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 Methyldibromoglutaronitrile

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
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
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
Development of a new in vitro skin sensitization assay (Epidermal Sensitization Assay; EpiSensA) using reconstructed human epidermis.
2013-12
NCTC 2544 and IL-18 production: a tool for the identification of contact allergens.
2013-04
Development of an in vitro dendritic cell-based test for skin sensitizer identification.
2013-03-18
An in vitro test to screen skin sensitizers using a stable THP-1-derived IL-8 reporter cell line, THP-G8.
2011-12
Patch testing with methyldibromoglutaronitrile in a localized population in the United States.
2010-12-15
Ethosome formulation of contact allergens may enhance patch test reactions in patients.
2010-10
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
Patents
Name Type Language
Methyldibromoglutaronitrile
Common Name English
METHYLDIBROMO GLUTARONITRILE
INCI  
INCI  
Preferred Name English
1,2-DIBROMO-2,4-DICYANOBUTANE [MI]
Common Name English
METHYLDIBROMOGLUTARONITRILE [VANDF]
Common Name English
BROMOTHALONIL
Common Name English
BROMOTHALONIL [HSDB]
Common Name English
Cosmoguard
Brand Name English
TEKTAMER 38
Brand Name English
1,2-DIBROMO-2,4-DICYANOBUTANE
MI  
Systematic Name English
Pentanedinitrile, 2-bromo-2-(bromomethyl)-
Systematic Name English
Classification Tree Code System Code
CFR 21 CFR 175.105
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
CFR 21 CFR 176.170
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
EPA PESTICIDE CODE 111001
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
CFR 21 CFR 175.320
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
NDF-RT N0000185508
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
Code System Code Type Description
EVMPD
SUB169811
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
FDA UNII
YX089CPS05
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
WIKIPEDIA
Methyldibromo glutaronitrile
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
ALANWOOD
bromothalonil
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
DAILYMED
YX089CPS05
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
SMS_ID
100000159535
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
CFR
21 CFR 176.300
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
CAS
35691-65-7
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
ECHA (EC/EINECS)
252-681-0
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
EVMPD
SUB176430
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
NDF-RT
N0000171131
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY Allergens [Chemical/Ingredient]
DRUG BANK
DB14199
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
MESH
C039411
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
PUBCHEM
61948
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
CHEBI
62823
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
EPA CompTox
DTXSID3024944
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
NDF-RT
N0000184306
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY Cell-mediated Immunity [PE]
MERCK INDEX
m4296
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY Merck Index
RXCUI
1307044
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY RxNorm
HSDB
7313
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY
NDF-RT
N0000175629
Created by admin on Mon Mar 31 18:38:12 GMT 2025 , Edited by admin on Mon Mar 31 18:38:12 GMT 2025
PRIMARY Increased Histamine Release [PE]