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

General Information of Drug (ID: DR0395)
Drug Name
Cyproheptadine
Synonyms
Ciproheptadina; Ciproheptadina [INN-Spanish]; Cypoheptadine; Cyproheptadiene; Cyproheptadine [INN:BAN]; Cyproheptadinum; Cyproheptadinum [INN-Latin]; Dihexazin; Dronactin; Eiproheptadine; MK 141; Periactin; Periactine; Periactinol; CYPROHEPTADINE; Peritol; 1-Methyl-4-(5-dibenzo(a,e)cycloheptatrienylidene)piperidine; 1-Methyl-4-(5H-dibenzo(a,d)cycloheptenylidene)piperidine; 129-03-3; 4-(5H-dibenzo[a,d][7]annulen-5-ylidene)-1-methylpiperidine; 5-(1-Methylpiperidylidene-4)-5H-dibenzo(a,d)cyclopheptene
Indication Rheumatoid arthritis [ICD11: FA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 287.4 Topological Polar Surface Area 3.2
Heavy Atom Count 22 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
2913
PubChem SID
9151 ; 597387 ; 3206368 ; 4509244 ; 7979013 ; 8151866 ; 10506298 ; 11110964 ; 11110965 ; 11113362 ; 11466131 ; 11467251 ; 11485761 ; 14751189 ; 26751603 ; 29222066 ; 46508613 ; 47216945 ; 47440433 ; 47440434 ; 47515490 ; 47589155 ; 47736665 ; 48110626 ; 48110627 ; 48185155 ; 48259431 ; 48415832 ; 49698345 ; 50015917 ; 50100203 ; 50104260 ; 51092057 ; 78634349 ; 85209714 ; 85279540 ; 85787813 ; 85788782 ; 90341656 ; 92309316 ; 92729717 ; 93166482 ; 94564370 ; 96079554 ; 103173872 ; 103928989 ; 104171133 ; 104301985 ; 108667051 ; 116933607
ChEBI ID
CHEBI:4046
CAS Number
129-03-3
TTD Drug ID
D00TLN
Formula
C21H21N
Canonical SMILES
CN1CCC(=C2C3=CC=CC=C3C=CC4=CC=CC=C42)CC1
InChI
1S/C21H21N/c1-22-14-12-18(13-15-22)21-19-8-4-2-6-16(19)10-11-17-7-3-5-9-20(17)21/h2-11H,12-15H2,1H3
InChIKey
JJCFRYNCJDLXIK-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
1-OH-CPH DM003756 N. A. Unclear 1 [5]
2-OH-CPH DM003754 N. A. Unclear 1 [5]
3-OH-CPH DM003758 N. A. Unclear 1 [5]
CPH-10,11-epoxide DM003757 N. A. Unclear 1 [5]
CPH-NO DM003752 N. A. Unclear 1 [5]
Cyproheptadine N-glucuronide DM003755
78173912
Conjugation - N-glucuronidation 1 [4]
Nor-CPH DM003750
159718
Unclear 1 [5]
2-OH-CPH-NO DM003753 N. A. Unclear 2 [5]
Nor-2-OH-CPH DM003751 N. A. Unclear 2 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004128 Cyproheptadine Nor-CPH Unclear Unclear [5]
MR004130 Cyproheptadine CPH-NO Unclear Unclear [5]
MR004132 Cyproheptadine 2-OH-CPH Unclear Unclear [5]
MR004135 Cyproheptadine Cyproheptadine N-glucuronide Conjugation - N-glucuronidation UGT1A3 ... [4]
MR004136 Cyproheptadine 1-OH-CPH Unclear Unclear [5]
MR004137 Cyproheptadine CPH-10,11-epoxide Unclear Unclear [5]
MR004138 Cyproheptadine 3-OH-CPH Unclear Unclear [5]
MR004133 2-OH-CPH 2-OH-CPH-NO Unclear Unclear [5]
MR004134 2-OH-CPH Nor-2-OH-CPH Unclear Unclear [5]
MR004131 CPH-NO 2-OH-CPH-NO Unclear Unclear [5]
MR004129 Nor-CPH Nor-2-OH-CPH Unclear Unclear [5]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[2]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[3]
UDP-glucuronosyltransferase 1A4 (UGT1A4) DME0048 Homo sapiens
UD14_HUMAN
2.4.1.17
[4]
UDP-glucuronosyltransferase 2B10 (UGT2B10) DME0205 Homo sapiens
UDB10_HUMAN
2.4.1.17
[4]
References
1 Cyproheptadine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Effect of common exon variant (p.P364L) on drug glucuronidation by the human UDP-glucuronosyltransferase 1 family. Basic Clin Pharmacol Toxicol. 2011 Dec;109(6):486-93.
3 Glucuronidation of amines and other xenobiotics catalyzed by expressed human UDP-glucuronosyltransferase 1A3. Drug Metab Dispos. 1998 Jun;26(6):507-12.
4 Human metabolism of cyproheptadine
5 Fungal transformations of antihistamines: metabolism of cyproheptadine hydrochloride by Cunninghamella elegans

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