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Compound Detail

CHEMBL291338

3,3',4',5-TETRACHLOROSALICYLANILIDE
💊 Approved Drug
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💊 Approved Drug
O=C(Nc1ccc(Cl)c(Cl)c1)c1cc(Cl)cc(Cl)c1O
ChEMBL ↗ Properties Compare Identifier

Basic Information

ChEMBL ID CHEMBL291338
Name 3,3',4',5-TETRACHLOROSALICYLANILIDE
Phase Approved
Structure Type MOL
InChI Key SJQBHPJLLIJASD-UHFFFAOYSA-N

Known Names

3,3',4',5-tetrachlorosalicylanilide Irgasan bs200
9
Targets
11
Activities
2
Assay Types
0
PK Parameters
20
Publications
2
Known Names
1
Mechanisms

Molecular Properties

351.0
MW (Da)
5.26
ALogP
2
HBA
2
HBD
49.3
PSA (Ų)
0.78
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn
USAN Stem -ilide; -sal-

Extended Properties

Molecular Formula C13H7Cl4NO2
MW 351.02
Aromatic Rings 2
Heavy Atoms 20
NP-Likeness -1.52

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - - ✓ ✓

Drug Warnings

Withdrawn
dermatological toxicity
Photosensitivity reactions
Country: Japan   Year: 1976
Withdrawn
dermatological toxicity
Photosensitivity reactions
Country: Japan   Year: 1976
Withdrawn
dermatological toxicity
potent photosensitizers and can cause disabling skin disorders
Country: United States   Year: 1975
Withdrawn
dermatological toxicity
potent photosensitizers and can cause disabling skin disorders
Country: United States   Year: 1975

Activity Summary

IC50 9 meas. best 6.27
EC50 2 meas. best 5.1

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Prostaglandin G/H synthase 2
CHEMBL230
 IC50 6.27 6.27 542.0 1
Prostaglandin G/H synthase 1
CHEMBL221
 IC50 6.18 6.18 666.0 1
Mitogen-activated protein kinase 1
CHEMBL4040
 IC50 6.05 6.05 886.0 1
Mitogen-activated protein kinase 14
CHEMBL260
 IC50 5.66 5.66 2176.0 1
Thromboxane-A synthase
CHEMBL1835
 IC50 5.31 5.31 4927.0 1
Trypanosoma cruzi
CHEMBL368
 EC50 5.1 5.1 8000.0 1
Hepatitis C virus
CHEMBL379
 IC50 5.07 5.07 8600.0 1
ADMET
CHEMBL612558
 EC50 4.58 4.58 26000.0 1
KinA/Spo0F (sporulation kinase A/sporulation initiation phosphotransferase F)
CHEMBL2111331
 IC50 4.43 4.3767 37000.0 3

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Prostaglandin G/H synthase 2 IC50 = 542.0 nM 6.27 DRUGMATRIX: Cyclooxygenase COX-2 enzyme inhibition (substrate: Arachidonic acid) -
Prostaglandin G/H synthase 1 IC50 = 666.0 nM 6.18 DRUGMATRIX: Cyclooxygenase COX-1 enzyme inhibition (substrate: Arachidonic acid) -
Mitogen-activated protein kinase 1 IC50 = 886.0 nM 6.05 DRUGMATRIX: Protein Serine/Threonine Kinase, ERK2 enzyme inhibition (substrate: ... -
Mitogen-activated protein kinase 14 IC50 = 2176.0 nM 5.66 DRUGMATRIX: Protein Serine/Threonine Kinase, p38alpha enzyme inhibition (substra... -
Thromboxane-A synthase IC50 = 4927.0 nM 5.31 DRUGMATRIX: Thromboxane Synthetase enzyme inhibition (substrate: PGH2) -
Trypanosoma cruzi EC50 = 8000.0 nM 5.1 Antitrypanosomal activity against Trypanosoma cruzi amastigotes infected in BESM... 20547819
Hepatitis C virus IC50 = 8600.0 nM 5.07 Inhibition of HCV 1b NS5B polymerase 18479921
ADMET EC50 = 26000.0 nM 4.58 Cytotoxicity against BESM cells after 88 hrs by HTS assay 20547819
KinA/Spo0F (sporulation kinase A/sporulation initiation phosphotransferase F) IC50 = 37000.0 nM 4.43 Ability to inhibit autophosphorylation of KinA/Sp0F assay 9873461
KinA/Spo0F (sporulation kinase A/sporulation initiation phosphotransferase F) IC50 = 45000.0 nM 4.35 Inhibition of autophosphorylation of the two-component signal transduction syste... 9685233
KinA/Spo0F (sporulation kinase A/sporulation initiation phosphotransferase F) IC50 = 45000.0 nM 4.35 Inhibition of histidine protein kinase (KinA) phosphorylation in the presence of... 9873460

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 405
21075637 10.1016/j.bmc.2010.10.036 Staphylococcus aureus 4
9685233 10.1021/jm9803572 Staphylococcus aureus 2
21075637 10.1016/j.bmc.2010.10.036 Unchecked 2
9873460 10.1016/s0960-894x(98)00326-6 Staphylococcus aureus 2
9685233 10.1021/jm9803572 Enterococcus faecalis 2
9873461 10.1016/s0960-894x(98)00325-4 Bacteria 1
9873460 10.1016/s0960-894x(98)00326-6 KinA/Spo0F (sporulation kinase A/sporulation initiation phosphotransferase F) 1
9873461 10.1016/s0960-894x(98)00325-4 KinA/Spo0F (sporulation kinase A/sporulation initiation phosphotransferase F) 1
9873460 10.1016/s0960-894x(98)00326-6 Enterococcus faecalis 1
9873460 10.1016/s0960-894x(98)00326-6 Enterococcus faecium 1
9873460 10.1016/s0960-894x(98)00326-6 No relevant target 1
18479921 10.1016/j.bmcl.2008.04.068 Hepatitis C virus 1
20547819 10.1128/aac.01777-09 ADMET 1
20547819 10.1128/aac.01777-09 Trypanosoma cruzi 1
20547819 10.1128/aac.01777-09 Unchecked 1
9685233 10.1021/jm9803572 Enterococcus faecium 1
21075637 10.1016/j.bmc.2010.10.036 Stenotrophomonas maltophilia 1
21075637 10.1016/j.bmc.2010.10.036 Serratia marcescens 1
21075637 10.1016/j.bmc.2010.10.036 Mycolicibacterium smegmatis 1

Data from ChEMBL 36 via Core Engine