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Compound Detail

CHEMBL3545252

DOCETAXEL
💊 Approved Drug
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💊 Approved Drug
CC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@@]1(C)C(=O)[C@H](O)C3=C(C)[C@@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)c4ccccc4)C[C@@](O)([C@@H](OC(=O)c4ccccc4)[C@H]21)C3(C)C.O.O.O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL3545252
Name DOCETAXEL
Phase Approved
Structure Type MOL
InChI Key XCDIRYDKECHIPE-QHEQPUDQSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL92
Active Moiety CHEMBL92

Known Names

Beizray Docetaxel Docetaxel (as trihydrate) Docetaxel accord Docetaxel hydrate Docetaxel teva Docetaxel trihydrate Docetaxel zentiva (previously docetaxel winthrop) Docivyx RP 56976 RP-56976 Taxceus +3 more
600
Targets
788
Activities
4
Assay Types
13
PK Parameters
20
Publications
15
Known Names
20
Indications
1
Mechanisms

Molecular Properties

807.9
MW (Da)
3.26
ALogP
14
HBA
5
HBD
224.4
PSA (Ų)
0.15
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1995
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning
USAN Stem -taxel
USAN Year 1994

Extended Properties

Molecular Formula C43H59NO17
MW 861.94
Aromatic Rings 2
Heavy Atoms 58
NP-Likeness 1.89

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Tubulin inhibitor INHIBITOR Tubulin ✓ ✓

Indications

Adenocarcinoma Adenocarcinoma Breast Neoplasms Breast Neoplasms Breast Neoplasms Carcinoma, Non-Small-Cell Lung Head and Neck Neoplasms Head and Neck Neoplasms Head and Neck Neoplasms Head and Neck Neoplasms Head and Neck Neoplasms Neoplasms Neoplasms Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms Prostatic Neoplasms Stomach Neoplasms Stomach Neoplasms Stomach Neoplasms

ATC Classification

L01CD02
docetaxel
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning
immune system toxicity
Country: United States
Black Box Warning
hepatotoxicity
Country: United States
Black Box Warning
hematological toxicity
Country: United States
Black Box Warning
respiratory toxicity
Country: United States
Black Box Warning
dermatological toxicity
Country: United States
Black Box Warning
gastrointestinal toxicity
Country: United States
Black Box Warning
vascular toxicity
Country: United States

Activity Summary

IC50 784 meas. best 10.94
EC50 2 meas. best 6.1
Kd 1 meas. best 9.09
Ki 1 meas. best 6.28

