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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

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
C-terminal sequence analysis of peptides using triphenylgermanyl isothiocyanate.
2002 Mar 1
Molecular printboards: monolayers of beta-cyclodextrins on silicon oxide surfaces.
2004 Jun 22
Diisothiocyanate derivatives as potent, insurmountable antagonists of P2Y6 nucleotide receptors.
2004 May 1
[Oligonucleotide microarray preparation using enhanced poly-L-lysine glass slides].
2004 Nov
Suppressive effect of 1,4-phenylene diisothiocyanate on N-butyl-N-(4-hydroxybutyl)nitrosamine-induced urinary bladder carcinogenesis in male ICR mice.
2005 Nov 20
A Novel Label-Free Optical Biosensor Using Synthetic Oligonucleotides from E. coli O157:H7: Elementary Sensitivity Tests.
2009
Surface immobilisation of antibody on cyclic olefin copolymer for sandwich immunoassay.
2009 Apr 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 Mar
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 Mar 24
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)
Name Type Language
BITOSCANATE
HSDB   INN   MI  
INN  
Official Name English
P-PHENYLENE BIS(ISOTHIOCYANATE)
Common Name English
16842
Code English
BITOSCANATE [MI]
Common Name English
BITOSCANATE [HSDB]
Common Name English
bitoscanate [INN]
Common Name English
NSC-758884
Code English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Sat Dec 16 16:52:37 GMT 2023 , Edited by admin on Sat Dec 16 16:52:37 GMT 2023
Code System Code Type Description
INN
2397
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PRIMARY
ChEMBL
CHEMBL2104676
Created by admin on Sat Dec 16 16:52:37 GMT 2023 , Edited by admin on Sat Dec 16 16:52:37 GMT 2023
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ECHA (EC/EINECS)
223-741-3
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PRIMARY
EPA CompTox
DTXSID3046532
Created by admin on Sat Dec 16 16:52:37 GMT 2023 , Edited by admin on Sat Dec 16 16:52:37 GMT 2023
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DRUG CENTRAL
3033
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HSDB
6435
Created by admin on Sat Dec 16 16:52:37 GMT 2023 , Edited by admin on Sat Dec 16 16:52:37 GMT 2023
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FDA UNII
6D1R3P86GX
Created by admin on Sat Dec 16 16:52:37 GMT 2023 , Edited by admin on Sat Dec 16 16:52:37 GMT 2023
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SMS_ID
100000086324
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EVMPD
SUB05861MIG
Created by admin on Sat Dec 16 16:52:37 GMT 2023 , Edited by admin on Sat Dec 16 16:52:37 GMT 2023
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PUBCHEM
19958
Created by admin on Sat Dec 16 16:52:37 GMT 2023 , Edited by admin on Sat Dec 16 16:52:37 GMT 2023
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MESH
C032582
Created by admin on Sat Dec 16 16:52:37 GMT 2023 , Edited by admin on Sat Dec 16 16:52:37 GMT 2023
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NSC
758884
Created by admin on Sat Dec 16 16:52:37 GMT 2023 , Edited by admin on Sat Dec 16 16:52:37 GMT 2023
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NCI_THESAURUS
C72149
Created by admin on Sat Dec 16 16:52:37 GMT 2023 , Edited by admin on Sat Dec 16 16:52:37 GMT 2023
PRIMARY
WIKIPEDIA
BITOSCANATE
Created by admin on Sat Dec 16 16:52:37 GMT 2023 , Edited by admin on Sat Dec 16 16:52:37 GMT 2023
PRIMARY
CAS
4044-65-9
Created by admin on Sat Dec 16 16:52:37 GMT 2023 , Edited by admin on Sat Dec 16 16:52:37 GMT 2023
PRIMARY
MERCK INDEX
m2579
Created by admin on Sat Dec 16 16:52:37 GMT 2023 , Edited by admin on Sat Dec 16 16:52:37 GMT 2023
PRIMARY Merck Index