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Compound Detail

CHEMBL185

FLUOROURACIL
💊 Approved Drug
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💊 Approved Drug
O=c1[nH]cc(F)c(=O)[nH]1
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL185
Name FLUOROURACIL
Phase Approved
Structure Type MOL
InChI Key GHASVSINZRGABV-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

5 FU 5-fluorouracil 5-fluoruracil 5-FU 5.f.u. Accusite Actikerall Adrucil Carac Efudex Efudix Fluoro-uracil roche +14 more
216
Targets
2,501
Activities
3
Assay Types
19
PK Parameters
20
Publications
26
Known Names
20
Indications
3
Mechanisms

Molecular Properties

130.1
MW (Da)
-0.80
ALogP
2
HBA
2
HBD
65.7
PSA (Ų)
0.48
QED
0
Ro5 Violations
0
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1962
Availability Prescription
Chirality Achiral

Routes of Administration

Parenteral Topical
USAN Stem -racil; -uracil
USAN Year 1962

Extended Properties

Molecular Formula C4H3FN2O2
MW 130.08
Aromatic Rings 1
Heavy Atoms 9
NP-Likeness -0.80

Mechanism of Action

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

Indications

Adenocarcinoma Adenocarcinoma Carcinoma, Basal Cell Keratosis Keratosis, Actinic Neoplasms Neoplasms Anus Neoplasms Anus Neoplasms Anus Neoplasms Biliary Tract Neoplasms Biliary Tract Neoplasms Breast Neoplasms Breast Neoplasms Carcinoma Carcinoma Carcinoma, Hepatocellular Carcinoma, Neuroendocrine Carcinoma, Pancreatic Ductal Carcinoma, Squamous Cell

ATC Classification

L01BC02
fluorouracil
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS
L01BC52
fluorouracil, combinations
Level 1: ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
Level 2: ANTINEOPLASTIC AGENTS

