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

General Information of Drug (ID: DR1227)
Drug Name
Paclitaxel
Synonyms
Paclitaxel (Taxol); Paxceed; Paxene; Plaxicel; QW 8184; TaxAlbin; Taxol A; Xorane; Yewtaxan; nab-paclitaxel; paclitaxel; Capxol; Ebetaxel; Genaxol; Genetaxyl; Genexol; Intaxel; LipoPac; MBT 0206; Mitotax; OncoGel; P88XT4IS4D; 33069-62-4; 7-Epipaclitaxel; 7-epi-Paclitaxel; ABI 007; ABI-007; Abraxane; BMS-181339-01; CHEBI:45863; CHEMBL428647; DRG-0190; EmPAC; HSDB 6839; MFCD00869953; NSC 125973; NSC-125973; NSC125973; Onxol; TAXOL; UNII-P88XT4IS4D; Zisu
Indication Ovarian cancer [ICD11: 2C73] Approved [1]
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
D0E2RD
Formula
C47H51NO14
Canonical SMILES
CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(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
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
3'-p-hydroxypaclitaxel DM001144
3081785
Oxidation - Hydroxylation 1 [7]
6alpha, 3'-p-dihydroxypaclitaxel DM001143
158371
Oxidation - Hydroxylation 1 [8]
6alpha-hydroxypaclitaxel DM001145
10056458
Oxidation - Hydroxylation 1 [9]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001907 Paclitaxel 6alpha, 3'-p-dihydroxypaclitaxel Oxidation - Hydroxylation CYP3A4 [8]
MR001908 Paclitaxel 3'-p-hydroxypaclitaxel Oxidation - Hydroxylation CYP3A4 [7]
MR001909 Paclitaxel 6alpha-hydroxypaclitaxel Oxidation - Hydroxylation CYP2C8 [9]
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
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[4]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[5]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1254 Bacteroides thetaiotaomicron Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1265 Escherichia coli Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1415 Eggerthella lenta Not Available Not Available [6]
Unclear metabolic mechanism (DME-unclear) DME1444 Odoribacter splanchnicus Not Available Not Available [6]
⏷ Show the Full List of 13  DME(s)
References
1 Taxol (paclitaxel) was approved by FDA for the treatment of patients with recurrent ovarian cancer. Gynecol Oncol. 1994 Jul;54(1):103.
2 Effects of acid and lactone forms of eight HMG-CoA reductase inhibitors on CYP-mediated metabolism and MDR1-mediated transport. Pharm Res. 2006 Mar;23(3):506-12.
3 Drug-interaction between paclitaxel and goshajinkigan extract and its constituents
4 Utilization of human liver microsomes to explain individual differences in paclitaxel metabolism by CYP2C8 and CYP3A4. J Pharmacol Sci. 2005 Jan;97(1):83-90.
5 Drug Interactions Flockhart Table
6 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
7 Update: influenza activity--United States MMWR Morb Mortal Wkly Rep. 1986 Mar 14;35(10):166-7.
8 [International council of nurses: the international voice of the nursing profession] Bol Oficina Sanit Panam. 1979 Aug;87(2):152-5.
9 Noise in an ac biased junction: Nonstationary Aharonov-Bohm effect Phys Rev Lett. 1994 Jan 24;72(4):538-541. doi: 10.1103/PhysRevLett.72.538.

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