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 10.94 7.87 0.0 29
KB
CHEMBL398
 IC50 10.0 8.8005 0.1 20
HSC-3
CHEMBL612279
 IC50 9.88 9.88 0.1 1
Growth hormone-releasing hormone receptor
CHEMBL2032
 IC50 9.85 9.85 0.1 1
5637
CHEMBL612565
 IC50 9.84 9.84 0.1 1
HT-144
CHEMBL2366291
 IC50 9.8 9.8 0.2 1
NCI-H292
CHEMBL614733
 IC50 9.8 9.8 0.2 1
HCE-T
CHEMBL2366139
 IC50 9.79 9.79 0.2 1
ESS-1
CHEMBL1075444
 IC50 9.75 9.75 0.2 1
D-566MG
CHEMBL2366336
 IC50 9.74 9.74 0.2 1
HCT-116
CHEMBL394
 IC50 9.74 8.8433 0.2 18
CAL-62
CHEMBL1075413
 IC50 9.73 9.73 0.2 1
GT3TKB
CHEMBL2366148
 IC50 9.63 9.63 0.2 1
HSC-4
CHEMBL1075469
 IC50 9.62 9.62 0.2 1
KOSC-2
CHEMBL1075481
 IC50 9.59 9.59 0.3 1
ES8
CHEMBL2366069
 IC50 9.59 9.59 0.3 1
NB14
CHEMBL2366212
 IC50 9.59 9.59 0.3 1
BFTC-905
CHEMBL1075396
 IC50 9.57 9.57 0.3 1
HO-1-N-1
CHEMBL1075466
 IC50 9.55 9.55 0.3 1
A498
CHEMBL614516
 IC50 9.55 9.55 0.3 1
HuO-3N1
CHEMBL1075475
 IC50 9.52 9.52 0.3 1
SF-539
CHEMBL614860
 IC50 9.52 9.52 0.3 1
HT-29
CHEMBL384
 IC50 9.48 8.7009 0.3 11
CAL-27
CHEMBL1075408
 IC50 9.47 9.47 0.3 1
NCI-H510A
CHEMBL2366332
 IC50 9.47 9.47 0.3 1
TE-8
CHEMBL2366182
 IC50 9.44 9.44 0.4 1
VA-ES-BJ
CHEMBL2366259
 IC50 9.43 9.43 0.4 1
RH-1
CHEMBL2366078
 IC50 9.41 9.41 0.4 1
COLO-800
CHEMBL2366224
 IC50 9.41 9.41 0.4 1
ES7
CHEMBL2366297
 IC50 9.41 9.41 0.4 1
GAMG
CHEMBL1075447
 IC50 9.38 9.38 0.4 1
Ca9-22
CHEMBL1075404
 IC50 9.37 9.37 0.4 1
SBC-1
CHEMBL2366327
 IC50 9.37 9.37 0.4 1
WiDr
CHEMBL614647
 IC50 9.37 9.37 0.4 1
RPMI-7951
CHEMBL612447
 IC50 9.35 9.35 0.4 1
HGC-27
CHEMBL1075463
 IC50 9.33 9.33 0.5 1
SW1710
CHEMBL1075590
 IC50 9.33 9.33 0.5 1
MC-IXC
CHEMBL1075495
 IC50 9.32 9.32 0.5 1
FTC-133
CHEMBL1075445
 IC50 9.31 9.31 0.5 1
HL-60
CHEMBL383
 IC50 9.3 8.526 0.5 5
A549
CHEMBL392
 IC50 9.3 8.1332 0.5 19
A2780
CHEMBL614004
 IC50 9.3 8.2969 0.5 13
MRC5
CHEMBL614181
 IC50 9.3 9.3 0.5 1
HT-1080
CHEMBL614580
 IC50 9.3 9.3 0.5 1
NMC-G1
CHEMBL2366349
 IC50 9.29 9.29 0.5 1
SK-OV-3
CHEMBL614925
 IC50 9.29 7.52 0.5 5
GI-1
CHEMBL2366272
 IC50 9.28 9.28 0.5 1
CGTH-W-1
CHEMBL2366300
 IC50 9.27 9.27 0.5 1
A2058
CHEMBL613503
 IC50 9.26 9.26 0.5 1
ETK-1
CHEMBL2366116
 IC50 9.25 9.25 0.6 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 646.0 ng.hr.mL-1 Rattus norvegicus
AUC 667.0 ng.hr.mL-1 Rattus norvegicus
CL 14.0 mL.min-1.kg-1 Homo sapiens
CL 14.0 mL.min-1.kg-1 Homo sapiens
CL 125.17 mL.min-1.kg-1 Rattus norvegicus
CL 17.78 mL.min-1.kg-1 Homo sapiens
Fu 0.04 - Homo sapiens
MRT 2.5 hr Homo sapiens
MRT 3.34 hr Rattus norvegicus
T1/2 11.0 hr Homo sapiens
T1/2 1.167 hr Homo sapiens
T1/2 7.37 hr Rattus norvegicus
Vd 78.8 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 0.01149 nM 10.94 Cytotoxicity against human HL60-0607-2 cells after 72 hrs by SRB assay 21396751
NON-PROTEIN TARGET IC50 = 0.018 nM 10.74 Cytotoxicity against human MDA231 cells after 72 hrs by MTS assay 21142180
