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Compound Detail

CHEMBL1637

GEMCITABINE HYDROCHLORIDE
💊 Approved Drug
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💊 Approved Drug
Cl.Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)C2(F)F)c(=O)n1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1637
Name GEMCITABINE HYDROCHLORIDE
Phase Approved
Structure Type MOL
InChI Key OKKDEIYWILRZIA-OSZBKLCCSA-N
Therapeutic ✓ Yes
Parent Compound CHEMBL888
Active Moiety CHEMBL888

Known Names

Gemcitabine (as hydrochloride) Gemcitabine hcl Gemcitabine hydrochloride Gemzar Infugem LY-188011 HYDROCHLORIDE LY188011 HYDROCHLORIDE
9
Targets
13
Activities
1
Assay Types
0
PK Parameters
20
Publications
7
Known Names
20
Indications
2
Mechanisms

Molecular Properties

263.2
MW (Da)
-1.29
ALogP
7
HBA
3
HBD
110.6
PSA (Ų)
0.61
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1996
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral
USAN Stem -citabine
USAN Year 1990

Extended Properties

Molecular Formula C9H12ClF2N3O4
MW 299.66
Aromatic Rings 1
Heavy Atoms 18
NP-Likeness 1.30

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Ribonucleoside-diphosphate reductase RR1 inhibitor INHIBITOR Ribonucleoside-diphosphate reductase RR1 ✓ ✓
DNA polymerase (alpha/delta/epsilon) inhibitor INHIBITOR DNA polymerase (alpha/delta/epsilon) ✓ ✓

Indications

Breast Neoplasms Breast Neoplasms Carcinoma, Non-Small-Cell Lung Ovarian Neoplasms Ovarian Neoplasms Pancreatic Neoplasms Pancreatic Neoplasms Carcinoma, Squamous Cell Cholangiocarcinoma Gallbladder Neoplasms Gallbladder Neoplasms Liver Neoplasms Lung Neoplasms Lymphoma Neoplasms Neoplasms Thromboembolism Triple Negative Breast Neoplasms Urethral Neoplasms Urinary Bladder Neoplasms

Activity Summary

IC50 13 meas. best 8.67

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
NCI-H460
CHEMBL396
 IC50 8.67 7.17 2.1 2
C2G cell line
CHEMBL613541
 IC50 8.43 8.43 3.7 1
TRAMP-C2H
CHEMBL614369
 IC50 8.33 8.33 4.7 1
TRAMP-C1A
CHEMBL614367
 IC50 8.05 8.05 9.0 1
C2D cell line
CHEMBL614368
 IC50 7.92 7.92 11.9 1
A2780
CHEMBL614004
 IC50 5.9 5.88 1250.0 2
A549
CHEMBL392
 IC50 5.64 5.235 2310.0 2
L02
CHEMBL4296457
 IC50 5.35 5.14 4510.0 2
MCF7
CHEMBL387
 IC50 5.2 5.2 6350.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
NCI-H460 IC50 = 2.13 nM 8.67 Cytotoxicity against human NCI-H460 cells by MTT assay 19345581
C2G cell line IC50 = 3.7 nM 8.43 Inhibitory concentration to inhibit growth of C2G prostate cancer cell line by u... 14971910
TRAMP-C2H IC50 = 4.7 nM 8.33 Inhibitory concentration to inhibit growth of C2H prostate cancer cell line by u... 14971910
TRAMP-C1A IC50 = 9.0 nM 8.05 Inhibitory concentration to inhibit growth of C1A prostate cancer cell line by u... 14971910
C2D cell line IC50 = 11.9 nM 7.92 Inhibitory concentration to inhibit growth of C2D prostate cancer cell line by u... 14971910
A2780 IC50 = 1250.0 nM 5.9 Cytotoxicity against human A2780 cells assessed as reduction in cell viability i... 33992863
A2780 IC50 = 1380.0 nM 5.86 Cytotoxicity against human A2780 cells assessed as reduction in cell viability i... 33992863
NCI-H460 IC50 = 2130.0 nM 5.67 Cytotoxicity against human NCI-H460 cells after 3 days by MTT assay 20356655
A549 IC50 = 2310.0 nM 5.64 Cytotoxicity against human A549 cells assessed as reduction in cell viability in... 33992863
L02 IC50 = 4510.0 nM 5.35 Cytotoxicity against human L02 cells assessed as reduction in cell viability inc... 33992863
MCF7 IC50 = 6350.0 nM 5.2 Cytotoxicity against human MCF7 cells assessed as reduction in cell viability in... 33992863
L02 IC50 = 11870.0 nM 4.93 Cytotoxicity against human L02 cells assessed as reduction in cell viability inc... 33992863
A549 IC50 = 14650.0 nM 4.83 Cytotoxicity against human A549 cells assessed as reduction in cell viability in... 33992863

Literature References

PubMed DOI Target Context # Activities
33992863 10.1016/j.bmc.2021.116214 A2780 18
24919854 10.1007/s10637-014-0120-7 Calu-6 2
33992863 10.1016/j.bmc.2021.116214 Unchecked 2
33992863 10.1016/j.bmc.2021.116214 L02 2
33992863 10.1016/j.bmc.2021.116214 A549 2
- 10.1101/2020.03.25.008482 Vero C1008 2
- 10.1101/2020.03.25.008482 SARS-CoV-2 2
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 3 1
24919854 10.1007/s10637-014-0120-7 Unchecked 1
- 10.1101/2020.04.21.054387 SARS-CoV-2 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 4 1
14971910 10.1021/jm0303711 TRAMP-C1A 1
23956101 10.1093/toxsci/kft176 ATP-binding cassette sub-family C member 2 1
23956101 10.1093/toxsci/kft176 Bile salt export pump 1
20356655 10.1016/j.ejmech.2010.02.011 NCI-H460 1
19860433 10.1021/jm901181h Blood 1
19860433 10.1021/jm901181h HCT-116 1
19345581 10.1016/j.bmcl.2009.03.069 NCI-H460 1
14971910 10.1021/jm0303711 TRAMP-C2H 1
14971910 10.1021/jm0303711 C2G cell line 1

Data from ChEMBL 36 via Core Engine