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 |
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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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Direct toxicity assessment of wastewater: Baroxymeter, a portable rapid toxicity device and the industry perspective. | 2002 |
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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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Determination of bronopol and its degradation products by HPLC. | 2002 Jun 20 |
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Detection of Mycobacterium avium subspecies paratuberculosis specific IS900 insertion sequences in bulk-tank milk samples obtained from different regions throughout Switzerland. | 2002 Jun 26 |
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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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[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations]. | 2004 May |
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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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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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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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The use of bronopol to control fungal infection in rainbow trout eggs. | 2007 Jun |
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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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Patch-test results of the North American Contact Dermatitis Group 2005-2006. | 2009 May-Jun |
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Formaldehyde-releasers in cosmetics in the USA and in Europe. | 2010 Apr |
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Effect of preservatives on the accuracy of mid-infrared milk component testing. | 2010 Dec |
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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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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 1. Characterization, frequency and relevance of sensitization, and frequency of use in cosmetics. | 2010 Jan |
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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 |
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
Fri Dec 15 15:09:37 GMT 2023
by
admin
on
Fri Dec 15 15:09:37 GMT 2023
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Record UNII |
6PU1E16C9W
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Record Status |
Validated (UNII)
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Record Version |
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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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admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
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CFR |
21 CFR 176.170
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admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
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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] |
Related Record | Type | Details | ||
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ACTIVE MOIETY |