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Showing metabocard for Chlorpheniramine (HMDB01944)

IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (5) Show 5 proteinsXML
enzymes (5) Show 5 proteins
Record Information
Version3.6
Creation Date2006-05-18 09:20:41 UTC
Update Date2016-02-11 01:05:08 UTC
HMDB IDHMDB01944
Secondary Accession Numbers
  • HMDB04994
Metabolite Identification
Common NameChlorpheniramine
DescriptionChlorpheniramine is a histamine H1 antagonist used in allergic reactions, hay fever, rhinitis, urticaria, and asthma. It has also been used in veterinary applications. One of the most widely used of the classical antihistaminics, it generally causes less drowsiness and sedation than Promethazine. -- Pubchem; Chlorphenamine or chlorpheniramine, commonly marketed as its salt chlorphenamine maleate (Chlor- Trimeton, Piriton, Chlor- Tripolon), is a first generation antihistamine used in the prevention of the symptoms of allergic conditions such as rhinitis and urticaria.- wikipedia.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
1-(P-Chlorophenyl)-1-(2-pyridyl)-3-dimethylaminopropaneChEBI
1-(P-Chlorophenyl)-1-(2-pyridyl)-3-N,N-dimethylpropylamineChEBI
2-[P-chloro-alpha-[2-(dimethylamino)Ethyl]benzyl]pyridineChEBI
3-(P-Chlorophenyl)-3-(2-pyridyl)-N,N-dimethylpropylamineChEBI
ChlorophenylpyridamineChEBI
ChlorphenaminChEBI
ChlorphenaminumChEBI
ChlorpheniramineChEBI
ChlorpheniraminumChEBI
ClofeniraminaChEBI
ClorfenaminaChEBI
ClorfeniraminaChEBI
gamma-(4-Chlorophenyl)-gamma-(2-pyridyl)propyldimethylamineChEBI
gamma-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamineChEBI
HaynonChEBI
Chlor-trimetonHMDB
Chloropheniramine maleateHMDB
Chlorphenamine hydrogen maleateHMDB
Chlorphenamine maleateHMDB
Chlorpheniaramine maleateHMDB
Chlorpheniramine maleateHMDB
TeldrinHMDB
Chemical FormulaC16H19ClN2
Average Molecular Weight274.788
Monoisotopic Molecular Weight274.123676325
IUPAC Name[3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
Traditional Namechlorpheniramine
CAS Registry Number113-92-8
SMILES
CN(C)CCC(C1=CC=C(Cl)C=C1)C1=CC=CC=N1
InChI Identifier
InChI=1S/C16H19ClN2/c1-19(2)12-10-15(16-5-3-4-11-18-16)13-6-8-14(17)9-7-13/h3-9,11,15H,10,12H2,1-2H3
InChI KeyInChIKey=SOYKEARSMXGVTM-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as pheniramines. These are compounds containing a pheniramine moiety, which is structurally characterized by the presence of a 2-benzylpyridine linked to an dimethyl(propyl)amine to form a dimethyl[3-phenyl-3-(pyridin-2-yl)propyl]amine skeleton.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassPheniramines
Direct ParentPheniramines
Alternative Parents
Substituents
  • Pheniramine
  • Phenylpropylamine
  • Aralkylamine
  • Halobenzene
  • Chlorobenzene
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Ontology
StatusExpected but not Quantified
Origin
  • Drug
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point130 - 135 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility160.0 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.052 mg/mLALOGPS
logP3.74ALOGPS
logP3.58ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)9.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.85 m3·mol-1ChemAxon
Polarizability30.82 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-01b9-3900000000-ea4ccfd2afe05f49fc7aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-004i-0090000000-9e46eb080de95d4f8f8eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-014i-1920000000-d2d2acf559d9070a1d47View in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (Unknown) , Positivesplash10-0zfr-6190000000-2ca3230cde716588805eView in MoNA
MSMass Spectrum (Electron Ionization)splash10-0zfr-6490000000-8e58cd1c686f23a7dac6View in MoNA
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Skin
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-4 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01114
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022759
KNApSAcK IDNot Available
Chemspider ID2624
KEGG Compound IDC06905
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkChlorpheniramine
NuGOwiki LinkHMDB01944
Metagene LinkHMDB01944
METLIN ID1734
PubChem Compound2725
PDB IDNot Available
ChEBI ID52010
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Bantz EW, Dolen WK, Chadwick EW, Nelson HS: Chronic chlorpheniramine therapy: subsensitivity, drug metabolism, and compliance. Ann Allergy. 1987 Nov;59(5):341-6. [3688558 ]
  2. Simons FE, Silver NA, Gu X, Simons KJ: Clinical pharmacology of H1-antihistamines in the skin. J Allergy Clin Immunol. 2002 Nov;110(5):777-83. [12417888 ]
  3. MSDS [Link]

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
Enzyme Details
2. Cytochrome P450 2D6
General function:
Involved in monooxygenase activity
Specific function:
Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:
CYP2D6
Uniprot ID:
P10635
Molecular weight:
55768.94
Enzyme Details
3. Serum albumin
General function:
Involved in transport
Specific function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc
Gene Name:
ALB
Uniprot ID:
P02768
Molecular weight:
69365.9
Enzyme Details
4. Histamine H1 receptor
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
Enzyme Details
5. Histamine H4 receptor
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
The H4 subclass of histamine receptors could mediate the histamine signals in peripheral tissues. Displays a significant level of constitutive activity (spontaneous activity in the absence of agonist)
Gene Name:
HRH4
Uniprot ID:
Q9H3N8
Molecular weight:
44495.4