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Identification
NameCarbinoxamine
Accession NumberDB00748  (APRD00765)
Typesmall molecule
Groupsapproved
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.

Structure
Thumb
Synonyms
SynonymLanguageCode
CarbinoxaminGermanINN
CarbinoxaminaSpanishINN
CarbinoxamineFrenchINN
CarbinoxaminumLatinINN
Salts
Name/CAS Structure Properties
Carbinoxamine Maleate
Thumb Not applicable DBSALT000963
Brand names
NameCompany
AllergefonSERP
ClistinNot Available
HistinKenyaku
PalgicNot Available
RotoxamineNot Available
SatinminShou Chan
Brand mixtures
Brand NameIngredients
AnpirinCarbinoxamine and Pseudoephedrine
Aseptobron CCarbinoxamine and Oxeladin
BecameCarbinoxamine and Pseudoephedrine
BiminingCarbinoxamine and Pseudoephedrine
BininCarbinoxamine and Pseudoephedrine
CarmineCarbinoxamine and Pseudoephedrine
FubininCarbinoxamine and Pseudoephedrine
Kenantist Carbinoxamine and Triamcinolone
KezinteaCarbinoxamine and Pseudoephedrine
KompiminCarbinoxamine and Pseudoephedrine
LondecCarbinoxamine and Pseudoephedrine
LontecCarbinoxamine and Pseudoephedrine
NasalconCarbinoxamine and Pseudoephedrine
NascoCarbinoxamine and Pseudoephedrine
Pseudo-CarbCarbinoxamine and Pseudoephedrine
PsubityCarbinoxamine and Pseudoephedrine
RhinarCarbinoxamine and Pseudoephedrine
RhinohistCarbinoxamine and Pseudoephedrine
Rhinomode PediatricCarbinoxamine and Phenylephrine
RhinoprontCarbinoxamine and Phenylephrine
RotecCarbinoxamine and Pseudoephedrine
SeuphenonCarbinoxamine and Pseudoephedrine
SubilinCarbinoxamine and Pseudoephedrine
Tai ChiCarbinoxamine and Pseudoephedrine
WeliminCarbinoxamine and Pseudoephedrine
Categories
CAS number486-16-8
WeightAverage: 290.788
Monoisotopic: 290.118590947
Chemical FormulaC16H19ClN2O
InChI KeyInChIKey=OJFSXZCBGQGRNV-UHFFFAOYSA-N
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
IUPAC Name
{2-[(4-chlorophenyl)(pyridin-2-yl)methoxy]ethyl}dimethylamine
SMILES
CN(C)CCOC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzylethers
Direct parentBenzylethers
Alternative parentsChlorobenzenes; Pyridines and Derivatives; Aryl Chlorides; Tertiary Amines; Dialkyl Ethers; Polyamines; Organochlorides
Substituentschlorobenzene; aryl chloride; aryl halide; pyridine; tertiary amine; polyamine; dialkyl ether; ether; organochloride; organohalogen; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).
Pharmacology
IndicationFor 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.
PharmacodynamicsCarbinoxamine 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.
Mechanism of actionCarbinoxamine 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. Carbinoxamine's anticholinergic action appears to be due to a central antimuscarinic effect, which also may be responsible for its antiemetic effects, although the exact mechanism is unknown.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half life10 to 20 hours
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9787
Blood Brain Barrier + 0.955
Caco-2 permeable + 0.7503
P-glycoprotein substrate Substrate 0.6804
P-glycoprotein inhibitor I Non-inhibitor 0.5997
P-glycoprotein inhibitor II Non-inhibitor 0.8382
Renal organic cation transporter Inhibitor 0.7956
CYP450 2C9 substrate Non-substrate 0.8203
CYP450 2D6 substrate Substrate 0.5558
CYP450 3A4 substrate Substrate 0.6473
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Inhibitor 0.8452
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.8403
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.5557
Ames test Non AMES toxic 0.8751
Carcinogenicity Non-carcinogens 0.9182
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.9003 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7085
hERG inhibition (predictor II) Inhibitor 0.6835
Pharmacoeconomics
Manufacturers
  • Mcneil pharmaceutical co div mcneilab inc
  • Boca pharmacal inc
  • Cypress pharmaceutical inc
  • Mikart inc
  • Invagen pharmaceuticals inc
  • Ortho mcneil pharmaceutical inc
Packagers
Dosage forms
FormRouteStrength
Solution / dropsOral
SyrupOral
TabletOral
Tablet, extended releaseOral
Prices
Unit descriptionCostUnit
Palgic 4 mg tablet0.87USDtablet
Carbinoxamine maleate 4 mg tablet0.65USDtablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
boiling point160 °C at 1.00E-01 mm HgPhysProp
logP2.6Not Available
Predicted Properties
PropertyValueSource
water solubility2.28e-01 g/lALOGPS
logP3.03ALOGPS
logP3.27ChemAxon
logS-3.1ALOGPS
pKa (strongest basic)8.87ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count0ChemAxon
polar surface area25.36ChemAxon
rotatable bond count6ChemAxon
refractivity82.13ChemAxon
polarizability31.7ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Tilford. C.H. and Shelton, R.S.; U.S. Patent 2,606,195;August 5,1952; assigned to The Wm.S. Merrell Company.
Swain, A.P.; U.S. Patent 2800,485; July 23,1957; assigned to McNeil Laboratories, Inc.

