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

General Information of Drug (ID: DR0322)
Drug Name
ADD-3878
Synonyms
Ciglitazona; Ciglitazona [Spanish]; Ciglitazone [USAN:INN]; Ciglitazonum; Ciglitazonum [Latin]; Ciglitizone; U 63287; U-63287; YZFWTZACSRHJQD-UHFFFAOYSA-N; ciglitazone; (+-)-5-(p-((1-Methylcyclohexyl)methoxy)benzyl)-2,4-thiazolidinedione; (+/-)-5-[4-(1-Methylcyclohexylmethoxy)benzyl]thiazolidine-2,4-dione; 5-(4-((1-methylcyclohexyl)methoxy)benzyl)thiazolidine-2,4-dione; 5-{4-[(1-methylcyclohexyl)methoxy]benzyl}-1,3-thiazolidine-2,4-dione; 74772-77-3; ADD 3878; ADD-3878; C18H23NO3S; CHEBI:64227; MFCD00865499; NCGC00164446-01
Indication Endometriosis [ICD11: GA10] Discontinued [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 333.4 Topological Polar Surface Area 80.7
Heavy Atom Count 23 Rotatable Bond Count 5
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
2750
PubChem SID
6897912 ; 7978942 ; 8151777 ; 11120025 ; 11120513 ; 11121001 ; 11121640 ; 11122120 ; 11147108 ; 11362709 ; 11365271 ; 11367833 ; 11370689 ; 11370690 ; 11373434 ; 11375995 ; 12012730 ; 14899936 ; 17397629 ; 22391558 ; 24892661 ; 26681499 ; 26752160 ; 26752161 ; 26752162 ; 26757865 ; 26758470 ; 29221905 ; 46488049 ; 47216537 ; 47810501 ; 48110200 ; 48334208 ; 50052262 ; 50104808 ; 50620095 ; 53788148 ; 56312056 ; 56314037 ; 57321433 ; 85788733 ; 91611856 ; 92309991 ; 95612759 ; 99300903 ; 99302423 ; 103165086 ; 103853966 ; 104046501 ; 104301499
ChEBI ID
CHEBI:64227
CAS Number
74772-77-3
TTD Drug ID
D03GWY
Formula
C18H23NO3S
Canonical SMILES
CC1(CCCCC1)COC2=CC=C(C=C2)CC3C(=O)NC(=O)S3
InChI
1S/C18H23NO3S/c1-18(9-3-2-4-10-18)12-22-14-7-5-13(6-8-14)11-15-16(20)19-17(21)23-15/h5-8,15H,2-4,9-12H2,1H3,(H,19,20,21)
InChIKey
YZFWTZACSRHJQD-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
Cis-3'-ol DM004144 N. A. Oxidation - Monohydroxylation 1 [3]
Cis-4'-ol DM004142 N. A. Oxidation - Monohydroxylation 1 [3]
Trans-3'-ol DM004143 N. A. Oxidation - Monohydroxylation 1 [3]
Trans-4'-ol DM004141 N. A. Oxidation - Monohydroxylation 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004538 ADD-3878 Trans-4'-ol Oxidation - Monohydroxylation Unclear [3]
MR004539 ADD-3878 Cis-4'-ol Oxidation - Monohydroxylation Unclear [3]
MR004540 ADD-3878 Trans-3'-ol Oxidation - Monohydroxylation Unclear [3]
MR004541 ADD-3878 Cis-3'-ol Oxidation - Monohydroxylation Unclear [3]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800004145)
2 Effects of gemfibrozil, itraconazole, and their combination on the pharmacokinetics of pioglitazone. Clin Pharmacol Ther. 2005 May;77(5):404-14.
3 Isomodal column switching high-performance liquid chromatographic technique for the analysis of ciglitazone and its metabolites in human serum

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