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Compound Detail

CHEMBL90555

VINCRISTINE
💊 Approved Drug
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💊 Approved Drug
CC[C@]1(O)C[C@H]2CN(CCc3c([nH]c4ccccc34)[C@@](C(=O)OC)(c3cc4c(cc3OC)N(C=O)[C@H]3[C@@](O)(C(=O)OC)[C@H](OC(C)=O)[C@]5(CC)C=CCN6CC[C@]43[C@@H]65)C2)C1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL90555
Name VINCRISTINE
Phase Approved
Structure Type MOL
InChI Key OGWKCGZFUXNPDA-XQKSVPLYSA-N
Therapeutic ✓ Yes

Known Names

22-oxovincaleukoblastine Leucristine Leurocristine Oncotcs Tecnocris Vincaleukoblastine, 22-oxo- Vincristin Vincristina Vincristine Vinkristin
77
Targets
361
Activities
3
Assay Types
12
PK Parameters
20
Publications
10
Known Names
20
Indications

Molecular Properties

825.0
MW (Da)
3.52
ALogP
12
HBA
3
HBD
171.2
PSA (Ų)
0.13
QED
2
Ro5 Violations
8
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1963
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product
USAN Stem vin-
USAN Year 1962

Extended Properties

Molecular Formula C46H56N4O10
MW 824.97
Aromatic Rings 3
Heavy Atoms 60
NP-Likeness 1.47

Indications

Neoplasms Brain Neoplasms Brain Neoplasms Central Nervous System Neoplasms Choroid Plexus Neoplasms Ependymoma Ependymoma Ependymoma Ganglioneuroblastoma Gestational Trophoblastic Disease Glioma Hepatoblastoma Histiocytosis, Langerhans-Cell HIV Infections Hodgkin Disease Hodgkin Disease Leukemia Leukemia, Lymphocytic, Chronic, B-Cell Leukemia, Lymphoid Leukemia, Myeloid, Acute

ATC Classification

L01CA02
vincristine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 339 meas. best 11.0
EC50 16 meas. best 8.62
Ki 6 meas. best 7.07

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HT-29
CHEMBL384
 IC50 11.0 7.8409 0.0 11
MES-SA/Dx5
CHEMBL613827
 IC50 10.7 10.7 0.0 1
ARO
CHEMBL612590
 IC50 10.0 9.76 0.1 2
K562
CHEMBL385
 IC50 10.0 7.49 0.1 7
NCI-H460
CHEMBL396
 IC50 9.89 9.89 0.1 1
CCRF-CEM
CHEMBL382
 IC50 9.77 8.252 0.2 5
Unchecked
CHEMBL612545
 IC50 9.7 7.3957 0.2 35
KB
CHEMBL398
 IC50 9.7 8.15 0.2 42
MDA-MB-435
CHEMBL614697
 IC50 9.54 8.505 0.3 4
HT-1080
CHEMBL614580
 IC50 9.52 9.52 0.3 1
MDA-MB-468
CHEMBL614335
 IC50 9.4 9.4 0.4 1
MCF7
CHEMBL387
 IC50 9.22 7.6507 0.6 14
L1210
CHEMBL386
 IC50 9.14 8.5133 0.7 6
HL-60
CHEMBL383
 IC50 9.06 7.3433 0.9 3
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 9.06 6.912 0.9 71
A2780
CHEMBL614004
 IC50 9.05 7.5767 0.9 6
Plasmodium falciparum
CHEMBL364
 IC50 9.0 9.0 1.0 1
HeLa
CHEMBL399
 IC50 9.0 8.1443 1.0 7
DU-145
CHEMBL613508
 IC50 8.95 8.51 1.1 2
P388
CHEMBL389
 IC50 8.92 8.266 1.2 5
786-0
CHEMBL613102
 IC50 8.92 8.175 1.2 2
MV4-11
CHEMBL613835
 IC50 8.88 8.88 1.3 1
BHK-21
CHEMBL614527
 IC50 8.82 7.6067 1.5 3
MDA-MB-231
CHEMBL400
 IC50 8.8 7.8088 1.6 8
Molecular identity unknown
CHEMBL612546
 EC50 8.62 8.62 2.4 5
COLO 205
CHEMBL614561
 IC50 8.59 8.59 2.6 3
BT-474
CHEMBL614529
 IC50 8.54 8.54 2.9 1
SMMC-7721
CHEMBL613831
 IC50 8.52 7.11 3.0 5
A2780
CHEMBL614004
 EC50 8.47 8.44 3.4 2
A-375
CHEMBL613859
 IC50 8.46 8.46 3.5 1
PT-45
CHEMBL612586
 IC50 8.4 8.4 4.0 2
Bel-7402
CHEMBL614279
 IC50 8.38 7.89 4.2 2
P388/ADR
CHEMBL614218
 IC50 8.35 7.435 4.5 2
MES-SA
CHEMBL614343
 IC50 8.31 8.31 4.9 1
CAKI-1
CHEMBL614067
 IC50 8.24 8.24 5.7 1
ADMET
CHEMBL612558
 IC50 8.22 7.095 6.0 4
HCT-116
CHEMBL394
 IC50 8.15 7.735 7.0 2
TERT-RPE1
CHEMBL615013
 IC50 8.12 8.12 7.6 1
SNU-423
CHEMBL1075584
 IC50 8.0 7.87 10.0 2
SNU-398
CHEMBL614454
 EC50 7.92 7.92 12.0 1
MX1
CHEMBL613704
 IC50 7.92 7.52 12.0 2
MIA PaCa-2
CHEMBL614725
 IC50 7.82 7.82 15.0 1
A549
CHEMBL392
 IC50 7.75 7.0725 18.0 12
4T1
CHEMBL612589
 IC50 7.7 7.7 20.0 1
P388
CHEMBL389
 EC50 7.7 7.7 20.0 1
Huh-7
CHEMBL614039
 IC50 7.7 7.7 20.0 1
OVCAR-3
CHEMBL614213
 IC50 7.7 7.7 20.0 2
HEK293
CHEMBL614818
 IC50 7.59 7.59 25.8 1
SNU-475
CHEMBL1075586
 IC50 7.53 7.53 29.3 1
OE33
CHEMBL1075556
 IC50 7.52 7.52 30.0 1

