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Details

Stereochemistry ACHIRAL
Molecular Formula C8H4N2S2
Molecular Weight 192.261
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 2
Charge 0

SHOW SMILES / InChI
Structure of BITOSCANATE

SMILES

S=C=NC1=CC=C(C=C1)N=C=S

InChI

InChIKey=OMWQUXGVXQELIX-UHFFFAOYSA-N
InChI=1S/C8H4N2S2/c11-5-9-7-1-2-8(4-3-7)10-6-12/h1-4H

HIDE SMILES / InChI

Molecular Formula C8H4N2S2
Molecular Weight 192.261
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 2
Optical Activity NONE

Description
Curator's Comment: The description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/769078 | https://www.ncbi.nlm.nih.gov/pubmed/955553 | https://www.ncbi.nlm.nih.gov/pubmed/769062 | https://www.ncbi.nlm.nih.gov/pubmed/26639764

Bitoscanate is a tasteless, odorless, colorless, needle-like crystalline solid material prepared from mustard powder acid and used as an anthelmintic against nematodes, especially hookworms (Necator sp.) and Ancylostoma duodenale. Side effects reported with therapeutic use have been nausea, vomiting, diarrhea, abdominal pain or discomfort, loss of appetite, dizziness or giddiness, vertigo, weakness, headache, and an itching sensation over the body. Such side effects have most often been mild and required no treatment. Bitoscanate is classified as an extremely hazardous substance in the United States as defined in Section 302 of the U.S. Emergency Planning and Community Right-to-Know Act (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities which produce, store, or use it in significant quantities.

Originator

Sources: Recueil des Travaux Chimiques des Pays-Bas et de la Belgique (1955), 74, 1262-8

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Immobilization of trypsin onto 1,4-diisothiocyanatobenzene-activated porous glass for microreactor-based peptide mapping by capillary electrophoresis: effect of calcium ions on the immobilization procedure.
2010-03-24
p-Isothiocyanatobenzyl-desferrioxamine: a new bifunctional chelate for facile radiolabeling of monoclonal antibodies with zirconium-89 for immuno-PET imaging.
2010-02
Electrochemical immunochip sensor for aflatoxin M1 detection.
2009-07-01
Surface immobilisation of antibody on cyclic olefin copolymer for sandwich immunoassay.
2009-04-15
The specific isolation of C-terminal peptides of proteins through a transamination reaction and its advantage for introducing functional groups into the peptide.
2009-03
Application of the functionalized congener approach to dendrimer-based signaling agents acting through A(2A) adenosine receptors.
2009-03
Different strategies of covalent attachment of oligonucleotide probe onto glass beads and the hybridization properties.
2009-01
A Novel Label-Free Optical Biosensor Using Synthetic Oligonucleotides from E. coli O157:H7: Elementary Sensitivity Tests.
2009
A method for N-terminal de novo sequence analysis of proteins by matrix-assisted laser desorption/ionization mass spectrometry.
2008-09-15
Supramolecular layer-by-layer assembly of 3D multicomponent nanostructures via multivalent molecular recognition.
2008-04
Suppressive effect of 1,4-phenylene diisothiocyanate on N-butyl-N-(4-hydroxybutyl)nitrosamine-induced urinary bladder carcinogenesis in male ICR mice.
2005-11-20
[Comparison of two amine-modified chemical platforms for DNA microarray preparation].
2005-07
Toxicity to Tetrahymena and abiotic thiol reactivity of aromatic isothiocyanates.
2004-12-22
[Oligonucleotide microarray preparation using enhanced poly-L-lysine glass slides].
2004-11
Molecular printboards: monolayers of beta-cyclodextrins on silicon oxide surfaces.
2004-06-22
Diisothiocyanate derivatives as potent, insurmountable antagonists of P2Y6 nucleotide receptors.
2004-05-01
C-terminal sequence analysis of peptides using triphenylgermanyl isothiocyanate.
2002-03-01
Dendrimer-activated solid supports for nucleic acid and protein microarrays.
2001-09-03
Optimizing the immobilization of single-stranded DNA onto glass beads.
2001-02-26
Patents

Patents

Sample Use Guides

In Vivo Use Guide
2X 50 mg (50 mg at. 12-hourly intervals)
Route of Administration: Oral
The antiproliferative activity of Bitoscanate was evaluated on the human colon adenocarcinoma cell line (LoVo) and the doxorubicin-resistant human colon adenocarcinoma cell line (LoVo/DX) by means of the sulforhodamine B (SRB) assay. The impact of the compounds under study on cells viability is presented as a 50% growth inhibitory concentration (IC50) with doxorubicin used as reference. Bitoscanate shows moderate antiproliferative activity with IC50 = 9.41 mkM (LoVo) and 11.6 mkM (LoVo/DX)
Substance Class Chemical
Created
by admin
on Wed Apr 02 08:29:05 GMT 2025
Edited
by admin
on Wed Apr 02 08:29:05 GMT 2025
Record UNII
6D1R3P86GX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
BITOSCANATE
HSDB   INN   MI  
INN  
Official Name English
BITOSCANATE [HSDB]
Preferred Name English
P-PHENYLENE BIS(ISOTHIOCYANATE)
Common Name English
16842
Code English
BITOSCANATE [MI]
Common Name English
bitoscanate [INN]
Common Name English
NSC-758884
Code English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
Code System Code Type Description
INN
2397
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
ChEMBL
CHEMBL2104676
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
ECHA (EC/EINECS)
223-741-3
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
EPA CompTox
DTXSID3046532
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
DRUG CENTRAL
3033
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
HSDB
6435
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
FDA UNII
6D1R3P86GX
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
SMS_ID
100000086324
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
EVMPD
SUB05861MIG
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
PUBCHEM
19958
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
MESH
C032582
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
NSC
758884
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
NCI_THESAURUS
C72149
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
WIKIPEDIA
BITOSCANATE
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
CAS
4044-65-9
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY
MERCK INDEX
m2579
Created by admin on Wed Apr 02 08:29:05 GMT 2025 , Edited by admin on Wed Apr 02 08:29:05 GMT 2025
PRIMARY Merck Index
Related Record Type Details
ACTIVE MOIETY