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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Occurrence of clinical and sub-clinical mastitis in dairy herds in the West Littoral Region in Uruguay. | 2002 |
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Evaluation of flow injection analysis for determination of urea in sheep's and cow's milk. | 2002 |
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Literature review--efficacy of various disinfectants against Legionella in water systems. | 2002 Nov |
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Efficacy of bronopol against infection of rainbow trout (Oncorhynchus mykiss) with the fungus Saprolegnia species. | 2002 Nov 2 |
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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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[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 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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Plasma surface modification of poly vinyl chloride for improvement of antibacterial properties. | 2006 Jan |
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Antifungal activities of bronopol and 2-methyl-4-isothiazolin-3-one (MT) against saprolegnia. | 2007 Dec |
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A method for estimation of urea using ammonia electrode and its applicability to milk samples. | 2008 Nov |
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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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Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography. | 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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Short communication: effect of storage and preservation on total bacterial counts determined by automated flow cytometry in bulk tank goat milk. | 2009 Oct |
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Toxicity of fungicides to natural bacterial communities in wetland water and sediment measured using leucine incorporation and potential denitrification. | 2010 Feb |
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Preservatives in cosmetics: reactivity of allergenic formaldehyde-releasers towards amino acids through breakdown products other than formaldehyde. | 2010 Oct |
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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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7195
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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