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Compound Detail

CHEMBL553025

VINORELBINE
💊 Approved Drug
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💊 Approved Drug
CCC1=C[C@@H]2CN(C1)Cc1c([nH]c3ccccc13)[C@@](C(=O)OC)(c1cc3c(cc1OC)N(C)[C@H]1[C@@](O)(C(=O)OC)[C@H](OC(C)=O)[C@]4(CC)C=CCN5CC[C@]31[C@@H]54)C2
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL553025
Name VINORELBINE
Phase Approved
Structure Type MOL
InChI Key GBABOYUKABKIAF-IELIFDKJSA-N
Therapeutic ✓ Yes

Known Names

Navelbin NSC-760087 Vinorelbina Vinorelbine Vinorelbine base
687
Targets
758
Activities
4
Assay Types
15
PK Parameters
20
Publications
5
Known Names
20
Indications

Molecular Properties

779.0
MW (Da)
4.75
ALogP
11
HBA
2
HBD
133.9
PSA (Ų)
0.20
QED
2
Ro5 Violations
7
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1994
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning Natural Product
USAN Stem vin-
USAN Year 1993

Extended Properties

Molecular Formula C45H54N4O8
MW 778.95
Aromatic Rings 3
Heavy Atoms 57
NP-Likeness 1.55

Indications

Neoplasms Neoplasms Breast Neoplasms Breast Neoplasms Breast Neoplasms Breast Neoplasms Carcinoma Carcinoma, Non-Small-Cell Lung Esophageal Neoplasms Hodgkin Disease Hodgkin Disease Lung Neoplasms Lung Neoplasms Lung Neoplasms Lymphoma, Non-Hodgkin Mesothelioma Mesothelioma Rhabdomyosarcoma, Alveolar Rhabdomyosarcoma, Embryonal Triple Negative Breast Neoplasms

ATC Classification

L01CA04
vinorelbine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 753 meas. best 10.15
EC50 2 meas. best 8.22
Ki 2 meas. best 6.27
Kd 1 meas. best 6.27

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 10.15 7.6073 0.1 11
Unchecked
CHEMBL612545
 IC50 10.0 7.5986 0.1 7
MDA-MB-468
CHEMBL614335
 IC50 10.0 9.075 0.1 2
HT-1080
CHEMBL614580
 IC50 10.0 9.3 0.1 2
COLO-829
CHEMBL2366275
 IC50 9.98 9.98 0.1 1
CGTH-W-1
CHEMBL2366300
 IC50 9.63 9.63 0.2 1
HeLa
CHEMBL399
 IC50 9.52 7.9767 0.3 6
CAKI-1
CHEMBL614067
 IC50 9.52 7.71 0.3 2
BT-474
CHEMBL614529
 IC50 9.52 8.53 0.3 2
Tubulin
CHEMBL2095182
 IC50 9.51 7.1233 0.3 3
BB30-HNC
CHEMBL2366271
 IC50 9.4 9.4 0.4 1
MES-SA
CHEMBL614343
 IC50 9.4 8.1967 0.4 3
ECC12
CHEMBL2366180
 IC50 9.29 9.29 0.5 1
NCI-H522
CHEMBL614387
 IC50 9.27 9.27 0.5 1
HT-144
CHEMBL2366291
 IC50 9.23 9.23 0.6 1
A-375
CHEMBL613859
 IC50 9.22 8.32 0.6 2
GT3TKB
CHEMBL2366148
 IC50 9.13 9.13 0.7 1
MCF7
CHEMBL387
 IC50 9.1 7.544 0.8 5
NTERA-2-cl-D1
CHEMBL614206
 IC50 9.03 9.03 0.9 1
KB
CHEMBL398
 IC50 9.0 8.2 1.0 2
TE-9
CHEMBL2366147
 IC50 8.97 8.97 1.1 1
A253 cell line
CHEMBL614255
 IC50 8.91 8.91 1.2 1
ACN
CHEMBL2366195
 IC50 8.88 8.88 1.3 1
COLO 205
CHEMBL614561
 IC50 8.86 8.86 1.4 1
LCLC-103H cell line
CHEMBL614066
 IC50 8.85 8.85 1.4 1
SK-LMS-1
CHEMBL2366096
 IC50 8.84 8.84 1.5 1
MC-IXC
CHEMBL1075495
 IC50 8.83 8.83 1.5 1
KS-1
CHEMBL2366228
 IC50 8.83 8.83 1.5 1
RKO
CHEMBL614879
 IC50 8.82 8.82 1.5 1
LCLC-97TM1
CHEMBL1075489
 IC50 8.81 8.81 1.6 1
OVCAR-4
CHEMBL614051
 IC50 8.76 8.76 1.7 1
COLO-679
CHEMBL1075426
 IC50 8.74 8.74 1.8 1
HGC-27
CHEMBL1075463
 IC50 8.73 8.73 1.9 1
NCI-H520
CHEMBL614099
 IC50 8.73 8.73 1.9 1
IGR-1
CHEMBL1075479
 IC50 8.72 8.72 1.9 1
BPH-1
CHEMBL2366131
 IC50 8.72 8.72 1.9 1
ATN-1
CHEMBL2366277
 IC50 8.71 8.71 1.9 1
HOP-62
CHEMBL614643
 IC50 8.71 8.71 1.9 1
HUVEC
CHEMBL613979
 IC50 8.7 8.7 2.0 1
SCC-9
CHEMBL1075571
 IC50 8.69 8.69 2.0 1
NB12
CHEMBL2366285
 IC50 8.68 8.68 2.1 1
SBC-5
CHEMBL614896
 IC50 8.68 8.68 2.1 1
IGROV-1
CHEMBL613984
 IC50 8.66 8.66 2.2 1
HuTu80
CHEMBL614582
 IC50 8.66 8.66 2.2 1
HSC-2
CHEMBL1075468
 IC50 8.65 8.65 2.2 1
SK-UT-1
CHEMBL2366316
 IC50 8.65 8.65 2.2 1
MKN-45
CHEMBL614354
 IC50 8.64 8.64 2.3 1
SW1710
CHEMBL1075590
 IC50 8.63 8.63 2.3 1
SIG-M5
CHEMBL2366251
 IC50 8.61 8.61 2.5 1
NCI-H2122
CHEMBL1075533
 IC50 8.59 8.59 2.6 1

