Explore a selection of our essential drug information below, or:
Identification
- Generic Name
- Bithionol
- DrugBank Accession Number
- DB04813
- Background
Bithionol, formerly marketed as an active ingredient in various topical drug products, was shown to be a potent photosensitizer with the potential to cause serious skin disorders. Approvals of the NDA's for bithionol drug products were withdrawn on October 24, 1967 (see the Federal Register of October 31, 1967 (32 FR 15046)).
- Type
- Small Molecule
- Groups
- Approved, Withdrawn
- Structure
Structure for Bithionol (DB04813)
- Weight
- Average: 356.052
Monoisotopic: 353.884260954 - Chemical Formula
- C12H6Cl4O2S
- Synonyms
- 2-Hydroxy-3,5-dichlorophenyl sulfide
- 2-Hydroxy-3,5-dichlorophenyl sulphide
- 2,2'-Dihydroxy-3,3',5,5'-tetrachlorodiphenyl sulfide
- 2,2'-Dihydroxy-3,3',5,5'-tetrachlorodiphenylsulfide
- 2,2'-sulfanediylbis(4,6-dichlorophenol)
- 2,2'-Thiobis(4,6-dichlorophenol)
- Bis(3,5-dichloro-2-hydroxyphenyl) sulfide
- Bithionol
- Bithionol sulfide
- Bithionolate
- Bithionolum
- Bitionol
- External IDs
- Caswell No. 852
- CP 3438
- USAF B-22
Pharmacology
- Indication
Not Available
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Not Available
- Mechanism of action
Target Actions Organism AEstrogen receptor inhibitorHumans ACalpain-2 catalytic subunit inhibitorHumans AEstrogen receptor beta inhibitorHumans AInduced myeloid leukemia cell differentiation protein Mcl-1 inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- Not Available
Products
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Ingredient UNII CAS InChI Key Bithionolate sodium 66V0139H9A 6385-58-6 FNYZFZRGBBCWBI-UHFFFAOYSA-L - International/Other Brands
- Actamer / Bidiphen / Bisoxyphen / Bithin / Bitin / Lorothidol / Lorothiodol / Neopellis / Nobacter / Vancide BL
Categories
- ATC Codes
- D10AB01 — Bithionol
- D10AB — Preparations containing sulfur
- D10A — ANTI-ACNE PREPARATIONS FOR TOPICAL USE
- D10 — ANTI-ACNE PREPARATIONS
- D — DERMATOLOGICALS
- Drug Categories
- Anthelmintics
- Anti-Acne Preparations
- Anti-Acne Preparations for Topical Use
- Anti-Infective Agents
- Anti-Infective Agents, Local
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiplatyhelmintic Agents
- Antitrematodals
- Benzene Derivatives
- Dermatologicals
- Phenols
- Preparations Containing Sulfur
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diarylthioethers. These are organosulfur compounds containing a thioether group that is substituted by two aryl groups.
- Kingdom
- Organic compounds
- Super Class
- Organosulfur compounds
- Class
- Thioethers
- Sub Class
- Aryl thioethers
- Direct Parent
- Diarylthioethers
- Alternative Parents
- Thiophenol ethers / P-chlorophenols / O-chlorophenols / Dichlorobenzenes / Aryl chlorides / Sulfenyl compounds / Organooxygen compounds / Organochlorides / Hydrocarbon derivatives
- Substituents
- 1,3-dichlorobenzene / 2-chlorophenol / 2-halophenol / 4-chlorophenol / 4-halophenol / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Benzenoid / Chlorobenzene
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- aryl sulfide, polyphenol, dichlorobenzene, organochlorine pesticide, bridged diphenyl fungicide, bridged diphenyl antifungal drug (CHEBI:3131)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- AMT77LS62O
- CAS number
- 97-18-7
- InChI Key
- JFIOVJDNOJYLKP-UHFFFAOYSA-N
- 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
- IUPAC Name
- 2,4-dichloro-6-[(3,5-dichloro-2-hydroxyphenyl)sulfanyl]phenol
- SMILES
- OC1=C(SC2=C(O)C(Cl)=CC(Cl)=C2)C=C(Cl)C=C1Cl
References
- General References
- Not Available
- External Links
- KEGG Drug
- D00802
- KEGG Compound
- C07967
- PubChem Compound
- 2406
- PubChem Substance
- 46508019
- ChemSpider
- 2313
- BindingDB
- 36880
- ChEBI
- 3131
- ChEMBL
- CHEMBL290106
- ZINC
- ZINC000000608213
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- B1T
- Wikipedia
- Bithionol
- PDB Entries
- 3etd / 5d0r / 7erh
Clinical Trials
- Clinical Trials
Clinical Trial & Rare Diseases Add-on Data Package
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Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 188 °C PhysProp water solubility 4 mg/L (at 25 °C) MERCK INDEX (1996) pKa 4.82 MERCK INDEX (1996) - Predicted Properties
