Compound Detail

CHEMBL888

GEMCITABINE

💊 Approved Drug

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💊 Approved Drug

Nc1ccn([C@@H]2O[C@H](CO)[C@@H](O)C2(F)F)c(=O)n1

ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID	CHEMBL888
Name	GEMCITABINE
Phase	Approved
Structure Type	MOL
InChI Key	SDUQYLNIPVEERB-QPPQHZFASA-N
Therapeutic	✓ Yes

Known Names

Gemcitabina Gemcitabine Gemzar LY-188011 LY188011 NSC-613327

697

Targets

1,050

Activities

Assay Types

PK Parameters

Publications

Known Names

Indications

Molecular Properties

263.2

MW (Da)

-1.29

ALogP

HBA

HBD

110.6

PSA (Å²)

0.61

QED

Ro5 Violations

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	1989

Extended Properties

Molecular Formula	C9H11F2N3O4
MW	263.20
Aromatic Rings	1
Heavy Atoms	18
NP-Likeness	1.30

Indications

Neoplasms Neoplasms Biliary Tract Neoplasms Biliary Tract Neoplasms Breast Neoplasms Breast Neoplasms Breast Neoplasms Carcinoma Carcinoma, Hepatocellular Carcinoma, Non-Small-Cell Lung Carcinoma, Pancreatic Ductal Carcinoma, Squamous Cell Carcinoma, Squamous Cell Carcinoma, Squamous Cell Cholangiocarcinoma Cholangiocarcinoma Fallopian Tube Neoplasms Fallopian Tube Neoplasms Gallbladder Neoplasms Gallbladder Neoplasms

ATC Classification

L01BC05

gemcitabine

Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS

Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 1,023 meas. best 10.98

EC50 27 meas. best 10.52

Target Activity Profile

Target	Type	Best pChEMBL	Mean pChEMBL	Best (nM)	# Data
SIG-M5 CHEMBL2366251	IC50	10.98	10.98	0.0	1
KGN CHEMBL2366154	IC50	10.97	10.97	0.0	1
EW-13 CHEMBL2366124	IC50	10.95	10.95	0.0	1
SNU1 CHEMBL614931	IC50	10.8	10.8	0.0	1
PSN1 CHEMBL614241	IC50	10.78	8.9267	0.0	3
HuTu80 CHEMBL614582	IC50	10.78	10.78	0.0	1
EW-16 CHEMBL2366358	IC50	10.64	10.64	0.0	1
786-0 CHEMBL613102	IC50	10.64	10.64	0.0	1
ES1 CHEMBL2366146	IC50	10.57	10.57	0.0	1
RKO CHEMBL614879	IC50	10.56	10.56	0.0	1
ESS-1 CHEMBL1075444	IC50	10.54	10.54	0.0	1
SK-UT-1 CHEMBL2366316	IC50	10.53	10.53	0.0	1
Ramos CHEMBL614629	EC50	10.52	10.52	0.0	1
LB2241-RCC CHEMBL2366330	IC50	10.5	10.5	0.0	1
CHL-1 CHEMBL1075422	IC50	10.49	10.49	0.0	1
SW1783 CHEMBL1075591	IC50	10.47	10.47	0.0	1
MEL-JUSO CHEMBL1075501	IC50	10.41	10.41	0.0	1
HT-29 CHEMBL384	IC50	10.38	7.2488	0.0	8
SNG-M CHEMBL1075582	IC50	10.37	10.37	0.0	1
TE-15 CHEMBL2366086	IC50	10.33	10.33	0.0	1
HOS CHEMBL614736	IC50	10.32	10.32	0.0	1
BB65-RCC CHEMBL2366247	IC50	10.29	10.29	0.1	1
HCE-4 CHEMBL2366207	IC50	10.28	10.28	0.1	1
MHH-ES-1 CHEMBL1075505	IC50	10.27	10.27	0.1	1
RPMI-7951 CHEMBL612447	IC50	10.27	10.27	0.1	1
IST-SL2 CHEMBL2366101	IC50	10.23	10.23	0.1	1
GR-ST CHEMBL2366111	IC50	10.23	10.23	0.1	1
CMK CHEMBL2366177	IC50	10.23	10.23	0.1	1
NALM-6 CHEMBL614187	IC50	10.21	10.21	0.1	1
RPMI-6666 CHEMBL2366187	IC50	10.19	10.19	0.1	1
LC-2-ad CHEMBL2366260	IC50	10.19	10.19	0.1	1
ARH-77 CHEMBL2366241	IC50	10.15	10.15	0.1	1
IST-MEL1 CHEMBL2366094	IC50	10.14	10.14	0.1	1
SW1710 CHEMBL1075590	IC50	10.12	10.12	0.1	1
DEL CHEMBL2366186	IC50	10.05	10.05	0.1	1
AGS CHEMBL613860	IC50	10.04	10.04	0.1	1
NCI-H2122 CHEMBL1075533	IC50	10.02	10.02	0.1	1
HSC-4 CHEMBL1075469	IC50	9.99	9.99	0.1	1
769-P CHEMBL1075385	IC50	9.91	9.91	0.1	1
AM-38 CHEMBL2366192	IC50	9.91	9.91	0.1	1
RT-112 CHEMBL614145	IC50	9.89	9.89	0.1	1
MCF7 CHEMBL387	IC50	9.87	6.8006	0.1	16
IGROV-1 CHEMBL613984	IC50	9.84	9.84	0.1	1
OCI-AML2 CHEMBL2366220	IC50	9.83	9.83	0.1	1
NCI-H1299 CHEMBL612255	IC50	9.8	9.8	0.2	1
A-431 CHEMBL614069	IC50	9.74	9.74	0.2	1
SW982 CHEMBL2366238	IC50	9.67	9.67	0.2	1
BB30-HNC CHEMBL2366271	IC50	9.64	9.64	0.2	1
647-V CHEMBL1075384	IC50	9.61	9.61	0.2	1
ACN CHEMBL2366195	IC50	9.61	9.61	0.2	1

