Ambroxol

Title: Ambroxol
CAS Registry Number: 18683-91-5
CAS Name: 4-[[(2-Amino-3,5-dibromophenyl)methyl]amino]cyclohexanol
Additional Names: N-(trans-p-hydroxycyclohexyl)-(2-amino-3,5-dibromobenzyl)amine
Manufacturers' Codes: NA-872
Molecular Formula: C13H18Br2N2O
Molecular Weight: 378.10
Percent Composition: C 41.30%, H 4.80%, Br 42.27%, N 7.41%, O 4.23%
Literature References: Metabolite of bromhexine, q.v. Structure: E. Schraven et al., Eur. J. Pharmacol. 7, 445 (1967). Synthesis: J. Keck, Ann. 707, 107 (1967); FR 1522709; J. Keck et al., US 3536713 (1968, 1970 both to Thomae). Toxicity: S. Püschmann, R. Engelhorn, Arzneim.-Forsch. 28, 889 (1978). Series of articles on pharmacology, metabolism, and clinical studies: ibid. 889-935; on pharmacology and clinical efficacy of combination with amoxicillin, q.v., in bronchopulmonary disease: ibid. 37, 965-971 (1987). Symposium on pharmacology and efficacy in multicenter studies: Respiration 51, Suppl. 1, 1-68 (1987).
Derivative Type: Hydrochloride
CAS Registry Number: 23828-92-4
Trademarks: Abramen (Mepha); Ambril (Cascan); Bronchopront (Mack, Illert.); Duramucal (Durachemie); Fluibron (Chiesi); Fluixol (Ripari-Gero); Frenopect (Hefa); Lindoxyl (Lindopharm); Motosol (Europharma); Mucofar (Farmakos); Mucosan (Fher); Mucosolvan (Thomae); Mucoclear (Mundipharma); Mucovent (Byk Gulden); Pect (Rentschler); Solvolan (Krka); Stas-Hustenlöser (Stada); Surbronc (Boehringer, Ing.); Surfactal (Boehringer, Ing.)
Molecular Formula: C13H18Br2N2O.HCl
Molecular Weight: 414.56
Percent Composition: C 37.66%, H 4.62%, Br 38.55%, N 6.76%, O 3.86%, Cl 8.55%
Properties: Crystals from ethanol, mp 233-234.5° (dec). LD50 in mice, rats (mg/kg): 268, 380 i.p.; 2720, 13400 orally (Püschmann, Engelhorn).
Melting point: mp 233-234.5° (dec)
Toxicity data: LD50 in mice, rats (mg/kg): 268, 380 i.p.; 2720, 13400 orally (Püschmann, Engelhorn)
Therap-Cat: Expectorant.
Keywords: Expectorant.
Ambucaine Ambucetamide Ambuphylline Ambuside Ambutonium Bromide

Ambroxol
Ambroxol structural formulae.png
Ambroxol ball-and-stick.png
Systematic (IUPAC) name
trans-4-(2-Amino-3,5-dibrombenzylamino)-cyclohexanol
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 18683-91-5 N
ATC code R05CB06
PubChem CID 2132
ChemSpider 10276826 YesY
UNII 200168S0CL YesY
KEGG D07442 YesY
ChEMBL CHEMBL153479 YesY
Chemical data
Formula C13H18Br2N2O 
Mol. mass 378.10
 N (what is this?)  (verify)

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, Mucobrox, Mucol, Lasolvan, Mucoangin, Surbronc, Ambolar, and Lysopain. 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. 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.[1][2] Ambroxol is often administered as an active ingredient in cough syrup.

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".[3]

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 hydrochloride syrups are widely being used all over the world for the treatment of Productive cough. It is widely marketed under the brand name Boxol® in Bangladesh by Opsonin Pharma Limited.

Ambroxol also provides pain relief in acute sore throat. Pain in sore throat is the hallmark of acute pharyngitis.[4] 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,[5][6] but explained and confirmed in more recent work.

Ambroxol is a potent inhibitor of the neuronal Na+ channels.[7] This property led to the development of a lozenge containing 20 mg of ambroxol. Many state-of-the-art clinical studies[4] 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.