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
| Molecular Formula | C3H6BrNO4 |
| Molecular Weight | 199.988 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|---|
Target ID: GO:1903409 Sources: http://aac.asm.org/content/32/11/1693.full.pdf |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effect of preservatives on the accuracy of mid-infrared milk component testing. | 2010-12 |
|
| Viability of Mycoplasma agalactiae and Mycoplasma mycoides subsp. capri in goat milk samples stored under different conditions. | 2010-10-26 |
|
| Preservatives in cosmetics: reactivity of allergenic formaldehyde-releasers towards amino acids through breakdown products other than formaldehyde. | 2010-10 |
|
| Pain control in the African context: the Ugandan introduction of affordable morphine to relieve suffering at the end of life. | 2010-07-08 |
|
| An in vitro bacterial adhesion assessment of surface-modified medical-grade PVC. | 2010-06-01 |
|
| Formaldehyde-releasers in cosmetics in the USA and in Europe. | 2010-04 |
|
| Positivity ratio and reaction index: patch-test quality-control metrics applied to the north american contact dermatitis group database. | 2010-03-18 |
|
| Consumer exposure to biocides--identification of relevant sources and evaluation of possible health effects. | 2010-02-03 |
|
| Toxicity of fungicides to natural bacterial communities in wetland water and sediment measured using leucine incorporation and potential denitrification. | 2010-02 |
|
| 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. | 2010-01 |
|
| Formaldehyde-releasers in cosmetics: relationship to formaldehyde contact allergy. Part 1. Characterization, frequency and relevance of sensitization, and frequency of use in cosmetics. | 2010-01 |
|
| Short communication: effect of storage and preservation on total bacterial counts determined by automated flow cytometry in bulk tank goat milk. | 2009-10 |
|
| Phage therapy and photodynamic therapy: low environmental impact approaches to inactivate microorganisms in fish farming plants. | 2009-07-30 |
|
| Contrasting short-term antibiotic effects on respiration and bacterial growth compromises the validity of the selective respiratory inhibition technique to distinguish fungi and bacteria. | 2009-07 |
|
| Patch-test results of the North American Contact Dermatitis Group 2005-2006. | 2009-05-28 |
|
| A method for estimation of urea using ammonia electrode and its applicability to milk samples. | 2008-11 |
|
| Reproducibility and repeatability of measures of milk coagulation properties and predictive ability of mid-infrared reflectance spectroscopy. | 2008-10 |
|
| Simultaneous determination of 21 preservatives in cosmetics by ultra performance liquid chromatography. | 2008-10 |
|
| Contact hypersensitivity to selected excipients of dermatological topical preparations and cosmetics in patients with chronic eczema. | 2008-06 |
|
| Examining the fungal and bacterial niche overlap using selective inhibitors in soil. | 2008-03 |
|
| Antifungal activities of bronopol and 2-methyl-4-isothiazolin-3-one (MT) against saprolegnia. | 2007-12 |
|
| Evaluation of the MilkoScan FT 6000 milk analyzer for determining the freezing point of goat's milk under different analytical conditions. | 2007-07 |
|
| The use of bronopol to control fungal infection in rainbow trout eggs. | 2007-06 |
|
| Evaluation of the overall accuracy of the DeLaval cell counter for somatic cell counts in ovine milk. | 2006-12 |
|
| Plasma surface modification of poly vinyl chloride for improvement of antibacterial properties. | 2006-01 |
|
| [Contact allergy to preservatives contained in cosmetics]. | 2006 |
|
| Patch testing with patients' own cosmetics and toiletries--results of the IVDK*, 1998-2002. | 2005-10 |
|
| 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. | 2005-10 |
|
| Influence of storage and preservation on fossomatic cell count and composition of goat milk. | 2005-09 |
|
| Preservatives in registered chemical products. | 2005-07 |
|
| Evaluation of phototoxic properties of antimicrobials used in topical preparations by a photohaemolysis test. | 2005 |
|
| 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. | 2004-11 |
|
| Evaluation of rapid somatic cell counters under different analytical conditions in ovine milk. | 2004-11 |
|
| Efficacy of three surface disinfectants for dental radiographic films and gloves. | 2004-07 |
|
| [Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations]. | 2004-05 |
|
| Prevalence of antibodies to Leptospira interrogans serovar hardjo in bulk tank milk from unvaccinated irish dairy herds. | 2004-04-01 |
|
| Optimization by experimental design and artificial neural networks of the ion-interaction reversed-phase liquid chromatographic separation of twenty cosmetic preservatives. | 2004-03-12 |
|
| Biofilms, homoserine lactones and biocide susceptibility. | 2004-02 |
|
| Reproducibility of patch tests: comparison of identical test allergens from different commercial sources. | 2004-01 |
|
| [Allergy to cosmetics. II. Preservatives]. | 2004 |
|
| Effect of freezing on Fossomatic cell counting in ewe milk. | 2003-08 |
|
| Fossomatic cell-counting on ewe milk: comparison with direct microscopy and study of variation factors. | 2003-01 |
|
| Efficacy of bronopol against infection of rainbow trout (Oncorhynchus mykiss) with the fungus Saprolegnia species. | 2002-11-02 |
|
| Literature review--efficacy of various disinfectants against Legionella in water systems. | 2002-11 |
|
| Evaluation of the repeatability of a crude adult indirect Ostertagia ostertagi ELISA and methods of expressing test results. | 2002-10-16 |
|
| Detection of Mycobacterium avium subspecies paratuberculosis specific IS900 insertion sequences in bulk-tank milk samples obtained from different regions throughout Switzerland. | 2002-06-26 |
|
| Occurrence of clinical and sub-clinical mastitis in dairy herds in the West Littoral Region in Uruguay. | 2002 |
|
| Evaluation of flow injection analysis for determination of urea in sheep's and cow's milk. | 2002 |
|
| Direct toxicity assessment of wastewater: Baroxymeter, a portable rapid toxicity device and the industry perspective. | 2002 |
|
| [Allergy to preservatives]. | 1982 |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:48:30 GMT 2025
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| Record UNII |
6PU1E16C9W
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| Record Status |
Validated (UNII)
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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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admin on Mon Mar 31 17:48:30 GMT 2025 , Edited by admin on Mon Mar 31 17:48:30 GMT 2025
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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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PRIMARY | |||
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N0000171131
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PRIMARY | Allergens [Chemical/Ingredient] | ||
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CHEMBL1408862
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PRIMARY | |||
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bronopol
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PRIMARY | |||
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C77031
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PRIMARY | |||
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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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PRIMARY | RxNorm | ||
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6PU1E16C9W
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N0000175629
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PRIMARY | Increased Histamine Release [PE] |
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