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

General Information of Drug (ID: DR5232)
Drug Name
Taxol
Synonyms
C47H51NO14; weekly paclitaxel; Micellar Paclitaxel; Paclitaxel [USAN:INN:BAN]; SCHEMBL15000506; Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, 6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester, (2aR-(2aalpha,4beta,4abeta,6beta,9alpha(alphaR*,betaS*),11alpha,12alpha,12aalpha,12balpha))-
Indication Breast cancer [ICD11: 2C60-2C6Y] Approved [1]
Solid tumour/cancer [ICD11: ICD11: 2A00-2F9Z] Approved [2]
Pancreatic cancer [ICD11: ICD11: 2C10] Phase 3 [3]
Ovarian cancer [ICD11: ICD11: 2C73] Phase 2 [4]
Stomach cancer [ICD11: ICD11: 2B72] Phase 2 [5]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 853.9 Topological Polar Surface Area 221
Heavy Atom Count 62 Rotatable Bond Count 14
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 14
Cross-matching ID
PubChem CID
36314
ChEBI ID
CHEBI:45863
CAS Number
33069-62-4
TTD Drug ID
D0C4RB
Formula
C47H51NO14
Canonical SMILES
CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
InChI
InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
InChIKey
RCINICONZNJXQF-MZXODVADSA-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
6alpha,3'p-dihydroxypaxlitaxel DM018265 N. A. Unclear - Unclear 1 [9]
6alpha-hydroxypaclitaxel DM001145
10056458
Unclear - Unclear 1 [8]
6alpha-hydroxypaclitaxel?(6alpha-OHP) DM018263 N. A. Unclear - Unclear 1 [8]
p-3'-hydroxypaclitaxel DM015723
10898214
Unclear - Unclear 1 [8]
p-3-hydroxypaclitaxel DM018264 N. A. Unclear - Unclear 1 [8]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR010218 Taxol 6alpha-hydroxypaclitaxel?(6alpha-OHP) Unclear - Unclear CYP2C8 [8]
MR010219 Taxol p-3-hydroxypaclitaxel Unclear - Unclear CYP3A4 [8]
MR010220 Taxol 6alpha,3'p-dihydroxypaxlitaxel Unclear - Unclear Unclear [9]
MR011040 Taxol 6alpha-hydroxypaclitaxel Unclear - Unclear CYP2C8 [8]
MR011041 Taxol p-3'-hydroxypaclitaxel Unclear - Unclear CYP3A4 [8]
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
[6] , [7] , [8]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[8]
References
1 Paclitaxel directly binds to Bcl-2 and functionally mimics activity of Nur77. Cancer Res. 2009 Sep 1;69(17):6906-14.
2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
4 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
5 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
6 Selective inhibition of CYP2C8 by fisetin and its methylated metabolite, geraldol, in human liver microsomes
7 Polymorphisms of CYP2C8 Alter First-Electron Transfer Kinetics and Increase Catalytic Uncoupling
8 The Quantification of Paclitaxel and Its Two Major Metabolites in Biological Samples by HPLC-MS/MS and Its Application in a Pharmacokinetic and Tumor Distribution Study in Xenograft Nude Mouse
9 Metabolism of paclitaxel in mice

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