2,2'-Dithiobisbenzothiazole

US Approved Allergenic Extract (1994)

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

Structure Search

SMILES

S(SC1=NC2=C(S1)C=CC=C2)C3=NC4=C(S3)C=CC=C4

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
Sources: http://www.accessdata.fda.gov/spl/data/b9c29578-0968-465e-a24b-19dabfb2d7dd/b9c29578-0968-465e-a24b-19dabfb2d7dd.xml
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

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Allergic contact dermatitis 14 Sources: http://www.fda.gov/downloads/BiologicsBloodVaccines/Allergenics/UCM294327.pdf	Diagnostic		Approved 8583	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.

Doses

Dose	Population	Adverse events
5 % single, topical Highest studied dose Dose: 5 % Route: topical Route: single Dose: 5 % Sources: https://pubmed.ncbi.nlm.nih.gov/3219832/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3219832/	Other AEs: Contact dematitis... Other AEs: Contact dematitis Sources: https://pubmed.ncbi.nlm.nih.gov/3219832/

AEs

AE	Significance	Dose	Population
Contact dematitis		5 % single, topical Highest studied dose Dose: 5 % Route: topical Route: single Dose: 5 % Sources: https://pubmed.ncbi.nlm.nih.gov/3219832/	unhealthy, CHILD Health Status: unhealthy Age Group: CHILD Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/3219832/

PubMed

Title	Date	PubMed
A case of airborne allergic contact dermatitis by rubber additives.	2010-02	20197752
Cancer risks in chemical production workers exposed to 2-mercaptobenzothiazole.	2009-04	19158128
Mercaptobenzothiazole-on-gold organic phase biosensor systems: 1. Enhanced organosphosphate pesticide determination.	2009-02	19130375
The oxidative degradation of 2-mercaptobenzothiazole at the interface of beta-MnO2 and water.	2008-06-15	18093735
Mercaptobenzothiazole allergenicity-role of the thiol group.	2008	18568896
Chemical changes in rubber allergens during vulcanization.	2007-09	17680862
Oxidation of 2-mercaptobenzothiazole in latex gloves and its possible haptenation pathway.	2007-08	17630704
Solid state differentiation of plasma thiols using a centrifugally activated mercaptobenzothiazole disulfide exchange indicator.	2007-02-14	17264901
Both mercaptobenzothiazole and mercapto mix should be part of the standard series.	2006-11	17026709
Mercaptobenzothiazole or the mercapto-mix: which should be in the standard series?	2006-07	16842552
Allergic contact dermatitis from mercapto compounds.	2006-06	16956455
Bikini dermatitis due to mercaptobenzothiazole.	2006-06	16787458
One-pot synthesis of high-quality zinc-blende CdS nanocrystals.	2004-11-10	15521736
[Allergy to mercaptobenzothiazole and mercapto mix].	2004-10-27	15505561
Contact dermatitis of the feet: a study of 53 cases.	2004-09	15724346
Homolytic cleavage and aggregation processes in cyclopentadienylchromium chemistry.	2004-03	15023086
Allergic contact dermatitis from rubber bands in 3 postal workers.	2003-12	15025711
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.	2003-02	12623669
Occupational rubber glove allergy: results of the Information Network of Departments of Dermatology (IVDK), 1995-2001.	2003-01	12641577
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.	2002-07-01	12062936
Diagnostic screening for contact allergy to mercaptobenzothiazole derivatives.	2002-06	12022122
Inactivation of the human papillomavirus-16 E6 oncoprotein by organic disulfides.	2000-11	11092540

Patents

Sample Use Guides

In Vivo Use Guide

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

In Vitro Use Guide

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 `Mon Mar 31 17:52:15 GMT 2025` Edited by `admin` on `Mon Mar 31 17:52:15 GMT 2025`
Record UNII	6OK753033Z
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

2,2'-Dithiobisbenzothiazole

Systematic Name

English

DIBENZOTHIAZYL DISULFIDE

Preferred Name

English

VULKACIT DM

Brand 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