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Identification
NameBithionol
Accession NumberDB04813
TypeSmall Molecule
GroupsWithdrawn
Description

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drug products were withdrawn on October 24, 1967 (see the Federal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)).

Structure
Thumb
Synonyms
SynonymLanguageCode
2-Hydroxy-3,5-dichlorophenyl sulfideNot AvailableNot Available
2-Hydroxy-3,5-dichlorophenyl sulphideNot AvailableNot Available
2,2'-Dihydroxy-3,3',5,5'-tetrachlorodiphenyl sulfideNot AvailableNot Available
2,2'-Dihydroxy-3,3',5,5'-tetrachlorodiphenylsulfideNot AvailableNot Available
2,2'-sulfanediylbis(4,6-dichlorophenol)Not AvailableNot Available
2,2'-Thiobis (4,6-dichlorophenol)Not AvailableNot Available
2,2'-Thiobis-(4,6-dichlorophenol)Not AvailableNot Available
2,2'-Thiobis(4,6-dichlorophenol)Not AvailableNot Available
2,2'-Thiobis[4,6-dichlorophenol]Not AvailableNot Available
Bis(2-hydroxy-3,5-dichlorophenyl) sulfideNot AvailableNot Available
Bis(3,5-dichloro-2-hydroxyphenyl) sulfideNot AvailableNot Available
BithionalNot AvailableNot Available
Bithionol sulfideNot AvailableNot Available
BithionolateNot AvailableNot Available
BithionolumLatinINN
BitionolSpanishINN
SaltsNot Available
Brand names
NameCompany
ActamerNot Available
BidiphenNot Available
BisoxyphenNot Available
BithinNot Available
BitinNot Available
BitionolNot Available
LorothidolNot Available
LorothiodolNot Available
NeopellisNot Available
NobacterNot Available
PrevenolNot Available
Vancide BLNot Available
Brand mixturesNot Available
Categories
CAS number97-18-7
WeightAverage: 356.052
Monoisotopic: 353.884260954
Chemical FormulaC12H6Cl4O2S
InChI KeyJFIOVJDNOJYLKP-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
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenols and Derivatives
Direct parentp-Chlorophenols
Alternative parentso-Chlorophenols; Dichlorobenzenes; Aryl Chlorides; Polyamines; Thioethers; Enols; Organochlorides
Substituentschlorobenzene; aryl halide; aryl chloride; thioether; enol; polyamine; organochloride; organohalogen
Classification descriptionThis compound belongs to the p-chlorophenols.
Pharmacology
IndicationNot Available
PharmacodynamicsNot Available
Mechanism of actionNot Available
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrate Inhibitor 0.9127
CYP450 2D6 substrate Non-inhibitor 0.8961
CYP450 2C19 substrate Inhibitor 0.8995
CYP450 3A4 substrate 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
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point188 °CPhysProp
water solubility4 mg/L (at 25 °C)MERCK INDEX (1996)
pKa4.82MERCK INDEX (1996)
Predicted Properties
PropertyValueSource
Water Solubility0.00166ALOGPS
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
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00802
KEGG CompoundC07967
PubChem Compound2406
PubChem Substance46508019
ChemSpider2313
ChEBI3131
ChEMBL
IUPHAR2338
Guide to Pharmacology2338
ATC CodesP02BX01D10AB01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on September 11, 2007 14:02 / Updated on September 16, 2013 17:25