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
[Allergy to preservatives].
1982
Antibacterial action of 2-bromo-2-nitropropane-1,3-diol (bronopol).
1988 Nov
[Cytotoxic and genotoxic activity of certain preservative agents in cosmetics].
2001 Sep
Occurrence of clinical and sub-clinical mastitis in dairy herds in the West Littoral Region in Uruguay.
2002
Allergic contact dermatitis from 2-bromo-2-nitropropane-1,3-diol in Metrogel.
2002 Jan
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
Evaluation of the repeatability of a crude adult indirect Ostertagia ostertagi ELISA and methods of expressing test results.
2002 Oct 16
Effect of freezing on Fossomatic cell counting in ewe milk.
2003 Aug
[Allergy to cosmetics. II. Preservatives].
2004
Prevalence of antibodies to Leptospira interrogans serovar hardjo in bulk tank milk from unvaccinated irish dairy herds.
2004 Apr 1
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
Evaluation of rapid somatic cell counters under different analytical conditions in ovine milk.
2004 Nov
Evaluation of phototoxic properties of antimicrobials used in topical preparations by a photohaemolysis test.
2005
Preservatives in registered chemical products.
2005 Jul
Patch testing with patients' own cosmetics and toiletries--results of the IVDK*, 1998-2002.
2005 Oct
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
Influence of storage and preservation on fossomatic cell count and composition of goat milk.
2005 Sep
[Contact allergy to preservatives contained in cosmetics].
2006
Evaluation of the overall accuracy of the DeLaval cell counter for somatic cell counts in ovine milk.
2006 Dec
Plasma surface modification of poly vinyl chloride for improvement of antibacterial properties.
2006 Jan
Evaluation of the MilkoScan FT 6000 milk analyzer for determining the freezing point of goat's milk under different analytical conditions.
2007 Jul
The use of bronopol to control fungal infection in rainbow trout eggs.
2007 Jun
Contact hypersensitivity to selected excipients of dermatological topical preparations and cosmetics in patients with chronic eczema.
2008 Jun
Examining the fungal and bacterial niche overlap using selective inhibitors in soil.
2008 Mar
Reproducibility and repeatability of measures of milk coagulation properties and predictive ability of mid-infrared reflectance spectroscopy.
2008 Oct
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
Phage therapy and photodynamic therapy: low environmental impact approaches to inactivate microorganisms in fish farming plants.
2009 Jul 30
Consumer exposure to biocides--identification of relevant sources and evaluation of possible health effects.
2010 Feb 3
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 Jan
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
An in vitro bacterial adhesion assessment of surface-modified medical-grade PVC.
2010 Jun 1
Positivity ratio and reaction index: patch-test quality-control metrics applied to the north american contact dermatitis group database.
2010 Mar-Apr
Viability of Mycoplasma agalactiae and Mycoplasma mycoides subsp. capri in goat milk samples stored under different conditions.
2010 Oct 26
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
BRONOPOL [HSDB]
Common Name English
2-BROMO-2-NITROPROPANE-1,3-DIOL [INCI]
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
2-BROMO-2-NITROPROPANE-1,3-DIOL
INCI  
INCI  
Official Name English
Classification Tree Code System Code
NCI_THESAURUS C28394
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
NDF-RT N0000185508
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
WHO-VATC QD01AE91
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
CFR 21 CFR 176.300
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
Food Contact Sustance Notif, (FCN No.) FCN NO. 810
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
EPA PESTICIDE CODE 216400
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
Food Contact Sustance Notif, (FCN No.) FCN NO. 407
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
CFR 21 CFR 176.170
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
Code System Code Type Description
PUBCHEM
2450
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY
MERCK INDEX
m2727
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
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
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY Allergens [Chemical/Ingredient]
ChEMBL
CHEMBL1408862
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY
ALANWOOD
bronopol
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY
NCI_THESAURUS
C77031
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY
NDF-RT
N0000184306
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY Cell-mediated Immunity [PE]
DRUG BANK
DB13960
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY
EVMPD
SUB05925MIG
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-143-0
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY
INN
1716
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY
FDA UNII
6PU1E16C9W
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID8024652
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY
WIKIPEDIA
BRONOPOL
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY
SMS_ID
100000088698
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY
RXCUI
1114345
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY RxNorm
DAILYMED
6PU1E16C9W
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY
NDF-RT
N0000175629
Created by admin on Fri Dec 15 15:09:37 GMT 2023 , Edited by admin on Fri Dec 15 15:09:37 GMT 2023
PRIMARY Increased Histamine Release [PE]