Bronidox (T3D1725)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesGene RegulationTargets (1)XML
Targets (1)
Record Information
Version2.0
Creation Date2009-06-22 16:08:30 UTC
Update Date2014-12-24 20:24:32 UTC
Accession NumberT3D1725
Identification
Common NameBronidox
ClassSmall Molecule
DescriptionBronidox is an organobromide that is a nitrobromo derivative of dioxane. It is used as a stabilizer, surfacant, bactericide, and a preservative in immunology and cosmetics. It is corrosive to metals. Bronidox has been used in cosmetics since the mid-1970s as preservative for shampoos and foam baths.
Compound Type
  • Bromide Compound
  • Inorganic Compound
  • Lachrymator
  • Organic Compound
  • Organobromide
  • Pesticide
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
Synonym
5-Brom-5-nitro-1,3-dioxan
5-Bromo-5-nitro-1,3-dioxane
5-Bromo-5-nitro-m-dioxane
Bronidox l
Chemical FormulaC4H6BrNO4
Average Molecular Mass211.999 g/mol
Monoisotopic Mass210.948 g/mol
CAS Registry Number30007-47-7
IUPAC Name5-bromo-5-nitro-1,3-dioxane
Traditional Name5-bromo-5-nitro-1,3-dioxane
SMILES[O-][N+](=O)C1(Br)COCOC1
InChI IdentifierInChI=1S/C4H6BrNO4/c5-4(6(7)8)1-9-3-10-2-4/h1-3H2
InChI KeyInChIKey=XVBRCOKDZVQYAY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as 1,3-dioxanes. These are organic compounds containing 1,3-dioxane, an aliphatic six-member ring with two oxygen atoms in ring positions 1 and 3.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDioxanes
Sub Class1,3-dioxanes
Direct Parent1,3-dioxanes
Alternative Parents
Substituents
  • Meta-dioxane
  • C-nitro compound
  • Organic nitro compound
  • Acetal
  • Organic oxoazanium
  • Allyl-type 1,3-dipolar organic compound
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Oxacycle
  • Organooxygen compound
  • Organonitrogen compound
  • Organobromide
  • Organic nitrogen compound
  • Organohalogen compound
  • Alkyl bromide
  • Alkyl halide
  • Organopnictogen compound
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • 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 Point60°C
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility12.1 g/LALOGPS
logP0.38ALOGPS
logP1.02ChemAxon
logS-1.2ALOGPS
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area64.28 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity35.01 m³·mol⁻¹ChemAxon
Polarizability14.04 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, Positivesplash10-03di-0190000000-d897d7481e9bf6c3b2142016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0002-0900000000-7a213bf457a73fe2834d2016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-1900000000-8d36be681c8333da53992016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00kf-0910000000-a1618c08e74f125e9ad02016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-1900000000-ece0e3aaab40b939a9942016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-02mi-5900000000-3072609e0fd072c5e2732016-08-03View Spectrum
MSMass Spectrum (Electron Ionization)splash10-002r-9700000000-e7f6debf1376cf9cb0842014-09-20View Spectrum
Toxicity Profile
Route of ExposureOral (6) ; inhalation (6) ; dermal (6)
Mechanism of ToxicityBronidox likely acts as an oxidizing agent that leads to oxidation of free sulfhydryls in essential enzymes. One of the most probable protein targets is the TRPA1 ion channel that is expressed in sensory nerves (trigeminal nerve) of the eyes, nose, mouth and lungs. This compromises their activity and can lead to cell damage, cell death and/or apoptosis. It may also react with amines and amides to form nitrosamines or nitrosamides. Nitrosamines can be carcinogenic.
