Bromothalonil

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Name
Bromothalonil
Accession Number
DB14199
Type
Small Molecule
Groups
Approved, Experimental
Description

Bromothalonil, also known as Methyldibromo glutaronitrile (MDBGN), is a widely used preservative that can be found in many personal hygiene and industrial products. It is also a known allergen and dermatological irritant that has been banned in many EU countries due to increasing rates of contact allergy [1]. In 2005, MDBGN was named in the top 15 most frequently positive allergens identified in patch tests by the North American Contact Dermatitis Group (NACDG)[3].

Sensitivity to Bromothalonil may be identified with a clinical patch test.

Structure
Thumb
Synonyms
  • 1,2-Dibromo-2,4-dicyanobutane
  • 2-Bromo-2-(bromomethyl) glutaronitrile
  • 2-Bromo-2-(bromomethyl) pentanedinitrile
  • BBMG
  • Glutaronitrile, 2-bromo-2-(bromomethyl)-
  • MDBGN
  • Methyldibromo Glutaronitrile
  • Methyldibromoglutaronitrile
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
T.R.U.E. Test Thin-Layer Rapid Use Patch TestBromothalonil (4 ug/48h) + 2,2'-Dibenzothiazyl disulfide (20 ug/48h) + 2-mercaptobenzothiazole (61 ug/48h) + 4-(Isopropylamino)diphenylamine (10 ug/48h) + Bacitracin (486 ug/48h) + Balsam of Peru (648 ug/48h) + Benzocaine (378 ug/48h) + Benzylparaben (162 ug/48h) + Bisphenol A diglycidyl ether (32 ug/48h) + Bronopol (203 ug/48h) + Budesonide (0.8 ug/48h) + Butylparaben (162 ug/48h) + Chlorquinaldol (77 ug/48h) + Cinchocaine hydrochloride (66 ug/48h) + Cinnamaldehyde (41 ug/48h) + Cinnamyl alcohol (63 ug/48h) + Clioquinol (77 ug/48h) + Cobalt chloride hexahydrate (4 ug/48h) + Diazolidinylurea (446 ug/48h) + Potassium dichromate (15.7 ug/48h) + Dipentamethylenethiuram disulfide (5.5 ug/48h) + Diphenylguanidine (68 ug/48h) + Disperse Blue 106 (41 ug/48h) + Disulfiram (5.5 ug/48h) + Ditiocarb Zinc (68 ug/48h) + Ethyl hydroxybenzoate (162 ug/48h) + Ethylenediamine (18 ug/48h) + Eugenol (41 ug/48h) + Evernia prunastri (81 ug/48h) + Formaldehyde (146 ug/48h) + Geraniol (81 ug/48h) + Hydrocortisone butyrate (16 ug/48h) + Hydroxycitronellal (63 ug/48h) + Imidurea (486 ug/48h) + Isoeugenol (17 ug/48h) + Lanolin alcohols (810 ug/48h) + Methylchloroisothiazolinone (3 ug/48h) + Methylparaben (162 ug/48h) + Morpholinylmercaptobenzothiazole (20 ug/48h) + N,N'-diphenyl-1,4-phenylenediamine (25 ug/48h) + N-Cyclohexyl-N'-phenyl-1,4-phenylenediamine (25 ug/48h) + Neomycin sulfate (486 ug/48h) + Nickel sulfate hexahydrate (36 ug/48h) + P-Tert-Butylphenol-Formaldehyde Resin (Low Molecular Weight) (36 ug/48h) + Parthenolide (2 ug/48h) + Propylparaben (162 ug/48h) + Quaternium-15 (81 ug/48h) + Rosin (972 ug/48h) + Sodium aurotiosulfate (23 ug/48h) + Tetracaine hydrochloride (66 ug/48h) + Tetramethylthiuram monosulfide (5.5 ug/48h) + Thimerosal (6 ug/48h) + Thiohexam (20 ug/48h) + Thiram (5.5 ug/48h) + Tixocortol pivalate (2 ug/48h) + Zinc Dibutyldithiocarbamate (68 ug/48h) + alpha-Amyl cinnamaldehyde (17 ug/48h) + p-Phenylenediamine (65 ug/48h)KitSmartPractice Denmark ApS2012-03-01Not applicableUs
Categories
UNII
YX089CPS05
CAS number
35691-65-7
Weight
Average: 265.936
Monoisotopic: 263.889774
Chemical Formula
C6H6Br2N2
InChI Key
DHVLDKHFGIVEIP-UHFFFAOYSA-N
InChI
InChI=1S/C6H6Br2N2/c7-4-6(8,5-10)2-1-3-9/h1-2,4H2
IUPAC Name
2-bromo-2-(bromomethyl)pentanedinitrile
SMILES
BrCC(Br)(CCC#N)C#N

Pharmacology

Indication

Bromothalonil is approved for use within allergenic epicutaneous patch tests which are indicated for use as an aid in the diagnosis of allergic contact dermatitis (ACD) in persons 6 years of age and older.

Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
Not Available
Food Interactions
Not Available

References

General References
  1. Johansen JD, Veien N, Laurberg G, Avnstorp C, Kaaber K, Andersen KE, Paulsen E, Sommerlund M, Thormann J, Nielsen NH, Vissing S, Kristensen O, Kristensen B, Agner T, Menne T: Decreasing trends in methyldibromo glutaronitrile contact allergy--following regulatory intervention. Contact Dermatitis. 2008 Jul;59(1):48-51. doi: 10.1111/j.1600-0536.2008.01364.x. Epub 2008 Jul 1. [PubMed:18537990]
  2. Aakhus AE, Warshaw EM: Allergy to methyldibromoglutaronitrile/phenoxyethanol (Euxyl k 400): regulatory issues, epidemiology, clinical characteristics, and management. Dermatitis. 2011 May;22(3):127-40. [PubMed:21569742]
  3. Zug KA, Warshaw EM, Fowler JF Jr, Maibach HI, Belsito DL, Pratt MD, Sasseville D, Storrs FJ, Taylor JS, Mathias CG, Deleo VA, Rietschel RL, Marks J: Patch-test results of the North American Contact Dermatitis Group 2005-2006. Dermatitis. 2009 May-Jun;20(3):149-60. [PubMed:19470301]
External Links
ChemSpider
55806
ChEBI
62823
ChEMBL
CHEMBL3188084
Wikipedia
Methyldibromo_glutaronitrile

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Kit
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0807 mg/mLALOGPS
logP2.14ALOGPS
logP1.76ChemAxon
logS-3.5ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area47.58 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity45.91 m3·mol-1ChemAxon
Polarizability17.96 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Classification
Not classified

Drug created on July 03, 2018 16:47 / Updated on November 02, 2018 07:51