Carbinoxamine

Carbinoxamine
Systematic (IUPAC) name
2-[(4-Chlorophenyl)-pyridin-2-yl-methoxy]-N,N-
dimethyl-ethanamine
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a606008
  • C
  • 4 mg is FDA approved
Oral: 4 mg tablet or 4 mg/5 mL liquid
Pharmacokinetic data
Half-life 10 to 20 hours
Identifiers
486-16-8 Yes
R06AA08
PubChem CID 2564
DrugBank DB00748 Yes
ChemSpider 2466 Yes
UNII VED9E376NC Yes
KEGG D07617 Yes
ChEBI CHEBI:3398 Yes
ChEMBL CHEMBL864 Yes
Chemical data
Formula C16H19ClN2O
290.788 g/mol
 Yes (what is this?)  (verify)

Carbinoxamine (Clistin, Palgic, Rondec, Rhinopront) is a antihistamine and anticholinergic agent. It was first launched in the United States by the McNeil Corporation under the brand name Clistin. It is now available under the brand name Palgic as 4 mg tablets or 4 mg/5 mL liquid. It is approved by the U.S. Food and Drug Administration (FDA) (specifically at the 4 mg dose/strength) for hay fever (a.k.a. allergic rhinitis, SAR and PAR); vasomotor rhinitis; mild urticaria; angioedema, dermatographism and allergic conjunctivitis. Carbinoxamine is a histamine antagonist, specifically an H1-antagonist. The maleic acid acid salt of the levorotatory isomer is sold as the prescription drug rotoxamine.

Carbinoxamine is available in various countries around the world by itself, combined with decongestants such as pseudoephedrine, and also with other ingredients including paracetamol, aspirin, and codeine.

In June 2006 the FDA announced that more than 120 branded pharmacy products containing carbinoxamine were being illegally marketed and demanded they be removed from the marketplace. This action was precipitated by twenty-one reported deaths in children under the age of two who had been administered carbinoxamine-containing products. Despite the fact that the drug had not been studied in this age group, a multitude of OTC preparations containing carbinoxamine were being marketed for infants and toddlers. At present, all carbinoxamine-containing formulations are approved only for adults or children ages 3 or older.[1]

Carbinoxamine is used in the treatment of severe itching in patients with CD5.

Synthesis

Carbinoxamine synthesis:[2][3]

In the preparation of rotoxamine, reaction of pyridine-2-carboxaldehyde with the Grignard reagent formed from p-bromochlorobenzene gives the carbinol; alkylation with 2-(dimethylamino)chloroethane and optical resolution gives rotoxamine.

See also

References

  1. ↑
  2. ↑ C. H. Tilford and R. S. Shelton, U.S. Patent 2,606,195 (1952).
  3. ↑ A. P. Swain, U.S. Patent 2,800,485 (1957).