has been approved as a safe and effective substance in the European Medicines Agency, but has not been approved in the USA by the Food and Drug Administration. Ambroxol is also not registered for use in Australia.

References

References

  1. (2006). "Analogue-based Drug Discovery". John Wiley & Sons.
  2. (August 2008). "Ambroxol in the 21st century: pharmacological and clinical update". Expert Opin Drug Metab Toxicol.
  3. (2008). "Efficacy and safety of ambroxol lozenges in the treatment of acute uncomplicated sore throat. EBM-based clinical documentation". Arzneimittel-Forschung.
  4. (1978). "[Pharmacological study on the bromhexine metabolite ambroxol (author's transl)]". Arzneimittel-Forschung.
  5. (December 1977). "[The local anesthetic effect of NA872-containing eyedrops]". Medizinische Monatsschrift.
  6. (2020). "Efficacy of high-dose ambroxol for paraquat poisoning: A meta-analysis of randomized controlled trials". Journal of Research in Medical Sciences.
  7. "Ambroxol". Drugs.com.
  8. (February 2005). "Cell-specific modulation of surfactant proteins by ambroxol treatment". Toxicology and Applied Pharmacology.
  9. (December 2015). "A new role for an old drug: Ambroxol triggers lysosomal exocytosis via pH-dependent Ca²⁺ release from acidic Ca²⁺ stores". Cell Calcium.
  10. (September 1976). "Morphological and physical basis for lung surfactant action". Respiration Physiology.
  11. (November 2004). "Secretory leukoprotease inhibitor and pulmonary surfactant serve as principal defenses against influenza A virus infection in the airway and chemical agents up-regulating their levels may have therapeutic potential". Biological Chemistry.
  12. (March 2006). "Comparison of the effects of four Na+ channel analgesics on TTX-resistant Na+ currents in rat sensory neurons and recombinant Nav1.2 channels". Neuroscience Letters.
  13. (August 2008). "Ambroxol in the 21st century: pharmacological and clinical update". Expert Opinion on Drug Metabolism & Toxicology.
  14. (May 2014). "Ambroxol improves lysosomal biochemistry in glucocerebrosidase mutation-linked Parkinson disease cells". Brain.
  15. (September 2018). "Ambroxol Induces Autophagy and Potentiates Rifampin Antimycobacterial Activity". Antimicrobial Agents and Chemotherapy.
  16. (October 2015). "Pharmaceutical screen identifies novel target processes for activation of autophagy with a broad translational potential". Nature Communications.
  17. (March 2019). "Enhancement of lung levels of antibiotics by ambroxol and bromhexine". Expert Opinion on Drug Metabolism & Toxicology.
  18. (6 May 2024). "Ambroxol (International)".
  19. (14 November 2023). "The Next Insulin Scandal". The American Prospect.
  20. (June 2016). "Bromhexine-containing cough and cold medicines – risk of allergy and skin reactions". Therapeutic Goods Administration.

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expectorantsanilinesbromobenzene-derivativessecondary-aminessecondary-alcoholshuman-drug-metabolites