Carbinoxamine

Basic Info

Common NameCarbinoxamine(F05455)
2D Structure
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.

FRCD IDF05455
CAS Number486-16-8
PubChem CID2564
FormulaC16H19ClN2O
IUPAC Name

2-[(4-chlorophenyl)-pyridin-2-ylmethoxy]-N,N-dimethylethanamine

InChI Key

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

Canonical SMILES

CN(C)CCOC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2

Isomeric SMILES

CN(C)CCOC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2

WikipediaCarbinoxamine
Synonyms
        
            Carbinoxamina
        
            carbinoxamine
        
            Paracarbinoxamine
        
            Allergefon
        
            486-16-8
        
            Carbinoxaminum
        
            Clistin
        
            Paracarinoxamine
        
            (+-)-Carbinoxamine
        
            McN-R 73Z
Classifies
                

                  
                    Predicted: Pesticide
Update DateNov 13, 2018 17:07

Chemical Taxonomy

KingdomOrganic compounds
SuperclassBenzenoids
ClassBenzene and substituted derivatives
SubclassBenzylethers
Intermediate Tree NodesNot available
Direct ParentBenzylethers
Alternative Parents
Molecular FrameworkAromatic heteromonocyclic compounds
SubstituentsBenzylether - Chlorobenzene - Halobenzene - Aryl chloride - Aryl halide - Pyridine - Heteroaromatic compound - Tertiary aliphatic amine - Tertiary amine - Dialkyl ether - Ether - Azacycle - Organoheterocyclic compound - Organohalogen compound - Organic nitrogen compound - Amine - Hydrocarbon derivative - Organopnictogen compound - Organochloride - Organonitrogen compound - Organooxygen compound - Organic oxygen compound - Aromatic heteromonocyclic compound
DescriptionThis compound belongs to the class of organic compounds known as benzylethers. These are aromatic ethers with the general formula ROCR' (R = alkyl, aryl; R'=benzene).

Properties

Property NameProperty Value
Molecular Weight290.791
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count6
Complexity267
Monoisotopic Mass290.119
Exact Mass290.119
XLogP2.9
Formal Charge0
Heavy Atom Count20
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Isotope Atom Count0
Covalently-Bonded Unit Count1

ADMET

Model Result Probability
Absorption
Blood-Brain BarrierBBB+0.9550
Human Intestinal AbsorptionHIA+0.9787
Caco-2 PermeabilityCaco2+0.7503
P-glycoprotein SubstrateSubstrate0.6804
P-glycoprotein InhibitorNon-inhibitor0.5997
Non-inhibitor0.8382
Renal Organic Cation TransporterInhibitor0.7956
Distribution
Subcellular localizationMitochondria0.7264
Metabolism
CYP450 2C9 SubstrateNon-substrate0.8203
CYP450 2D6 SubstrateSubstrate0.5558
CYP450 3A4 SubstrateSubstrate0.6473
CYP450 1A2 InhibitorNon-inhibitor0.9045
CYP450 2C9 InhibitorNon-inhibitor0.9071
CYP450 2D6 InhibitorInhibitor0.8452
CYP450 2C19 InhibitorNon-inhibitor0.9025
CYP450 3A4 InhibitorNon-inhibitor0.8403
CYP Inhibitory PromiscuityHigh CYP Inhibitory Promiscuity0.5557
Excretion
Toxicity
Human Ether-a-go-go-Related Gene InhibitionWeak inhibitor0.7085
Inhibitor0.6835
AMES ToxicityNon AMES toxic0.8751
CarcinogensNon-carcinogens0.9182
Fish ToxicityLow FHMT0.6218
Tetrahymena Pyriformis ToxicityHigh TPT0.7655
Honey Bee ToxicityLow HBT0.8413
BiodegradationNot ready biodegradable1.0000
Acute Oral ToxicityII0.5344
Carcinogenicity (Three-class)Non-required0.5865
Model Value Unit
Absorption
Aqueous solubility-2.9647LogS
Caco-2 Permeability1.3570LogPapp, cm/s
Distribution
Metabolism
Excretion
Toxicity
Rat Acute Toxicity2.9003LD50, mol/kg
Fish Toxicity1.4076pLC50, mg/L
Tetrahymena Pyriformis Toxicity0.6539pIGC50, ug/L

Targets

Target Details

Histamine H1 receptor

General Function:
Histamine receptor activity
Specific Function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system.
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular Weight:
55783.61 Da
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]