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 IDs Not Available
Product Ingredients
IngredientUNIICASInChI KeyDetails
Chloropyramine hydrochlorideFWA92Z14NN 6170-42-9VEYWWAGBHABATA-UHFFFAOYSA-NDetails
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
Categories
UNII2K3L8O9SOV
CAS number59-32-5
WeightAverage: 289.803
Monoisotopic: 289.134575362
Chemical FormulaC16H20ClN3
InChI KeyICKFFNBDFNZJSX-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
Pharmacology
Indication

For the treatment of allergic conjunctivitis, allergic rhinitis, bronchial asthma, and other atopic (allergic) conditions.

Structured Indications Not Available
Pharmacodynamics

Chloropyramine 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 action

Chloropyramine 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.

TargetKindPharmacological actionActionsOrganismUniProt ID
Histamine H1 receptorProteinyes
antagonist
HumanP35367 details
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
Toxicity

Oral (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
Pharmacogenomic Effects/ADRs Not Available
Interactions
Drug Interactions
DrugInteractionDrug group
2,5-Dimethoxy-4-ethylamphetamine2,5-Dimethoxy-4-ethylamphetamine may decrease the sedative activities of Chloropyramine.Experimental, Illicit
3,4-Methylenedioxyamphetamine3,4-Methylenedioxyamphetamine may decrease the sedative activities of Chloropyramine.Experimental, Illicit
3,4-Methylenedioxymethamphetamine3,4-Methylenedioxymethamphetamine may decrease the sedative activities of Chloropyramine.Experimental, Illicit
4-Bromo-2,5-dimethoxyamphetamine4-Bromo-2,5-dimethoxyamphetamine may decrease the sedative activities of Chloropyramine.Experimental, Illicit
AmphetamineAmphetamine may decrease the sedative activities of Chloropyramine.Approved, Illicit
BenzphetamineBenzphetamine may decrease the sedative activities of Chloropyramine.Approved, Illicit
Benzylpenicilloyl PolylysineChloropyramine may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Betahistine can be decreased when used in combination with Chloropyramine.Approved
ChlorphentermineChlorphentermine may decrease the sedative activities of Chloropyramine.Illicit, Withdrawn
DextroamphetamineDextroamphetamine may decrease the sedative activities of Chloropyramine.Approved, Illicit
DiethylpropionDiethylpropion may decrease the sedative activities of Chloropyramine.Approved, Illicit
HyaluronidaseThe therapeutic efficacy of Hyaluronidase can be decreased when used in combination with Chloropyramine.Approved, Investigational
HydroxyamphetamineHydroxyamphetamine hydrobromide may decrease the sedative activities of Chloropyramine.Approved
LisdexamfetamineLisdexamfetamine may decrease the sedative activities of Chloropyramine.Approved, Investigational
MephedroneMephedrone may decrease the sedative activities of Chloropyramine.Investigational
MephentermineMephentermine may decrease the sedative activities of Chloropyramine.Approved
MethamphetamineMethamphetamine may decrease the sedative activities of Chloropyramine.Approved, Illicit
MMDAMMDA may decrease the sedative activities of Chloropyramine.Experimental, Illicit
PhenterminePhentermine may decrease the sedative activities of Chloropyramine.Approved, Illicit
PseudoephedrinePseudoephedrine may decrease the sedative activities of Chloropyramine.Approved
RitobegronRitobegron may decrease the sedative activities of Chloropyramine.Investigational
Food InteractionsNot Available
References
Synthesis ReferenceUS2607778
General ReferencesNot Available
External Links
ATC CodesD04AA09 — ChloropyramineR06AC03 — ChloropyramineR06AC53 — Chloropyramine, combinations
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (49.4 KB)
Clinical Trials
Clinical Trials Not Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point (°C)< 25 °CPhysProp
boiling point (°C)154.5 °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 RuleNoChemAxon
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 )
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
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as 2-benzylaminopyridines. These are aromatic compounds containing pyridine ring substituted at the 2-position by a benzylamine group.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct Parent2-benzylaminopyridines
Alternative ParentsDialkylarylamines / Chlorobenzenes / Aminopyridines and derivatives / Imidolactams / Aryl chlorides / Heteroaromatic compounds / Trialkylamines / Azacyclic compounds / Organopnictogen compounds / Organochlorides
Substituents2-benzylaminopyridine / Dialkylarylamine / Aminopyridine / Chlorobenzene / Halobenzene / Aryl chloride / Aryl halide / Imidolactam / Pyridine / Heteroaromatic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot 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 ]
Drug created on October 14, 2010 14:21 / Updated on June 11, 2017 17:11