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Compound Detail

CHEMBL1130

DOXIFLURIDINE
🧪 Phase III
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🧪 Phase III
C[C@H]1O[C@@H](n2cc(F)c(=O)[nH]c2=O)[C@H](O)[C@@H]1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1130
Name DOXIFLURIDINE
Phase Phase III
Structure Type MOL
InChI Key ZWAOHEXOSAUJHY-ZIYNGMLESA-N
Active Moiety CHEMBL185

Known Names

5'-deoxy-5-fluorouridine (5'-dfur) Capecitabine related compound b Doxifluridina Doxifluridine Flutron Fulturon Furtulon NSC-758890 RO 219738 RO-219738
3
Targets
12
Activities
3
Assay Types
10
PK Parameters
20
Publications
10
Known Names
1
Indications
3
Mechanisms

Molecular Properties

246.2
MW (Da)
-1.69
ALogP
6
HBA
3
HBD
104.5
PSA (Ų)
0.55
QED
0
Ro5 Violations
1
Rot. Bonds

Drug Information

Molecule Type Small molecule
Chirality Single Enantiomer

Flags

Prodrug
USAN Stem -uridine

Extended Properties

Molecular Formula C9H11FN2O5
MW 246.19
Aromatic Rings 1
Heavy Atoms 17
NP-Likeness 0.79

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
DNA disrupting agent DISRUPTING AGENT DNA ✓ ✓
RNA disrupting agent DISRUPTING AGENT RNA ✓ ✓
Thymidylate synthase inhibitor INHIBITOR Thymidylate synthase ✓ ✓

Indications

Stomach Neoplasms

Activity Summary

IC50 9 meas. best 5.52
EC50 2 meas. best 4.57
Ki 1 meas.

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
L1210
CHEMBL386
 IC50 5.52 5.48 3000.0 2
Unchecked
CHEMBL612545
 IC50 4.93 4.5917 11820.0 6
CCRF-CEM
CHEMBL382
 IC50 4.66 4.66 22000.0 1
Unchecked
CHEMBL612545
 EC50 4.57 4.465 26750.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 11.0 mL.min-1.kg-1 Homo sapiens
CL 6.7 mL.min-1.kg-1 Homo sapiens
CL 11.0 mL.min-1.kg-1 Homo sapiens
CL 11.0 mL.min-1.kg-1 Homo sapiens
Fu 0.61 - Homo sapiens
Fu 0.61 - Homo sapiens
MRT 0.46 hr Homo sapiens
T1/2 250.0 hr -
T1/2 - hr -
T1/2 0.35 hr Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
L1210 IC50 = 3000.0 nM 5.52 Inhibition of cell growth of L1210 mouse Leukemia cells 2967375
L1210 IC50 = 3600.0 nM 5.44 Concentration required for the 50% inhibition of growth of L1210 mouse leukemia ... 7120290
Unchecked IC50 = 11820.0 nM 4.93 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
Unchecked IC50 = 13247.0 nM 4.88 PUBCHEM_BIOASSAY: A screen for inhibitors of the PhoP region in Salmonella Typhi... -
CCRF-CEM IC50 = 22000.0 nM 4.66 Concentration required for the 50% inhibition of growth of CCRF-CEM human leukem... 7120290
Unchecked IC50 = 22800.0 nM 4.64 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
Unchecked EC50 = 26750.0 nM 4.57 PUBCHEM_BIOASSAY: A cytotoxicity screen of small molecule inhibitors of the PhoP... -
Unchecked IC50 = 32180.0 nM 4.49 PUBCHEM_BIOASSAY: A small molecule screen for inhibitors of the PhoP region in S... -
Unchecked IC50 = 38600.0 nM 4.41 PUBCHEM_BIOASSAY: A Counter Screen to identiry small molecule screen for inhibit... -
Unchecked EC50 = 43770.0 nM 4.36 PUBCHEM_BIOASSAY: A cytotoxicity screen of small molecule inhibitors of the PhoP... -
Unchecked IC50 = 63680.0 nM 4.2 PUBCHEM_BIOASSAY: A counter screen for small molecule screen for inhibitors of t... -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 405
7131481 10.1021/jm00351a006 Mus musculus 24
8277499 10.1021/jm00078a006 Mus musculus 20
20070106 10.1021/jm901371v Homo sapiens 8
533880 10.1021/jm00197a010 Sarcoma-180 6
7120290 10.1021/jm00350a024 Mus musculus 6
17683933 10.1016/j.bmcl.2007.07.033 SW-620 5
18426954 10.1124/dmd.108.020479 ADMET 4
- 10.6019/CHEMBL4495565 SARS-CoV-2 4
7120290 10.1021/jm00350a024 L1210 4
20014752 10.1021/tx900326k Hepatotoxicity 3
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
19445515 10.1021/jm900403j Homo sapiens 2
2967375 10.1021/jm00401a008 Uridine phosphorylase 1 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
533880 10.1021/jm00197a010 Mus musculus 2
2967375 10.1021/jm00401a008 ADMET 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2

Data from ChEMBL 36 via Core Engine