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Compound Detail

CHEMBL92

DOCETAXEL ANHYDROUS
💊 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
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL92
Name DOCETAXEL ANHYDROUS
Phase Approved
Structure Type MOL
InChI Key ZDZOTLJHXYCWBA-VCVYQWHSSA-N
Therapeutic ✓ Yes

Known Names

Bind 014 Cabazitaxel metabolite (rp56976) CKD-810 Docefrez Docetaxel anhydrous Docetaxel kabi Docetaxel mylan Docetaxel teva pharma Docetaxel winthrop Docetaxel, anhydrous NSC-628503 Rp56976
50
Targets
173
Activities
2
Assay Types
23
PK Parameters
20
Publications
12
Known Names
7
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 Natural Product
USAN Stem -taxel
USAN Year 1994

Extended Properties

Molecular Formula C43H53NO14
MW 807.89
Aromatic Rings 2
Heavy Atoms 58
NP-Likeness 1.89

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Tubulin stabiliser STABILISER Tubulin ✓ ✓

Indications

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

Activity Summary

IC50 171 meas. best 10.0
EC50 2 meas. best 8.22

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
DU-145
CHEMBL613508
 IC50 10.0 7.9267 0.1 12
LNCaP
CHEMBL612518
 IC50 9.7 8.3275 0.2 4
HeLa
CHEMBL399
 IC50 9.52 7.4908 0.3 13
Calu-1
CHEMBL613505
 IC50 9.4 9.4 0.4 1
MCF7
CHEMBL387
 IC50 9.3 7.9386 0.5 7
PC-3
CHEMBL390
 IC50 9.3 8.1182 0.5 11
U-251
CHEMBL615022
 IC50 9.15 9.15 0.7 1
SK-OV-3
CHEMBL614925
 IC50 9.12 8.21 0.8 2
HT-1080
CHEMBL614580
 IC50 8.82 8.82 1.5 1
Unchecked
CHEMBL612545
 IC50 8.77 6.5026 1.7 31
HCT-116
CHEMBL394
 IC50 8.77 8.1783 1.7 6
SH-SY5Y
CHEMBL614910
 IC50 8.74 8.74 1.8 1
LN-229
CHEMBL4296459
 IC50 8.7 8.7 2.0 1
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.7 6.57 2.0 7
CWR22R
CHEMBL612657
 IC50 8.68 8.68 2.1 1
NCI-H460
CHEMBL396
 IC50 8.62 7.805 2.4 4
CAKI-1
CHEMBL614067
 IC50 8.57 8.57 2.7 1
T84
CHEMBL613531
 IC50 8.57 8.57 2.7 1
A2780
CHEMBL614004
 IC50 8.54 8.3367 2.9 3
MDA-MB-468
CHEMBL614335
 IC50 8.51 8.51 3.1 1
MES-SA
CHEMBL614343
 IC50 8.47 8.47 3.4 1
1A9
CHEMBL614075
 IC50 8.45 8.45 3.5 1
Z-138
CHEMBL4483276
 IC50 8.4 7.455 4.0 4
A-375
CHEMBL613859
 IC50 8.35 8.35 4.5 1
SW-620
CHEMBL612262
 IC50 8.33 8.015 4.7 2
DU-145
CHEMBL613508
 EC50 8.22 8.22 6.0 1
HL-60
CHEMBL383
 IC50 8.14 7.12 7.2 4
KB
CHEMBL398
 IC50 8.14 7.655 7.3 4
HEK293
CHEMBL614818
 IC50 8.12 6.5967 7.5 3
PC-3
CHEMBL390
 EC50 8.12 8.12 7.6 1
TERT-RPE1
CHEMBL615013
 IC50 8.09 6.65 8.2 3
CAPAN-1
CHEMBL614536
 IC50 8.06 7.35 8.8 4
K562
CHEMBL385
 IC50 8.05 7.32 9.0 5
A549
CHEMBL392
 IC50 8.01 7.014 9.8 5
MDA-MB-231
CHEMBL400
 IC50 8.0 6.9233 10.0 6
MM1.S
CHEMBL4296471
 IC50 7.93 7.93 11.8 1
BT-474
CHEMBL614529
 IC50 7.67 7.67 21.4 1
SK-HEP1
CHEMBL614912
 IC50 7.52 7.52 30.0 1
HEp-2
CHEMBL614735
 IC50 7.22 7.22 60.0 1
SiHa
CHEMBL612542
 IC50 7.05 7.05 90.0 1
Vero
CHEMBL391
 IC50 6.89 6.89 130.0 1
Tubulin
CHEMBL2095182
 IC50 6.7 6.7 200.0 2
ECa-109 cell line
CHEMBL614668
 IC50 6.11 6.11 773.0 1
A549/TR
CHEMBL4483226
 IC50 6.08 6.08 836.2 1
HEY
CHEMBL613869
 IC50 6.07 6.07 860.0 1
NCI/ADR-RES
CHEMBL613829
 IC50 5.82 5.82 1530.5 1
L132
CHEMBL613999
 IC50 5.78 5.78 1680.0 1
RWPE-1
CHEMBL4296492
 IC50 5.76 5.76 1730.0 1
HepG2
CHEMBL395
 IC50 5.54 5.54 2860.0 1
Nucleotide-binding oligomerization domain-containing protein 2
CHEMBL1293266
 IC50 5.3 5.3 5011.9 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 667.0 ng.hr.mL-1 Rattus norvegicus
AUC 646.0 ng.hr.mL-1 Rattus norvegicus
AUC 5263.4 ng.hr.mL-1 Homo sapiens
AUC 930.0 ng.hr.mL-1 Rattus norvegicus
AUC 867.0 ng.hr.mL-1 Rattus norvegicus
AUC 21813.03 ng.hr.mL-1 Mus musculus
AUC 1809.67 ng.hr.mL-1 Mus musculus
AUC 12.76 ng.hr.mL-1 Mus musculus
AUC 18.9 ng.hr.mL-1 Mus musculus
CL 125.17 mL.min-1.kg-1 Rattus norvegicus
CL 46.0 mL.min-1.kg-1 Rattus norvegicus
Cmax 950.0 nM Mus musculus
Cmax 8090.0 nM Mus musculus
MRT 3.76 hr Rattus norvegicus
MRT 73.3 hr Mus musculus
MRT 2.29 hr Mus musculus
T1/2 5.75 hr Rattus norvegicus
T1/2 49.1 hr Mus musculus
T1/2 3.62 hr Mus musculus
Tmax 0.5 hr Mus musculus
Tmax 0.03 hr Mus musculus
Vd 78.8 L.kg-1 Rattus norvegicus
Vd 22.6 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
DU-145 IC50 = 0.1 nM 10.0 Cytotoxicity against human DU145 cells after 72 hrs by MTS assay 29406710
DU-145 IC50 = 0.1 nM 10.0 Antiproliferative activity against human DU145 cells 31251599
LNCaP IC50 = 0.2 nM 9.7 Antiproliferative activity against docetaxel-sensitive human LNCAP cells after 3... 29784275
LNCaP IC50 = 0.2 nM 9.7 Antiproliferative activity against androgen-insensitive human LNCaP cells assess... 33753258
HeLa IC50 = 0.3 nM 9.52 Antiproliferative activity against human HeLa cells after 72 hrs by MTT assay 30629433
Calu-1 IC50 = 0.4 nM 9.4 Antiproliferative activity against human Calu1 cells after 72 hrs by MTT assay 30629433
PC-3 IC50 = 0.5 nM 9.3 Antiproliferative activity against human PC3 cells 31251599
MCF7 IC50 = 0.5 nM 9.3 Antiproliferative activity against human MCF7 cells after 72 hrs by MTT assay 30629433
PC-3 IC50 = 0.5 nM 9.3 Cytotoxicity against human PC3 cells after 72 hrs by MTS assay 29406710
PC-3 IC50 = 0.6 nM 9.22 Cytotoxicity against human PC-3 cells assessed as inhibition of cell growth and ... 36126331
PC-3 IC50 = 0.6 nM 9.22 Antiproliferative activity against human PC3 cells after 72 hrs by MTT assay 30629433
HeLa IC50 = 0.7 nM 9.15 Antiproliferative activity against human HeLa cells assessed as inhibition of ce... 38294341
U-251 IC50 = 0.7 nM 9.15 Antiproliferative activity against human U251MG cells after 72 hrs by MTT assay 30629433
HeLa IC50 = 0.7 nM 9.15 Antiproliferative activity against human HeLa cells assessed as inhibition of ce... 37490800
SK-OV-3 IC50 = 0.75 nM 9.12 Cytotoxicity against human SKOV3 cells after 72 to 120 hrs by sulforhodamine B a... 29517223
HeLa IC50 = 1.0 nM 9.0 Antiproliferative activity against human HeLa cells assessed as reduction in cel... 38959729
LNCaP IC50 = 1.0 nM 9.0 Cytotoxicity against human LNCaP cells assessed as reduction in cell viability 34464875
DU-145 IC50 = 1.2 nM 8.92 Antiproliferative activity against docetaxel-sensitive human DU145 cells after 3... 29784275
DU-145 IC50 = 1.2 nM 8.92 Antiproliferative activity against androgen-insensitive human DU-145 cells asses... 33753258
HT-1080 IC50 = 1.5 nM 8.82 Antiproliferative activity against human HT-1080 cells assessed as reduction in ... 38959729

