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Compound Detail

CHEMBL290106

BITHIONOL
💊 Approved Drug
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💊 Approved Drug
Oc1c(Cl)cc(Cl)cc1Sc1cc(Cl)cc(Cl)c1O

Basic Information

ChEMBL ID CHEMBL290106
Name BITHIONOL
Phase Approved
Structure Type MOL
InChI Key JFIOVJDNOJYLKP-UHFFFAOYSA-N

Known Names

Bithin Bithionol Bitionol Lorothidol NSC-47129
37
Targets
79
Activities
4
Assay Types
0
PK Parameters
20
Publications
5
Known Names
2
Indications
1
Mechanisms

Molecular Properties

356.1
MW (Da)
5.86
ALogP
3
HBA
2
HBD
40.5
PSA (Ų)
0.71
QED
1
Ro5 Violations
2
Rot. Bonds

Drug Information

Molecule Type Small molecule
Availability Withdrawn
Chirality Achiral

Flags

Withdrawn Natural Product
USAN Year 1962

Extended Properties

Molecular Formula C12H6Cl4O2S
MW 356.06
Aromatic Rings 2
Heavy Atoms 19
NP-Likeness -0.45

Mechanism of Action

Mechanism Action Type Target Direct Efficacy
Unknown - -

Indications

Acne Vulgaris Helminthiasis

ATC Classification

D10AB01
bithionol
Level 1: DERMATOLOGICALS
Level 2: ANTI-ACNE PREPARATIONS
P02BX01
bithionol
Level 1: ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
Level 2: ANTHELMINTICS

Drug Warnings

Withdrawn
dermatological toxicity
shown to be a potent photosensitizer with the potential to cause serious skin disorders
Country: United States; Japan   Year: 1967
Withdrawn
dermatological toxicity
shown to be a potent photosensitizer with the potential to cause serious skin disorders
Country: United States; Japan   Year: 1967
Withdrawn
dermatological toxicity
shown to be a potent photosensitizer with the potential to cause serious skin disorders
Country: United States; Japan   Year: 1967
Withdrawn
dermatological toxicity
Dermatologic Toxicity
Country: United States; Japan   Year: 1967
Withdrawn
dermatological toxicity
Dermatologic Toxicity
Country: United States; Japan   Year: 1967
Withdrawn
dermatological toxicity
Photosensitivity reactions
Country: United States; Japan   Year: 1967
Withdrawn
dermatological toxicity
Photosensitivity reactions
Country: United States; Japan   Year: 1967

Activity Summary

IC50 58 meas. best 9.0
Ki 13 meas. best 6.33
EC50 6 meas. best 6.0
Kd 2 meas. best 7.21

