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Compound Detail

CHEMBL1228

OXYPHENBUTAZONE ANHYDROUS
💊 Approved Drug
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💊 Approved Drug
CCCCC1C(=O)N(c2ccccc2)N(c2ccc(O)cc2)C1=O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL1228
Name OXYPHENBUTAZONE ANHYDROUS
Phase Approved
Structure Type MOL
InChI Key HFHZKZSRXITVMK-UHFFFAOYSA-N
Therapeutic ✓ Yes

Known Names

Californit Crovaril Flogitolo Flogoril Frabel G-27202 Neo-farmadol NSC-526053 Oxalid Oxyphenbutazone anhydrous Rapostan Reozon +3 more
5
Targets
11
Activities
2
Assay Types
0
PK Parameters
20
Publications
15
Known Names

Molecular Properties

324.4
MW (Da)
3.49
ALogP
3
HBA
1
HBD
60.9
PSA (Ų)
0.86
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1960
Availability Withdrawn
Chirality Racemic

Routes of Administration

Oral

Flags

Withdrawn Natural Product
USAN Stem -butazone

Extended Properties

Molecular Formula C19H20N2O3
MW 324.38
Aromatic Rings 2
Heavy Atoms 24
NP-Likeness 0.26

Drug Warnings

Withdrawn
hematological toxicity
serious blood dyscrasias
Country: France; United States; United Kingdom; Germany; Sweden; Bangladesh; Ethiopia; Cyprus   Year: 1984
Withdrawn
General Warning
severe adverse reactions.
Country: France; United States; United Kingdom; Germany; Sweden; Bangladesh; Ethiopia; Cyprus   Year: 1984

Activity Summary

IC50 8 meas. best 5.78
Ki 3 meas. best 9.52

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Nicotinate phosphoribosyltransferase
CHEMBL4523354
 Ki 9.52 9.52 0.3 1
Unchecked
CHEMBL612545
 IC50 5.78 5.405 1662.8 4
Glucose-6-phosphate dehydrogenase-6-phosphogluconolactonase
CHEMBL1741212
 IC50 4.9 4.9 12500.0 1
Plasmodium falciparum
CHEMBL364
 IC50 4.82 4.82 15000.0 1
Solute carrier family 22 member 6
CHEMBL1777665
 Ki 4.5 4.5 32000.0 1
Unchecked
CHEMBL612545
 Ki 4.35 4.35 44500.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Nicotinate phosphoribosyltransferase Ki = 0.3 nM 9.52 Inhibition of NAPRT (unknown origin) -
Unchecked IC50 = 1662.8 nM 5.78 PubChem BioAssay. Decreased HeLa cell count-IC50. (Class of assay: confirmator... -
Unchecked IC50 = 3293.7 nM 5.48 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture CD31-stained tube area de... -
Unchecked IC50 = 4918.9 nM 5.31 PubChem BioAssay. alkaline phosphatase stimulation in WNT3A conditioned C2C12 ce... -
Unchecked IC50 = 8826.44 nM 5.05 PubChem BioAssay. VEGF stimulated ADSC/ECFC co-culture nuclear area decrease (vi... -
Glucose-6-phosphate dehydrogenase-6-phosphogluconolactonase IC50 = 12500.0 nM 4.9 PUBCHEM_BIOASSAY: Dose Response confirmation of uHTS small molecule inhibitors o... -
Plasmodium falciparum IC50 = 15000.0 nM 4.82 Antimicrobial activity against Plasmodium falciparum 20185316
Solute carrier family 22 member 6 Ki = 32000.0 nM 4.5 TP_TRANSPORTER: inhibition of PAH uptake in Xenopus laevis oocytes 10220563
Unchecked Ki = 44500.0 nM 4.35 Binding affinity to EZH2-EED (unknown origin) protein interaction assessed as in... 35093670

Literature References

PubMed DOI Target Context # Activities
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
20299217 10.1016/j.bmcl.2010.02.093 Mus musculus 4
33422907 10.1016/j.bmc.2020.115971 Rattus norvegicus 4
20014752 10.1021/tx900326k Hepatotoxicity 3
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
22931300 10.1021/tx300075j Liver microsomes 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
35093670 10.1016/j.ejmech.2022.114144 Unchecked 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
20185316 10.1016/j.bmc.2010.01.068 NON-PROTEIN TARGET 1
20185316 10.1016/j.bmc.2010.01.068 Leishmania mexicana 1
20185316 10.1016/j.bmc.2010.01.068 Leishmania major 1
38318365 10.1016/j.isci.2024.108907 Deoxynucleoside triphosphate triphosphohydrolase SAMHD1 1
20185316 10.1016/j.bmc.2010.01.068 Trypanosoma brucei 1
20185316 10.1016/j.bmc.2010.01.068 Trypanosoma brucei brucei 1

Data from ChEMBL 36 via Core Engine