Activity Summary

IC50 2,468 meas. best 8.4
EC50 32 meas. best 6.85
Ki 1 meas. best 4.89

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
HepG2
CHEMBL395
 IC50 8.4 4.7997 4.0 155
KB
CHEMBL398
 IC50 8.35 5.32 4.5 20
NON-PROTEIN TARGET
CHEMBL3879801
 IC50 8.0 5.0581 10.0 282
A549
CHEMBL392
 IC50 8.0 5.0207 10.0 184
OVCAR-3
CHEMBL614213
 IC50 8.0 6.36 10.0 2
PC-3
CHEMBL390
 IC50 7.8 5.0193 16.0 75
A-431
CHEMBL614069
 IC50 7.75 6.975 18.0 2
HT-29
CHEMBL384
 IC50 7.73 5.1927 18.8 51
Thymidylate synthase
CHEMBL3160
 IC50 7.7 6.592 20.0 5
LNCaP
CHEMBL612518
 IC50 7.52 5.4338 30.0 8
MOLT-4
CHEMBL614177
 IC50 7.52 5.6617 30.0 6
THP-1
CHEMBL614245
 IC50 7.4 6.2367 40.0 3
RPMI-8226
CHEMBL614882
 IC50 7.4 7.4 40.0 1
NCI-H460
CHEMBL396
 IC50 7.3 4.9777 50.0 31
HCC 2998
CHEMBL613855
 IC50 7.3 5.4033 50.0 6
Malme-3M
CHEMBL614021
 IC50 7.3 7.3 50.0 1
HL-60
CHEMBL383
 IC50 7.22 5.1082 60.0 28
SF-539
CHEMBL614860
 IC50 7.22 5.2967 60.0 3
MCF7
CHEMBL387
 IC50 7.16 5.0049 70.0 222
CAKI-1
CHEMBL614067
 IC50 7.16 7.16 70.0 1
MDA-MB-435
CHEMBL614697
 IC50 7.16 5.97 70.0 3
SW-620
CHEMBL612262
 IC50 7.1 5.3913 80.0 24
HCT-15
CHEMBL612263
 IC50 6.96 5.0156 110.0 18
Unchecked
CHEMBL612545
 IC50 6.96 4.9121 110.0 61
HeLa
CHEMBL399
 IC50 6.95 5.1508 113.0 130
L1210
CHEMBL386
 IC50 6.92 6.2049 120.0 37
CFPAC-1
CHEMBL613506
 IC50 6.85 6.356 140.0 5
BXPC-3
CHEMBL614530
 EC50 6.85 6.85 140.0 1
COLO 205
CHEMBL614561
 IC50 6.82 5.256 150.0 15
LX-2
CHEMBL5465457
 IC50 6.75 6.75 178.0 1
FM3A
CHEMBL614297
 IC50 6.75 6.75 180.0 1
WI-38
CHEMBL614391
 IC50 6.72 5.1717 192.0 18
Vero
CHEMBL391
 IC50 6.7 5.2717 200.0 6
KM12
CHEMBL614709
 IC50 6.68 5.2543 210.0 7
HCT-116
CHEMBL394
 IC50 6.66 4.9991 220.0 122
HeLa
CHEMBL399
 EC50 6.64 5.37 230.0 2
Caco-2
CHEMBL614058
 IC50 6.58 5.2973 266.0 15
ACHN
CHEMBL614519
 IC50 6.57 6.57 270.0 1
HaCaT
CHEMBL614392
 IC50 6.52 5.6325 300.0 4
HEp-2
CHEMBL614735
 IC50 6.52 5.545 300.0 4
NON-PROTEIN TARGET
CHEMBL3879801
 EC50 6.51 5.1244 310.0 9
ADMET
CHEMBL612558
 IC50 6.51 4.8773 310.0 26
NCI/ADR-RES
CHEMBL613829
 IC50 6.51 5.385 310.0 2
SK-MES-1
CHEMBL614923
 IC50 6.51 5.695 310.0 2
NCI-H23
CHEMBL614997
 IC50 6.48 6.48 330.0 1
A498
CHEMBL614516
 IC50 6.46 6.46 350.0 1
DU-145
CHEMBL613508
 IC50 6.44 5.295 360.0 26
Ehrlich
CHEMBL614641
 IC50 6.42 5.4933 380.0 3
HOP-62
CHEMBL614643
 IC50 6.41 6.41 390.0 1
HUVEC
CHEMBL613979
 IC50 6.37 4.6175 430.0 8

Pharmacokinetic Data

Parameter Value Units Species
AUC 76550.0 ng.hr.mL-1 Mus musculus
AUC 13551.0 ng.hr.mL-1 Rattus norvegicus
CL 26.0 mL.min-1.kg-1 Homo sapiens
CL 26.0 mL.min-1.kg-1 Homo sapiens
CL 98.38 mL.min-1.kg-1 Rattus norvegicus
Cmax 326337638.38 nM Mus musculus
Cmax 29266.61 nM Rattus norvegicus
F 49.0 % Homo sapiens
Fu 0.64 - Homo sapiens
MRT 0.15 hr Homo sapiens
MRT 2.484 hr Rattus norvegicus
T1/2 0.12 hr Homo sapiens
T1/2 4.36 hr Mus musculus
T1/2 2.354 hr Rattus norvegicus
T1/2 0.1333 hr Homo sapiens
T1/2 0.2667 hr Mus musculus
T1/2 1.36 hr Mus musculus
Vd 24.12 L.kg-1 Mus musculus
Vd 20.06 L.kg-1 Rattus norvegicus

