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Compound Detail

CHEMBL348000

CINCHOPHEN
💊 Approved Drug
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💊 Approved Drug
O=C(O)c1cc(-c2ccccc2)nc2ccccc12

Basic Information

ChEMBL ID CHEMBL348000
Name CINCHOPHEN
Phase Approved
Structure Type MOL
InChI Key YTRMTPPVNRALON-UHFFFAOYSA-N

Known Names

Cinchophen Cinchophene Cincofeno NSC-2617
1
Targets
4
Activities
2
Assay Types
0
PK Parameters
20
Publications
4
Known Names
1
Indications

Molecular Properties

249.3
MW (Da)
3.60
ALogP
2
HBA
1
HBD
50.2
PSA (Ų)
0.75
QED
0
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn Natural Product

Extended Properties

Molecular Formula C16H11NO2
MW 249.27
Aromatic Rings 3
Heavy Atoms 19
NP-Likeness -0.88

Indications

Gout

ATC Classification

M04AC02
cinchophen
Level 1: MUSCULO-SKELETAL SYSTEM
Level 2: ANTIGOUT PREPARATIONS

Drug Warnings

Withdrawn
hepatotoxicity
Hepatic toxicity, including jaundice, hepatitis and cirrhosis and a greater incidence of gastric ulceration than is associated with other nonsteroidal antiinflammatory agents
Country: Germany; Italy   Year: 1991
Withdrawn
hepatotoxicity
Hepatic toxicity, including jaundice, hepatitis and cirrhosis and a greater incidence of gastric ulceration than is associated with other nonsteroidal antiinflammatory agents
Country: Germany; Italy   Year: 1991
Withdrawn
General Warning
Unfavourable risk-benefit ratio
Country: Germany; Italy   Year: 1991
Withdrawn
hepatotoxicity
Hepatic toxicity, including jaundice, hepatitis and cirrhosis and a greater incidence of gastric ulceration than is associated with other nonsteroidal antiinflammatory agents
Country: Germany; Italy   Year: 1991
Withdrawn
gastrointestinal toxicity
Hepatic toxicity, including jaundice, hepatitis and cirrhosis and a greater incidence of gastric ulceration than is associated with other nonsteroidal antiinflammatory agents
Country: Germany; Italy   Year: 1991
Withdrawn
hepatotoxicity
Hepatic toxicity, including jaundice, hepatitis and cirrhosis and a greater incidence of gastric ulceration than is associated with other nonsteroidal antiinflammatory agents
Country: Germany; Italy   Year: 1991
Withdrawn
hepatotoxicity
Hepatic toxicity, including jaundice, hepatitis and cirrhosis and a greater incidence of gastric ulceration than is associated with other nonsteroidal antiinflammatory agents
Country: Germany; Italy   Year: 1991

Activity Summary

IC50 3 meas.
Kd 1 meas. best 3.9

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A
CHEMBL4409
Kd 3.9 3.9 127000.0 1

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
20014752 10.1021/tx900326k Hepatotoxicity 3
- 10.6019/CHEMBL4495565 SARS-CoV-2 2
- 10.6019/CHEMBL4513161 Pseudomonas aeruginosa 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 2
23509991 10.1021/jm301665y cAMP and cAMP-inhibited cGMP 3',5'-cyclic phosphodiesterase 10A 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
21965623 10.1124/dmd.111.040758 Bile salt export pump 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
26948801 10.1016/j.drudis.2016.02.015 Homo sapiens 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
21965623 10.1124/dmd.111.040758 Plasma 1
29727569 10.1021/acs.jmedchem.7b01862 MIA PaCa-2 1
22961681 10.1124/dmd.112.047068 Bile salt export pump 1
21624500 10.1016/j.drudis.2011.05.007 Hepatotoxicity 1
20843939 10.1124/dmd.110.035113 Hepatotoxicity 1
20553011 10.1021/tx1000865 Hepatotoxicity 1
17201408 10.1021/jm0602256 P-selectin glycoprotein ligand 1 1

Data from ChEMBL 36 via Core Engine