Human Metabolome Database Version 3.5

Showing metabocard for Chlorpheniramine (HMDB01944)

Record Information
Version 3.5
Creation Date 2006-05-18 03:20:41 -0600
Update Date 2013-10-17 16:15:57 -0600
HMDB ID HMDB01944
Secondary Accession Numbers
  • HMDB04994
Metabolite Identification
Common Name Chlorpheniramine
Description Chlorpheniramine 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
Download: MOL | SDF | PDB | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. Chlor-trimeton
  2. Chloropheniramine maleate
  3. Chlorphenamine hydrogen maleate
  4. Chlorphenamine Maleate
  5. Chlorpheniaramine maleate
  6. Chlorpheniramine
  7. Chlorpheniramine Maleate
  8. Teldrin
Chemical Formula C16H19ClN2
Average Molecular Weight 274.788
Monoisotopic Molecular Weight 274.123676325
IUPAC Name [3-(4-chlorophenyl)-3-(pyridin-2-yl)propyl]dimethylamine
Traditional IUPAC Name chlorpheniramine
CAS Registry Number 113-92-8
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 Key SOYKEARSMXGVTM-UHFFFAOYSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Aromatic Heteropolycyclic Compounds
Class Pheniramines
Sub Class N/A
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
  • pyridines(ChEBI)
Substituents
  • Aryl Chloride
  • Chlorobenzene
  • Organochloride
  • Phenylpropylamine
  • Pyridine
  • Tertiary Aliphatic Amine (Trialkylamine)
Direct Parent Pheniramines
Ontology
Status Expected and Not Quantified
Origin
  • Drug
Biofunction Not Available
Application Not Available
Cellular locations
  • Membrane (predicted from logP)
Physical Properties
State Solid
Experimental Properties
Property Value Reference
Melting Point 130 - 135 °C Not Available
Boiling Point Not Available Not Available
Water Solubility 160.0 mg/mL at 25 °C Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
LogP 3.74 ALOGPS
LogP 3.58 ChemAxon
LogS -3.72 ALOGPS
pKa (strongest basic) 9.47 ChemAxon
Hydrogen Acceptor Count 2 ChemAxon
Hydrogen Donor Count 0 ChemAxon
Polar Surface Area 16.13 A2 ChemAxon
Rotatable Bond Count 5 ChemAxon
Refractivity 80.85 ChemAxon
Polarizability 30.82 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge 1 ChemAxon
Spectra
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
MS/MS Spectrum EI-B (Unknown)
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biofluid Locations Not Available
Tissue Location
  • Skin
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID DB01114 Link_out
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB022759
KNApSAcK ID Not Available
Chemspider ID 2624 Link_out
KEGG Compound ID C06905 Link_out
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Chlorpheniramine Link_out
NuGOwiki Link HMDB01944 Link_out
Metagene Link HMDB01944 Link_out
METLIN ID 1734 Link_out
PubChem Compound 2725 Link_out
PDB ID Not Available
ChEBI ID 52010 Link_out
References
Synthesis Reference Not 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 Link_out
  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 Link_out
  3. MSDS Link_out

Enzymes
Name: Cytochrome P450 3A4
Reactions: Not Available
Gene Name: CYP3A4
Uniprot ID: P08684 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Cytochrome P450 2D6
Reactions: Not Available
Gene Name: CYP2D6
Uniprot ID: P10635 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Serum albumin
Reactions: Not Available
Gene Name: ALB
Uniprot ID: P02768 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Histamine H1 receptor
Reactions: Not Available
Gene Name: HRH1
Uniprot ID: P35367 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
Name: Histamine H4 receptor
Reactions: Not Available
Gene Name: HRH4
Uniprot ID: Q9H3N8 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA