U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C6H6Br2N2
Molecular Weight 265.933
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHYLDIBROMO GLUTARONITRILE

SMILES

BrCC(Br)(CCC#N)C#N

InChI

InChIKey=DHVLDKHFGIVEIP-UHFFFAOYSA-N
InChI=1S/C6H6Br2N2/c7-4-6(8,5-10)2-1-3-9/h1-2,4H2

HIDE SMILES / InChI
Methyldibromo glutaronitrile (MDBGN) is a bromine-containing preservative that has been used in cosmetic and toiletry preparations as well as in some industrial products. A maximum concentration of 0.1% MDBGN in stay-on and rinse-off cosmetics was approved for use in the mid 1980’s and animal tests showed it to be a weak sensitiser compared to other preservatives used at the time. By the 1990’s it became a commonly used preservative, particularly in cosmetic and self-hygiene products. However, methyldibromo glutaronitrile was soon discovered to cause allergic contact dermatitis reactions in eczema patients. Rates of sensitisation to MDBGN increased from 0.7% in 1991 to 3.5% in 2000 in patch test studies from 16 European centres. In the United States, sensitivity rates were up to 11.7%. In 2005, the European Union, banned the use of MDBGN in stay-on products, and then later in 2007 also in rinse-off products. Recent data from Europe observed a significant decrease in positive patch test reactions since the ban of MDBGN.

Approval Year

PubMed

PubMed

TitleDatePubMed
Allergic contact dermatitis due to deer-fat cream (Hirschtalgcreme).
2001 Jan
Occupational contact allergy to methyldibromo glutaronitrile in abrasive cleansers and work creams.
2001 May
Contact allergy to methyldibromo glutaronitrile in Euxyl K 400 in a cosmetic cream for protection against a permanent wave solution.
2002 Apr
Monitoring levels of preservative sensitivity in Europe. A 10-year overview (1991-2000).
2002 Apr
Increased positive patch test reactivity to methyldibromo glutaronitrile.
2003 Aug
Methyldibromo glutaronitrile: clinical experience and exposure-based risk assessment.
2003 Mar
Hypersensitivity to preservatives.
2004
Post-coital contact dermatitis from methyldibromo glutaronitrile.
2004 Jan
Influence of a detergent on skin response to methyldibromo glutaronitrile in sensitized individuals.
2004 Jan
Methyldibromoglutaronitrile in rinse-off products causes allergic contact dermatitis: an experimental study.
2004 Jan
Determination of methyldibromoglutaronitrile in cosmetic products by high-performance liquid chromatography with electrochemical detection. Method validation.
2004 Mar 26
Methyldibromoglutaronitrile in leave-on products elicits contact allergy at low concentration.
2004 Oct
Quantitative patch and repeated open application testing in methyldibromo glutaronitrile-sensitive patients.
2005 Apr
Methyldibromo glutaronitrile contact allergy: effect of single versus repeated daily exposure.
2005 Feb
[Will methyldibromo glutaronitrile (Euxyl K400) be the contact allergen of the year 2005 in Navarra?].
2005 Jan-Mar
Allergic contact dermatitis from methyldibromoglutaronitrile.
2005 Jun
Contact allergy to methyldibromo glutaronitrile--data from a 'front line' network.
2005 Mar
Increased retest reactivity by both patch and use test with methyldibromoglutaronitrile in sensitized individuals.
2006
A clinically relevant contact allergy to methyldibromo glutaronitrile at 1% (0.32 mg/cm) detected by a patch test.
2006 Jan
Occupational allergic contact dermatitis to methyldibromoglutaronitrile in hand degreasing toilet paper.
2007 Aug
Repeated open application tests with methyldibromoglutaronitrile in dermatitis patients with and without hypersensitivity to methyldibromoglutaronitrile.
2007 Dec
Variation in the amount of petrolatum preparation applied at patch testing.
2007 Jan
A further characteristic of susceptibility to contact allergy: sensitization to a weak contact allergen is associated with polysensitization. Results of the IVDK.
2007 Jun
Decreasing trends in methyldibromo glutaronitrile contact allergy--following regulatory intervention.
2008 Jul
[Contact sensitization to Euxyl K-400].
2009 Apr
Hand dermatitis: a focus on allergic contact dermatitis to biocides.
2009 Jul
The dose-response relationship between the patch test and ROAT and the potential use for regulatory purposes.
2009 Oct
Temporal trends of preservative allergy in Denmark (1985-2008).
2010 Feb
Methyldibromoglutaronitrile: skin sensitization and quantitative risk assessment.
2010 Mar
Patch testing in allergic contact dermatitis: is it useful to perform the cosmetic series in addition to the European standard series?
2010 Oct
An in vitro test to screen skin sensitizers using a stable THP-1-derived IL-8 reporter cell line, THP-G8.
2011 Dec
Development of an in vitro dendritic cell-based test for skin sensitizer identification.
2013 Mar 18
Genes specifically modulated in sensitized skins allow the detection of sensitizers in a reconstructed human skin model. Development of the SENS-IS assay.
2015 Jun
Dual regulation of skin sensitizer-induced HMOX1 expression by Bach1 and Nrf2: Comparison to regulation of the AKR1C2-ARE element in the KeratinoSens cell line.
2015 Nov 1
Patents
Name Type Language
METHYLDIBROMO GLUTARONITRILE
INCI  
INCI  
Official Name English
1,2-DIBROMO-2,4-DICYANOBUTANE [MI]
Common Name English
METHYLDIBROMO GLUTARONITRILE [INCI]
Common Name English
METHYLDIBROMOGLUTARONITRILE [VANDF]
Common Name English
BROMOTHALONIL
Common Name English
BROMOTHALONIL [HSDB]
Common Name English
TEKTAMER 38
Brand Name English
METHYLDIBROMOGLUTARONITRILE
VANDF  
Systematic Name English
1,2-DIBROMO-2,4-DICYANOBUTANE
MI  
Systematic Name English
Classification Tree Code System Code
CFR 21 CFR 175.105
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
CFR 21 CFR 176.170
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
EPA PESTICIDE CODE 111001
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
CFR 21 CFR 175.320
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
NDF-RT N0000185508
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
Code System Code Type Description
EVMPD
SUB169811
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
FDA UNII
YX089CPS05
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
WIKIPEDIA
Methyldibromo glutaronitrile
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
ALANWOOD
bromothalonil
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
DAILYMED
YX089CPS05
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
SMS_ID
100000159535
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
CFR
21 CFR 176.300
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
CAS
35691-65-7
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
ECHA (EC/EINECS)
252-681-0
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
EVMPD
SUB176430
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY Allergens [Chemical/Ingredient]
DRUG BANK
DB14199
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
MESH
C039411
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
PUBCHEM
61948
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
CHEBI
62823
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
EPA CompTox
DTXSID3024944
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
NDF-RT
N0000184306
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY Cell-mediated Immunity [PE]
MERCK INDEX
m4296
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY Merck Index
RXCUI
1307044
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY RxNorm
HSDB
7313
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY
NDF-RT
N0000175629
Created by admin on Fri Dec 15 16:56:54 GMT 2023 , Edited by admin on Fri Dec 15 16:56:54 GMT 2023
PRIMARY Increased Histamine Release [PE]