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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
Chloropyramine
Chlorpyramine
Halopyramine
External Identifiers Not Available
Approved Prescription ProductsNot Available
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AvapenaNot Available
SuprastinNot Available
SynopenNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Chloropyramine hydrochloride
ThumbNot applicableDBSALT000909
Categories
UNII2K3L8O9SOV
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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylmethylamines. These are compounds containing a phenylmethtylamine moiety, which consists of a phenyl group substituted by an methanamine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylmethylamines
Direct ParentPhenylmethylamines
Alternative Parents
Substituents
  • Dialkylarylamine
  • Phenylmethylamine
  • Benzylamine
  • Halobenzene
  • Chlorobenzene
  • Aminopyridine
  • Imidolactam
  • Pyridine
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organoheterocyclic compound
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.941
Blood Brain Barrier+0.9171
Caco-2 permeable+0.7061
P-glycoprotein substrateSubstrate0.783
P-glycoprotein inhibitor INon-inhibitor0.9316
P-glycoprotein inhibitor IINon-inhibitor0.927
Renal organic cation transporterInhibitor0.741
CYP450 2C9 substrateNon-substrate0.8112
CYP450 2D6 substrateNon-substrate0.734
CYP450 3A4 substrateSubstrate0.5631
CYP450 1A2 substrateInhibitor0.8437
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorInhibitor0.8994
CYP450 3A4 inhibitorNon-inhibitor0.9686
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6062
Ames testNon AMES toxic0.9301
CarcinogenicityNon-carcinogens0.8833
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5294 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.6398
hERG inhibition (predictor II)Inhibitor0.8005
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
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 Solubility0.441 mg/mLALOGPS
logP3.79ALOGPS
logP3.81ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area19.37 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity86.08 m3·mol-1ChemAxon
Polarizability32.25 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
References
Synthesis ReferenceUS2607778
General ReferencesNot Available
External Links
ATC CodesD04AA09R06AC03R06AC53
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (49.4 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
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. 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:19610651 ]
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Drug created on October 14, 2010 14:21 / Updated on January 15, 2016 17:38