Identification
- Summary
Bronopol is an antimicrobial compound used as a biocide and preservative.
- Generic Name
- Bronopol
- DrugBank Accession Number
- DB13960
- Background
Bronopol, or 2-Bromo-2-nitro-1,3-propanediol, is an organic compound with wide-spectrum antimicrobial properties. First synthesized in 1897, bronopol was primarily used as a preservative for pharmaceuticals and was registered in the United States in 1984 for use in industrial bactericides, slimicides and preservatives 9. Bronopol is used as a microbicide or microbiostat in various commercial and industrial applications, including oil field systems, air washer systems, air conditioning or humidifying systems, cooling water systems, papermills, absorbent clays, metal working fluids, printing inks, paints, adhesives and consumer products 9. Compared to other aliphatic halogen-nitro compounds, bronopol is more stable to hydrolysis in aqueous media under normal conditions 3. The inhibitory activity against various bacteria, including Pseudomonas aeruginosa, was demonstrated in vitro 3. The agent is largely available commercially as an antibacterial for a variety of industrial purposes while it is predominantly available for purchase as a pet animal litter antibacterial at the domestic consumer level 11. Nevertheless, ongoing contemporary re-evaluations of bronopol use in large markets such as Canada now place various compositional and product restrictions on the use of the agent in cosmetic products 7 and in other products where it may not primarily be used in the role of a non-medicinal preservative antimicrobial 8.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Bronopol (DB13960)
- Weight
- Average: 199.988
Monoisotopic: 198.948020332 - Chemical Formula
- C3H6BrNO4
- Synonyms
- 2-Bromo-2-nitropropane-1,3-diol
- 2-Nitro-2-bromo-1,3-propanediol
- beta-Bromo-beta-nitrotrimethyleneglycol
- Bronopol
- Bronopolu
- Bronopolum
- External IDs
- AI3-61639
- BRN 1705868
- NSC 141021
Pharmacology
- Indication
Bronopol as an active ingredient is registered as a commercial biocide and preservative in many industrial processes. Registered biocidal uses include pulp and paper mills, water cooling towers, waste water treatment, evaporative condensers, heat exchangers, food pasteurizing plants, metalworking fluids, and oilfield applications 11. In addition, preservative uses include household products (e.g., dishwashing liquids, laundry products), latex emulsions, polymer lattices, pigments, leather and milk samples for analysis 11. Bronopol is also formulated into granular domestic end-use products in the form of cat litter 11.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Prevention of Bacterial infection •••••••••••• - Contraindications & Blackbox Warnings
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At concentrations of 12.5 to 50 μg/mL, bronopol mediated an inhibitory activity against various strains of Gram negative and positive bacteria in vitro 3. The bactericidal activity is reported to be greater against Gram-negative bacteria than against Gram-positive cocci 3. Bronopol was also demonstrated to be effective against various fungal species, but the inhibitory action is reported to be minimal compared to that of against bacterial species 3. The inhibitory activity of bronopol decreases with increasing pH of the media 3,9. Bronopol also elicits an anti-protozoal activity, as demonstrated with Ichthyophthirius multifiliis in vitro and in vivo 2. It is proposed that bronopol affects the survival of all free-living stages of I. multifiliis 2.
- Mechanism of action
It is proposed that bronopol generates biocide-induced bacteriostasis followed by a growth at an inhibited rate in bacteria, via two distinct reactions between bronopol and essential thiols within the bacterial cell 1. Under aerobic conditions, bronopol catalyzes the oxidation of thiol groups, such as cysteine, to disulfides. This reaction is accompanied by rapid consumption of oxygen, where oxygen acts as the final oxidant. During the conversion of cysteine to cystine, radical anion intermediates such as superoxide and peroxide are formed from bronopol to exert a direct bactericidal activity. The oxidation of excess thiols alters the redox state to create anoxic conditions, leading to a second reaction involving the oxidation of intracellular thiols such as glutathione to its disulfide. The resulting effects are inhibition of enzyme function, and reduced growth rate following the bacteriostatic period 1. Under the anoxic conditions, the reaction between thiol and bronopol decelerates without the involvement of oxygen and the consumption of bronopol predominates. Bronopol is ultimately removed from the reaction via consumption and resumption of bacterial growth occurs 1.
Target Actions Organism AThiol groups oxidizerHumans - Absorption
Bronopol was rapidly absorbed in animal studies. It may be absorbed via aerosol inhalation, dermal contact, and ingestion 6. In rats, approximately 40% of the topically applied dose of bronopol was absorbed through the skin within 24 hr 6. Following oral administration of 1 mg/kg in rats, the peak plasma concentrations of bronopol were reached up to 2 hours post-dosing 5.