Pharmacokinetic Data

Parameter	Value	Units	Species
AUC	5617800.0	ng.hr.mL-1	Rattus norvegicus
AUC	26692900.0	ng.hr.mL-1	Rattus norvegicus
CL	32.0	mL.min-1.kg-1	Homo sapiens
CL	32.0	mL.min-1.kg-1	Homo sapiens
CL	402800.0	mL.min-1.g-1	Homo sapiens
CL	814100.0	mL.min-1.g-1	Homo sapiens
CL	477100.0	mL.min-1.g-1	Homo sapiens
CL	491900.0	mL.min-1.g-1	Homo sapiens
CL	300.0	mL.min-1.g-1	Homo sapiens
CL	350.0	mL.min-1.g-1	Homo sapiens
CL	250.0	mL.min-1.g-1	Homo sapiens
Cmax	5028875.38	nM	Rattus norvegicus
Cmax	27009878.42	nM	Rattus norvegicus
F	3.2	%	Rattus norvegicus
Fu	1.0	-	Homo sapiens
MRT	0.81	hr	Homo sapiens
T1/2	1.0	hr	Homo sapiens
T1/2	2.3	hr	Rattus norvegicus
T1/2	4.4	hr	Rattus norvegicus
T1/2	0.15	hr	Homo sapiens
T1/2	0.1333	hr	-
T1/2	0.15	hr	Homo sapiens
T1/2	1.298	hr	Homo sapiens
Tmax	1.7	hr	Rattus norvegicus
Tmax	0.5	hr	Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target	Type	Rel.	Value	Units	pChEMBL	Assay	PubMed
SIG-M5	IC50	=	0.01042	nM	10.98	SANGER: Inhibition of human SIG-M5 cell growth in a cell viability assay.	-
KGN	IC50	=	0.01081	nM	10.97	SANGER: Inhibition of human KGN cell growth in a cell viability assay.	-
EW-13	IC50	=	0.01122	nM	10.95	SANGER: Inhibition of human EW-13 cell growth in a cell viability assay.	-
SNU1	IC50	=	0.01596	nM	10.8	SANGER: Inhibition of human NCI-SNU-1 cell growth in a cell viability assay.	-
HuTu80	IC50	=	0.01664	nM	10.78	SANGER: Inhibition of human HUTU-80 cell growth in a cell viability assay.	-
PSN1	IC50	=	0.01652	nM	10.78	SANGER: Inhibition of human PSN1 cell growth in a cell viability assay.	-
EW-16	IC50	=	0.02299	nM	10.64	SANGER: Inhibition of human EW-16 cell growth in a cell viability assay.	-
786-0	IC50	=	0.023	nM	10.64	SANGER: Inhibition of human 786-0 cell growth in a cell viability assay.	-
ES1	IC50	=	0.02682	nM	10.57	SANGER: Inhibition of human ES1 cell growth in a cell viability assay.	-
RKO	IC50	=	0.02785	nM	10.56	SANGER: Inhibition of human RKO cell growth in a cell viability assay.	-
ESS-1	IC50	=	0.02858	nM	10.54	SANGER: Inhibition of human ESS-1 cell growth in a cell viability assay.	-
