WordNet

a salt or ester of maleic acid; used as a nontricyclic antidepressant drug for psychomotor activation

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2015/03/06 15:00:05」(JST)

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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.^{[clarification needed]}

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.

References

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

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English Journal

The cooperative effect of Lewis pairs in the Friedel-Crafts hydroxyalkylation reaction: a simple and effective route for the synthesis of (±)-carbinoxamine.

Harikrishnan A1, Sanjeevi J, Ramanathan CR.
Organic & biomolecular chemistry.Org Biomol Chem.2015 Mar 28;13(12):3633-47. doi: 10.1039/c4ob02597k.
An efficient C-C bond formation strategy between aromatic/heteroaromatic π-nucleophiles and Lewis acid activated aldehydes is described. This aromatic electrophilic substitution reaction of arenes or heteroarenes is facilitated by Lewis acid AlBr3. Aromatic rings with electron donating substituents
PMID 25672597

Pro-arrhythmic potential of oral antihistamines (H1): combining adverse event reports with drug utilization data across Europe.

Poluzzi E1, Raschi E1, Godman B2, Koci A1, Moretti U3, Kalaba M4, Wettermark B5, Sturkenboom M6, De Ponti F1.
PloS one.PLoS One.2015 Mar 18;10(3):e0119551. doi: 10.1371/journal.pone.0119551. eCollection 2015.
BACKGROUND: There is appreciable utilisation of antihistamines (H1) in European countries, either prescribed by physician and purchased by patients for self-medication. Terfenadine and astemizole underwent regulatory restrictions in '90 because of their cardiac toxicity, but only scarce clinical dat
PMID 25785934

Theoretical study on the proton shuttle mechanism of saccharopine dehydrogenase.

Sheng X1, Gao J, Liu Y, Liu C.
Journal of molecular graphics & modelling.J Mol Graph Model.2013 Jul;44:17-25. doi: 10.1016/j.jmgm.2013.04.009. Epub 2013 May 9.
Saccharopine dehydrogenase (SDH) is the last enzyme in the AAA pathway of l-lysine biosynthesis. On the basis of crystal structures of SDH, the whole catalytic cycle of SDH has been studied by using density functional theory (DFT) method. Calculation results indicate that hydride transfer is the rat
PMID 23732302

Japanese Journal

症例報告パブロンS中のマレイン酸カルビノキサミンによる各層下膿疱型薬疹の1例

前田知子,中島武之,宮島進 [他]
臨床皮膚科 55(9), 697-699, 2001-08
NAID 40020002506

グラジエント高速液体クロマトグラフィーによるかぜ薬中の9成分同時定量

増田光宏,佐藤智子,半田光一 [他],伊藤裕二,相楽和彦
分析化学 46(10), 777-783, 1997-10-05
… Nine components in the preparation, such as acetaminophen, anhydrous caffeine, riboflavin, dihydrocodeine phosphate, DL-methylephedrine hydrochloride, carbinoxamine maleate, noscapine, bisibuthiamine and bromhexine hydrochloride, could be completely separated by changing from water-acetonitrile (95 : 5) to water-acetonitrile (1 : 1) as the mobile phase containing 0.1% of phosphoric acid and 0.08 w/v% of sodium heptansulfonate by a linear gradient program. …
NAID 110002907349

テトラフェニルホウ素ナトリウムによる塩化ベルベリンの直接滴定

海東常敏 [他],富岡勇,相楽和彦,伊藤裕二
分析化学 22(9), 1175-1179, 1973
… Coexistent components, such as acrinol, papaverine hydrochloride, carbinoxamine maleate and riboflavin did not interfere. …
NAID 130000943464

Related Pictures

★リンクテーブル★

リンク元	「カルビノキサミン」「マレイン酸カルビノキサミン」
関連記事	「maleate」「carbinoxamine」

「カルビノキサミン」

Carbinoxamine
Systematic (IUPAC) name
	2-[(4-Chlorophenyl)-pyridin-2-yl-methoxy]-N,N-; dimethyl-ethanamine
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a606008
Pregnancy; category	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
ATC code	R06AA08
PubChem	CID 2564
DrugBank	DB00748
ChemSpider	2466
UNII	VED9E376NC
KEGG	D07617
ChEBI	CHEBI:3398
ChEMBL	CHEMBL864
Chemical data
Formula	C16H19ClN2O
Molecular mass	290.788 g/mol
	SMILES Clc1ccc(cc1)C(OCCN(C)C)c2ncccc2;
	InChI InChI=1S/C16H19ClN2O/c1-19(2)11-12-20-16(15-5-3-4-10-18-15)13-6-8-14(17)9-7-13/h3-10,16H,11-12H2,1-2H3 ; Key:OJFSXZCBGQGRNV-UHFFFAOYSA-N ;
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