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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Determination of bronopol in cosmetic products by HPLC with electrochemical detection. | 2001 Apr |
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[Cytotoxic and genotoxic activity of certain preservative agents in cosmetics]. | 2001 Sep |
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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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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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Literature review--efficacy of various disinfectants against Legionella in water systems. | 2002 Nov |
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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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Fossomatic cell-counting on ewe milk: comparison with direct microscopy and study of variation factors. | 2003 Jan |
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Optimization by experimental design and artificial neural networks of the ion-interaction reversed-phase liquid chromatographic separation of twenty cosmetic preservatives. | 2004 Mar 12 |
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[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations]. | 2004 May |
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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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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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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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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 UTC 2023
by
admin
on
Fri Dec 15 15:09:37 UTC 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 UTC 2023 , Edited by admin on Fri Dec 15 15:09:37 UTC 2023
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CFR |
21 CFR 176.170
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admin on Fri Dec 15 15:09:37 UTC 2023 , Edited by admin on Fri Dec 15 15:09:37 UTC 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 |