Details of the Drug

General Information of Drug (ID: DMPJKRL)

Drug Name

BITHIONOL

Synonyms

bithionol; 97-18-7; Actamer; Bithin; 2,2'-Thiobis(4,6-dichlorophenol); Lorothidol; Bitionol; Bithionol sulfide; Bisoxyphen; Bidiphen; Lorothiodol; Bitin; Nobacter; Bithionolate; Neopellis; Vancide BL; Usaf B-22; Bithional; Bithionolum; 2-Hydroxy-3,5-dichlorophenyl sulfide; TKhsd; Bis(2-hydroxy-3,5-dichlorophenyl) sulfide; Bis(3,5-dichloro-2-hydroxyphenyl) sulfide; 2,2'-sulfanediylbis(4,6-dichlorophenol); Caswell No. 852; Bitionol [INN-Spanish]; XL 7; Bithionolum [INN-Latin]; 2,2'-Dihydroxy-3,3',5,5'-tetrachlorodiphenyl sulfide

Indication

Disease Entry	ICD 11	Status	REF
Trematode infection	1F8Y	Withdrawn from market	[1]
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Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 1

Molecular Weight (mw)

356

Logarithm of the Partition Coefficient (xlogp)

5.8

Rotatable Bond Count (rotbonds)

2

Hydrogen Bond Donor Count (hbonddonor)

2

Hydrogen Bond Acceptor Count (hbondacc)

3

Chemical Identifiers

Formula: C12H6Cl4O2S
IUPAC Name: 2,4-dichloro-6-(3,5-dichloro-2-hydroxyphenyl)sulfanylphenol
Canonical SMILES: C1=C(C=C(C(=C1SC2=C(C(=CC(=C2)Cl)Cl)O)O)Cl)Cl
InChI: InChI=1S/C12H6Cl4O2S/c13-5-1-7(15)11(17)9(3-5)19-10-4-6(14)2-8(16)12(10)18/h1-4,17-18H
InChIKey: JFIOVJDNOJYLKP-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 2406
ChEBI ID: CHEBI:3131
CAS Number: 97-18-7
DrugBank ID: DB04813
TTD ID: D0QQ1J
VARIDT ID: DR00936

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Calpain-2 (CAPN2)	TTG5QB7	CAN2_HUMAN	Inhibitor	[2]
Estrogen receptor (ESR)	TTZAYWL	ESR1_HUMAN	Inhibitor	[2]
Estrogen receptor beta (ESR2)	TTOM3J0	ESR2_HUMAN	Inhibitor	[2]
Induced myeloid leukemia cell differentiation protein Mcl-1 (MCL1)	TTL53M6	MCL1_HUMAN	Inhibitor	[2]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Gene/Protein Processing	[3]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Trematode infection

ICD Disease Classification

1F8Y

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Calpain-2 (CAPN2)	DTT	CAPN2	5.15E-14	0.35	1.04

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2338).
2	In silico identification and biochemical evaluation of novel inhibitors of NRH:quinone oxidoreductase 2 (NQO2). Bioorg Med Chem Lett. 2010 Dec 15;20(24):7331-6.
3	Identification of environmental chemicals that activate p53 signaling after in vitro metabolic activation. Arch Toxicol. 2022 Jul;96(7):1975-1987. doi: 10.1007/s00204-022-03291-5. Epub 2022 Apr 18.