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Compound Detail

CHEMBL917

FLOXURIDINE
💊 Approved Drug
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💊 Approved Drug
O=c1[nH]c(=O)n([C@H]2C[C@H](O)[C@@H](CO)O2)cc1F
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL917
Name FLOXURIDINE
Phase Approved
Structure Type MOL
InChI Key ODKNJVUHOIMIIZ-RRKCRQDMSA-N
Therapeutic ✓ Yes

Known Names

5-fluoro-2-deoxyuridine 5-fudr F.u.d.r. Floxuridina Floxuridine Fluoruridine deoxyribose FUDR NSC-27640
55
Targets
177
Activities
3
Assay Types
20
PK Parameters
20
Publications
8
Known Names
19
Indications
1
Mechanisms

Molecular Properties

246.2
MW (Da)
-1.68
ALogP
6
HBA
3
HBD
104.5
PSA (Ų)
0.58
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1970
Availability Prescription
Chirality Single Enantiomer

Routes of Administration

Parenteral

Flags

Black Box Warning
USAN Stem -uridine
USAN Year 1965

Extended Properties

Molecular Formula C9H11FN2O5
MW 246.19
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness 0.70

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Thymidylate synthase inhibitor INHIBITOR Thymidylate synthase ✓ ✓

Indications

Neoplasms Neoplasms Colorectal Neoplasms Colorectal Neoplasms Colorectal Neoplasms Carcinoid Tumor Carcinoma, Hepatocellular Cholangiocarcinoma Cholangiocarcinoma Esophageal Neoplasms Gastrointestinal Stromal Tumors Liver Neoplasms Ovarian Neoplasms Peritoneal Neoplasms Stomach Neoplasms Stomach Neoplasms Colonic Neoplasms Fallopian Tube Neoplasms Rectal Neoplasms

ATC Classification

L01BC09
floxuridine
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Drug Warnings

Black Box Warning
General Warning
Country: United States

Activity Summary

IC50 155 meas. best 9.4
EC50 21 meas. best 8.48
Ki 1 meas. best 5.82

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Thymidylate synthase
CHEMBL3160
 IC50 9.4 7.4921 0.4 14
L1210
CHEMBL386
 IC50 9.3 7.7807 0.5 15
L5178Y
CHEMBL614720
 IC50 9.12 7.238 0.8 15
Unchecked
CHEMBL612545
 IC50 9.05 8.4986 0.9 7
CCRF-CEM
CHEMBL382
 IC50 8.7 6.8391 2.0 11
SNU-C2A
CHEMBL614304
 IC50 8.48 8.48 3.3 1
Jurkat
CHEMBL397
 EC50 8.48 8.48 3.3 1
Cryptosporidium parvum
CHEMBL612855
 EC50 8.3 8.16 5.0 2
Ramos
CHEMBL614629
 EC50 8.12 8.12 7.5 1
FM3A
CHEMBL614297
 IC50 8.03 8.03 9.4 1
HL-60
CHEMBL383
 IC50 7.92 7.92 12.0 2
A549
CHEMBL392
 IC50 7.91 6.342 12.4 5
HCT-8
CHEMBL613510
 EC50 7.82 7.82 15.0 1
NUGC-3
CHEMBL614208
 IC50 7.82 7.82 15.0 1
HeLa
CHEMBL399
 IC50 7.68 6.01 21.0 11
A2780
CHEMBL614004
 IC50 7.58 7.58 26.0 1
HCT-15
CHEMBL612263
 IC50 7.31 7.31 49.0 1
AZ-521 cell line
CHEMBL614274
 IC50 7.3 7.3 50.0 1
TSU
CHEMBL613973
 IC50 7.24 7.24 58.0 1
LNCaP
CHEMBL612518
 IC50 7.16 7.16 69.2 1
DLD-1
CHEMBL614285
 IC50 7.04 7.04 92.0 1
MKN-28
CHEMBL614353
 IC50 6.92 6.92 120.0 1
T-24
CHEMBL614774
 IC50 6.92 6.155 120.0 2
HT-1080
CHEMBL614580
 IC50 6.92 6.835 120.0 2
SW48
CHEMBL614055
 IC50 6.89 6.89 130.0 1
MDA-MB-231
CHEMBL400
 IC50 6.68 5.55 210.0 2
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 6.62 5.092 240.0 10
C170
CHEMBL614705
 IC50 6.4 6.4 400.0 1
NIH3T3
CHEMBL614822
 IC50 6.3 5.41 500.0 6
BJ
CHEMBL614358
 EC50 6.22 5.23 596.0 2
COLO 320DM
CHEMBL614562
 IC50 6.19 6.19 650.0 1
Streptokinase A
CHEMBL1293228
 EC50 6.16 6.16 689.0 1
KKLS
CHEMBL613996
 IC50 6.12 6.12 760.0 1
Toxoplasma gondii
CHEMBL612888
 EC50 6.04 5.9825 910.0 4
Streptococcus sp. 'group A'
CHEMBL612389
 EC50 6.04 6.04 916.0 1
SW-620
CHEMBL612262
 IC50 6.02 5.925 960.0 2
Streptococcus
CHEMBL612313
 EC50 5.87 5.87 1338.0 1
Unchecked
CHEMBL612545
 Ki 5.82 5.82 1500.0 1
791T cell line
CHEMBL614254
 IC50 5.5 5.5 3200.0 1
MKN-45
CHEMBL614354
 IC50 5.46 5.46 3500.0 1
ADMET
CHEMBL612558
 IC50 5.35 5.115 4500.0 2
T47D
CHEMBL614361
 IC50 5.25 5.25 5610.0 1
T98G
CHEMBL614775
 IC50 5.25 5.25 5570.0 1
143B
CHEMBL614508
 IC50 5.22 5.035 6020.0 2
U-87 MG
CHEMBL614247
 IC50 5.21 5.21 6140.0 1
L929
CHEMBL612267
 IC50 5.11 5.11 7700.0 1
KB
CHEMBL398
 IC50 5.06 5.06 8690.0 4
HepG2
CHEMBL395
 IC50 5.05 5.05 8910.0 3
A549
CHEMBL392
 EC50 5.01 4.615 9740.0 2
HeLa
CHEMBL399
 EC50 4.99 4.99 10260.0 1