General Reference
  1. 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
ResourceLink
KEGG CompoundC06871
PubChem Compound2564
PubChem Substance46506787
ChemSpider2466
BindingDB50240487
ChEBI3398
ChEMBLCHEMBL864
Therapeutic Targets DatabaseDAP001069
PharmGKBPA164746898
RxListhttp://www.rxlist.com/cgi/generic3/rondecsyr.htm
Drugs.comhttp://www.drugs.com/cdi/carbinoxamine-maleate.html
WikipediaCarbinoxamine
ATC CodesR06AA08
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(74.6 KB)
Interactions
Drug Interactions
Drug
Benzylpenicilloyl PolylysineAntihistamines may diminish the diagnostic effect of Benzylpenicilloyl Polylysine. Treatment with systemic histamine H1 antagonists such as carbinoxamine should be suspended for benzylpenicilloyl-polylysine skin testing to minimize the potential for false negative results. Delay skin testing until the systemic effects of the antihistamine have dissipated. A histamine skin test may be used to assess residual antihistaminic effects.
DonepezilPossible antagonism of action
GalantaminePossible antagonism of action
PramlintidePramlintide may enhance the anticholinergic effect of Anticholinergics such as carbinoxamine. These effects are specific to the gastrointestinal tract. Use caution during concomitant therapy with pramlintide and anticholinergics. Additive effects on reduced gastrointestinal motility may occur.
TacrineThe therapeutic effects of the central acetylcholinesterase inhibitor, Tacrine, and/or the anticholinergic, Carbinoxamine, may be reduced due to antagonism. The interaction may be beneficial when the anticholinergic action is a side effect. Monitor for decreased efficacy of both agents.
TrimethobenzamideTrimethobenzamide and Carbinoxamine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Monitor for enhanced anticholinergic effects.
TriprolidineTriprolidine and Carbinoxamine, two anticholinergics, may cause additive anticholinergic effects and enhance their adverse/toxic effects. Additive CNS depressant effects may also occur. Monitor for enhanced anticholinergic and CNS depressant effects.
TrospiumTrospium and Carbinoxamine, two anticholinergics, may cause additive anticholinergic effects and enhanced adverse/toxic effects. Monitor for enhanced anticholinergic effects.
Food InteractionsNot Available

1. Histamine H1 receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: antagonist

Components

Name UniProt ID Details
Histamine H1 receptor P35367 Details

References:

  1. Oishi R, Shishido S, Yamori M, Saeki K: Comparison of the effects of eleven histamine H1-receptor antagonists on monoamine turnover in the mouse brain. Naunyn Schmiedebergs Arch Pharmacol. 1994 Feb;349(2):140-4. Pubmed
  2. Ramadan AA, Mandil H: Spectrophotometric determination of carbinoxamine maleate in pharmaceutical formulations by ternary complex formation with Cu(II) and eosin. Anal Biochem. 2006 Jun 1;353(1):133-7. Epub 2006 Mar 9. Pubmed
  3. Darby WJ: Nutrition, food needs and technologic priorities: the World Food Conference. Nutr Rev. 1975 Aug;33(8):225-34. Pubmed
  4. Yang J, Dudley GB: [1,2]-Anionic rearrangement of 2-benzyloxypyridine and related pyridyl ethers. J Org Chem. 2009 Oct 16;74(20):7998-8000. Pubmed
  5. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

1. Cytochrome P450 2B6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2B6 P20813 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

2. Cytochrome P450 2C19

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C19 P33261 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

3. Cytochrome P450 2C8

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C8 P10632 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

4. Cytochrome P450 2C9

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2C9 P11712 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

5. Cytochrome P450 2D6

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 2D6 P10635 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

6. Cytochrome P450 2E1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 2E1 P05181 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

7. Cytochrome P450 3A4

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 3A4 P08684 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on April 02, 2014 14:13