1,3-Dibromo-5,5-dimethylhydantoin (T3D1792)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-06-22 16:08:37 UTC
Update Date2014-12-24 20:24:38 UTC
Accession NumberT3D1792
Identification
Common Name1,3-Dibromo-5,5-dimethylhydantoin
ClassSmall Molecule
Description1,3-Dibromo-5,5-dimethylhydantoin is an organobromide compound derived from the heterocycle called dimethylhydantoin. It is widely used as a disinfectant used for drinking water purification, recreational water treatment, as a bleaching agent in pulp and paper mills, and for treating industrial/commercial water cooling systems. Bromine is a halogen element with the symbol Br and atomic number 35. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock. (3, 6)
Compound Type
  • Amide
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
1, 3-Dibromo-5,5-dimethylhydantoin
1,3-Dibromo-5,5-dimethyl-2,4-imidazolidinedione
5,5-Dimethyl-1,3-dibromohydantoin
Hydantoin, 1,3-dibromo-5,5-dimethyl- (8CI)
N,n'-dibromodimethylhydantoin
Takecharge orange
Chemical FormulaC5H6Br2N2O2
Average Molecular Mass285.921 g/mol
Monoisotopic Mass283.880 g/mol
CAS Registry Number77-48-5
IUPAC Name1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione
Traditional Namedbdmh
SMILESCC1(C)N(Br)C(=O)N(Br)C1=O
InChI IdentifierInChI=1S/C5H6Br2N2O2/c1-5(2)3(10)8(6)4(11)9(5)7/h1-2H3
InChI KeyInChIKey=VRLDVERQJMEPIF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydantoins. These are heterocyclic compounds containing an imidazolidine substituted by ketone group at positions 2 and 4.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassAzolidines
Sub ClassImidazolidines
Direct ParentHydantoins
Alternative Parents
Substituents
  • Hydantoin
  • Alpha-amino acid or derivatives
  • Dicarboximide
  • Carbonic acid derivative
  • Azacycle
  • Carboxylic acid derivative
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point198°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility7.18 g/LALOGPS
logP-0.16ALOGPS
logP1.38ChemAxon
logS-1.6ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area40.62 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity46.12 m³·mol⁻¹ChemAxon
Polarizability18.69 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-001i-0090000000-2e1d8d02ccfd1129905d2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001i-0190000000-749e908cf1f7ecf7e2ca2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-0940000000-7e0dca7aa50fb3e53ec42016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-001i-0090000000-ed13c4d91117c1714ec12016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-001i-0090000000-8a696ae6aeb814dcad952016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-2900000000-83ebe697e373fd4beb662016-08-03View Spectrum
Toxicity Profile
Route of ExposureOral (4) ; inhalation (4) ; dermal (4)
Mechanism of ToxicityBromine is a powerful oxidizing agent and is able to release oxygen free radicals from the water in mucous membranes. These free radicals are also potent oxidizers and produce tissue damage. In additon, the formation of hydrobromic and bromic acids will result in secondary irritation. The bromide ion is also known to affect the central nervous system, causing bromism. This is believed to be a result of bromide ions substituting for chloride ions in the in actions of neurotransmitters and transport systems, thus affecting numerous synaptic processes. (4, 5, 1)
MetabolismBromine is mainly absorbed via inhalation, but may also enter the body through dermal contact. Bromine salts can be ingested. Due to its reactivity, bromine quickly forms bromide and may be deposited in the tissues, displacing other halogens. (4)
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/Sources1,3-Dibromo-5,5-dimethylhydantoin is an organobromide compound derived from the heterocycle called dimethylhydantoin. It is widely used as a disinfectant used for drinking water purification, recreational water treatment, as a bleaching agent in pulp and paper mills, and for treating industrial/commercial water cooling systems. Diatomic bromine does not occur naturally, but bromine salts can be found in crustal rock.
Minimum Risk LevelNot Available
Health EffectsBromine vapour causes irritation and direct damage to the mucous membranes. Elemental bromine also burns the skin. The bromide ion is a central nervous system depressant and chronic exposure produces neuronal effects. This is called bromism and can result in central reactions reaching from somnolence to coma, cachexia, exicosis, loss of reflexes or pathologic reflexes, clonic seizures, tremor, ataxia, loss of neural sensitivity, paresis, papillar edema of the eyes, abnormal speech, cerebral edema, delirium, aggressiveness, and psychoses. (3, 4, 5)
SymptomsBromine vapour causes irritation and direct damage to the mucous membranes. Symptoms include lacrimation, rhinorrhoea, eye irritation with mucous secretions from the oropharyngeal and upper airways, coughing, dyspnoea, choking, wheezing, epistaxis, and headache. The bromide ion is a central nervous system depressant producing ataxia, slurred speech, tremor, nausea, vomiting, lethargy, dizziness, visual disturbances, unsteadiness, headaches, impaired memory and concentration, disorientation and hallucinations. This is called bromism. (4, 5)
TreatmentEYES: irrigate opened eyes for several minutes under running water. INGESTION: do not induce vomiting. Rinse mouth with water (never give anything by mouth to an unconscious person). Seek immediate medical advice. SKIN: should be treated immediately by rinsing the affected parts in cold running water for at least 15 minutes, followed by thorough washing with soap and water. If necessary, the person should shower and change contaminated clothing and shoes, and then must seek medical attention. INHALATION: supply fresh air. If required provide artificial respiration.
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDNot Available
HMDB IDNot Available
PubChem Compound ID6479
ChEMBL IDNot Available
ChemSpider ID6234
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC056578
Stitch ID1,3-Dibromo-5,5-dimethylhydantoin
PDB IDNot Available
ACToR ID9074
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1792.pdf
General References
  1. Ziouzenkova O, Orasanu G, Sharlach M, Akiyama TE, Berger JP, Viereck J, Hamilton JA, Tang G, Dolnikowski GG, Vogel S, Duester G, Plutzky J: Retinaldehyde represses adipogenesis and diet-induced obesity. Nat Med. 2007 Jun;13(6):695-702. Epub 2007 May 27. [17529981 ]
  2. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  3. Wikipedia. Bromine. Last Updated 9 June 2009. [Link]
  4. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
  5. Wikipedia. Potassium bromide. Last Updated 9 June 2009. [Link]
  6. Wikipedia. DBDMH. Last Updated 16 May 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Cytochrome P450 4F12
General Function:
Leukotriene-b4 20-monooxygenase activity
Specific Function:
Catalyzes leukotriene B4 omega-hydroxylation and arachidonic acid omega-hydroxylation but with an activity much lower than that of CYP4F2. Catalyzes the hydroxylation of the antihistamine ebastine.
Gene Name:
CYP4F12
Uniprot ID:
Q9HCS2
Molecular Weight:
60269.165 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
AC502.08 uMNVS_ADME_hCYP4F12Novascreen
References
  1. Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]