NAV

Bromothalonil

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

Identification

Generic Name
Bromothalonil
DrugBank Accession Number
DB14199
Background

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.

Type
Small Molecule
Groups
Approved, Experimental
Structure
3D
Similar Structures
Weight
Average: 265.936
Monoisotopic: 263.889774
Chemical Formula
C6H6Br2N2
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
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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.

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Contraindications & Blackbox Warnings
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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

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
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Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
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) + 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) + p-tert-Butylphenol-formaldehyde resin (low molecular weight) (36 ug/48h)KitCutaneousSmartPractice Denmark ApS2012-03-01Not applicableUS flag

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
YX089CPS05
CAS number
35691-65-7
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

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. [Article]
  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. [Article]
  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. [Article]
ChemSpider
55806
RxNav
1307044
ChEBI
62823
ChEMBL
CHEMBL3188084
Wikipedia
Methyldibromo_glutaronitrile

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2CompletedDiagnosticAllergic Contact Dermatitis1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
KitCutaneous
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/MSsplash10-053r-0910000000-d7348bb3f6cd82a21af5
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-03di-1090000000-b3a37e258ba6fb052797
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1920000000-165a83b17a856341aaa8
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-513ffe4cb2bdd03dc73a
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-004i-9000000000-e12030acfd6808e5163c
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-5900000000-02387f56e17efbfb5db6
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-130.93622
predicted
DeepCCS 1.0 (2019)
[M+H]+133.15363
predicted
DeepCCS 1.0 (2019)
[M+Na]+142.08934
predicted
DeepCCS 1.0 (2019)

Drug created at July 03, 2018 22:47 / Updated at June 12, 2020 16:53