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Compound Detail

CHEMBL428647

PACLITAXEL
💊 Approved Drug
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💊 Approved Drug
CC(=O)O[C@H]1C(=O)[C@@]2(C)[C@H]([C@H](OC(=O)c3ccccc3)[C@]3(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c4ccccc4)c4ccccc4)C(C)=C1C3(C)C)[C@]1(OC(C)=O)CO[C@@H]1C[C@@H]2O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL428647
Name PACLITAXEL
Phase Approved
Structure Type MOL
InChI Key RCINICONZNJXQF-MZXODVADSA-N
Therapeutic ✓ Yes

Known Names

(-)-paclitaxel ABI-007 Abraxane Apealea Apexelsin BMS 181339-01 BMS-181339-01 Capxol Cyclopax DHP 107 DHP-107 Ebetaxel +18 more
596
Targets
3,023
Activities
4
Assay Types
30
PK Parameters
20
Publications
30
Known Names
20
Indications
1
Mechanisms

Molecular Properties

853.9
MW (Da)
3.74
ALogP
14
HBA
4
HBD
221.3
PSA (Ų)
0.13
QED
2
Ro5 Violations
10
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1992
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product Chemical Probe
USAN Stem -taxel
USAN Year 1993

Extended Properties

Molecular Formula C47H51NO14
MW 853.92
Aromatic Rings 3
Heavy Atoms 62
NP-Likeness 1.87

Mechanism of Action

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

Indications

Breast Neoplasms Breast Neoplasms Breast Neoplasms Breast Neoplasms Carcinoma Carcinoma Carcinoma, Non-Small-Cell Lung Neoplasms Neoplasms Ovarian Neoplasms Ovarian Neoplasms Ovarian Neoplasms Pancreatic Neoplasms Pancreatic Neoplasms Pancreatic Neoplasms Sarcoma, Kaposi Adenocarcinoma Adenocarcinoma Adenocarcinoma of Lung Anemia