Pharmacokinetic Data

Parameter Value Units Species
AUC 308.0 ng.hr.mL-1 Rattus norvegicus
AUC 209.0 ng.hr.mL-1 Rattus norvegicus
AUC - - Rattus norvegicus
AUC - - Rattus norvegicus
AUC 232.0 ng/g.hr Rattus norvegicus
AUC 34.0 ng/g.hr Rattus norvegicus
AUC 4107.2 ng.hr.mL-1 Mus musculus
AUC 3419.0 ng.hr.mL-1 Mus musculus
Cmax 731.14 nM Rattus norvegicus
Cmax 686.46 nM Rattus norvegicus
Cmax - - Rattus norvegicus
Cmax - - Rattus norvegicus
Cmax 60.0 ng/g Rattus norvegicus
Cmax 9.0 ng/g Rattus norvegicus
Cmax 1763.27 nM Mus musculus
Cmax 374.4 ng/g Mus musculus
T1/2 0.17 hr -
T1/2 0.22 hr Homo sapiens
T1/2 0.26 hr Homo sapiens
T1/2 0.385 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Thymidylate synthase IC50 = 0.4 nM 9.4 Inhibition of thymidylate synthase in mouse L1210 cells assessed as inhibition o... 21330014
Thymidylate synthase IC50 = 0.4 nM 9.4 Inhibition of thymidylate synthase in mouse L1210 cells assessed as inhibition o... 21330014
L1210 IC50 = 0.5 nM 9.3 In vitro concentration required for 50% inhibition (IC50) of growth of L1210 mou... 6228661
Thymidylate synthase IC50 = 0.6 nM 9.22 Inhibition of thymidylate synthase in mouse L1210 cells assessed as inhibition o... 21330014
Thymidylate synthase IC50 = 0.6 nM 9.22 Inhibition of thymidylate synthase in mouse L1210 cells assessed as inhibition o... 21330014
L1210 IC50 = 0.63 nM 9.2 Cytostatic activity against mouse L1210 cells in presence of 500 uM uracil 21330014
L1210 IC50 = 0.64 nM 9.19 Growth inhibition in L1210 mouse leukemia cells after 48 hr treatment 11728193
Thymidylate synthase IC50 = 0.7 nM 9.15 Inhibition of thymidylate synthase in mouse L1210 cells assessed as inhibition o... 21330014
Thymidylate synthase IC50 = 0.7 nM 9.15 Inhibition of thymidylate synthase in mouse L1210 cells assessed as inhibition o... 21330014
L5178Y IC50 = 0.76 nM 9.12 Comparative inhibition of L5178Y cell growth in vitro (concentration required fo... 6779007
Unchecked IC50 = 0.9 nM 9.05 Cytostatic activity against mouse L1210/0 cells after 48 hrs by cell counting 21892829
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (... -
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
L1210 IC50 = 1.1 nM 8.96 Cytostatic activity against mouse L1210 cells after 2 days by coulter counting a... 21330014
CCRF-CEM IC50 = 2.0 nM 8.7 In vitro cytotoxicity of compounds were determined on Inhibition of human leukem... 8917645
L5178Y IC50 = 2.0 nM 8.7 In vitro growth inhibition of L5178Y-Parental murine leukemia cells by incorpora... 11101356
L5178Y IC50 = 2.0 nM 8.7 In vitro growth inhibition of L5178Y-Parental murine leukemia cells 11101356
L1210 IC50 = 2.3 nM 8.64 Cytostatic activity against mouse L1210 cells in presence of 500 uM uridine 21330014

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 405
7288823 10.1021/jm00141a013 Mus musculus 24
7966151 10.1021/jm00049a009 Mus musculus 18
7853342 10.1021/jm00003a012 Mus musculus 18
16472241 10.2174/1570163043334794 Hepatotoxicity 18
25644674 10.1016/j.ejmech.2015.01.045 Staphylococcus aureus 14
32882127 10.1021/acs.jmedchem.0c00149 ADMET 14
25644674 10.1016/j.ejmech.2015.01.045 Staphylococcus epidermidis 12
3397995 10.1021/jm00403a016 L1210 11
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
21892829 10.1021/jm200815w CCRF-CEM 10
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
8246229 10.1021/jm00075a016 NIH3T3 8
8246229 10.1021/jm00075a016 L5178Y 8
11101356 10.1021/jm000975u L5178Y 6
27022837 10.1021/acs.jmedchem.5b01807 Liver 6
27022837 10.1021/acs.jmedchem.5b01807 Plasma 6
21330014 10.1016/j.ejmech.2011.01.005 Thymidylate synthase 6
6447210 10.1021/jm00182a008 NON-PROTEIN TARGET 5
6447210 10.1021/jm00182a008 Sarcoma-180 5

Data from ChEMBL 36 via Core Engine