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Details

Stereochemistry ACHIRAL
Molecular Formula C14H8N2S4
Molecular Weight 332.487
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2,2'-DITHIOBISBENZOTHIAZOLE

SMILES

S(SC1=NC2=CC=CC=C2S1)C3=NC4=CC=CC=C4S3

InChI

InChIKey=AFZSMODLJJCVPP-UHFFFAOYSA-N
InChI=1S/C14H8N2S4/c1-3-7-11-9(5-1)15-13(17-11)19-20-14-16-10-6-2-4-8-12(10)18-14/h1-8H

HIDE SMILES / InChI

Molecular Formula C14H8N2S4
Molecular Weight 332.487
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: https://www.google.com/patents/US4755608; https://www.ncbi.nlm.nih.gov/pubmed/19158128; https://www.ncbi.nlm.nih.gov/pubmed/20197752; https://www.ncbi.nlm.nih.gov/pubmed/20197752; http://www.fda.gov/downloads/BiologicsBloodVaccines/Allergenics/UCM294327.pdf

2,2'-dithiobisbenzothiazole is a Standardized Chemical Allergen as labeled by US Food and Drug Administration. and can cause an allergic contact dermatitis.Its physiologic effect is by means of increased histamine release, and cell-mediated immunity. 2,2'-dithiobis(benzothiazole) is a useful compound in the rubber industry as a vulcanization accelerator. 2,2'-dithiobis(benzothiazole) was marketed to the rubber industry under the tradename Altax(TM) by the R. T. Vanderbilt Company, Inc. and was originally developed for safe processing of rubber compounds cured at above 142° C. 2,2'-dithiobis(benzothiazole) is widely used in compounds of all types for many major commercial applications. It may be carcinogenic for human. The mortality (1955-2005) and cancer morbidity experience (1971-2005) of a cohort of 363 male production workers exposed to MBT while employed at a chemical factory in north Wales showed a significant excess mortality for cancers of the large intestine.

Originator

Curator's Comment: was marketed to the rubber industry under the tradename Altax(TM) by the R. T. Vanderbilt Company, Inc.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
T.R.U.E. TEST

Approved Use

T.R.U.E. TEST(R) is an epicutaneous patch test indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 18 years of age and older whose history suggests sensitivity to one or more of the 35 substances included on the T.R.U.E. TEST panels.
PubMed

PubMed

TitleDatePubMed
Inactivation of the human papillomavirus-16 E6 oncoprotein by organic disulfides.
2000 Nov
Determination of the sensitising activity of the rubber contact sensitisers TMTD, ZDMC, MBT and DEA in a modified local lymph node assay and the effect of sodium dodecyl sulfate pretreatment on local lymph node responses.
2002 Jul 1
Diagnostic screening for contact allergy to mercaptobenzothiazole derivatives.
2002 Jun
Allergic contact dermatitis from rubber bands in 3 postal workers.
2003 Dec
Development and application of an LC-MS method to determine possible migration of mercaptobenzothiazole, benzothiazole and related vulcanization residues from rubber used in contact with food and drink.
2003 Feb
Occupational rubber glove allergy: results of the Information Network of Departments of Dermatology (IVDK), 1995-2001.
2003 Jan
[Allergy to mercaptobenzothiazole and mercapto mix].
2004 Aug-Sep
Homolytic cleavage and aggregation processes in cyclopentadienylchromium chemistry.
2004 Mar
One-pot synthesis of high-quality zinc-blende CdS nanocrystals.
2004 Nov 10
Contact dermatitis of the feet: a study of 53 cases.
2004 Sep
Mercaptobenzothiazole or the mercapto-mix: which should be in the standard series?
2006 Jul
Allergic contact dermatitis from mercapto compounds.
2006 Jun
Bikini dermatitis due to mercaptobenzothiazole.
2006 Jun
Both mercaptobenzothiazole and mercapto mix should be part of the standard series.
2006 Nov
Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway.
2007 Aug
Solid state differentiation of plasma thiols using a centrifugally activated mercaptobenzothiazole disulfide exchange indicator.
2007 Feb 14
Chemical changes in rubber allergens during vulcanization.
2007 Sep
Mercaptobenzothiazole allergenicity-role of the thiol group.
2008
The oxidative degradation of 2-mercaptobenzothiazole at the interface of beta-MnO2 and water.
2008 Jun 15
Cancer risks in chemical production workers exposed to 2-mercaptobenzothiazole.
2009 Apr
Mercaptobenzothiazole-on-gold organic phase biosensor systems: 1. Enhanced organosphosphate pesticide determination.
2009 Feb
A case of airborne allergic contact dermatitis by rubber additives.
2010 Feb
Patents