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
HepG2 IC50 = 4.0 nM 8.4 Cytotoxicity against human HepG2 cells assessed as cell growth inhibition 35964428
KB IC50 = 4.46 nM 8.35 Cytotoxicity against human KB cells by MTT assay 19345581
A549 IC50 = 10.0 nM 8.0 Cytotoxicity against human A549 cells after 48 hrs by SRB assay 25259515
NON-PROTEIN TARGET IC50 = 10.0 nM 8.0 Cytotoxicity against human THP1 cells assessed as inhibition of cell growth afte... -
OVCAR-3 IC50 = 10.0 nM 8.0 Cytotoxicity against human OVCAR-3 cells assessed as cell growth inhibition 36470105
PC-3 IC50 = 16.0 nM 7.8 Antiproliferative activity against human PC3 cells after 48 hrs by MTT assay 19423198
A-431 IC50 = 18.0 nM 7.75 Antiproliferative activity against human A431 cells after 48 hrs by MTT assay 19423198
HT-29 IC50 = 18.77 nM 7.73 Antiproliferative activity against human HT-29 cells assessed as reduction in ce... 36269639
Thymidylate synthase IC50 = 20.0 nM 7.7 Inhibition of thymidylate synthase in mouse L1210 cells assessed as inhibition o... 21330014
MOLT-4 IC50 = 30.0 nM 7.52 Antitumor activity against human MOLT4 cells after 24 hrs by MTT assay 20211564
LNCaP IC50 = 30.0 nM 7.52 Cytotoxicity against human LNCAP cells assessed as growth inhibition after 24 hr... 27156770
NON-PROTEIN TARGET IC50 = 30.0 nM 7.52 Cytotoxicity against human PC3 cells assessed as growth inhibition after 24 hrs ... 27156770
THP-1 IC50 = 40.0 nM 7.4 Cytotoxicity against human THP1 cells after 48 hrs by SRB assay 25259515
RPMI-8226 IC50 = 40.0 nM 7.4 Cytotoxicity against human RPMI-8226 cells assessed as cell growth inhibition 36470105
NCI-H460 IC50 = 50.0 nM 7.3 Cytotoxicity against human NCI-H460 cells assessed as cell growth inhibition 36470105
HCC 2998 IC50 = 50.0 nM 7.3 Cytotoxicity against human HCC 2998 cells assessed as cell growth inhibition 36470105
Malme-3M IC50 = 50.0 nM 7.3 Cytotoxicity against human Malme-3M cells assessed as cell growth inhibition 36470105
HL-60 IC50 = 60.0 nM 7.22 Cytotoxicity against human HL60 cells after 72 hrs by MTT assay 22959518
SF-539 IC50 = 60.0 nM 7.22 Cytotoxicity against human SF-539 cells assessed as cell growth inhibition 36470105
Thymidylate synthase IC50 = 60.0 nM 7.22 Inhibition of thymidylate synthase in mouse L1210 cells assessed as inhibition o... 21330014

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 259
23994328 10.1016/j.ejmech.2013.07.027 NON-PROTEIN TARGET 30
24469112 10.1016/j.ejmech.2014.01.004 NON-PROTEIN TARGET 27
23683592 10.1016/j.bmcl.2013.04.056 NON-PROTEIN TARGET 27
22995621 10.1016/j.bmcl.2012.08.095 NON-PROTEIN TARGET 27
27554444 10.1016/j.bmcl.2016.08.022 NON-PROTEIN TARGET 27
23474899 10.1016/j.ejmech.2013.02.006 NON-PROTEIN TARGET 27
20930123 10.1124/dmd.110.033613 NON-PROTEIN TARGET 25
22056277 10.1016/j.ejmech.2011.10.023 NON-PROTEIN TARGET 24
19704126 10.1128/aac.00607-09 Candida dubliniensis 21
22119151 10.1016/j.ejmech.2011.11.013 NON-PROTEIN TARGET 21
8277499 10.1021/jm00078a006 Mus musculus 20
32485532 10.1016/j.ejmech.2020.112439 MCF7 20
7328578 10.1021/jm00142a011 P388 18
20350811 10.1016/j.bmc.2010.03.019 NON-PROTEIN TARGET 18
16472241 10.2174/1570163043334794 Hepatotoxicity 18
32795627 10.1016/j.bmcl.2020.127470 Heat shock protein HSP90 17
18950904 10.1016/j.ejmech.2008.09.015 NON-PROTEIN TARGET 16
32485532 10.1016/j.ejmech.2020.112439 A549 16
7853342 10.1021/jm00003a012 Mus musculus 15

Data from ChEMBL 36 via Core Engine