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

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

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
Direct toxicity assessment of wastewater: Baroxymeter, a portable rapid toxicity device and the industry perspective.
2002
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
Determination of bronopol and its degradation products by HPLC.
2002 Jun 20
Detection of Mycobacterium avium subspecies paratuberculosis specific IS900 insertion sequences in bulk-tank milk samples obtained from different regions throughout Switzerland.
2002 Jun 26
Prevalence of antibodies to Leptospira interrogans serovar hardjo in bulk tank milk from unvaccinated irish dairy herds.
2004 Apr 1
[Contact sensitization to pharmaceutic aids in dermatologic cosmetic and external use preparations].
2004 May
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
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
Plasma surface modification of poly vinyl chloride for improvement of antibacterial properties.
2006 Jan
Antifungal activities of bronopol and 2-methyl-4-isothiazolin-3-one (MT) against saprolegnia.
2007 Dec
The use of bronopol to control fungal infection in rainbow trout eggs.
2007 Jun
Phage therapy and photodynamic therapy: low environmental impact approaches to inactivate microorganisms in fish farming plants.
2009 Jul 30
Patch-test results of the North American Contact Dermatitis Group 2005-2006.
2009 May-Jun
Formaldehyde-releasers in cosmetics in the USA and in Europe.
2010 Apr
Effect of preservatives on the accuracy of mid-infrared milk component testing.
2010 Dec
Toxicity of fungicides to natural bacterial communities in wetland water and sediment measured using leucine incorporation and potential denitrification.
2010 Feb
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 1. Characterization, frequency and relevance of sensitization, and frequency of use in cosmetics.
2010 Jan
Positivity ratio and reaction index: patch-test quality-control metrics applied to the north american contact dermatitis group database.
2010 Mar-Apr
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:09:37 GMT 2023
Edited
by admin
on Fri Dec 15 15:09:37 GMT 2023
Record UNII
6PU1E16C9W
Record Status Validated (UNII)
Record Version
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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
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
HSDB
7195
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
CAS
52-51-7
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
MESH
C006827
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
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]
Related Record Type Details
ACTIVE MOIETY