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

General Information of Drug (ID: DR1645)
Drug Name
Trilostane
Synonyms
Trilostane; Trilostano; Trilostanum; Vetoryl; WIN 24,540; Win-24540; Desopan; L0FPV48Q5R; Modrastane; Modrenal; (1aR,4aR,4bS,6aS,7S,9aS,9bS,11aS)-2,7-dihydroxy-4a,6a-dimethyl-1a,4,4a,4b,5,6,6a,7,8,9,9a,9b,10,11-tetradecahydrocyclopenta[7,8]phenanthro[1,10a-b]oxirene-3-carbonitrile; (4alpha,5alpha,17beta)-3,17-dihydroxy-4,5-epoxyandrost-2-ene-2-carbonitrile; 13647-35-3; CHEBI:32260; DSSTox_CID_3706; DSSTox_GSID_23706; DSSTox_RID_77157; MFCD00199295; UNII-L0FPV48Q5R
Indication Cushing syndrome [ICD11: 5A70] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 329.4 Topological Polar Surface Area 76.8
Heavy Atom Count 24 Rotatable Bond Count 0
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
656583
PubChem SID
582970 ; 7848243 ; 9268061 ; 14753126 ; 14850960 ; 46507062 ; 48416665 ; 53789389 ; 56352900 ; 57408348 ; 77191778 ; 92716671 ; 99437135 ; 103770890 ; 113527831 ; 124757227 ; 125164031 ; 126591224 ; 126622687 ; 126654263 ; 127324070 ; 127324071 ; 127324072 ; 127324073 ; 127324074 ; 134337470 ; 134990249 ; 135692137 ; 136946482 ; 137005257 ; 143492476 ; 144206007 ; 144212723 ; 152103462 ; 152164604 ; 152242918 ; 160964442 ; 162170394 ; 163138502 ; 164194095 ; 165702349 ; 170465836 ; 175265964 ; 176262060 ; 176484985 ; 178103456 ; 179149866 ; 196105623 ; 210275073 ; 210280711
ChEBI ID
ChEBI:32260
CAS Number
13647-35-3
TTD Drug ID
D03XOC
Formula
C20H27NO3
Canonical SMILES
CC12CCC3C(C1CCC2O)CCC45C3(CC(=C(C4O5)O)C#N)C
InChI
1S/C20H27NO3/c1-18-7-6-14-12(13(18)3-4-15(18)22)5-8-20-17(24-20)16(23)11(10-21)9-19(14,20)2/h12-15,17,22-23H,3-9H2,1-2H3/t12-,13-,14-,15-,17+,18-,19+,20+/m0/s1
InChIKey
KVJXBPDAXMEYOA-CXANFOAXSA-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
17-ketotrilostane DM002393
21122657
Unclear 1 [3] , [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR002455 Trilostane 17-ketotrilostane Unclear Unclear [3], [4]
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]
References
1 Trilostane was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Long-term low-dose ketoconazole treatment in bilateral macronodular adrenal hyperplasia. Endocrinol Diabetes Metab Case Rep. 2014;2014:140083.
3 High-performance liquid chromatographic assay for trilostane and its major metabolite, 17-ketotrilostane, in human plasma J Chromatogr. 1985 May 3;339(2):440-4. doi: 10.1016/s0378-4347(00)84678-2.
4 The bioavailability and metabolism of trilostane in normal subjects, a comparative study using high pressure liquid chromatographic and quantitative cytochemical assays J Steroid Biochem. 1984 Nov;21(5):601-5. doi: 10.1016/0022-4731(84)90337-6.

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