SK-UT-1	IC50	=	0.02969	nM	10.53	SANGER: Inhibition of human SK-UT-1 cell growth in a cell viability assay.	-
Ramos	EC50	=	0.03	nM	10.52	Cytotoxicity against human Ramos cells assessed as reduction in cell viability a...	27032331
LB2241-RCC	IC50	=	0.03179	nM	10.5	SANGER: Inhibition of human LB2241-RCC cell growth in a cell viability assay.	-
CHL-1	IC50	=	0.03241	nM	10.49	SANGER: Inhibition of human CHL-1 cell growth in a cell viability assay.	-
SW1783	IC50	=	0.03355	nM	10.47	SANGER: Inhibition of human SW1783 cell growth in a cell viability assay.	-
MEL-JUSO	IC50	=	0.03908	nM	10.41	SANGER: Inhibition of human MEL-JUSO cell growth in a cell viability assay.	-
HT-29	IC50	=	0.04128	nM	10.38	SANGER: Inhibition of human HT-29 cell growth in a cell viability assay.	-
SNG-M	IC50	=	0.04247	nM	10.37	SANGER: Inhibition of human SNG-M cell growth in a cell viability assay.	-
TE-15	IC50	=	0.04637	nM	10.33	SANGER: Inhibition of human TE-15 cell growth in a cell viability assay.	-

Literature References

PubMed	DOI	Target Context	# Activities
-	10.6019/CHEMBL3885881	Rattus norvegicus	295
27117260	10.1016/j.bmc.2016.03.052	Unchecked	25
35439009	10.1021/acs.jmedchem.1c02207	MIA PaCa-2	23
16472241	10.2174/1570163043334794	Hepatotoxicity	18
25874330	10.1016/j.ejmech.2015.03.064	A549	17
11356111	10.1021/jm0005149	Mus musculus	14
22194678	10.1371/journal.pcbi.1002310	Hepatotoxicity	14
19929004	10.1021/jm901428k	CCRF-CEM	14
15646539	10.1016/s0399-8320(04)95062-2	Unchecked	11
25874330	10.1016/j.ejmech.2015.03.064	MRC5	10
23230131	10.1124/dmd.112.048769	ADMET	10
32827851	10.1016/j.ejmech.2020.112661	T-24	10
23230131	10.1124/dmd.112.048769	Cytidine deaminase	9
28234466	10.1021/acs.jmedchem.7b00049	Rattus norvegicus	9
15646539	10.1016/s0399-8320(04)95062-2	NON-PROTEIN TARGET	8
26295308	10.18632/oncotarget.4919	HT-29	8
20930123	10.1124/dmd.110.033613	NON-PROTEIN TARGET	7
37634418	10.1016/j.bmc.2023.117458	BXPC-3	7
24120088	10.1016/j.bmc.2013.08.023	Human immunodeficiency virus 1	7
24471998	10.1021/jm401853a	NON-PROTEIN TARGET	7

Data from ChEMBL 36 via Core Engine