{2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]ethyl}dimethylamine

• ChemBase ID: 628
• Molecular Formular: C16H19ClN2O
• Molecular Mass: 290.78786
• Monoisotopic Mass: 290.11859092
• SMILES: Clc1ccc(C(OCCN(C)C)c2ncccc2)cc1
• Canonical SMILES: CN(CCOC(c1ccccn1)c1ccc(cc1)Cl)C
• 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
• InChIKey: OJFSXZCBGQGRNV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]ethyl}dimethylamine
• IUPAC Traditional name: carbinoxamine
• Brand Name: Allergefon; Clistin; Rotoxamine; Twiston
• Synonyms: Carbinoxamine Maleate; Paracarbinoxamine; Paracarinoxamine; Carbinoxamine

Database IDs

• CAS Number: 486-16-8
• PubChem SID: 160964091; 46506787
• PubChem CID: 2564

CALCULATED PROPERTIES

JChem

• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 0.14102614
• LogD (pH = 7.4): 1.7942975
• Log P: 3.2719407
• Molar Refractivity: 82.1278 cm^3
• Polarizability: 32.299973 Å^3
• Polar Surface Area: 25.36 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.03
• LOG S: -3.11
• Solubility (Water): 2.28e-01 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.6

DETAILS

DrugBank - DB00748

• Drug Groups: approved
• Description: Carbinoxamine is a first generation antihistamine that competes with free histamine for binding at HA-receptor sites. This antagonizes the effects of histamine on HA-receptors, leading to a reduction of the negative symptoms brought on by histamine HA-receptor binding. The product label for carbinoxamine as an over the counter cough and cold medicine is being modified to state "do not use" in children under 4 years of age in order to prevent and reduce misuse, as many unapproved carbinoxamine-containing preparations contained inappropriate labeling, which promoted unapproved uses (including management of congestion, cough, the common cold, and the use in children under 2 years of age), which can potentially cause serious health risks.
• Indication: For symptomatic relief of seasonal and perennial allergic rhinitis and vasomotor rhinitis, as well as allergic conjunctivitis caused by foods and inhaled allergens. Also for the relief of allergic reactions to blood or plasma, and the symptomatic management of mild, uncomplicated allergic skin manifestations of urticaria and angioedema.
• Pharmacology: Carbinoxamine is a first generation antihistamine of the ethanolamine class. Ethanolamine antihistamines have significant antimuscarinic activity and produce marked sedation in most patients. In addition to the usual allergic symptoms, the drug also treats irritant cough and nausea, vomiting, and vertigo associated with motion sickness. It also is used commonly to treat drug-induced extrapyramidal symptoms as well as to treat mild cases of Parkinson's disease. Rather than preventing the release of histamine, as do cromolyn and nedocromil, carbinoxamine competes with free histamine for binding at HA-receptor sites. Carbinoxamine competitively antagonizes the effects of histamine on HA-receptors in the GI tract, uterus, large blood vessels, and bronchial muscle. Ethanolamine derivatives have greater anticholinergic activity than do other antihistamines, which probably accounts for the antidyskinetic action of carbinoxamine.
• Affected Organisms: Humans and other mammals
• Half Life: 10 to 20 hours
• References: BEALE HD, RAWLING FF, FIGLEY KD: Clistin maleate; a clinical appraisal of a new antihistaminic. J Allergy. 1954 Nov;25(6):521-4. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• BEALE HD, RAWLING FF, FIGLEY KD: Clistin maleate; a clinical appraisal of a new antihistaminic. J Allergy. 1954 Nov;25(6):521-4. Pubmed