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Identification
Name Bithionol
Accession Number DB04813
Type small molecule
Groups withdrawn
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drug products were withdrawn on October 24, 1967 (see the Federal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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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)
2,2'-Thiobis-(4,6-dichlorophenol)
2,2'-Thiobis(4,6-dichlorophenol)
2,2'-Thiobis[4,6-dichlorophenol]
Bis(2-hydroxy-3,5-dichlorophenyl) sulfide
Bis(3,5-dichloro-2-hydroxyphenyl) sulfide
Bithional
Bithionol sulfide
Bithionolate
Bithionolum [inn-latin]
Bitionol [inn-spanish]
Caswell No. 852
Usaf B-22
First Prev Next Last
Salts Not Available
Brand names
Name Company
Actamer
Bidiphen
Bisoxyphen
Bithin
Bitin
Bitionol
Lorothidol
Lorothiodol
Neopellis
Nobacter
Prevenol
Vancide BL
First Prev Next Last
Brand mixtures Not Available
Categories
  • Anti-Infective Agents, Local
  • Antiplatyhelmintic Agents
CAS number 97-18-7
Weight Average: 356.052
Monoisotopic: 353.884260954
Chemical Formula C12H6Cl4O2S
InChI Key InChIKey=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
Plain Text
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
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Not Available
Classes Not Available
Substructures Not Available
Pharmacology
Indication Not Available
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
Toxicity Not Available
Affected organisms Not Available
Pathways Not Available
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 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 1.66e-03 g/l 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 ChemAxon
rotatable bond count 2 ChemAxon
refractivity 81.92 ChemAxon
polarizability 31.3 ChemAxon
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00802 Link_out
KEGG Compound C07967 Link_out
PubChem Compound 2406 Link_out
PubChem Substance 46508019 Link_out
ChemSpider 2313 Link_out
ChEBI 3131 Link_out
ChEMBL 3131 Link_out
IUPHAR 2338 Link_out
Guide to Pharmacology 2338 Link_out
ATC Codes
  • P02BX01
  • D10AB01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Comments
Drug created on September 11, 2007 14:02 / Updated on February 08, 2013 16:23