You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2006-05-18 09:20:41 UTC
Update Date2017-10-23 19:03:55 UTC
HMDB IDHMDB0001944
Secondary Accession Numbers
  • HMDB01944
  • 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
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
ChlorpheniraminumChEBI
ClofeniraminaChEBI
ClorfenaminaChEBI
ClorfeniraminaChEBI
gamma-(4-Chlorophenyl)-gamma-(2-pyridyl)propyldimethylamineChEBI
gamma-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamineChEBI
HaynonChEBI
2-[P-chloro-a-[2-(dimethylamino)Ethyl]benzyl]pyridineGenerator
2-[P-chloro-α-[2-(dimethylamino)ethyl]benzyl]pyridineGenerator
g-(4-Chlorophenyl)-g-(2-pyridyl)propyldimethylamineGenerator
γ-(4-chlorophenyl)-γ-(2-pyridyl)propyldimethylamineGenerator
g-(4-Chlorophenyl)-N,N-dimethyl-2-pyridinepropanamineGenerator
γ-(4-chlorophenyl)-N,N-dimethyl-2-pyridinepropanamineGenerator
Chlor-trimetonHMDB
Chloropheniramine maleateHMDB
Chlorphenamine hydrogen maleateHMDB
Chlorphenamine maleateHMDB
Chlorpheniaramine maleateHMDB
Chlorpheniramine maleateHMDB
TeldrinHMDB
Aller-chlorMeSH
Chlor-tripolonMeSH
ChlorproMeSH
cloro-TrimetonMeSH
KlorominMeSH
Maleate, chlorpheniramineMeSH
PiritonMeSH
Rugby brand OF chlorpheniramine maleateMeSH
Schering-plough brand OF chlorpheniramine maleateMeSH
Tannate, chlorpheniramineMeSH
Bayer brand OF chlorpheniramine maleateMeSH
chlo-AmineMeSH
ChlorphenamineMeSH
Hogil brand 1 OF chlorpheniramine maleateMeSH
Llorens brand OF chlorpheniramine maleateMeSH
Schering brand OF chlorpheniramine maleateMeSH
Vortech brand 1 OF chlorpheniramine maleateMeSH
antihistaminico LlorensMeSH
ChlorprophenpyridamineMeSH
Chlorspan 12MeSH
Chlortab-4MeSH
Halsey drug brand OF chlorpheniramine maleateMeSH
Stafford-miller brand OF chlorpheniramine maleateMeSH
Vortech brand 3 OF chlorpheniramine maleateMeSH
Chlor-100MeSH
Chlorpheniramine tannateMeSH
Efidac 24MeSH
Hogil brand 2 OF chlorpheniramine maleateMeSH
Intra brand OF chlorpheniramine maleateMeSH
Schein brand OF chlorpheniramine maleateMeSH
Vortech brand 2 OF chlorpheniramine maleateMeSH
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 KeySOYKEARSMXGVTM-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
  • Chlorobenzene
  • Halobenzene
  • Aralkylamine
  • Aryl chloride
  • Benzenoid
  • Monocyclic benzene moiety
  • Aryl halide
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Azacycle
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Ontology
Process

Naturally occurring process:

  Biological process:

    Biochemical pathway:

Disposition

Biological Location:

  Subcellular:

  Organ and components:

Route of exposure:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point130 - 135 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility160 mg/mL at 25 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.052 g/LALOGPS
logP3.74ALOGPS
logP3.58ChemAxon
logS-3.7ALOGPS
pKa (Strongest Basic)9.47ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area16.13 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity80.85 m³·mol⁻¹ChemAxon
Polarizability30.82 ųChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0zfr-6290000000-2ca3230cde716588805eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-9380000000-f4a0f7b13adeafb1762dView in MoNA
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
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0uy0-0960000000-1f750af75fe542c6c06fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-001i-0290000000-03651b7b90a1745fdf23View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0uy0-0960000000-1f750af75fe542c6c06fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0090000000-9b4d486e9c2c7712ca4dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0059-0190000000-2c96b165338a445b284dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ue9-3960000000-73025748bd5a00459938View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0090000000-90a6e640c735788d17caView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-1090000000-89ac3cf688134ba8a50bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01tc-6490000000-4242ef7cec7b0b0a7393View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0zfr-6490000000-8e58cd1c686f23a7dac6View in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid LocationsNot Available
Tissue Location
  • Skin
Pathways
NameSMPDB/PathwhizKEGG
Chlorphenamine ActionPw057579Pw057579 greyscalePw057579 simpleNot Available
Displaying 1 entry
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
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. [PubMed: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. [PubMed:12417888 ]
  3. MSDS [Link]

Enzymes

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
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
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
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
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