U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of BRONOPOL

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

HIDE SMILES / InChI

Description
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

Curator's Comment: Chronic Effects on Humans: May cause damage to the nervous system (CNS).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
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

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.
Name Type Language
BRONOPOL
HSDB   INN   JAN   MART.   MI   VANDF   WHO-DD  
INN  
Official Name English
2-BROMO-2-NITROPROPANE-1,3-DIOL
INCI  
INCI  
Preferred Name English
BRONOPOL [HSDB]
Common Name English
BRONOPOL [VANDF]
Common Name English
NSC-141021
Code English
Bronopol [WHO-DD]
Common Name English
bronopol [INN]
Common Name English
BRONOPOL [MI]
Common Name English
BRONOPOL [MART.]
Common Name English
BRONOPOL [JAN]
Common Name English
2-BROMO-2-NITRO-1,3-PROPANEDIOL
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C28394
Created by admin on Mon Mar 31 17:48:30 GMT 2025 , Edited by admin on Mon Mar 31 17:48:30 GMT 2025
NDF-RT N0000185508
Created by admin on Mon Mar 31 17:48:30 GMT 2025 , Edited by admin on Mon Mar 31 17:48:30 GMT 2025
WHO-VATC QD01AE91
Created by admin on Mon Mar 31 17:48:30 GMT 2025 , Edited by admin on Mon Mar 31 17:48:30 GMT 2025
CFR 21 CFR 176.300
Created by admin on Mon Mar 31 17:48:30 GMT 2025 , Edited by admin on Mon Mar 31 17:48:30 GMT 2025
Food Contact Sustance Notif, (FCN No.) FCN NO. 810
Created by admin on Mon Mar 31 17:48:30 GMT 2025 , Edited by admin on Mon Mar 31 17:48:30 GMT 2025
EPA PESTICIDE CODE 216400
Created by admin on Mon Mar 31 17:48:30 GMT 2025 , Edited by admin on Mon Mar 31 17:48:30 GMT 2025
Food Contact Sustance Notif, (FCN No.) FCN NO. 407
Created by admin on Mon Mar 31 17:48:30 GMT 2025 , Edited by admin on Mon Mar 31 17:48:30 GMT 2025
CFR 21 CFR 176.170
Created by admin on Mon Mar 31 17:48:30 GMT 2025 , Edited by admin on Mon Mar 31 17:48:30 GMT 2025
Code System Code Type Description
PUBCHEM
2450
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PRIMARY
MERCK INDEX
m2727
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PRIMARY Merck Index
NSC
141021
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PRIMARY
HSDB
7195
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PRIMARY
CAS
52-51-7
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PRIMARY
MESH
C006827
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PRIMARY
NDF-RT
N0000171131
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PRIMARY Allergens [Chemical/Ingredient]
ChEMBL
CHEMBL1408862
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PRIMARY
ALANWOOD
bronopol
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PRIMARY
NCI_THESAURUS
C77031
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PRIMARY
NDF-RT
N0000184306
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PRIMARY Cell-mediated Immunity [PE]
DRUG BANK
DB13960
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PRIMARY
EVMPD
SUB05925MIG
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PRIMARY
ECHA (EC/EINECS)
200-143-0
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PRIMARY
INN
1716
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PRIMARY
FDA UNII
6PU1E16C9W
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PRIMARY
EPA CompTox
DTXSID8024652
Created by admin on Mon Mar 31 17:48:30 GMT 2025 , Edited by admin on Mon Mar 31 17:48:30 GMT 2025
PRIMARY
WIKIPEDIA
BRONOPOL
Created by admin on Mon Mar 31 17:48:30 GMT 2025 , Edited by admin on Mon Mar 31 17:48:30 GMT 2025
PRIMARY
SMS_ID
100000088698
Created by admin on Mon Mar 31 17:48:30 GMT 2025 , Edited by admin on Mon Mar 31 17:48:30 GMT 2025
PRIMARY
RXCUI
1114345
Created by admin on Mon Mar 31 17:48:30 GMT 2025 , Edited by admin on Mon Mar 31 17:48:30 GMT 2025
PRIMARY RxNorm
DAILYMED
6PU1E16C9W
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PRIMARY
NDF-RT
N0000175629
Created by admin on Mon Mar 31 17:48:30 GMT 2025 , Edited by admin on Mon Mar 31 17:48:30 GMT 2025
PRIMARY Increased Histamine Release [PE]