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

General Information of Drug (ID: DR1900)
Drug Name
DX-8951
Synonyms
DX-8951f; Dx 8951; Exatecan; Exatecan [INN]; OC71PP0F89; (1S,9S)-1-Amino-9-ethyl-5-fluoro-1,2,3,9,12,15-hexahydro-9-hydroxy-4-methyl-10H,13H-benzo(de)pyrano(3',4':6,7)indolizino(1,2-b)quinoline-10,13-dione; 10H,13H-Benzo(de)pyrano(3',4':6,7)indolizino(1,2-b)quinoline-10,13-dione, 1-amino-9-ethyl-5-fluoro-1,2,3,9,12,15-hexahydro-9-hydroxy-4-methyl-, (1S-trans)-; 171335-80-1; C24H22FN3O4; UNII-OC71PP0F89
Indication Pancreatic cancer [ICD11: 2C10] Phase 3 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 435.4 Topological Polar Surface Area 106
Heavy Atom Count 32 Rotatable Bond Count 1
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 7
Cross-matching ID
PubChem CID
151115
ChEBI ID
CHEBI:135709
CAS Number
171335-80-1
TTD Drug ID
D01FUC
Formula
C24H22FN3O4
Canonical SMILES
CCC1(C2=C(COC1=O)C(=O)N3CC4=C5C(CCC6=C5C(=CC(=C6C)F)N=C4C3=C2)N)O
InChI
1S/C24H22FN3O4/c1-3-24(31)14-6-18-21-12(8-28(18)22(29)13(14)9-32-23(24)30)19-16(26)5-4-11-10(2)15(25)7-17(27-21)20(11)19/h6-7,16,31H,3-5,8-9,26H2,1-2H3/t16-,24-/m0/s1
InChIKey
ZVYVPGLRVWUPMP-FYSMJZIKSA-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
UM-1 DM003171
151115
Oxidation - 4-hydroxymethylation 1 [3]
UM-2 DM003172 N. A. Oxidation - 3-hydroxylation 1 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003614 DX-8951 UM-1 Oxidation - 4-hydroxymethylation Unclear [3]
MR003615 DX-8951 UM-2 Oxidation - 3-hydroxylation Unclear [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 ClinicalTrials.gov (NCT00023972) Gemcitabine With or Without Exatecan Mesylate in Treating Patients With Locally Advanced or Metastatic Pancreatic Cancer.
2 Phase I and pharmacological study of a new camptothecin derivative, exatecan mesylate (DX-8951f), infused over 30 minutes every three weeks. Clin Cancer Res. 2001 Oct;7(10):3056-64.
3 Validation study of assay method for DX-8951 and its metabolite in human plasma and urine by high-performance liquid chromatography/atmospheric pressure chemical ionization tandem mass spectrometry
4 Urinary metabolites of DX-8951, a novel camptothecin analog, in rats and humans

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