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Compound Detail

CHEMBL501867

VINCRISTINE SULFATE
💊 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.O=S(=O)(O)O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL501867
Name VINCRISTINE SULFATE
Phase Approved
Structure Type MOL
InChI Key AQTQHPDCURKLKT-JKDPCDLQSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL90555
Active Moiety CHEMBL90555

Known Names

37231 Kyocristine Leurocristine sulfate LILLY-37231 Marqibo Marqibo kit Novopharm NSC-67574 Oncovin Vincasar pfs Vincrex Vincristine sulfate +5 more
19
Targets
45
Activities
2
Assay Types
0
PK Parameters
20
Publications
17
Known Names
20
Indications
1
Mechanisms

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 C46H58N4O14S
MW 923.05
Aromatic Rings 3
Heavy Atoms 60
NP-Likeness 1.47

Mechanism of Action

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

Indications

Astrocytoma Brain Neoplasms Carcinoma Central Nervous System Neoplasms Colorectal Neoplasms Ganglioneuroblastoma Glioma Head and Neck Neoplasms Hepatoblastoma Hodgkin Disease Hodgkin Disease Kidney Neoplasms Leukemia Leukemia, Biphenotypic, Acute Leukemia, Biphenotypic, Acute Leukemia, Biphenotypic, Acute Leukemia, Lymphocytic, Chronic, B-Cell Leukemia, Lymphoid Leukemia-Lymphoma, Adult T-Cell Lung Neoplasms

Drug Warnings

Black Box Warning
misuse
Country: United States

Activity Summary

IC50 42 meas. best 9.0
EC50 3 meas. best 7.33

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 9.0 7.4286 1.0 7
LNCaP
CHEMBL612518
 IC50 8.54 8.375 2.9 2
OVCAR-3
CHEMBL614213
 IC50 8.0 8.0 10.0 1
IGROV-1
CHEMBL613984
 IC50 8.0 8.0 10.0 1
MCF7
CHEMBL387
 IC50 8.0 7.145 10.0 2
PC-3
CHEMBL390
 IC50 7.96 7.142 11.0 5
NFF
CHEMBL614198
 IC50 7.77 7.77 16.9 2
A549
CHEMBL392
 IC50 7.7 7.235 20.0 2
KB
CHEMBL398
 IC50 7.7 7.7 20.0 1
ADMET
CHEMBL612558
 IC50 7.51 7.51 31.0 1
HeLa
CHEMBL399
 IC50 7.45 7.445 35.8 2
Unchecked
CHEMBL612545
 EC50 7.33 7.2633 47.0 3
Plasmodium falciparum
CHEMBL364
 IC50 7.3 6.4714 50.1 7
BT-549
CHEMBL614072
 IC50 7.26 7.26 54.7 1
DU-145
CHEMBL613508
 IC50 7.14 5.64 72.3 2
HepG2
CHEMBL395
 IC50 7.0 6.58 100.0 2
HT-29
CHEMBL384
 IC50 7.0 7.0 100.0 1
MDA-MB-231
CHEMBL400
 IC50 6.93 6.93 116.6 1
Lu1
CHEMBL613290
 IC50 6.32 6.32 480.0 1
Unchecked
CHEMBL612545
 IC50 5.51 5.51 3120.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 1.0 nM 9.0 Cytotoxic activity against human tumor SW 13 cell line 15857148
LNCaP IC50 = 2.9 nM 8.54 Cytotoxicity against human LNCAP cells after 72 hrs by alamar blue assay 20732809
LNCaP IC50 = 6.1 nM 8.21 Cytotoxicity against human LNCAP cells after 72 hrs by alamar blue assay 23215348
OVCAR-3 IC50 = 10.0 nM 8.0 Cytotoxic activity against human tumor Ovcar-3 cell line 15857148
IGROV-1 IC50 = 10.0 nM 8.0 Cytotoxic activity against human tumor Igrov-1 cell line 15857148
MCF7 IC50 = 10.0 nM 8.0 Cytotoxic activity against human tumor MCF-7 cell line 15857148
NON-PROTEIN TARGET IC50 = 10.0 nM 8.0 Cytotoxic activity against human tumor Mia Paca 2 cell line 15857148
PC-3 IC50 = 11.0 nM 7.96 Cytotoxicity against human PC3 cells after 72 hrs by alamar blue assay 20732809
PC-3 IC50 = 15.0 nM 7.82 Cytotoxicity against human PC3 cells after 72 hrs by alamar blue assay 23215348
PC-3 IC50 = 15.3 nM 7.82 Cytotoxicity against human PC3 cells assessed as inhibition of cell viability af... 23489291
NFF IC50 = 17.0 nM 7.77 Cytotoxicity against human NFF cells after 72 hrs by alamar blue assay 23215348
NFF IC50 = 16.9 nM 7.77 Cytotoxicity against human NFF cells assessed as inhibition of cell viability af... 23489291
KB IC50 = 20.0 nM 7.7 Cytotoxicity against human KB cells after 72 hrs by SRB assay 26522953
A549 IC50 = 20.0 nM 7.7 Cytotoxicity against human A549 cells after 72 hrs by alamar blue assay 23215348
PC-3 IC50 = 27.6 nM 7.56 Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay 28038323
ADMET IC50 = 31.0 nM 7.51 Cytotoxicity against human HEK cells after 72 hrs by alamar blue assay 23215348
HeLa IC50 = 35.8 nM 7.45 Cytotoxicity against human HeLa cells assessed as inhibition of cell viability a... 23489291
HeLa IC50 = 36.0 nM 7.44 Cytotoxicity against human HeLa cells after 72 hrs by alamar blue assay 23215348
Unchecked EC50 = 47.0 nM 7.33 PUBCHEM_BIOASSAY: Luminescence Cell-Based Dose Response to Identify Inhibitors o... -
Plasmodium falciparum IC50 = 50.12 nM 7.3 Antiplasmodial activity against Plasmodium falciparum W2 after 72 hrs by SYBR gr... 19734910

Literature References

PubMed DOI Target Context # Activities
18598018 10.1021/jm800194k NON-PROTEIN TARGET 27
24747749 10.1016/j.ejmech.2014.04.004 NON-PROTEIN TARGET 27
20684599 10.1021/jm1007165 NON-PROTEIN TARGET 24
19006285 10.1021/jm800827q NON-PROTEIN TARGET 24
17559205 10.1021/jm070235m NON-PROTEIN TARGET 24
412968 10.1021/jm00199a016 B16 20
22283430 10.1021/jm2012694 NON-PROTEIN TARGET 16
20395150 10.1016/j.bmc.2010.03.063 NON-PROTEIN TARGET 16
412968 10.1021/jm00199a016 P388 9
15857148 10.1021/jm049387x NON-PROTEIN TARGET 8
19734910 10.1038/nchembio.215 Plasmodium falciparum 7
430477 10.1021/jm00190a008 P388/VCR 6
430477 10.1021/jm00190a008 NON-PROTEIN TARGET 5
430477 10.1021/jm00190a008 P388/S 4
412968 10.1021/jm00199a016 Mus musculus 4
19006285 10.1021/jm800827q NSCLC 4
19006285 10.1021/jm800827q Melanoma cell 4
19006285 10.1021/jm800827q Leukemia cell 4
16107161 10.1021/jm050353e Panel NCI-60 (60 carcinoma cell lines) 3
12036377 10.1021/jm011123c Panel melanoma (Carcinoma cell lines) 3

Data from ChEMBL 36 via Core Engine