KB IC50 = 0.1 nM 10.0 Cytotoxicity against human KB cells after 72 hrs 17064914
NON-PROTEIN TARGET IC50 = 0.114 nM 9.94 Cytotoxicity against multidrug-resistant human HL60OR-0604-2 cells after 72 hrs ... 21396751
NON-PROTEIN TARGET IC50 = 0.1317 nM 9.88 Cytotoxicity against multidrug-resistant human KBR-0530 cells after 72 hrs by SR... 21396751
HSC-3 IC50 = 0.1315 nM 9.88 SANGER: Inhibition of human HSC-3 cell growth in a cell viability assay. -
Growth hormone-releasing hormone receptor IC50 = 0.14 nM 9.85 Displacement of [125I]JV1-42 from GHRH receptor expressed in human MX1 cells 17261802
5637 IC50 = 0.1433 nM 9.84 SANGER: Inhibition of human 5637 cell growth in a cell viability assay. -
KB IC50 = 0.15 nM 9.82 Cytotoxicity against human KB cells 19572612
KB IC50 = 0.15 nM 9.82 Cytotoxicity against human KB cells after 72 hrs by neutral red based colorimetr... 21443172
HT-144 IC50 = 0.1574 nM 9.8 SANGER: Inhibition of human HT-144 cell growth in a cell viability assay. -
NCI-H292 IC50 = 0.1585 nM 9.8 SANGER: Inhibition of human NCI-H292 cell growth in a cell viability assay. -
HCE-T IC50 = 0.1617 nM 9.79 SANGER: Inhibition of human HCE-T cell growth in a cell viability assay. -
KB IC50 = 0.17 nM 9.77 Cytotoxicity against human KB cells incubated for 72 hrs by MTS assay 23072299
KB IC50 = 0.17 nM 9.77 Cytotoxicity against human KB cells after 72 hrs by MTS assay 21142180
ESS-1 IC50 = 0.1787 nM 9.75 SANGER: Inhibition of human ESS-1 cell growth in a cell viability assay. -
HCT-116 IC50 = 0.18 nM 9.74 Antiproliferative activity against IC95 biaryl selected drug-resistant against h... 17922005
D-566MG IC50 = 0.1823 nM 9.74 SANGER: Inhibition of human D-566MG cell growth in a cell viability assay. -
CAL-62 IC50 = 0.1849 nM 9.73 SANGER: Inhibition of human CAL-62 cell growth in a cell viability assay. -
KB IC50 = 0.2 nM 9.7 Cytotoxicity against human KB cells 16989521

Literature References

PubMed DOI Target Context # Activities
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
25047938 10.1016/j.bmc.2014.05.048 Unchecked 9
25740159 10.1016/j.bmcl.2015.02.013 No relevant target 9
8831755 10.1021/jm9604080 Mus musculus 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
22320354 10.1021/jm200848t NON-PROTEIN TARGET 8
17922005 10.1038/nchembio.2007.34 HCT-116 8
15887962 10.1021/jm049343o Albumin 6
11212122 10.1016/s0960-894x(00)00682-x Mus musculus 6
12482420 10.1016/s0960-894x(02)00891-0 Mus musculus 6
21396751 10.1016/j.ejmech.2011.02.027 Rattus norvegicus 5
21396751 10.1016/j.ejmech.2011.02.027 NON-PROTEIN TARGET 5
22320354 10.1021/jm200848t SNU-398 5
23202849 10.1016/j.ejmech.2012.10.051 HL-60 4
23202849 10.1016/j.ejmech.2012.10.051 HT-29 4
23202849 10.1016/j.ejmech.2012.10.051 CAL-33 4
21443232 10.1021/jm101505d Mus musculus 4
18426954 10.1124/dmd.108.020479 ADMET 4

Data from ChEMBL 36 via Core Engine