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

General Information of Drug (ID: DR1091)
Drug Name
Mifepristone
Synonyms
Mifegyne; Mifeprex; Mifepriston; Mifepristona; Mifepristona [Spanish]; Mifepristone [USAN:INN:BAN]; Mifepristone(Mifeprex); Mifepristone, 98%; Mifepristonum; Mifepristonum [Latin]; R 38486; RU 38486; RU 486; RU 486-6; RU-38486; RU-486; Corlux; Korlym; VGX-410; VGX-410C; mifepristone; 320T6RNW1F; 84371-65-3; BRN 5779404; C-1073; CHEBI:50692; DSSTox_CID_3322; DSSTox_RID_76976; HSDB 6841; MLS000069785; NCGC00025179-05; RU486; SMR000058481; UNII-320T6RNW1F
Indication Cushing syndrome [ICD11: 5A70] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 429.6 Topological Polar Surface Area 40.5
Heavy Atom Count 32 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
55245
PubChem SID
9854 ; 610895 ; 827617 ; 7847651 ; 7885329 ; 7979988 ; 8184037 ; 10321543 ; 11466327 ; 11467447 ; 11486193 ; 11533034 ; 12013919 ; 12146248 ; 14758749 ; 14905326 ; 17405362 ; 24278572 ; 26752199 ; 26759172 ; 34719152 ; 46386955 ; 46505795 ; 46518693 ; 47573358 ; 47720589 ; 47795017 ; 47795018 ; 48018884 ; 48318385 ; 48393908 ; 48416281 ; 49698423 ; 49835339 ; 49965772 ; 50124354 ; 50576278 ; 53777907 ; 53788556 ; 56312231 ; 56313355 ; 56313657 ; 56313765 ; 56352854 ; 56424093 ; 57313727 ; 85752924 ; 85789352 ; 90341299 ; 92125204
ChEBI ID
CHEBI:50692
CAS Number
84371-65-3
TTD Drug ID
D0Z4EI
Formula
C29H35NO2
Canonical SMILES
CC#CC1(CCC2C1(CC(C3=C4CCC(=O)C=C4CCC23)C5=CC=C(C=C5)N(C)C)C)O
InChI
1S/C29H35NO2/c1-5-15-29(32)16-14-26-24-12-8-20-17-22(31)11-13-23(20)27(24)25(18-28(26,29)2)19-6-9-21(10-7-19)30(3)4/h6-7,9-10,17,24-26,32H,8,11-14,16,18H2,1-4H3/t24-,25+,26-,28-,29-/m0/s1
InChIKey
VKHAHZOOUSRJNA-GCNJZUOMSA-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
17alpha-hydroxymifepristone DM004435
13605512
Oxidation - Aliphatic hydroxylation 1 [5] , [6]
Monodemethylated mifepristone DM004431
10070462
Oxidation - N-dealkylation 1 [5] , [7]
Mifepristone Metabolite M2 DM004432 N. A. Unclear 2 [8]
Mifepristone Metabolite M4 DM004434 N. A. Unclear 2 [8]
Mifepristone Metabolite M6 DM004436 N. A. Unclear 2 [8]
Mifepristone Metabolite M5 DM004433 N. A. Unclear 3 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR004757 Mifepristone Monodemethylated mifepristone Oxidation - N-dealkylation CYP3A4 [5], [7]
MR004762 Mifepristone 17alpha-hydroxymifepristone Oxidation - Aliphatic hydroxylation CYP3A4 [5], [6]
MR004763 17alpha-hydroxymifepristone Mifepristone Metabolite M4 Unclear Unclear [8]
MR004764 17alpha-hydroxymifepristone Mifepristone Metabolite M6 Unclear Unclear [8]
MR004758 Monodemethylated mifepristone Mifepristone Metabolite M2 Unclear Unclear [8]
MR004760 Monodemethylated mifepristone Mifepristone Metabolite M4 Unclear Unclear [8]
MR004759 Mifepristone Metabolite M2 Mifepristone Metabolite M5 Unclear Unclear [8]
MR004761 Mifepristone Metabolite M4 Mifepristone Metabolite M5 Unclear Unclear [8]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1393 Blautia hansenii Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [4]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [4]
⏷ Show the Full List of 8  DME(s)
References
1 Mifepristone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Evaluation of strategies for the assessment of drug-drug interactions involving cytochrome P450 enzymes. Eur J Drug Metab Pharmacokinet. 2018 Dec;43(6):737-750.
3 Comparative analysis of substrate and inhibitor interactions with CYP3A4 and CYP3A5. Xenobiotica. 2006 Apr;36(4):287-99.
4 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
5 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.
6 PAT Program report: background and current status. Proficiency Analytical Testing
7 Respirator performance terminology
8 In vitro metabolism of mifepristone (RU-486) in rat, monkey and human hepatic S9 fractions: identification of three new mifepristone metabolites

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