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

General Information of Drug (ID: DR0900)
Drug Name
Ixabepilone
Synonyms
Ixabepilone; Ixempra; Aza-epothilone B; Azaepothilone B; K27005NP0A; 17-oxa-4-azabicyclo(14.1.0)heptadecane-5,9-dione, 7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-((1E)-1-methyl-2-(2-methyl-4-thiazolyl)ethenyl)-, (1S,3S,7S,10R,11S,12S,16R)-; 1S,3S,7S,10R,11S,12S,16R)-7,11-Dihydroxy-8,8,10,12,16-pentamethyl-3-((1E)-1-methyl-2-(2-methylthiazol-4-yl)ethenyl)-17-oxa-4-azabicyclo(14.1.0)heptadecane-5,9-dione; 219989-84-1; BMS 247550; BMS 247550-01; BMS 247550-1; BMS-247550; BMS-247550-01; CHEBI:63605; NSC747973; UNII-K27005NP0A
Indication Breast cancer [ICD11: 2C60] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 506.7 Topological Polar Surface Area 140
Heavy Atom Count 35 Rotatable Bond Count 2
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
6445540
PubChem SID
11969810 ; 14786763 ; 14933557 ; 34184371 ; 47206488 ; 49684213 ; 49999545 ; 57369862 ; 76567192 ; 91148449 ; 103771488 ; 114573104 ; 126623101 ; 126665598 ; 127325936 ; 127325937 ; 127325938 ; 127325939 ; 134223036 ; 135135146 ; 135610851 ; 137240334 ; 137248706 ; 140173305 ; 152258135 ; 160646974 ; 162202446 ; 175267394 ; 176484667 ; 178103430 ; 179150167 ; 184022005 ; 184529017 ; 184812276 ; 221678841 ; 223664545 ; 226399596 ; 228058699 ; 241053227 ; 248880927 ; 251910828 ; 252448545
ChEBI ID
CHEBI:63605
CAS Number
219989-84-1
TTD Drug ID
D0W2EK
Formula
C27H42N2O5S
Canonical SMILES
CC1CCCC2(C(O2)CC(NC(=O)CC(C(C(=O)C(C1O)C)(C)C)O)C(=CC3=CSC(=N3)C)C)C
InChI
1S/C27H42N2O5S/c1-15-9-8-10-27(7)22(34-27)12-20(16(2)11-19-14-35-18(4)28-19)29-23(31)13-21(30)26(5,6)25(33)17(3)24(15)32/h11,14-15,17,20-22,24,30,32H,8-10,12-13H2,1-7H3,(H,29,31)/b16-11+/t15-,17+,20-,21-,22-,24-,27+/m0/s1
InChIKey
FABUFPQFXZVHFB-PVYNADRNSA-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
11-hydroxy ixabepilone DM001056
156028064
Oxidation - Hydroxylation 1 [3]
Deg-1 DM001053
59070255
Unclear 1 [3] , [2]
Deg-2 DM001054 N. A. Unclear 1 [3]
Deg-3 DM001055 N. A. Unclear 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001292 Ixabepilone Deg-1 Unclear Unclear [3], [2]
MR001293 Ixabepilone Deg-2 Unclear Unclear [3]
MR001294 Ixabepilone Deg-3 Unclear Unclear [3]
MR001295 Ixabepilone 11-hydroxy ixabepilone Oxidation - Hydroxylation Unclear [3]
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 Ixabepilone was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 The effect of ketoconazole on the pharmacokinetics and pharmacodynamics of ixabepilone: a first in class epothilone B analogue in late-phase clinical development. Clin Cancer Res. 2008 May 1;14(9):2701-9.
3 Biotransformation profiling of [(14)C]ixabepilone in human plasma, urine and feces samples using accelerator mass spectrometry (AMS) Drug Metab Pharmacokinet. 2009;24(6):511-22. doi: 10.2133/dmpk.24.511.

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