MetabolismBronidox can be metabolized to 2-bromo-2-nitropropane-1,3-diol, a well known nitrosating agent.(6)
Toxicity ValuesLD50: 590 mg/kg (mouse, Oral); LD50: 455 mg/kg (rat, Oral) LD50: 31 mg/kg (rat, ipr.); LD50: 2500 µg (mouse, skin); LD50: 2500 µg (rat, skin)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity (not listed by IARC). (7)
Uses/SourcesBronidox is used as a stabilizer, surfacant, bactericide, and preservative in immunology and cosmetics. (4)
Minimum Risk LevelNot Available
Health EffectsCan cause significant skin and eye irritation at concentrations >0.1%. A formaldehyde releaser, bromonitrodioxane can cause allergic contact dermatitis in hairdressers and in workers handling cleaners containing bromonitrodioxane. It is neither mutagenic nor teratogenic.
SymptomsAcute doses cause skin and eye irritation. May cause respiratory tract and mucous membrane irritation if inhaled. Harmful if ingested. May affect behavior/central nervous system (tremor, convulsions, excitement).
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 ID1807
ChEMBL IDNot Available
ChemSpider ID1741
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDNot Available
Stitch IDBronidox
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1725.pdf
General References
  1. Ghannoum M, Thomson M, Bowman W, Al-Khalil S: Mode of action of the antimicrobial compound 5-bromo-5-nitro-1,3-dioxane (bronidox). Folia Microbiol (Praha). 1986;31(1):19-31. [3082729 ]
  2. Eisenbrand G, Blankart M, Sommer H, Weber B: N-nitrosoalkanolamines in cosmetics. IARC Sci Publ. 1991;(105):238-41. [1855860 ]
  3. Golomb, BA (1999). A Review of the Scientific Literature As It Pertains to Gulf War Illnesses. Volume 2: Pyridostigmine Bromide. Washington, DC: RAND.
  4. Wikipedia. Bronidox. Last Updated 19 February 2009. [Link]
  5. Material Safety Data Sheet. 5-Bromo-5-nitro-1,3-dioxane MSDS [Link]
  6. International Programme on Chemical Safety (IPCS) INCHEM (1992). Poison Information Monograph for Bromine. [Link]
  7. International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

Target Details
1. Transient receptor potential cation channel subfamily A member 1
General Function:
Temperature-gated cation channel activity
Specific Function:
Receptor-activated non-selective cation channel involved in detection of pain and possibly also in cold perception and inner ear function (PubMed:25389312, PubMed:25855297). Has a central role in the pain response to endogenous inflammatory mediators and to a diverse array of volatile irritants, such as mustard oil, cinnamaldehyde, garlic and acrolein, an irritant from tears gas and vehicule exhaust fumes (PubMed:25389312, PubMed:20547126). Is also activated by menthol (in vitro)(PubMed:25389312). Acts also as a ionotropic cannabinoid receptor by being activated by delta(9)-tetrahydrocannabinol (THC), the psychoactive component of marijuana (PubMed:25389312). May be a component for the mechanosensitive transduction channel of hair cells in inner ear, thereby participating in the perception of sounds. Probably operated by a phosphatidylinositol second messenger system (By similarity).
Gene Name:
TRPA1
Uniprot ID:
O75762
Molecular Weight:
127499.88 Da
References
  1. Ghannoum M, Thomson M, Bowman W, Al-Khalil S: Mode of action of the antimicrobial compound 5-bromo-5-nitro-1,3-dioxane (bronidox). Folia Microbiol (Praha). 1986;31(1):19-31. [3082729 ]
  2. Eisenbrand G, Blankart M, Sommer H, Weber B: N-nitrosoalkanolamines in cosmetics. IARC Sci Publ. 1991;(105):238-41. [1855860 ]
  3. Nilius B, Prenen J, Owsianik G: Irritating channels: the case of TRPA1. J Physiol. 2011 Apr 1;589(Pt 7):1543-9. doi: 10.1113/jphysiol.2010.200717. Epub 2010 Nov 15. [21078588 ]
  4. Wikipedia. Bronidox. Last Updated 19 February 2009. [Link]