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Compound Detail

CHEMBL267744

TICRYNAFEN
💊 Approved Drug
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💊 Approved Drug
O=C(O)COc1ccc(C(=O)c2cccs2)c(Cl)c1Cl

Basic Information

ChEMBL ID CHEMBL267744
Name TICRYNAFEN
Phase Approved
Structure Type MOL
InChI Key AGHANLSBXUWXTB-UHFFFAOYSA-N

Known Names

Acide tienilique Acido tienilico Selacryn SK&F 62698 SK&F-62698 Ticrynafen Tienilic acid
2
Targets
3
Activities
2
Assay Types
5
PK Parameters
20
Publications
7
Known Names
1
Indications
1
Mechanisms

Molecular Properties

331.2
MW (Da)
3.75
ALogP
4
HBA
1
HBD
63.6
PSA (Ų)
0.85
QED
0
Ro5 Violations
5
Rot. Bonds

Drug Information

Molecule Type Small molecule
First Approval 1979
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn Natural Product
USAN Year 1975

Extended Properties

Molecular Formula C13H8Cl2O4S
MW 331.18
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -1.22

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - -

Indications

Cardiovascular Diseases

ATC Classification

C03CC02
tienilic acid
Level 1: CARDIOVASCULAR SYSTEM
Level 2: DIURETICS

Drug Warnings

Withdrawn
hepatotoxicity
Liver Toxicity and Death
Country: France; United States; United Kingdom; Germany; Philippines   Year: 1980
Withdrawn
hepatotoxicity
Liver Toxicity and Death
Country: France; United States; United Kingdom; Germany; Philippines   Year: 1980
Withdrawn
hepatotoxicity
Liver Toxicity and Death
Country: France; United States; United Kingdom; Germany; Philippines   Year: 1980
Withdrawn
hepatotoxicity
deaths due to liver dysfunction
Country: France; United States; United Kingdom; Germany; Philippines   Year: 1980
Withdrawn
hepatotoxicity
deaths due to liver dysfunction
Country: France; United States; United Kingdom; Germany; Philippines   Year: 1980
Withdrawn
hepatotoxicity
deaths due to liver dysfunction
Country: France; United States; United Kingdom; Germany; Philippines   Year: 1980
Withdrawn
hepatotoxicity
Liver Toxicity
Country: France; United States; United Kingdom; Germany; Philippines   Year: 1980
Withdrawn
hepatotoxicity
Liver Toxicity
Country: France; United States; United Kingdom; Germany; Philippines   Year: 1980

Activity Summary

Ki 2 meas. best 5.37
IC50 1 meas. best 5.49

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Aldo-keto reductase family 1 member B1
CHEMBL2622
IC50 5.49 5.49 3206.0 1
Cytochrome P450 2C9
CHEMBL3397
Ki 5.37 5.165 4300.0 2

Pharmacokinetic Data

Parameter Value Units Species
CL 61.0 uL.min-1.(10^6cells)-1 Rattus norvegicus
CL 82.0 mL.min-1.g-1 Homo sapiens
CL 4.2e-05 mL.min-1.g-1 Homo sapiens
CL 6.9e-05 mL.min-1.g-1 Homo sapiens
CL 0.111 uL/min Homo sapiens

Activity Data Samples

Top measurements by pChEMBL value

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 270
15646539 10.1016/s0399-8320(04)95062-2 Unchecked 11
7086820 10.1021/jm00343a008 Canis familiaris 8
7277395 10.1021/jm00139a019 Canis familiaris 8
15646539 10.1016/s0399-8320(04)95062-2 NON-PROTEIN TARGET 8
16248836 10.2174/138920005774330639 Cytochrome P450 2C9 4
7277395 10.1021/jm00139a019 Rattus norvegicus 4
21467212 10.1124/dmd.111.039180 Liver microsome 3
6431103 10.1021/jm00374a014 Mus musculus 3
21321060 10.1124/dmd.110.037259 Cytochrome P450 2C9 3
20014752 10.1021/tx900326k Hepatotoxicity 3
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 2
22931300 10.1021/tx300075j Cytochrome P450 3A4 2
22931300 10.1021/tx300075j Liver microsomes 2
- 10.6019/CHEMBL3301361 ADMET 2
19939518 10.1016/j.ejmech.2009.10.025 Hematopoietic prostaglandin D synthase 2
21467212 10.1124/dmd.111.039180 ADMET 2
7086820 10.1021/jm00343a008 Mus musculus 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
6431103 10.1021/jm00374a014 Canis familiaris 2

Data from ChEMBL 36 via Core Engine