Literature References

PubMed DOI Target Context # Activities
29357251 10.1021/acs.jmedchem.7b01407 4T1 43
29120172 10.1021/acs.jnatprod.7b00177 Unchecked 28
29357251 10.1021/acs.jmedchem.7b01407 ADMET 25
34717125 10.1016/j.ejmech.2021.113936 ADMET 23
32203786 10.1016/j.ejmech.2020.112194 ADMET 18
36786551 10.1021/acs.jmedchem.2c01115 Unchecked 16
29517223 10.1021/acs.jnatprod.7b01047 Unchecked 12
28462831 10.1016/j.bmcl.2017.04.047 PC-3 9
29406710 10.1021/acs.jmedchem.7b01858 Unchecked 7
31288149 10.1016/j.ejmech.2019.07.001 CWR22R 6
31199640 10.1021/acs.jmedchem.9b00260 Mus musculus 6
25787766 10.1126/scitranslmed.aaa4642 ADMET 5
38959729 10.1016/j.ejmech.2024.116617 Unchecked 5
29359935 10.1021/acs.jnatprod.7b00857 Unchecked 5
39102508 10.1021/acs.jmedchem.4c01188 A-427 4
26922231 10.1016/j.ejmech.2016.02.007 Rattus norvegicus 4
29784275 10.1016/j.bmc.2018.05.026 Unchecked 4
31251599 10.1021/acs.jmedchem.9b00706 Unchecked 4
39102508 10.1021/acs.jmedchem.4c01188 ADMET 4
31767266 10.1016/j.bmcl.2019.126760 Transcription factor p65 4

Data from ChEMBL 36 via Core Engine