ATC Classification

L01CD01
paclitaxel
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

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

Activity Summary

IC50 2,950 meas. best 11.0
EC50 63 meas. best 8.7
Ki 6 meas. best 6.08
Kd 4 meas. best 7.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
SW626
CHEMBL1075593
 IC50 11.0 11.0 0.0 1
BGC-823
CHEMBL614526
 IC50 10.96 7.8596 0.0 23
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 10.8 7.1501 0.0 325
A549
CHEMBL392
 IC50 10.52 7.4916 0.0 198
KB
CHEMBL398
 IC50 10.4 7.6926 0.0 65
MES-SA/Dx5
CHEMBL613827
 IC50 10.4 7.494 0.0 5
PC-9
CHEMBL614102
 IC50 10.25 8.0833 0.1 3
Plasmodium falciparum
CHEMBL364
 IC50 10.15 8.2167 0.1 15
L1210
CHEMBL386
 IC50 10.05 7.526 0.1 15
HT-29
CHEMBL384
 IC50 10.0 8.0264 0.1 64
MCF7
CHEMBL387
 IC50 10.0 7.4359 0.1 201
P388
CHEMBL389
 IC50 10.0 7.3294 0.1 16
ECC-1
CHEMBL6066738
 IC50 10.0 10.0 0.1 1
Unchecked
CHEMBL612545
 IC50 10.0 6.4216 0.1 133
BT-549
CHEMBL614072
 IC50 10.0 8.64 0.1 3
OVCAR-3
CHEMBL614213
 IC50 10.0 8.1412 0.1 25
EL4
CHEMBL614293
 IC50 10.0 7.885 0.1 2
BeWo
CHEMBL614525
 IC50 10.0 10.0 0.1 1
SK-MEL
CHEMBL614914
 IC50 10.0 7.695 0.1 2
SK-OV-3
CHEMBL614925
 IC50 10.0 7.6009 0.1 54
NCI-H460
CHEMBL396
 IC50 9.85 7.869 0.1 31
HT-1080
CHEMBL614580
 IC50 9.82 8.504 0.1 5
HepG2
CHEMBL395
 IC50 9.72 6.9442 0.2 79
HCT-116
CHEMBL394
 IC50 9.7 7.9393 0.2 71
MDA-MB-231
CHEMBL400
 IC50 9.7 7.4451 0.2 96
ARO
CHEMBL612590
 IC50 9.7 9.7 0.2 2
MDA-MB-435
CHEMBL614697
 IC50 9.7 8.1728 0.2 36
CCRF-CEM
CHEMBL382
 IC50 9.57 7.4591 0.3 34
TE-15
CHEMBL2366086
 IC50 9.54 9.54 0.3 1
PG-49 cell line
CHEMBL614847
 IC50 9.51 9.09 0.3 2
LC-2-ad
CHEMBL2366260
 IC50 9.5 9.5 0.3 1
WM 266-4
CHEMBL4296510
 IC50 9.49 9.49 0.3 1
U-87 MG
CHEMBL614247
 IC50 9.42 7.2217 0.4 6
PC-3
CHEMBL390
 IC50 9.4 7.2104 0.4 45
A2780
CHEMBL614004
 IC50 9.4 7.7939 0.4 94
Jurkat
CHEMBL397
 IC50 9.3 7.9525 0.5 4
M14
CHEMBL614317
 IC50 9.3 8.392 0.5 5
MKN-45
CHEMBL614354
 IC50 9.3 7.3133 0.5 3
KB 3-1
CHEMBL614590
 IC50 9.3 8.402 0.5 5
Ishikawa
CHEMBL614649
 IC50 9.3 9.3 0.5 1
MRC5
CHEMBL614181
 IC50 9.28 7.6367 0.5 6
K562
CHEMBL385
 IC50 9.22 6.9788 0.6 41
MES-SA
CHEMBL614343
 IC50 9.22 8.7725 0.6 4
SNU-398
CHEMBL614454
 IC50 9.22 9.22 0.6 1
RL95-2
CHEMBL2366168
 IC50 9.18 9.18 0.7 1
HeLa
CHEMBL399
 IC50 9.15 7.6548 0.7 129
MDA-MB-453
CHEMBL614334
 IC50 9.15 9.15 0.7 1
MZ1-PC
CHEMBL2366204
 IC50 9.14 9.14 0.7 1
CAKI-1
CHEMBL614067
 IC50 9.05 9.05 0.9 1
RPTEC
CHEMBL614883
 IC50 9.05 9.05 0.9 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 8720.0 ng.hr.mL-1 Mus musculus
AUC 35320.0 ng.hr.mL-1 Mus musculus
AUC 2519.06 ng.hr.mL-1 Mus musculus
AUC 10161.65 ng.hr.mL-1 Rattus norvegicus
AUC 622.0 ng.hr.mL-1 Rattus norvegicus
AUC 113.0 ng.hr.mL-1 Rattus norvegicus
AUC 746.0 ng.hr.mL-1 Rattus norvegicus
AUC 88.0 ng.hr.mL-1 Rattus norvegicus
AUC 375.0 ng.hr.mL-1 Rattus norvegicus
AUC 171.0 ng.hr.mL-1 Rattus norvegicus
AUC 303.0 ng.hr.mL-1 Rattus norvegicus
AUC 172.0 ng.hr.mL-1 Rattus norvegicus
AUC 197.35 ng.hr.mL-1 Mus musculus
AUC 12603.86 ng.hr.mL-1 Homo sapiens
AUC 1734.95 ng.hr.mL-1 Rattus norvegicus
AUC 610.89 ng.hr.mL-1 Rattus norvegicus
AUC 4488.38 ng.hr.mL-1 Rattus norvegicus
AUC 308.5 ng.hr.mL-1 Rattus norvegicus
AUC 2728.1 ng.hr.mL-1 Rattus norvegicus
AUC 3756.5 ng.hr.mL-1 Rattus norvegicus
AUC 1734.95 ng.hr.mL-1 Rattus norvegicus
AUC 610.89 ng.hr.mL-1 Rattus norvegicus
AUC 3131.51 ng.hr.mL-1 Rattus norvegicus
AUC 95.5 ng.hr.mL-1 Mus musculus
AUC 98.8 ng.hr.mL-1 Mus musculus
AUC 95.9 ng.hr.mL-1 Rattus norvegicus
CL 6.4 mL.min-1.kg-1 Homo sapiens
CL 6.4 mL.min-1.kg-1 Homo sapiens
CL 151.67 mL.min-1.kg-1 Rattus norvegicus
CL 101.67 mL.min-1.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
SW626 IC50 = 0.01 nM 11.0 Cytotoxicity against human SW626 cells after 72 hrs by SRB assay 12088425
BGC-823 IC50 = 0.011 nM 10.96 Cytotoxicity against human BGC-823 cells assessed as reduction in cell growth me... 37336771
NON-PROTEIN TARGET IC50 = 0.016 nM 10.8 Cytotoxicity against human Hep3B2 cells after 72 hrs by MTS assay 21812410
NON-PROTEIN TARGET IC50 = 0.016 nM 10.8 Cytotoxicity against human Hep3B2 cells assessed as reduction in cell viability ... 25760674
A549 IC50 = 0.03 nM 10.52 Antiproliferative activity against human A549 cells after 3 days by SRB assay 26865176
MES-SA/Dx5 IC50 = 0.04 nM 10.4 In vitro cytotoxic activity against uterine sarcoma (MES-SA) cells assayed by in... 11728191
KB IC50 = 0.04 nM 10.4 Antiproliferative activity against human KB cells after 3 days by SRB assay 26865176
PC-9 IC50 = 0.056 nM 10.25 Antiproliferation activity against human PC9 cells assessed as reduction in cell... 32546298
Plasmodium falciparum IC50 = 0.07 nM 10.15 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910
BGC-823 IC50 = 0.077 nM 10.11 Antiproliferation activity against human BGC823 cells assessed as reduction in c... 32546298
L1210 IC50 = 0.09 nM 10.05 Cytotoxicity expressed as concentration required to inhibit cell growth by 50% o... 12392737
Plasmodium falciparum IC50 = 0.09 nM 10.05 Antiplasmodial activity against Plasmodium falciparum 3D7 after 72 hrs by SYBR g... 19734910
OVCAR-3 IC50 = 0.1 nM 10.0 Cytotoxicity against human OVCAR-3 cells treated for 72 hrs 38964520
MCF7 IC50 = 0.1 nM 10.0 Antiproliferative activity against human MCF7 cells assessed as reduction in cel... 27010926
KB IC50 = 0.1 nM 10.0 Antiproliferative activity against human KB cells assessed as reduction in cell ... 27010926
SK-MEL IC50 = 0.1 nM 10.0 Antiproliferative activity against human SK-MEL cells assessed as reduction in c... 27010926
EL4 IC50 = 0.1 nM 10.0 Antiproliferative activity against mouse EL4 cells assessed as cell growth inhib... 27010926
Unchecked IC50 = 0.1 nM 10.0 Antiproliferative activity against human YD-10B cells assessed as cell growth in... 27010926
SK-OV-3 IC50 = 0.1 nM 10.0 Antiproliferative activity against human SK-OV-3 cells assessed as reduction in ... 27010926
ECC-1 IC50 = 0.1 nM 10.0 Antiproliferative activity against human ECC-1 cells assessed as reduction in ce... 38911148

