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Identification
NameChloropyramine
Accession NumberDB08800  (DB07523)
Typesmall molecule
Groupsapproved
Description

Chloropyramine is a first generation antihistamine drug approved in some Eastern European countries for the treatment of allergic conjunctivitis, allergic rhinitis, bronchial asthma, and other atopic (allergic) conditions. Related indications for clinical use include Quincke’s edema, allergic reactions to insect bites, food and drug allergies, and anaphylactic shock.

Structure
Thumb
Synonyms
SynonymLanguageCode
ChlorpyramineNot AvailableNot Available
HalopyramineNot AvailableNot Available
Salts
Name/CAS Structure Properties
Chloropyramine hydrochloride
Thumb Not applicable DBSALT000909
Brand names
NameCompany
AvapenaNot Available
SuprastinNot Available
SynopenNot Available
Brand mixturesNot Available
Categories
CAS number59-32-5
WeightAverage: 289.803
Monoisotopic: 289.134575362
Chemical FormulaC16H20ClN3
InChI KeyInChIKey=ICKFFNBDFNZJSX-UHFFFAOYSA-N
InChI
InChI=1S/C16H20ClN3/c1-19(2)11-12-20(16-5-3-4-10-18-16)13-14-6-8-15(17)9-7-14/h3-10H,11-13H2,1-2H3
IUPAC Name
N-[(4-chlorophenyl)methyl]-N-[2-(dimethylamino)ethyl]pyridin-2-amine
SMILES
CN(C)CCN(CC1=CC=C(Cl)C=C1)C1=CC=CC=N1
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassHeterocyclic Compounds
ClassPyridines and Derivatives
SubclassAminopyridines and Derivatives
Direct parentAminopyridines and Derivatives
Alternative parentsChlorobenzenes; Aryl Chlorides; Tertiary Amines; Polyamines; Organochlorides
Substituentsaryl chloride; aryl halide; benzene; tertiary amine; polyamine; organochloride; organohalogen; amine; organonitrogen compound
Classification descriptionThis compound belongs to the aminopyridines and derivatives. These are organic heterocyclic compounds containing an amino group attached to a pyridine ring.
Pharmacology
IndicationFor the treatment of allergic conjunctivitis, allergic rhinitis, bronchial asthma, and other atopic (allergic) conditions.
PharmacodynamicsChloropyramine is known as a competitive reversible H1-receptor antagonist (also known as an H1 inverse agonist), meaning that it exerts its pharmacological action by competing with histamine for the H1 subtype histamine receptor. By blocking the effects of histamine, the drug inhibits the vasodilation, increased vascular permeability, and tissue edema associated with histamine release in the tissue. In addition, chloropyramine has some anticholinergic properties. Chloropyramine's anticholinergic properties and the fact that it can pass through the blood-brain barrier are linked to its clinical side effects: drowsiness, weakness, vertigo, fatigue, dryness in the mouth, constipation, and rarely - visual disturbances and increase of intraocular pressure.
Mechanism of actionChloropyramine binds to the histamine H1 receptor. This blocks the action of endogenous histamine, which subsequently leads to temporary relief of the negative symptoms brought on by histamine.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityOral (LD50): Acute: 142 mg/kg [Rat]. 135 mg/kg [Mouse]. DUST (LC50): Acute: 209 mg/m 2 hours [Rat].
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 + 0.941
Blood Brain Barrier + 0.9171
Caco-2 permeable + 0.7061
P-glycoprotein substrate Substrate 0.783
P-glycoprotein inhibitor I Non-inhibitor 0.9316
P-glycoprotein inhibitor II Non-inhibitor 0.927
Renal organic cation transporter Inhibitor 0.741
CYP450 2C9 substrate Non-substrate 0.8112
CYP450 2D6 substrate Non-substrate 0.734
CYP450 3A4 substrate Substrate 0.5631
CYP450 1A2 substrate Inhibitor 0.8437
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Inhibitor 0.8994
CYP450 3A4 substrate Non-inhibitor 0.9686
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6062
Ames test Non AMES toxic 0.9301
Carcinogenicity Non-carcinogens 0.8833
Biodegradation Not ready biodegradable 1.0
Rat acute toxicity 2.5294 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.6398
hERG inhibition (predictor II) Inhibitor 0.8005
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
boiling point154.5 °C at 2.00E-01 mm HgPhysProp
water solubilityInsolubleMSDS
Predicted Properties
PropertyValueSource
water solubility4.41e-01 g/lALOGPS
logP3.79ALOGPS
logP3.81ChemAxon
logS-2.8ALOGPS
pKa (strongest basic)8.76ChemAxon
physiological charge1ChemAxon
hydrogen acceptor count3ChemAxon
hydrogen donor count0ChemAxon
polar surface area19.37ChemAxon
rotatable bond count6ChemAxon
refractivity86.08ChemAxon
polarizability32.25ChemAxon
number of rings2ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceUS2607778
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD07195
ChemSpider23628
PharmGKBPA165958419
HETC4C
ATC CodesD04AA09R06AC03
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(49.4 KB)
Interactions
Drug InteractionsNot Available
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. Kurenova EV, Hunt DL, He D, Magis AT, Ostrov DA, Cance WG: Small molecule chloropyramine hydrochloride (C4) targets the binding site of focal adhesion kinase and vascular endothelial growth factor receptor 3 and suppresses breast cancer growth in vivo. J Med Chem. 2009 Aug 13;52(15):4716-24. doi: 10.1021/jm900159g. Pubmed

Comments
Drug created on October 14, 2010 14:21 / Updated on March 28, 2014 11:06