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 |
|---|---|---|
| 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. | 2015-11-01 |
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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. | 2015-06 |
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| Development of a new in vitro skin sensitization assay (Epidermal Sensitization Assay; EpiSensA) using reconstructed human epidermis. | 2013-12 |
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| NCTC 2544 and IL-18 production: a tool for the identification of contact allergens. | 2013-04 |
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| Development of an in vitro dendritic cell-based test for skin sensitizer identification. | 2013-03-18 |
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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. | 2011-12 |
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| Patch testing with methyldibromoglutaronitrile in a localized population in the United States. | 2010-12-15 |
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| Ethosome formulation of contact allergens may enhance patch test reactions in patients. | 2010-10 |
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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? | 2010-10 |
|
| NTP technical report on the toxicology and carcinogenesis studies of 1,2-dibromo-2,4-dicyanobutane (CAS No. 35691-65-7) in F344/N rats and B6C3F1 mice (dermal studies). | 2010-06 |
|
| Quantitative repeated open application testing with a rinse-off product in methyldibromo glutaronitrile-sensitive patients: results of the IVDK. | 2010-06 |
|
| Methyldibromoglutaronitrile: skin sensitization and quantitative risk assessment. | 2010-03 |
|
| Temporal trends of preservative allergy in Denmark (1985-2008). | 2010-02 |
|
| The dose-response relationship between the patch test and ROAT and the potential use for regulatory purposes. | 2009-10 |
|
| Hand dermatitis: a focus on allergic contact dermatitis to biocides. | 2009-07 |
|
| [Contact sensitization to Euxyl K-400]. | 2009-04 |
|
| Patch test dose-response study: polysensitized individuals do not express lower elicitation thresholds than single/double-sensitized individuals. | 2009-01 |
|
| Methyldibromoglutaronitrile allergy: relationship between patch test and repeated open application test thresholds. | 2008-11 |
|
| New aspects in allergic contact dermatitis. | 2008-10 |
|
| Proliferative responses in the local lymph node assay associated with concomitant exposure to 1,4-phenylenediamine and methyldibromo glutaronitrile: evidence for synergy? | 2008-08 |
|
| Decreasing trends in methyldibromo glutaronitrile contact allergy--following regulatory intervention. | 2008-07 |
|
| Repeated open application tests with methyldibromoglutaronitrile in dermatitis patients with and without hypersensitivity to methyldibromoglutaronitrile. | 2007-12 |
|
| Occupational allergic contact dermatitis to methyldibromoglutaronitrile in hand degreasing toilet paper. | 2007-08 |
|
| Consort allergic dermatitis to cosmetic agents in a 10-year-old young girl. | 2007-07 |
|
| A further characteristic of susceptibility to contact allergy: sensitization to a weak contact allergen is associated with polysensitization. Results of the IVDK. | 2007-06 |
|
| Contact allergy epidemics and their controls. | 2007-04 |
|
| Allergic contact dermatitis from methyldibromo glutaronitrile in a sanitary pad and review of Australian clinic data. | 2007-03 |
|
| Variation in the amount of petrolatum preparation applied at patch testing. | 2007-01 |
|
| Identification and classification of skin sensitizers: identifying false positives and false negatives. | 2006-11 |
|
| Preservatives sensitivity in Israel: a 10-year overview (1995-2004). | 2006-10 |
|
| [The most frequent allergens in allergic contact dermatitis]. | 2006-07-14 |
|
| Methyldibromoglutaronitrile contact allergy--the beginning of the end? | 2006-04 |
|
| Connubial allergic contact dermatitis to Euxyl K 400. | 2006-02 |
|
| A clinically relevant contact allergy to methyldibromo glutaronitrile at 1% (0.32 mg/cm) detected by a patch test. | 2006-01 |
|
| Increased retest reactivity by both patch and use test with methyldibromoglutaronitrile in sensitized individuals. | 2006 |
|
| Allergic contact dermatitis due to methyldibromo glutaronitrile in make-up removal wipes. | 2005-12 |
|
| Patch testing with patients' own cosmetics and toiletries--results of the IVDK*, 1998-2002. | 2005-10 |
|
| Allergic contact dermatitis from methyldibromoglutaronitrile. | 2005-06 |
|
| Contact sensitivity to preservatives in Turkey. | 2005-06 |
|
| [Allergy to methyldibromoglutaronitrile (dibromodicyanobutane)]. | 2005-05 |
|
| [Will methyldibromo glutaronitrile (Euxyl K400) be the contact allergen of the year 2005 in Navarra?]. | 2005-04-14 |
|
| Quantitative patch and repeated open application testing in methyldibromo glutaronitrile-sensitive patients. | 2005-04 |
|
| Contact allergy to methyldibromo glutaronitrile--data from a 'front line' network. | 2005-03 |
|
| Methyldibromo glutaronitrile contact allergy: effect of single versus repeated daily exposure. | 2005-02 |
|
| Recommendation to include methyldibromo glutaronitrile in the European standard patch test series. | 2005-01 |
|
| Repeated open application test with methyldibromo glutaronitrile, a multicentre study within the EECDRG. | 2005-01 |
|
| Patch testing with methyldibromo glutaronitrile, a multicentre study within the EECDRG. | 2005-01 |
|
| Allergic contact dermatitis from methyldibromo glutaronitrile--clinical cases from 2003. | 2005-01 |
|
| Stability of patch test preparations of methyldibromo glutaronitrile in petrolatum. | 2004-12-21 |
|
| Methyldibromoglutaronitrile in leave-on products elicits contact allergy at low concentration. | 2004-10 |
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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
Created by
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EPA PESTICIDE CODE |
111001
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CFR |
21 CFR 175.320
Created by
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NDF-RT |
N0000185508
Created by
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| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
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SUB169811
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YX089CPS05
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Methyldibromo glutaronitrile
Created by
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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