Details
Stereochemistry | ACHIRAL |
Molecular Formula | C3H6BrNO4 |
Molecular Weight | 199.988 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OCC(Br)(CO)[N+]([O-])=O
InChI
InChIKey=LVDKZNITIUWNER-UHFFFAOYSA-N
InChI=1S/C3H6BrNO4/c4-3(1-6,2-7)5(8)9/h6-7H,1-2H2
DescriptionCurator's Comment: description was created based on several sources,including
https://archive.epa.gov/pesticides/reregistration/web/pdf/2770red.pdf
https://echa.europa.eu/registration-dossier/-/registered-dossier/11419/7/1
http://www.ncbi.nlm.nih.gov/pubmed/3075439
http://www.croplifescience.com/pdf/binato.pdf
http://pubs.acs.org/doi/full/10.1021/es503724k
Curator's Comment: description was created based on several sources,including
https://archive.epa.gov/pesticides/reregistration/web/pdf/2770red.pdf
https://echa.europa.eu/registration-dossier/-/registered-dossier/11419/7/1
http://www.ncbi.nlm.nih.gov/pubmed/3075439
http://www.croplifescience.com/pdf/binato.pdf
http://pubs.acs.org/doi/full/10.1021/es503724k
Bronopol is used as a preservative in various cosmetic, pharmaceutical, toiletry and household preparations at concentrations of up to 0.1% (wt/vol) particularly because of its high activity against Gram-negative bacteria, especially Pseudomonas aeruginosa and other pseudomonad. Bronopol hydrolyzes within 3 h at 60 °C and pH 8, producing formaldehyde, nitrosamines, and other molecules. Although the parent compound (bronopol) is rather short-lived in the environment, its degradation products are toxic and more persistent. The protection against the bactericidal activity of bronopol afforded by catalase or superoxide dismutase suggests that the activity stems from the aerobic interaction and the generation of active oxygen species from oxygen diffusing into the suspensions during bronopol treatment. The acute oral LD50 was 307 mg/kg for rat males and 342 mg/kg for females. Bronopol is moderately toxic by the oral route. Results from an acute dermal toxicity study while inadequate, suggest bronopol is highly toxic by the dermal route.
CNS Activity
Sources: http://www.croplifescience.com/pdf/binato.pdf
Curator's Comment: Chronic Effects on Humans: May cause damage to the nervous system (CNS).
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:1903409 Sources: http://aac.asm.org/content/32/11/1693.full.pdf |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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PubMed
Title | Date | PubMed |
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[Allergy to preservatives]. | 1982 |
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Antibacterial action of 2-bromo-2-nitropropane-1,3-diol (bronopol). | 1988 Nov |
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[Cytotoxic and genotoxic activity of certain preservative agents in cosmetics]. | 2001 Sep |
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Occurrence of clinical and sub-clinical mastitis in dairy herds in the West Littoral Region in Uruguay. | 2002 |
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Allergic contact dermatitis from 2-bromo-2-nitropropane-1,3-diol in Metrogel. | 2002 Jan |
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Reduction of mastitis caused by experimental challenge with Staphylococcus aureus and Streptococcus agalactiae by use of a quaternary ammonium and halogen-mixture teat dip. | 2002 Jan |
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Evaluation of the repeatability of a crude adult indirect Ostertagia ostertagi ELISA and methods of expressing test results. | 2002 Oct 16 |
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Effect of freezing on Fossomatic cell counting in ewe milk. | 2003 Aug |
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[Allergy to cosmetics. II. Preservatives]. | 2004 |
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Prevalence of antibodies to Leptospira interrogans serovar hardjo in bulk tank milk from unvaccinated irish dairy herds. | 2004 Apr 1 |
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Assessing the residual antibacterial activity of clinical materials disinfected with glutaraldehyde, o-phthalaldehyde, hydrogen peroxide or 2-bromo-2-nitro-1,3-propanediol by means of a bacterial toxicity assay. | 2004 Nov |
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Evaluation of rapid somatic cell counters under different analytical conditions in ovine milk. | 2004 Nov |
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Evaluation of phototoxic properties of antimicrobials used in topical preparations by a photohaemolysis test. | 2005 |
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Preservatives in registered chemical products. | 2005 Jul |
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Patch testing with patients' own cosmetics and toiletries--results of the IVDK*, 1998-2002. | 2005 Oct |
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The relative cytotoxicity of personal care preservative systems in Balb/C 3T3 clone A31 embryonic mouse cells and the effect of selected preservative systems upon the toxicity of a standard rinse-off formulation. | 2005 Oct |
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Influence of storage and preservation on fossomatic cell count and composition of goat milk. | 2005 Sep |
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[Contact allergy to preservatives contained in cosmetics]. | 2006 |
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Evaluation of the overall accuracy of the DeLaval cell counter for somatic cell counts in ovine milk. | 2006 Dec |
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Plasma surface modification of poly vinyl chloride for improvement of antibacterial properties. | 2006 Jan |
