Carbinoxamine

Title: Carbinoxamine
CAS Registry Number: 486-16-8
CAS Name: 2-[(4-Chlorophenyl)-2-pyridinylmethoxy]-N,N-dimethylethanamine
Additional Names: 2-[p-chloro-a-(2-dimethylaminoethoxy)benzyl]pyridine; paracarbinoxamine
Molecular Formula: C16H19ClN2O
Molecular Weight: 290.79
Percent Composition: C 66.09%, H 6.59%, Cl 12.19%, N 9.63%, O 5.50%
Literature References: Prepn: Tilford, Shelton, US 2606195 (1952 to Wm. S. Merrell); Swain, US 2800485 (1957 to McNeil Labs.). Prepn of l-form: GB 905993 (1962 to McNeil Labs.), C.A. 58, 5644a (1962). Abs config of l-form: V. Barouh et al., J. Med. Chem. 14, 834 (1971). Pharmacology and toxicology: R. Cahen, Ann. Pharm. Fr. 20, 463 (1962). GLC determn in serum: D. J. Hoffman et al., J. Pharm. Sci. 72, 1342 (1983).
Properties: Liquid, bp0.1 158-162°.
Boiling point: bp0.1 158-162°
Derivative Type: Hydrochloride
Molecular Formula: C16H19ClN2O.HCl
Molecular Weight: 327.25
Percent Composition: C 58.72%, H 6.16%, Cl 21.67%, N 8.56%, O 4.89%
Properties: Crystals from isopropanol + ethyl acetate, dec 162-164°. Sol in water.
Derivative Type: Maleate
CAS Registry Number: 3505-38-2
Trademarks: Allergefon (Lafon); Clistin (McNeil); Ciberon (Taisho); Lergefin (Larma); Polistin T-Caps (Trommsdorff)
Molecular Formula: C16H19ClN2O.C4H4O4
Molecular Weight: 406.86
Percent Composition: C 59.04%, H 5.70%, Cl 8.71%, N 6.89%, O 19.66%
Properties: Bitter crystals from ethyl acetate, mp 117-119°. Freely sol in water, alcohol, chloroform. Very slightly sol in ether. pH of 1% aq soln 4.6-5.1. LD50 in mice (mg/kg): 166 i.p. (Cahen).
Melting point: mp 117-119°
Toxicity data: LD50 in mice (mg/kg): 166 i.p. (Cahen)
Derivative Type: l-Form
Additional Names: Levocarbinoxamine; rotoxamine
Manufacturers' Codes: McN-R-73-Z
Properties: bp0.5 143-144°. nD20 1.5522. [a]D25 -6.8° (c = 2 in methanol).
Boiling point: bp0.5 143-144°
Optical Rotation: [a]D25 -6.8° (c = 2 in methanol)
Index of refraction: nD20 1.5522
Derivative Type: l-Form d-tartrate
CAS Registry Number: 49746-00-1
Trademarks: Twiston (McNeil)
Molecular Formula: C16H19ClN2O.C4H6O6
Molecular Weight: 440.87
Percent Composition: C 54.49%, H 5.72%, Cl 8.04%, N 6.35%, O 25.40%
Properties: Crystals from isopropanol, mp 143-144.5°. [a]D25 +37.2° (c = 20 in methanol).
Melting point: mp 143-144.5°
Optical Rotation: [a]D25 +37.2° (c = 20 in methanol)
Therap-Cat: Antihistaminic.
Keywords: Antihistaminic; Aminoalkylethers.
Carbiphene Carbitol? Carbobenzoxy Chloride Carbocloral Carbocysteine

Carbinoxamine
Systematic (IUPAC) name
2-[(4-chlorophenyl)-pyridin-2-yl-methoxy]-N,N-
dimethyl-ethanamine
Clinical data
AHFS/Drugs.com monograph
MedlinePlus a606008
Pregnancy cat. C
Legal status 4 mg is FDA approved
Routes Oral: 4 mg tablet or 4 mg/5 mL liquid
Pharmacokinetic data
Half-life 10 to 20 hours
Identifiers
CAS number 486-16-8 YesY
ATC code R06AA08
PubChem CID 2564
DrugBank DB00748
ChemSpider 2466 YesY
UNII VED9E376NC YesY
KEGG D07617 YesY
ChEBI CHEBI:3398 YesY
ChEMBL CHEMBL864 YesY
Chemical data
Formula C16H19ClN2O 
Mol. mass 290.788 g/mol
 YesY (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, codeine hydrochloride &c.

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]

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