NAV

Bithionol

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 Approvals of the NDA's for bithionol drug products were withdrawn on October 24, 1967 (see the Federal Register of October 31, 1967 (32 FR 15046)).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Approved, Withdrawn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
3D
Similar Structures
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
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Pharmacology

Indication

Not Available

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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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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Product Ingredients
IngredientUNIICASInChI Key
Bithionolate sodium66V0139H9A6385-58-6FNYZFZRGBBCWBI-UHFFFAOYSA-L
International/Other Brands
Actamer / Bidiphen / Bisoxyphen / Bithin / Bitin / Lorothidol / Lorothiodol / Neopellis / Nobacter / Vancide BL

Categories

ATC Codes
D10AB01 — BithionolP02BX01 — Bithionol
Drug Categories
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
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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)188 °CPhysProp
water solubility4 mg/L (at 25 °C)MERCK INDEX (1996)
pKa4.82MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.00166 mg/mLALOGPS
logP6.12ALOGPS
logP5.97Chemaxon
logS-5.3ALOGPS
pKa (Strongest Acidic)4.89Chemaxon
pKa (Strongest Basic)-7.2Chemaxon
Physiological Charge-1Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area40.46 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity81.92 m3·mol-1Chemaxon
Polarizability31.3 Å3Chemaxon
Number of Rings2Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9909
Blood Brain Barrier+0.8869
Caco-2 permeable+0.7873
P-glycoprotein substrateNon-substrate0.7822
P-glycoprotein inhibitor INon-inhibitor0.943
P-glycoprotein inhibitor IINon-inhibitor0.9609
Renal organic cation transporterNon-inhibitor0.819
CYP450 2C9 substrateNon-substrate0.7194
CYP450 2D6 substrateNon-substrate0.8524
CYP450 3A4 substrateNon-substrate0.6484
CYP450 1A2 substrateInhibitor0.9107
CYP450 2C9 inhibitorInhibitor0.9127
CYP450 2D6 inhibitorNon-inhibitor0.8961
CYP450 2C19 inhibitorInhibitor0.8995
CYP450 3A4 inhibitorNon-inhibitor0.6459
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9131
Ames testNon AMES toxic0.9133
CarcinogenicityNon-carcinogens0.733
BiodegradationNot ready biodegradable0.9922
Rat acute toxicity3.1921 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9401
hERG inhibition (predictor II)Non-inhibitor0.8592
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0309000000-0f3b02346cac8d14ae58
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-c061d6a6d41550c7855c
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-0209000000-6af9d7721225b75d95c7
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0209000000-3c32a2c7a486da7be0ad
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-0901000000-d4f662611bc1b0a954c5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001i-9530000000-fcdf9ec606ff8e8e1743
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-157.6218299
predicted
DarkChem Lite v0.1.0
[M-H]-160.41953
predicted
DeepCCS 1.0 (2019)
[M+H]+162.8789501
predicted
DarkChem Lite v0.1.0
[M+H]+162.77753
predicted
DeepCCS 1.0 (2019)
[M+Na]+173.5716334
predicted
DarkChem Lite v0.1.0
[M+Na]+168.87067
predicted
DeepCCS 1.0 (2019)

Drug created at September 11, 2007 20:02 / Updated at February 21, 2021 18:51