Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0303)
Drug Name
Chlorphenamine
Synonyms
Chloropheniramine; Chlorophenylpyridamine; Chloropiril; Chloroprophenpyridamine; Chlorphenamin; Chlorphenamine; Chlorphenaminum; Chlorpheniramine maleate; Chlorpheniramine polistirex; Chlorpheniraminum; Chlorprophenpyridamine; Clorfenamina; Clorfeniramina; Clorfeniramina [Italian]; Cloropiril; Aller-Chlor; Allergican; Allergisan; Antagonate; Chlor-trimeton; Haynon; Histadur; Kloromin; Phenetron; Polaramine; Polaronil; Telachlor; Teldrin; chlorpheniramine; 132-22-9; 4-Chloropheniramine
Indication Allergy [ICD11: 4A80] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 274.79 Topological Polar Surface Area 16.1
Heavy Atom Count 19 Rotatable Bond Count 5
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
2725
ChEBI ID
CHEBI:52010
CAS Number
132-22-9
Formula
C16H19ClN2
Canonical SMILES
CN(C)CCC(C1=CC=C(C=C1)Cl)C2=CC=CC=N2
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/t15-/m1/s1
InChIKey
SOYKEARSMXGVTM-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
Chlorpheniramine N-oxide DM001822
46781011
Unclear 1 [4]
Monodesmethylchlorpheniramine DM001819
161321
Unclear 1 [4]
Didesmethylchlorpheniramine DM001820
161322
Unclear 2 [4]
3-(p-chlorophenyl)-3-(2-pyridyl) propanol DM001821
24128772
Unclear 3 [4]
3-(p-chlorophenyl)-3-(2-pyridyl)-N-acetylaminopropane DM001660
524031
Unclear 3 [4]
3-(p-chlorophenyl)-3-(2-pyridyl)-propionic acid DM001672
20741471
Unclear 4 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000633 Chlorphenamine Monodesmethylchlorpheniramine Unclear CYP2D6 [4]
MR000634 Chlorphenamine Chlorpheniramine N-oxide Unclear Unclear [4]
MR000629 Monodesmethylchlorpheniramine Didesmethylchlorpheniramine Unclear Unclear [4]
MR000630 Didesmethylchlorpheniramine 3-(p-chlorophenyl)-3-(2-pyridyl)-N-acetylaminopropane Unclear Unclear [4]
MR000631 Didesmethylchlorpheniramine 3-(p-chlorophenyl)-3-(2-pyridyl) propanol Unclear Unclear [4]
MR000632 3-(p-chlorophenyl)-3-(2-pyridyl) propanol 3-(p-chlorophenyl)-3-(2-pyridyl)-propionic acid Unclear Unclear [4]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[3]
References
1 The Drugs.com International Drug Name Database: Chlorpheniramine-maleate-dexchlorpheniramine-maleate
2 The roles of CYP2D6 and stereoselectivity in the clinical pharmacokinetics of chlorpheniramine. Br J Clin Pharmacol. 2002 May;53(5):519-25.
3 Drug Interactions Flockhart Table
4 Metabolism of chlorpheniramine in rat and human by use of stable isotopes Xenobiotica. 1991 Jan;21(1):97-109. doi: 10.3109/00498259109039454.

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