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
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
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
Title | Date | PubMed |
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Allergic contact dermatitis due to deer-fat cream (Hirschtalgcreme). | 2001 Jan |
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Occupational contact allergy to methyldibromo glutaronitrile in abrasive cleansers and work creams. | 2001 May |
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Contact allergy to methyldibromo glutaronitrile in Euxyl K 400 in a cosmetic cream for protection against a permanent wave solution. | 2002 Apr |
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Monitoring levels of preservative sensitivity in Europe. A 10-year overview (1991-2000). | 2002 Apr |
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Increased positive patch test reactivity to methyldibromo glutaronitrile. | 2003 Aug |
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Methyldibromo glutaronitrile: clinical experience and exposure-based risk assessment. | 2003 Mar |
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Hypersensitivity to preservatives. | 2004 |
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Post-coital contact dermatitis from methyldibromo glutaronitrile. | 2004 Jan |
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Influence of a detergent on skin response to methyldibromo glutaronitrile in sensitized individuals. | 2004 Jan |
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Methyldibromoglutaronitrile in rinse-off products causes allergic contact dermatitis: an experimental study. | 2004 Jan |
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Determination of methyldibromoglutaronitrile in cosmetic products by high-performance liquid chromatography with electrochemical detection. Method validation. | 2004 Mar 26 |
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Methyldibromoglutaronitrile in leave-on products elicits contact allergy at low concentration. | 2004 Oct |
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Quantitative patch and repeated open application testing in methyldibromo glutaronitrile-sensitive patients. | 2005 Apr |
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Methyldibromo glutaronitrile contact allergy: effect of single versus repeated daily exposure. | 2005 Feb |
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[Will methyldibromo glutaronitrile (Euxyl K400) be the contact allergen of the year 2005 in Navarra?]. | 2005 Jan-Mar |
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Allergic contact dermatitis from methyldibromoglutaronitrile. | 2005 Jun |
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Contact allergy to methyldibromo glutaronitrile--data from a 'front line' network. | 2005 Mar |
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Increased retest reactivity by both patch and use test with methyldibromoglutaronitrile in sensitized individuals. | 2006 |
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A clinically relevant contact allergy to methyldibromo glutaronitrile at 1% (0.32 mg/cm) detected by a patch test. | 2006 Jan |
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Occupational allergic contact dermatitis to methyldibromoglutaronitrile in hand degreasing toilet paper. | 2007 Aug |
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Repeated open application tests with methyldibromoglutaronitrile in dermatitis patients with and without hypersensitivity to methyldibromoglutaronitrile. | 2007 Dec |
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Variation in the amount of petrolatum preparation applied at patch testing. | 2007 Jan |
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A further characteristic of susceptibility to contact allergy: sensitization to a weak contact allergen is associated with polysensitization. Results of the IVDK. | 2007 Jun |
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Decreasing trends in methyldibromo glutaronitrile contact allergy--following regulatory intervention. | 2008 Jul |
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[Contact sensitization to Euxyl K-400]. | 2009 Apr |
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Hand dermatitis: a focus on allergic contact dermatitis to biocides. | 2009 Jul |
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The dose-response relationship between the patch test and ROAT and the potential use for regulatory purposes. | 2009 Oct |
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Temporal trends of preservative allergy in Denmark (1985-2008). | 2010 Feb |
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Methyldibromoglutaronitrile: skin sensitization and quantitative risk assessment. | 2010 Mar |
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Patch testing in allergic contact dermatitis: is it useful to perform the cosmetic series in addition to the European standard series? | 2010 Oct |
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An in vitro test to screen skin sensitizers using a stable THP-1-derived IL-8 reporter cell line, THP-G8. | 2011 Dec |
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Development of an in vitro dendritic cell-based test for skin sensitizer identification. | 2013 Mar 18 |
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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 |
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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 |
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Classification Tree | Code System | Code | ||
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CFR |
21 CFR 175.105
Created by
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CFR |
21 CFR 176.170
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EPA PESTICIDE CODE |
111001
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CFR |
21 CFR 175.320
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NDF-RT |
N0000185508
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SUB169811
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YX089CPS05
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Methyldibromo glutaronitrile
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bromothalonil
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YX089CPS05
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100000159535
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21 CFR 176.300
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35691-65-7
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252-681-0
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SUB176430
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N0000171131
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PRIMARY | Allergens [Chemical/Ingredient] | ||
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DB14199
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C039411
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61948
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62823
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DTXSID3024944
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N0000184306
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PRIMARY | Cell-mediated Immunity [PE] | ||
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m4296
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PRIMARY | Merck Index | ||
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1307044
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PRIMARY | RxNorm | ||
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7313
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N0000175629
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PRIMARY | Increased Histamine Release [PE] |
SUBSTANCE RECORD