Target Activity Profile

Target Type Best pChEMBL Mean pChEMBL Best (nM) # Data
Unchecked
CHEMBL612545
IC50 9.0 6.3511 1.0 19
Transthyretin
CHEMBL3194
Kd 7.21 6.585 62.0 2
Mitogen-activated protein kinase 14
CHEMBL260
IC50 6.5 6.5 318.0 1
Mitogen-activated protein kinase 1
CHEMBL4040
IC50 6.42 6.42 385.0 1
Adenosine receptor A3
CHEMBL256
Ki 6.33 6.33 468.0 1
Alpha-2B adrenergic receptor
CHEMBL1942
Ki 6.25 6.25 560.0 1
Epidermal growth factor receptor
CHEMBL203
IC50 6.21 6.21 614.0 1
Alpha-2C adrenergic receptor
CHEMBL1916
Ki 6.2 6.2 638.0 1
Adenosine receptor A2a
CHEMBL251
Ki 6.18 6.18 655.0 1
Adenosine receptor A3
CHEMBL256
IC50 6.08 6.08 829.0 1
Nuclear receptor subfamily 1 group I member 2
CHEMBL3401
EC50 6.0 5.45 1000.0 2
Adenosine receptor A2a
CHEMBL251
IC50 5.93 5.93 1167.0 1
Unchecked
CHEMBL612545
EC50 5.92 5.28 1210.0 4
Alpha-2B adrenergic receptor
CHEMBL1942
IC50 5.91 5.91 1226.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
Ki 5.91 5.91 1225.0 1
Sodium-dependent noradrenaline transporter
CHEMBL222
IC50 5.91 5.91 1235.0 1
D(3) dopamine receptor
CHEMBL234
Ki 5.84 5.84 1433.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
Ki 5.84 5.84 1434.0 1
Substance-K receptor
CHEMBL2327
Ki 5.81 5.81 1553.0 1
Sodium-dependent dopamine transporter
CHEMBL238
Ki 5.76 5.76 1733.0 1
Thromboxane-A synthase
CHEMBL1835
IC50 5.74 5.74 1840.0 1
Solute carrier family 22 member 2
CHEMBL1743122
IC50 5.72 5.72 1900.0 1
Induced myeloid leukemia cell differentiation protein Mcl-1
CHEMBL4361
IC50 5.72 5.72 1898.9 1
Receptor tyrosine-protein kinase erbB-2
CHEMBL1824
IC50 5.67 5.67 2147.0 1
Sodium-dependent dopamine transporter
CHEMBL238
IC50 5.66 5.66 2181.0 1
Tyrosine-protein kinase Lck
CHEMBL258
IC50 5.65 5.65 2255.0 1
Solute carrier family 22 member 1
CHEMBL5685
IC50 5.65 5.53 2230.0 2
Mu-type opioid receptor
CHEMBL233
Ki 5.65 5.65 2236.0 1
Transthyretin
CHEMBL3194
IC50 5.62 5.57 2400.0 2
HSP60/HSP10
CHEMBL4106131
IC50 5.55 5.55 2800.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
Ki 5.5 5.5 3152.0 1
Alpha-2A adrenergic receptor
CHEMBL1867
IC50 5.42 5.42 3824.0 1
Estrogen receptor
CHEMBL206
IC50 5.4 5.4 3940.9 1
D(3) dopamine receptor
CHEMBL234
IC50 5.38 5.38 4218.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
Ki 5.37 5.37 4320.0 1
GroEL/GroES
CHEMBL4106139
IC50 5.37 5.13 4300.0 2
Alpha-2C adrenergic receptor
CHEMBL1916
IC50 5.36 5.36 4392.0 1
5-hydroxytryptamine receptor 2C
CHEMBL225
Ki 5.34 5.34 4599.0 1
Substance-K receptor
CHEMBL2327
IC50 5.33 5.33 4659.0 1
Calpain-2 catalytic subunit
CHEMBL4143
IC50 5.32 5.32 4751.1 1
Multidrug and toxin extrusion protein 1
CHEMBL1743126
IC50 5.28 5.28 5200.0 1
5-hydroxytryptamine receptor 1A
CHEMBL273
IC50 5.26 5.26 5515.0 1
Mu-type opioid receptor
CHEMBL233
IC50 5.26 5.26 5507.0 1
Solute carrier family 22 member 3
CHEMBL2073673
IC50 5.26 5.26 5500.0 1
Envelope glycoprotein gp160
CHEMBL1293311
IC50 5.21 5.21 6160.0 1
Multidrug and toxin extrusion protein 2
CHEMBL1743127
IC50 5.18 5.18 6600.0 1
5-hydroxytryptamine receptor 2B
CHEMBL1833
IC50 5.17 5.17 6789.0 1
Estrogen receptor beta
CHEMBL242
IC50 5.09 5.09 8147.1 1
5-hydroxytryptamine receptor 2C
CHEMBL225
IC50 5.06 5.06 8780.0 1
Pup--protein ligase
CHEMBL5169231
IC50 4.8 4.8 15900.0 1

