386. Ambroxol

Nomenclature

CAS number: 18683-91-5
trans-4-[[(2-Amino-3,5-dibromophenyl)methyl]amino]cyclohexanol; N-(trans-p-hydroxycyclohexyl)-(2-amino-3,5-dibromobenzyl)amine; NA-872.
C13H18Br2N2O; mol wt 378.10.
C 41.30%, H 4.80%, Br 42.27%, N 7.41%, O 4.23%.

Description and 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).

Chemical structure

Derivative

Hydrochloride.

Nomenclature

CAS number: 23828-92-4
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-Hustenlser (Stada); Surbronc (Boehringer, Ing.); Surfactal (Boehringer, Ing.).
C13H18Br2N2O.HCl; mol wt 414.56.
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).

Therapeutic Category

Expectorant.

Keywords

Expectorant