BITOSCANATE

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/769080
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

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hookworm infection 2 Sources: https://www.ncbi.nlm.nih.gov/pubmed/769078	Primary		Withdrawn	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Optimizing the immobilization of single-stranded DNA onto glass beads.	2001 Feb 26	11245893
Dendrimer-activated solid supports for nucleic acid and protein microarrays.	2001 Sep 3	11828505
C-terminal sequence analysis of peptides using triphenylgermanyl isothiocyanate.	2002 Mar 1	11846383
Molecular printboards: monolayers of beta-cyclodextrins on silicon oxide surfaces.	2004 Jun 22	15986687
Diisothiocyanate derivatives as potent, insurmountable antagonists of P2Y6 nucleotide receptors.	2004 May 1	15081875
[Oligonucleotide microarray preparation using enhanced poly-L-lysine glass slides].	2004 Nov	15567766
[Comparison of two amine-modified chemical platforms for DNA microarray preparation].	2005 Jul	16027070
Toxicity to Tetrahymena and abiotic thiol reactivity of aromatic isothiocyanates.	2005 May-Jul	16328896
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	15929075
Supramolecular layer-by-layer assembly of 3D multicomponent nanostructures via multivalent molecular recognition.	2008 Apr	19325764
A method for N-terminal de novo sequence analysis of proteins by matrix-assisted laser desorption/ionization mass spectrometry.	2008 Sep 15	18577371
A Novel Label-Free Optical Biosensor Using Synthetic Oligonucleotides from E. coli O157:H7: Elementary Sensitivity Tests.	2009	22408559
Surface immobilisation of antibody on cyclic olefin copolymer for sandwich immunoassay.	2009 Apr 15	19250814
Different strategies of covalent attachment of oligonucleotide probe onto glass beads and the hybridization properties.	2009 Jan	18491234
Electrochemical immunochip sensor for aflatoxin M1 detection.	2009 Jul 1	19489595
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	19165755
Application of the functionalized congener approach to dendrimer-based signaling agents acting through A(2A) adenosine receptors.	2009 Mar	18600474
p-Isothiocyanatobenzyl-desferrioxamine: a new bifunctional chelate for facile radiolabeling of monoclonal antibodies with zirconium-89 for immuno-PET imaging.	2010 Feb	19763566
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	20206011

Patents

Sample Use Guides

In Vivo Use Guide

2X 50 mg (50 mg at. 12-hourly intervals)

Route of Administration: Oral

In Vitro Use Guide

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

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Name

Type

Language

BITOSCANATE

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