Sample Use Guides

Apply the three adhesive panels of allergens and allergen mixes on healthy skin of the back. Remove panels and evaluate the skin 48 hours after application. Re-evaluate the skin 72 to 96 hours after application. Three adhesive panels consisting of 35 allergen and allergen mix patches and a negative control. Panel 3.3 contains 12 allergens and allergen mixes including mercaptobenzothiazole (Position 32) (purity ≥98.5%) The gel vehicle is povidone. The product is formulated to contain 75 ug/cm2 of mercaptobenzothiazole, which corresponds to 61 ug of mercaptobenzothiazole per patch.
Route of Administration: Topical
The cytotoxicity of 2-mercaptobenzothiazole [MBT] on bacteria was evaluated by the SOS/umu test using Salmonella typhimurium TA1535/pSK1002. MBT showed more than 50% cytotoxicity at its highest concentrations in a dose-dependent manner with LC50 of 19 mg/L.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:16:13 GMT 2023
Edited
by admin
on Fri Dec 15 15:16:13 GMT 2023
Record UNII
6OK753033Z
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2,2'-DITHIOBISBENZOTHIAZOLE
MI  
Systematic Name English
VULKACIT DM
Brand Name English
DIBENZOTHIAZYL DISULFIDE
VANDF  
Common Name English
2,2'-DIBENZOTHIAZYL DISULFIDE [HSDB]
Common Name English
MBTS
Common Name English
NSC-2
Code English
DIBENZOTHIAZYL DISULFIDE [VANDF]
Common Name English
2,2'-DITHIOBIS(BENZOTHIAZOLE)
Systematic Name English
2,2'-DITHIOBISBENZOTHIAZOLE [MI]
Common Name English
THIOFIDE
Brand Name English
BENZOTHIAZOLE, 2,2'-DITHIOBIS-
Systematic Name English
BIS(2-BENZOTHIAZYL) DISULPHIDE
Common Name English
BIS(2-BENZOTHIAZYL) DISULFIDE
Common Name English
DIBENZOTHIAZYL DISULPHIDE
Common Name English
Classification Tree Code System Code
NDF-RT N0000185508
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
EPA PESTICIDE CODE 9202
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
Code System Code Type Description
MERCK INDEX
m4683
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY Merck Index
NDF-RT
N0000171131
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY Allergens [Chemical/Ingredient]
SMS_ID
100000134275
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY
NDF-RT
N0000184306
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY Cell-mediated Immunity [PE]
CHEBI
53239
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY
CAS
120-78-5
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY
MESH
C028000
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY
EVMPD
SUB61034
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY
HSDB
1137
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY
FDA UNII
6OK753033Z
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY
PUBCHEM
8447
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY
DAILYMED
6OK753033Z
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY
NSC
2
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY
NDF-RT
N0000175629
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY Increased Histamine Release [PE]
RXCUI
1306112
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY RxNorm
EPA CompTox
DTXSID1020146
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-424-9
Created by admin on Fri Dec 15 15:16:13 GMT 2023 , Edited by admin on Fri Dec 15 15:16:13 GMT 2023
PRIMARY