Pharmacokinetic Data

Parameter Value Units Species
CL 20.0 mL.min-1.kg-1 Homo sapiens
CL 12.0 mL.min-1.kg-1 Homo sapiens
CL 20.0 mL.min-1.kg-1 Canis lupus familiaris
CL 20.0 mL.min-1.kg-1 Homo sapiens
CL 21.0 mL.min-1.kg-1 Homo sapiens
CL 23.6 mL.min-1.kg-1 Macaca
CL 31.7 mL.min-1.kg-1 Rattus norvegicus
CL 16.17 mL.min-1.kg-1 Mus musculus
Fu 0.87 - Homo sapiens
MRT 17.0 hr Homo sapiens
MRT 18.0 hr Homo sapiens
T1/2 18.0 hr Homo sapiens
T1/2 26.0 hr Homo sapiens
T1/2 24.8 hr Mus musculus
T1/2 27.7 hr Mus musculus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NON-PROTEIN TARGET IC50 = 0.07 nM 10.15 Antiproliferative activity against exponentially growing adherent human SCC114 c... 25872984
HT-1080 IC50 = 0.1 nM 10.0 Antiproliferative activity against human HT-1080 cells assessed as reduction in ... 38959729
Unchecked IC50 = 0.1 nM 10.0 Antiproliferative activity against human Melmet 5 cells assessed as reduction in... 38959729
MDA-MB-468 IC50 = 0.1 nM 10.0 Antiproliferative activity against human MDA-MB-468 cells assessed as reduction ... 38959729
COLO-829 IC50 = 0.1051 nM 9.98 SANGER: Inhibition of human COLO-829 cell growth in a cell viability assay. -
CGTH-W-1 IC50 = 0.2316 nM 9.63 SANGER: Inhibition of human CGTH-W-1 cell growth in a cell viability assay. -
CAKI-1 IC50 = 0.3 nM 9.52 Antiproliferative activity against human CAKI-1 cells assessed as reduction in c... 38959729
HeLa IC50 = 0.3 nM 9.52 Antiproliferative activity against human HeLa cells assessed as reduction in cel... 38959729
BT-474 IC50 = 0.3 nM 9.52 Antiproliferative activity against human BT-474 cells assessed as reduction in c... 38959729
Tubulin IC50 = 0.308 nM 9.51 Inhibition of tubulin polymerization (unknown origin) 38516587
BB30-HNC IC50 = 0.3988 nM 9.4 SANGER: Inhibition of human BB30-HNC cell growth in a cell viability assay. -
MES-SA IC50 = 0.4 nM 9.4 Antiproliferative activity against human MES-SA cells assessed as reduction in c... 38959729
Unchecked IC50 = 0.5 nM 9.3 Antiproliferative activity against human Hermes 3C cells assessed as reduction i... 38959729
ECC12 IC50 = 0.509 nM 9.29 SANGER: Inhibition of human ECC12 cell growth in a cell viability assay. -
NCI-H522 IC50 = 0.5354 nM 9.27 SANGER: Inhibition of human NCI-H522 cell growth in a cell viability assay. -
HT-144 IC50 = 0.5909 nM 9.23 SANGER: Inhibition of human HT-144 cell growth in a cell viability assay. -
A-375 IC50 = 0.6 nM 9.22 Antiproliferative activity against human A-375 cells assessed as reduction in ce... 38959729
GT3TKB IC50 = 0.7477 nM 9.13 SANGER: Inhibition of human GT3TKB cell growth in a cell viability assay. -
MCF7 IC50 = 0.8 nM 9.1 Antiproliferative activity against human MCF7 cells assessed as reduction in cel... 38959729
Unchecked IC50 = 0.9 nM 9.05 Antiproliferative activity against human WM1366 cells assessed as reduction in c... 38959729

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 405
32473523 10.1016/j.ejmech.2020.112332 NCI-H1975 22
32473523 10.1016/j.ejmech.2020.112332 HCT-116 19
32473523 10.1016/j.ejmech.2020.112332 HepG2 19
16472241 10.2174/1570163043334794 Hepatotoxicity 18
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 14
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
38833507 10.1021/acs.jmedchem.4c00388 A2058 11
21051535 10.1124/dmd.110.034629 ADMET 9
16621936 10.1124/dmd.105.006619 ADMET 8
18426954 10.1124/dmd.108.020479 ADMET 8
11602674 - ATP-dependent translocase ABCB1 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
27428868 10.1021/acs.jmedchem.6b00777 Unchecked 8
36728755 10.1021/acs.jmedchem.2c01424 KBv200 7
33588178 10.1016/j.ejmech.2021.113169 MES-SA/Dx5 5
23202849 10.1016/j.ejmech.2012.10.051 HT-29 4
27753480 10.1021/acs.jmedchem.6b00525 Unchecked 4
23202849 10.1016/j.ejmech.2012.10.051 CAL-33 4
23202849 10.1016/j.ejmech.2012.10.051 HL-60 4

Data from ChEMBL 36 via Core Engine