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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
Optimizing the immobilization of single-stranded DNA onto glass beads.
2001 Feb 26
C-terminal sequence analysis of peptides using triphenylgermanyl isothiocyanate.
2002 Mar 1
Diisothiocyanate derivatives as potent, insurmountable antagonists of P2Y6 nucleotide receptors.
2004 May 1
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
p-Isothiocyanatobenzyl-desferrioxamine: a new bifunctional chelate for facile radiolabeling of monoclonal antibodies with zirconium-89 for immuno-PET imaging.
2010 Feb
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)
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:52:37 GMT 2023
Edited
by admin
on Sat Dec 16 16:52:37 GMT 2023
Record UNII
6D1R3P86GX
Record Status Validated (UNII)
Record Version
  • Download
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
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
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
PRIMARY
ECHA (EC/EINECS)
223-741-3
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
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
PRIMARY
DRUG CENTRAL
3033
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
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
PRIMARY
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
PRIMARY
SMS_ID
100000086324
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
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
PRIMARY
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
Related Record Type Details
ACTIVE MOIETY