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

General Information of Drug (ID: DR0304)
Drug Name
Chlorpheniramine
Synonyms
Chlorphenamine, (R)-; Chlorpheniramine, (-)-; Chlorpheniramine, (R)-; EY9131E63D; Lopac-C-3025; CHLORPHENIRAMINE (S) MALEATE; Lopac-C-4915; SCHEMBL4220; SPBio_000292; Spectrum2_000156; Spectrum3_000345; Spectrum4_000282; Spectrum5_001442; Spectrum_000140; l-chlorpheniramine; levochlorpheniramine; (-)-Chloropheniramine; (-)-chlorpheniramine; (3R)-3-(4-chlorophenyl)-N,N-dimethyl-3-pyridin-2-ylpropan-1-amine; 32188-09-3; AC1LEQ0Y; BSPBio_002009; CAS-113-92-8; CHEBI:52013; GTPL1213; KBioGR_000804; KBioSS_000600; UNII-EY9131E63D
Indication Allergic rhinitis [ICD11: CA08] Approved [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
716121
PubChem SID
9299815 ; 11110931 ; 11110932 ; 11112256 ; 11363014 ; 11365576 ; 11368138 ; 11371329 ; 11373943 ; 11376300 ; 11484028 ; 11487972 ; 11490161 ; 11492097 ; 11493954 ; 15442268 ; 33774101 ; 47719847 ; 48018097 ; 50064683 ; 50100400 ; 50225325 ; 57304992 ; 85789162 ; 109896795 ; 135650086 ; 135774423 ; 137002507 ; 160666558 ; 174007153 ; 175269603 ; 179039539 ; 226396260
ChEBI ID
ChEBI:52010
CAS Number
132-22-9
TTD Drug ID
D0B7NG
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-OAHLLOKOSA-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
MR000639 Chlorpheniramine Monodesmethylchlorpheniramine Unclear CYP2D6 [4]
MR000640 Chlorpheniramine Chlorpheniramine N-oxide Unclear Unclear [4]
MR000635 Monodesmethylchlorpheniramine Didesmethylchlorpheniramine Unclear Unclear [4]
MR000636 Didesmethylchlorpheniramine 3-(p-chlorophenyl)-3-(2-pyridyl)-N-acetylaminopropane Unclear Unclear [4]
MR000637 Didesmethylchlorpheniramine 3-(p-chlorophenyl)-3-(2-pyridyl) propanol Unclear Unclear [4]
MR000638 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 Chlorpheniramine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
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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