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Evaluation of the MilkoScan FT 6000 milk analyzer for determining the freezing point of goat's milk under different analytical conditions. | 2007 Jul |
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The use of bronopol to control fungal infection in rainbow trout eggs. | 2007 Jun |
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Contact hypersensitivity to selected excipients of dermatological topical preparations and cosmetics in patients with chronic eczema. | 2008 Jun |
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Examining the fungal and bacterial niche overlap using selective inhibitors in soil. | 2008 Mar |
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Reproducibility and repeatability of measures of milk coagulation properties and predictive ability of mid-infrared reflectance spectroscopy. | 2008 Oct |
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Contrasting short-term antibiotic effects on respiration and bacterial growth compromises the validity of the selective respiratory inhibition technique to distinguish fungi and bacteria. | 2009 Jul |
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Phage therapy and photodynamic therapy: low environmental impact approaches to inactivate microorganisms in fish farming plants. | 2009 Jul 30 |
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Consumer exposure to biocides--identification of relevant sources and evaluation of possible health effects. | 2010 Feb 3 |
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Formaldehyde-releasers in cosmetics: relationship to formaldehyde contact allergy. Part 2. Patch test relationship to formaldehyde contact allergy, experimental provocation tests, amount of formaldehyde released, and assessment of risk to consumers allergic to formaldehyde. | 2010 Jan |
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Formaldehyde-releasers in cosmetics: relationship to formaldehyde contact allergy. Part 1. Characterization, frequency and relevance of sensitization, and frequency of use in cosmetics. | 2010 Jan |
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An in vitro bacterial adhesion assessment of surface-modified medical-grade PVC. | 2010 Jun 1 |
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Positivity ratio and reaction index: patch-test quality-control metrics applied to the north american contact dermatitis group database. | 2010 Mar-Apr |
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Viability of Mycoplasma agalactiae and Mycoplasma mycoides subsp. capri in goat milk samples stored under different conditions. | 2010 Oct 26 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: The volunteer study showed that Bronopol is slightly irritant to human skin at 0.25% in aqueous buffer at pH 5.5.
0.25% in aqueous buffer at pH 5.5
Route of Administration:
Other
To prepare the plates for inhibitory activity determination, 1 ml of diluted distilled solution of bronopol was added to 9 ml of various media to give a final concentration of 100, 50, 25, 12.5, 6.25, 3.13,1.56, 0.78, 0.39 and 0.2 mcg/ml. Bronopol had the strongest antibacterial action (MIC = 6.25 ug/ml) against Shigella dysenteriae and V. parahaemolyticus and on the contrary the weakest one (MIC = 25-50 ug/ml) against C. albicans, S. haemolyticus and C. diphtheriae. All the bacteria tested except for those were supressed to grow at a concentration of 12.5 ug/ml.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C28394
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NDF-RT |
N0000185508
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WHO-VATC |
QD01AE91
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CFR |
21 CFR 176.300
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Food Contact Sustance Notif, (FCN No.) |
FCN NO. 810
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EPA PESTICIDE CODE |
216400
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Food Contact Sustance Notif, (FCN No.) |
FCN NO. 407
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CFR |
21 CFR 176.170
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2450
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m2727
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141021
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52-51-7
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C006827
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N0000171131
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PRIMARY | Allergens [Chemical/Ingredient] | ||
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CHEMBL1408862
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bronopol
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C77031
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N0000184306
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PRIMARY | Cell-mediated Immunity [PE] | ||
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DB13960
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SUB05925MIG
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200-143-0
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1716
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6PU1E16C9W
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DTXSID8024652
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BRONOPOL
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100000088698
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1114345
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6PU1E16C9W
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N0000175629
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PRIMARY | Increased Histamine Release [PE] |
ACTIVE MOIETY