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Trematode infection 1F8Y Withdrawn from market [1], [2]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 356
Topological Polar Surface Area (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 [3]
Estrogen receptor (ESR) TTZAYWL ESR1_HUMAN Inhibitor [3]
Estrogen receptor beta (ESR2) TTOM3J0 ESR2_HUMAN Inhibitor [3]
Induced myeloid leukemia cell differentiation protein Mcl-1 (MCL1) TTL53M6 MCL1_HUMAN Inhibitor [3]
Molecular Interaction Atlas (MIA) 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) Jump to Detail Molecular Expression Atlas of This Drug

References

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2 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3 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.
4 Interpreting expression profiles of cancers by genome-wide survey of breadth of expression in normal tissues. Genomics 2005 Aug;86(2):127-41.
5 An updated patent review of calpain inhibitors (2012 - 2014).Expert Opin Ther Pat. 2015 Jan;25(1):17-31.
6 Phase II study of obatoclax mesylate (GX15-070), a small-molecule BCL-2 family antagonist, for patients with myelofibrosis. Clin Lymphoma Myeloma Leuk. 2010 Aug;10(4):285-9.
7 Clinical pipeline report, company report or official report of the Pharmaceutical Research and Manufacturers of America (PhRMA)
8 Clinical pipeline report, company report or official report of Prelude Therapeutics.
9 Clinical pipeline report, company report or official report of AbbVie.
10 MCL1 inhibitors S63845/MIK665 plus Navitoclax synergistically kill difficult-to-treat melanoma cells. Cell Death Dis. 2020 Jun 8;11(6):443.
11 Clinical pipeline report, company report or official report of Amgen.
12 Mcl-1 inhibitors: a patent review.Expert Opin Ther Pat. 2017 Feb;27(2):163-178.
13 Differential biochemical and cellular actions of Premarin estrogens: distinct pharmacology of bazedoxifene-conjugated estrogens combination. Mol Endocrinol. 2009 Jan;23(1):74-85.
14 Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services.
15 Benzothiophene selective estrogen receptor modulators with modulated oxidative activity and receptor affinity. J Med Chem. 2007 May 31;50(11):2682-92.
16 Estrogen inhibits the vascular injury response in estrogen receptor beta-deficient female mice. Proc Natl Acad Sci U S A. 1999 Dec 21;96(26):15133-6.
17 Lovastatin and beyond: the history of the HMG-CoA reductase inhibitors. Nat Rev Drug Discov. 2003 Jul;2(7):517-26.
18 MF101, a selective estrogen receptor beta modulator for the treatment of menopausal hot flushes: a phase II clinical trial. Menopause. 2009 May-Jun;16(3):458-65.
19 Company report (Axcentua)
20 S-equol, a potent ligand for estrogen receptor beta, is the exclusive enantiomeric form of the soy isoflavone metabolite produced by human intestinal bacterial flora. Am J Clin Nutr. 2005 May;81(5):1072-9.
21 Erb-041, an estrogen receptor-beta agonist, inhibits skin photocarcinogenesis in SKH-1 hairless mice by downregulating the WNT signaling pathway. Cancer Prev Res (Phila). 2014 Feb;7(2):186-98.
22 Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800031986)
23 Modulators of vascular sex hormone receptors and their effects in estrogen-deficiency states associated with menopause. Recent Pat Cardiovasc Drug Discov. 2008 Nov;3(3):165-86.
24 Reprint of Are all estrogens the same Maturitas. 2008 Sep-Oct;61(1-2):195-201.
25 17alpha-Ethinylestradiol hinders nucleotide excision repair in zebrafish liver cells. Aquat Toxicol. 2009 Dec 13;95(4):273-8.
26 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. (Target id: 620).
27 Clinical pipeline report, company report or official report of Shionogi (2011).
28 Effect of selective estrogen receptor modulators on cell proliferation and estrogen receptor activities in normal human prostate stromal and epithe... Prostate Cancer Prostatic Dis. 2009;12(4):375-81.