Bithionol

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Withdrawn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 Approvals of the NDA's for bithionol drug products were withdrawn on October 24, 1967 (see the Federal Register of October 31, 1967 (32 FR 15046)).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
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
  • Bitionol
External IDs
Caswell No. 852 / Usaf B-22
International/Other Brands
Actamer / Bidiphen / Bisoxyphen / Bithin / Bitin / Bitionol / Lorothidol / Lorothiodol / Neopellis / Nobacter / Prevenol / Vancide BL
Categories
UNII
AMT77LS62O
CAS number
97-18-7
Weight
Average: 356.052
Monoisotopic: 353.884260954
Chemical Formula
C12H6Cl4O2S
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

Pharmacology

Indication
Not Available
Structured Indications
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
AmodiaquineThe serum concentration of Bithionol can be decreased when it is combined with Amodiaquine.Approved, Investigational
ChloroquineThe serum concentration of Bithionol can be decreased when it is combined with Chloroquine.Approved, Vet Approved
HydroxychloroquineThe serum concentration of Bithionol can be decreased when it is combined with Hydroxychloroquine.Approved
PrimaquineThe serum concentration of Bithionol can be decreased when it is combined with Primaquine.Approved
Food Interactions
Not Available

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
IUPHAR
2338
Guide to Pharmacology
GtP Drug Page
HET
B1T
ATC Codes
D10AB01 — BithionolP02BX01 — Bithionol
PDB Entries
3etd / 5d0r

Clinical Trials

Clinical Trials
Not Available

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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Diarylthioether / 1,3-dichlorobenzene / 4-halophenol / 2-halophenol / 2-chlorophenol / 4-chlorophenol / Thiophenol ether / Chlorobenzene / Halobenzene / Phenol
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
aryl sulfide, polyphenol, dichlorobenzene, organochlorine pesticide, bridged diphenyl fungicide, bridged diphenyl antifungal drug (CHEBI:3131)

Drug created on September 11, 2007 14:02 / Updated on November 09, 2017 03:47