Property Value Source Water Solubility 0.00166 mg/mL ALOGPS logP 6.12 ALOGPS logP 5.97 Chemaxon logS -5.3 ALOGPS pKa (Strongest Acidic) 4.89 Chemaxon pKa (Strongest Basic) -7.2 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 40.46 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 81.92 m3·mol-1 Chemaxon Polarizability 31.3 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9909 Blood Brain Barrier + 0.8869 Caco-2 permeable + 0.7873 P-glycoprotein substrate Non-substrate 0.7822 P-glycoprotein inhibitor I Non-inhibitor 0.943 P-glycoprotein inhibitor II Non-inhibitor 0.9609 Renal organic cation transporter Non-inhibitor 0.819 CYP450 2C9 substrate Non-substrate 0.7194 CYP450 2D6 substrate Non-substrate 0.8524 CYP450 3A4 substrate Non-substrate 0.6484 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Inhibitor 0.9127 CYP450 2D6 inhibitor Non-inhibitor 0.8961 CYP450 2C19 inhibitor Inhibitor 0.8995 CYP450 3A4 inhibitor Non-inhibitor 0.6459 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9131 Ames test Non AMES toxic 0.9133 Carcinogenicity Non-carcinogens 0.733 Biodegradation Not ready biodegradable 0.9922 Rat acute toxicity 3.1921 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9401 hERG inhibition (predictor II) Non-inhibitor 0.8592
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0309000000-0f3b02346cac8d14ae58 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0009000000-c061d6a6d41550c7855c Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udi-0209000000-6af9d7721225b75d95c7 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0209000000-3c32a2c7a486da7be0ad Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-0901000000-d4f662611bc1b0a954c5 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-9530000000-fcdf9ec606ff8e8e1743 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 157.6218299 predictedDarkChem Lite v0.1.0 [M-H]- 160.41953 predictedDeepCCS 1.0 (2019) [M+H]+ 162.8789501 predictedDarkChem Lite v0.1.0 [M+H]+ 162.77753 predictedDeepCCS 1.0 (2019) [M+Na]+ 173.5716334 predictedDarkChem Lite v0.1.0 [M+Na]+ 168.87067 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3 (PubMed:17922032). Maintains neuronal survival in response to ischemic reperfusion injury when in the presence of circulating estradiol (17-beta-estradiol/E2) (By similarity)
- Specific Function
- 14-3-3 protein binding
- Gene Name
- ESR1
- Uniprot ID
- P03372
- Uniprot Name
- Estrogen receptor
- Molecular Weight
- 66215.45 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Calcium-regulated non-lysosomal thiol-protease which catalyzes limited proteolysis of substrates involved in cytoskeletal remodeling and signal transduction. Proteolytically cleaves MYOC at 'Arg-226' (PubMed:17650508). Proteolytically cleaves CPEB3 following neuronal stimulation which abolishes CPEB3 translational repressor activity, leading to translation of CPEB3 target mRNAs (By similarity)
- Specific Function
- calcium ion binding
- Gene Name
- CAPN2
- Uniprot ID
- P17655
- Uniprot Name
- Calpain-2 catalytic subunit
- Molecular Weight
- 79994.545 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Nuclear hormone receptor. Binds estrogens with an affinity similar to that of ESR1/ER-alpha, and activates expression of reporter genes containing estrogen response elements (ERE) in an estrogen-dependent manner (PubMed:20074560)
- Specific Function
- DNA binding
- Gene Name
- ESR2
- Uniprot ID
- Q92731
- Uniprot Name
- Estrogen receptor beta
- Molecular Weight
- 59215.765 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Involved in the regulation of apoptosis versus cell survival, and in the maintenance of viability but not of proliferation. Mediates its effects by interactions with a number of other regulators of apoptosis. Isoform 1 inhibits apoptosis. Isoform 2 promotes apoptosis
- Specific Function
- BH domain binding
- Gene Name
- MCL1
- Uniprot ID
- Q07820
- Uniprot Name
- Induced myeloid leukemia cell differentiation protein Mcl-1
- Molecular Weight
- 37336.975 Da
References
- Zhou Y, Zhang Y, Zhao D, Yu X, Shen X, Zhou Y, Wang S, Qiu Y, Chen Y, Zhu F: TTD: Therapeutic Target Database describing target druggability information. Nucleic Acids Res. 2024 Jan 5;52(D1):D1465-D1477. doi: 10.1093/nar/gkad751. [Article]
Drug created at September 11, 2007 20:02 / Updated at October 03, 2024 04:25