Activity Data Samples

Top measurements by pChEMBL value

Target Type Rel. Value Units pChEMBL Assay PubMed
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. RKO viability from Cell TiterGlo-IC50. (Class of assay: conf... -
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. SW480 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. HCT116 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. DLD-1 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Unchecked IC50 = 1.0 nM 9.0 PubChem BioAssay. GSK3B-pretreated HCT116 viability from Cell TiterGlo-IC50. (... -
Unchecked IC50 = 8.67 nM 8.06 PubChem BioAssay. SNU-C1 viability from Cell TiterGlo-IC50. (Class of assay: c... -
Unchecked IC50 = 15.05 nM 7.82 PubChem BioAssay. Colo320 viability from Cell TiterGlo-IC50. (Class of assay: ... -
Transthyretin Kd = 62.0 nM 7.21 Binding affinity to TTR V30M mutant (unknown origin) by isothermal titration cal... 34547896
Mitogen-activated protein kinase 14 IC50 = 318.0 nM 6.5 DRUGMATRIX: Protein Serine/Threonine Kinase, p38alpha enzyme inhibition (substra... -
Mitogen-activated protein kinase 1 IC50 = 385.0 nM 6.42 DRUGMATRIX: Protein Serine/Threonine Kinase, ERK2 enzyme inhibition (substrate: ... -
Adenosine receptor A3 Ki = 468.0 nM 6.33 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
Alpha-2B adrenergic receptor Ki = 560.0 nM 6.25 DRUGMATRIX: Alpha-2B adrenergic receptor radioligand binding (ligand: Rauwolscin... -
Epidermal growth factor receptor IC50 = 614.0 nM 6.21 DRUGMATRIX: Protein Tyrosine Kinase, EGF Receptor enzyme inhibition (substrate: ... -
Alpha-2C adrenergic receptor Ki = 638.0 nM 6.2 DRUGMATRIX: Adrenergic Alpha-2C radioligand binding (ligand: [3H] MK-912) -
Adenosine receptor A2a Ki = 655.0 nM 6.18 DRUGMATRIX: Adenosine A2A radioligand binding (ligand: AB-MECA) -
Adenosine receptor A3 IC50 = 829.0 nM 6.08 DRUGMATRIX: Adenosine A3 radioligand binding (ligand: AB-MECA) -
Unchecked IC50 = 995.9 nM 6.0 PubChem BioAssay. HT-29 viability from Cell TiterGlo-IC50. (Class of assay: co... -
Nuclear receptor subfamily 1 group I member 2 EC50 = 1000.0 nM 6.0 Competitive binding affinity to human PXR LBD (111 to 434) by TR-FRET assay 20966043
Transthyretin Kd = 1100.0 nM 5.96 Binding affinity to TTR V30M mutant (unknown origin) expressed in Escherichia co... 34547896
Adenosine receptor A2a IC50 = 1167.0 nM 5.93 DRUGMATRIX: Adenosine A2A radioligand binding (ligand: AB-MECA) -

Literature References

PubMed DOI Target Context # Activities
- 10.6019/CHEMBL3885881 Rattus norvegicus 434
34547896 10.1021/acs.jmedchem.1c00823 Transthyretin 13
- 10.6019/CHEMBL4495565 SARS-CoV-2 6
20966043 10.1124/dmd.110.035105 Nuclear receptor subfamily 1 group I member 2 6
30852084 10.1016/j.bmcl.2019.02.028 GroEL/GroES 4
32171615 10.1016/j.bmcl.2020.127099 Staphylococcus aureus 4
23241029 10.1021/jm301302s Multidrug and toxin extrusion protein 1 2
- 10.6019/CHEMBL4495564 Replicase polyprotein 1ab 2
35926511 10.1021/acs.jmedchem.2c00289 Pup--protein ligase 2
- 10.6019/CHEMBL4495565 Vero C1008 2
- 10.6019/CHEMBL4808148 Histone deacetylase 6 2
34825185 10.1039/D1MD00211B Cell membrane 2
37468498 10.1038/s41467-023-40064-9 Prostaglandin G/H synthase 1 2
37468498 10.1038/s41467-023-40064-9 Muscarinic acetylcholine receptor M1 2
- 10.6019/CHEMBL4495565 ADMET 2
34458737 10.1039/D1MD00151E Staphylococcus aureus 2
- 10.6019/CHEMBL4651402 SARS-CoV-2 2
37468498 10.1038/s41467-023-40064-9 Thromboxane A2 receptor 2
37468498 10.1038/s41467-023-40064-9 Alpha-1A adrenergic receptor 2
22194678 10.1371/journal.pcbi.1002310 Hepatotoxicity 1

Data from ChEMBL 36 via Core Engine