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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:52 UTC
Update Date2017-12-07 02:52:39 UTC
HMDB IDHMDB0015690
Secondary Accession Numbers
  • HMDB15690
Metabolite Identification
Common NameChloropyramine
DescriptionChloropyramine 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
ValueSource
HALOPYRAMINEChEMBL
AnaphyllineHMDB
ChlorpyramineHMDB
ChlorpyraminumHMDB
SuprastinMeSH
AvapenaMeSH
N-(P-Chlorobenzyl)-N-(2-pyridyl)-n',n''-dimethylethylenediamineMeSH
Chloropyramine hydrochlorideMeSH
Chloropyramine monohydrochlorideMeSH
Chemical FormulaC16H20ClN3
Average Molecular Weight289.803
Monoisotopic Molecular Weight289.134575362
IUPAC NameN-[(4-chlorophenyl)methyl]-N-[2-(dimethylamino)ethyl]pyridin-2-amine
Traditional Namechloropyramine
CAS Registry Number59-32-5
SMILES
CN(C)CCN(CC1=CC=C(Cl)C=C1)C1=CC=CC=N1
InChI Identifier
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
InChI KeyICKFFNBDFNZJSX-UHFFFAOYSA-N
Chemical 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 Parents
Substituents
  • 2-benzylaminopyridine
  • Dialkylarylamine
  • Aminopyridine
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Imidolactam
  • Pyridine
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Organoheterocyclic compound
  • Azacycle
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Amine
  • Organic nitrogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point60 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.44 g/LALOGPS
logP3.79ALOGPS
logP3.81ChemAxon
logS-2.8ALOGPS
pKa (Strongest Basic)8.76ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area19.37 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity86.08 m³·mol⁻¹ChemAxon
Polarizability32.25 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a6r-9530000000-b6ae851a4ae80a823d03View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2090000000-2e81afab100f5ed6a72fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dj-6090000000-2bca247e25b9a1ac267fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00dl-9630000000-b6412f2e6b488b87f820View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-000i-0090000000-fba4fce50ff94474bf1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0190000000-ec3530ff95df29bd9547View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02t9-2930000000-1f1e66b2bf505d9191a1View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
Pathways
NameSMPDB/PathwhizKEGG
Chloropyramine H1-Antihistamine ActionPw058510Pw058510 greyscalePw058510 simpleNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08800 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB08800 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB08800
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID23628
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound25295
PDB IDC4C
ChEBI ID768237
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
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:
55783.6
References
  1. Budihna M, Drevensek G, Burjak M, Kocijancic S: Effects of chloropyramine and famotidine on postischaemic and posthypoxic myocardial damage in isolated rat hearts. Pflugers Arch. 1996;431(6 Suppl 2):R217-8. [PubMed:8739342 ]