Cloperastine

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Template:Short description Template:Drugbox

Cloperastine (INN) or cloperastin, in the forms of cloperastine hydrochloride (JAN) (brand names Hustazol, Nitossil, Seki) and cloperastine fendizoate, is an antitussive and antihistamine that is marketed as a cough suppressant in Japan, Hong Kong, Brazil and in some European countries.[1][2][3] It was first introduced in 1972 in Japan, and then in Italy in 1981.[4]

Side effects

Adverse effects may include sedation, drowsiness, heartburn, and thickening of bronchial secretions.[5]

Pharmacology

The precise mechanism of action of cloperastine is not fully clear, but several different biological activities have been identified for the drug, of which include: ligand of the σ1 receptor (Ki = 20 nM) (likely an agonist),[6] GIRK channel blocker (described as "potent"),[7][8][9][10] antihistamine (Ki = 3.8 nM for the H1 receptor),[3][6] and anticholinergic.[3][11] It is thought that the latter two properties contribute to side effects, such as sedation and somnolence, while the former two may be involved in or responsible for the antitussive efficacy of cloperastine.[6][7]

Synthesis

File:Cloperastine synthesis.svg
Synthesis:[12] Patents:[13][14] Isomers:[15] China:[16]

The halogenation of 4-Chlorobenzhydrol [119-56-2] (1) with phosphorus tribromide in tetrachloromethane gives 1-(Bromophenylmethyl)-4-chlorobenzene [948-54-9] (2). Treatment with ethylenechlorohydrin (2-Chloroethanol) [107-07-3] (3) gives 1-(4-Chlorobenzhydryl)oxy-2-chloroethane [5321-46-0] (4). Reaction with piperidine (5) completes the synthesis of Cloperastine (6).

See also

References

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  7. ↑ a b Script error: No such module "citation/CS1".
  8. ↑ Script error: No such module "Citation/CS1".
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  10. ↑ Script error: No such module "Citation/CS1".
  11. ↑ Script error: No such module "citation/CS1".
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  13. ↑ Anon., <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (1970 to Yoshitomi Pharmaceutical).
  14. ↑ Anon., <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (1952 to Parke Davis & Co).
  15. ↑ Laura Puricelli, <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (1999 to AESCULAPIUS FARMACEUTICI S.r.l.).
  16. ↑ 陶文潘, 潘文驰, 潘兴长, 罗泳萍, 樊希祥, <templatestyles src="Citation/styles.css"/>Template:Citation/make link Script error: No such module "Check for unknown parameters". (2015 to 重庆市恒安化工有限公司).

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