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL4689842 U2OS 756
- 10.6019/CHEMBL4689842 Fibroblast 756
- 10.6019/CHEMBL4689842 HEK-293T 756
- 10.6019/CHEMBL5058577 Fibroblast 304
- 10.6019/CHEMBL5303300 HEK-293T 304
- 10.6019/CHEMBL5303300 Fibroblast 304
- 10.6019/CHEMBL5303300 U2OS 304
- 10.6019/CHEMBL5058577 HEK-293T 304
- 10.6019/CHEMBL5058577 U2OS 304
- 10.6019/CHEMBL5724801 U2OS 152
- 10.6019/CHEMBL5724801 Fibroblast 152
- 10.6019/CHEMBL5724801 HEK-293T 152
- 10.5281/zenodo.13943903 ADMET 83
31158845 10.1038/s41586-019-1291-3 ADMET 65
33729781 10.1021/acs.jmedchem.0c01826 ADMET 55
22711747 10.1124/dmd.112.046508 Rattus norvegicus 36
35247755 10.1016/j.ejmech.2022.114231 ADMET 31
17206139 10.1038/nchembio853 Unchecked 30
17158054 10.1016/j.bmc.2006.09.024 HT-1080 28
33938746 10.1021/acs.jmedchem.1c00246 ADMET 21

Data from ChEMBL 36 via Core Engine