Description
Ambroxol HCl (18683-91-5) is a radical scavenger with anti-inflammatory activity. Blocks the generation of reactive oxygen species by bronchoalveolar lavage cells, inhibits doxorubicin-induced lipid peroxidation (70 mg/kg in rat), and inhibits the release of inflammatory mediators from human leukocytes and mast cells (effective dose ~ 100 μM)
Originator
Mucosolvan,Thomae,W. Germany,1980
Uses
Ambroxol is a metabolite of Bromohexine. Ambroxol Hydrochloride is a bronchosecretolytic drug. Free base of Ambroxol Hydrochloride (A575900).
Definition
ChEBI: Ambroxol is an aromatic amine.
Manufacturing Process
6.5 g of N-(trans-p-hydroxycyclohexyl)-(2-aminobenzyl)-amine were dissolved
in a mixture of 80 cc of glacial acetic acid and 20 cc of water, and then 9.6 g
of bromine were added dropwise at room temperature while stirring the
solution. After all of the bromine had been added, the reaction mixture was
stirred for two hours more and was then concentrated in a water aspirator
vacuum. The residue was taken up in 2 N ammonia, the solution was
extracted several times with chloroform, and the organic extract solutions
were combined and evaporated. The residue, raw N-(trans-phydroxycyclohexyl)-(
2-amino-3,5-dibromobenzyl)-amine, was purified with
chloroform and ethyl acetate over silica gel in a chromatographic column, the
purified product was dissolved in a mixture of ethanol and ether, and the
solution was acidified with concentrated hydrochloric acid. The precipitate
formed thereby was collected and recrystallized from ethanol and ether,
yielding N-(trans-p-hydroxycyclohexyl)-(2-amino-3,5-dibromobenzyl)-amine
hydrochloride, MP 233-234.5°C (decomposition).
Therapeutic Function
Expectorant
References
1) Teramoto et al. (1999), Effects of ambroxol on spontaneous or stimulated generation of reactive oxygen species by bronchoalveolar lavage cells harvested from patients with or without chronic obstructive pulmonary diseases; Pharmacology, 59 135
2) Nowak et al. (1995), Ambroxol inhibits doxorubicin-induced lipid peroxidation in heart of mice; Free Radic. Biol. Med., 19 659
3) Gibbs et al. (1999), Ambroxol inhibits the release of histamine, leukotrienes and cytokines from human leukocytes and mast cells; Inflamm. Res., 48 86
