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Record Information
Version2.0
Creation Date2009-06-22 16:08:37 UTC
Update Date2014-12-24 20:24:39 UTC
Accession NumberT3D1798
Identification
Common NameDibrompropamidine
ClassSmall Molecule
DescriptionDibrompropamidine is an organobromide compound. It is an antiseptic and disinfectant. As dibrompropamidine isethionate, it is also used in eyedrops and ointment for the treatment of infections. 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
  • Amine
  • Bromide Compound
  • Ether
  • Industrial/Workplace Toxin
  • Organic Compound
  • Organobromide
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
4,4'-(Trimethylenedioxy)bis(3-bromobenzamidine)
Brolene
Brulidine
Dibromopropamidine
Golden eye
Chemical FormulaC17H18Br2N4O2
Average Molecular Mass470.158 g/mol
Monoisotopic Mass467.980 g/mol
CAS Registry Number496-00-4
IUPAC Name3-bromo-4-[3-(2-bromo-4-carbamimidoylphenoxy)propoxy]benzene-1-carboximidamide
Traditional Namebrolene
SMILESNC(=N)C1=CC=C(OCCCOC2=CC=C(C=C2Br)C(N)=N)C(Br)=C1
InChI IdentifierInChI=1S/C17H18Br2N4O2/c18-12-8-10(16(20)21)2-4-14(12)24-6-1-7-25-15-5-3-11(17(22)23)9-13(15)19/h2-5,8-9H,1,6-7H2,(H3,20,21)(H3,22,23)
InChI KeyInChIKey=GMJFVGRUYJHMCO-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenoxy compound
  • Phenol ether
  • Alkyl aryl ether
  • Bromobenzene
  • Halobenzene
  • Aryl bromide
  • Aryl halide
  • Monocyclic benzene moiety
  • Amidine
  • Carboximidamide
  • Carboxylic acid amidine
  • Ether
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organooxygen compound
  • Organohalogen compound
  • Organobromide
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
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 PointNot Available
Boiling PointNot Available
SolubilityNot Available
LogPNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.013 g/LALOGPS
logP2.36ALOGPS
logP2.9ChemAxon
logS-4.6ALOGPS
pKa (Strongest Basic)11.81ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area118.2 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity126.53 m³·mol⁻¹ChemAxon
Polarizability40.74 ųChemAxon
Number of Rings2ChemAxon
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, Positivesplash10-014i-0020900000-4e27395f08642e69729e2016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-07vi-0190700000-cffa581a34ee8e3b61a92016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-03fv-4490000000-5615b11f0b05a3f1b9d92016-08-02View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-0040900000-90572efd4494e3536bcf2016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0191400000-f4ec0a2d7b83ed827dd52016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-03di-4390000000-950ac975bd087a4e626e2016-08-03View 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/SourcesAs dibrompropamidine isethionate, it is also used in eyedrops and ointment for the treatment of infections. 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 ID11974
ChEMBL IDCHEMBL30044
ChemSpider ID11479
KEGG IDNot Available
UniProt IDNot Available
OMIM ID
ChEBI IDNot Available
BioCyc IDNot Available
CTD IDC053597
Stitch IDDibrompropamidine
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkNot Available
References
Synthesis ReferenceNot Available
MSDST3D1798.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. Dibrompropamidine. Last Updated 20 May 2009. [Link]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Thrombospondin receptor activity
Specific Function:
Thrombin, which cleaves bonds after Arg and Lys, converts fibrinogen to fibrin and activates factors V, VII, VIII, XIII, and, in complex with thrombomodulin, protein C. Functions in blood homeostasis, inflammation and wound healing.
Gene Name:
F2
Uniprot ID:
P00734
Molecular Weight:
70036.295 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.946 uMNot AvailableBindingDB 50098554
References
  1. Enyedy IJ, Lee SL, Kuo AH, Dickson RB, Lin CY, Wang S: Structure-based approach for the discovery of bis-benzamidines as novel inhibitors of matriptase. J Med Chem. 2001 Apr 26;44(9):1349-55. [11311057 ]
General Function:
Serine-type peptidase activity
Specific Function:
Degrades extracellular matrix. Proposed to play a role in breast cancer invasion and metastasis. Exhibits trypsin-like activity as defined by cleavage of synthetic substrates with Arg or Lys as the P1 site. Involved in the terminal differentiation of keratinocytes through prostasin (PRSS8) activation and filaggrin (FLG) processing.
Gene Name:
ST14
Uniprot ID:
Q9Y5Y6
Molecular Weight:
94769.01 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory0.535 uMNot AvailableBindingDB 50098554
References
  1. Enyedy IJ, Lee SL, Kuo AH, Dickson RB, Lin CY, Wang S: Structure-based approach for the discovery of bis-benzamidines as novel inhibitors of matriptase. J Med Chem. 2001 Apr 26;44(9):1349-55. [11311057 ]
General Function:
Serine-type endopeptidase activity
Specific Function:
Specifically cleaves the zymogen plasminogen to form the active enzyme plasmin.
Gene Name:
PLAU
Uniprot ID:
P00749
Molecular Weight:
48507.09 Da
Binding/Activity Constants
TypeValueAssay TypeAssay Source
Inhibitory1.57 uMNot AvailableBindingDB 50098554
References
  1. Enyedy IJ, Lee SL, Kuo AH, Dickson RB, Lin CY, Wang S: Structure-based approach for the discovery of bis-benzamidines as novel inhibitors of matriptase. J Med Chem. 2001 Apr 26;44(9):1349-55. [11311057 ]