Pharmacokinetic Data

Parameter Value Units Species
CL 1.8 mL.min-1.kg-1 Homo sapiens
CL 2.0 mL.min-1.kg-1 Rattus norvegicus
CL 2.0 mL.min-1.kg-1 Homo sapiens
CL 4.8 mL.min-1.kg-1 Macaca
CL 9.8 mL.min-1.kg-1 Canis lupus familiaris
CL 84.87 mL.min-1.kg-1 Rattus norvegicus
CL 33.1 mL.min-1.kg-1 Rattus norvegicus
CL 0.523 mL.min-1.kg-1 Homo sapiens
CL 0.209 mL.min-1.kg-1 Homo sapiens
Fu 0.4 - Homo sapiens
MRT 20.0 hr Homo sapiens
T1/2 23.0 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HT-29 IC50 = 0.01 nM 11.0 In vitro cytotoxic activity against colon adenocarcinoma (HT-29) cells assayed b... 11728191
MES-SA/Dx5 IC50 = 0.02 nM 10.7 In vitro cytotoxic activity against uterine sarcoma (MES-SA) cells assayed by in... 11728191
K562 IC50 = 0.1 nM 10.0 Cytotoxicity against human K562 cells assessed as cell viability after 48 hrs by... 22582991
ARO IC50 = 0.1 nM 10.0 Cytotoxicity against human Aro cells by MTT assay 16539377
NCI-H460 IC50 = 0.13 nM 9.89 In vitro cytotoxic activity against nonsmall cell lung carcinoma (NCI-H460) cell... 11728191
CCRF-CEM IC50 = 0.17 nM 9.77 Cytotoxicity against human CCRF-CEM cells assessed as cell viability after 48 hr... 22582991
Unchecked IC50 = 0.2 nM 9.7 Antiproliferative activity against human Melmet 5 cells assessed as reduction in... 38959729
KB IC50 = 0.2 nM 9.7 Antiproliferative activity against human KB cells after 72 hrs by SRB assay 28333459
KB IC50 = 0.21 nM 9.68 Cytotoxicity against human KB cells after 48 hrs by MTT assay 30455148
MDA-MB-435 IC50 = 0.29 nM 9.54 Antiproliferative activity against MDA435/LCC6 cells by ELISA 17154505
HT-1080 IC50 = 0.3 nM 9.52 Antiproliferative activity against human HT-1080 cells assessed as reduction in ... 38959729
Unchecked IC50 = 0.3 nM 9.52 Growth inhibition of human KB/S cells after 72 hrs by MTT assay 29746134
ARO IC50 = 0.3 nM 9.52 Cytotoxicity against human Aro cells after 72 hrs by MTT assay 17915851
KB IC50 = 0.4 nM 9.4 Growth inhibition of human KB cells after 72 hrs by methylene blue assay 22060033
KB IC50 = 0.4 nM 9.4 Growth inhibition of human KB cells after 72 hrs by methylene blue dye assay 19053773
KB IC50 = 0.4 nM 9.4 Antiproliferative activity against human KB cells 25059503
MDA-MB-468 IC50 = 0.4 nM 9.4 Antiproliferative activity against human MDA-MB-468 cells assessed as reduction ... 38959729
Unchecked IC50 = 0.4 nM 9.4 Cytotoxicity against human KB/S cells after 72 hrs by MTT assay 30869890
MCF7 IC50 = 0.6 nM 9.22 Growth inhibition of Pgp deficient MCF7 cells expressing MRP1 17567121
KB IC50 = 0.6 nM 9.22 Cytotoxicity against human KB cells assessed as growth inhibition after 72 hrs b... 24106982

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 270
4020828 10.1021/jm00146a017 Mus musculus 61
23685944 10.1016/j.ejmech.2013.03.033 NON-PROTEIN TARGET 27
17181164 10.1021/jm0605031 Molecular identity unknown 25
19220018 10.1021/jm801338r Molecular identity unknown 25
17973361 10.1021/jm0708984 Molecular identity unknown 25
16472241 10.2174/1570163043334794 Hepatotoxicity 18
21051535 10.1124/dmd.110.034629 ADMET 15
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
32171161 10.1016/j.ejmech.2020.112158 Unchecked 13
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
36167009 10.1016/j.ejmech.2022.114784 Unchecked 9
17915851 10.1021/jm070534b A549 9
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
22320354 10.1021/jm200848t NON-PROTEIN TARGET 8
21664138 10.1016/j.bmc.2011.05.031 HCT-116 8
15920768 10.1002/jps.20373 ADMET 8
8277312 10.1021/np50100a011 NON-PROTEIN TARGET 8
32171161 10.1016/j.ejmech.2020.112158 Tubulin 8
- 10.1016/S0960-894X(00)80225-5 P388 7

Data from ChEMBL 36 via Core Engine