- Volume of distribution
The highest concentrations of bronopol were detected in the excretory organs of rat such as kidney, liver, and lung 5. The lowest concentration was in the fat 5.
- Protein binding
No data available.
- Metabolism
Bronopol undergoes degradation in aqueous medium to form bromonitroethanol from a retroaldol reaction with the liberation of an equimolar amount of formaldehyde 4. Formaldehyde is a degradation product of bronopol, which may cause sensitization 6. Bromonitroethanol further decomposes to formaldehyde and bromonitromethane. Bromonitroethanol may also break down to release a nitrite ion and 2-bromoethanol 4.
Hover over products below to view reaction partners
- Route of elimination
Metabolism studies indicate that bronopol is primarily excreted in the urine 9. In rats, about 19% of dermally-applied bronopol was excreted in the urine, feces and expired air 6. Following oral administration of 1 mg/kg radiolabelled bronopol in rats, approximately 81% and 6% of the administered radioactivity was recovered in the urine and expired air, respectively, within a period of 24 hours 5. Following intravenous administration in rat, the recoveries in the urine and expired air were 74% and 9% of the dose, respectively 5.
- Half-life
The half-life of bronopol in the biological systems is not reported in the literature. The half-life value reported for bronopol reflects the environment fate of the compound. When released into the air as vapours, bronopol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals where the half life for this reaction is approximately 11 days 6. The photolysis half-life is 24 hours in water but may be up to 2 days under natural sunlight 6.
- Clearance
No data available.
- Adverse Effects
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Oral LD50, dermal LD50, and inhalation LD50 in rat are 180 mg/kg MSDS, 64-160 mg/kg 6, and > 5000 mg/m^3 MSDS , respectively. In a 90-day dermal toxicity study in rabbits, the NOEL for systemic toxicity was 2 mg/kg/day 9. In a rat 90-day oral toxicity study, bronopol was associated with a severe gastrointestinal irritation 9. A chronic feeding or carcinogenicity study with rats resulted in high mortality, stomach lesions, and severe reduction in body weight gain. A reduction in weight gain was also observed in a chronic dermal or carcinogenicity study of mice 9. Bronopol was not mutagenic in four mutagenicity studies 9.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareTenofovir alafenamide The serum concentration of Tenofovir alafenamide can be increased when it is combined with Bronopol. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 75% Alcohol Wipes Bronopol (0.0969 g/51) + Benzalkonium chloride (0.0969 g/51) + Benzethonium chloride (0.0646 g/51) + Ethanol (242.25 g/51) + Phenoxyethanol (0.1938 g/51) Cloth Topical Baijieyuan Biotechnology (Shandong) Co., Ltd. 2020-06-10 2020-06-16 US 
Aiweier Alcohol Wipes Bronopol (0.0969 g/201) + Benzalkonium chloride (0.0969 g/201) + Benzethonium chloride (0.0646 g/201) + Ethanol (242.25 g/201) + Phenoxyethanol (0.1938 g/201) Cloth Topical Baijieyuan Biotechnology (Shandong) Co., Ltd. 2020-06-10 Not applicable US Aiweier Disinfecttant Wipes Bronopol (0.09 g/1001) + Benzalkonium chloride (0.09 g/1001) + Benzethonium chloride (0.06 g/1001) + Ethanol (225 g/1001) + Phenoxyethanol (0.18 g/1001) Cloth Topical Baijieyuan Biotechnology (Shandong) Co., Ltd. 2020-06-10 Not applicable US Aiweier Disinfecttant Wipes Bronopol (0.0405 g/601) + Benzalkonium chloride (0.0405 g/601) + Benzethonium chloride (0.027 g/601) + Ethanol (101.25 g/601) + Phenoxyethanol (0.081 g/601) Cloth Topical Baijieyuan Biotechnology (Shandong) Co., Ltd. 2020-06-10 Not applicable US Alcohol wipes Bronopol (0.015 g/101) + Benzalkonium chloride (0.015 g/101) + Benzethonium chloride (0.01 g/101) + Ethanol (37.5 g/101) + Phenoxyethanol (0.03 g/101) Cloth Topical Baijieyuan Biotechnology (Shandong) Co., Ltd. 2020-06-10 Not applicable US - Unapproved/Other Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Antibacterial Wet Wipes Bronopol (0.061 g/100g) + Benzalkonium chloride (0.156 g/100g) + Didecyldimethylammonium chloride (0.012 g/100g) + Iodopropynyl butylcarbamate (0.077 g/100g) Swab Topical SHANDONG PROVINCE RUNHE SANITARY MATERIALS CO.,LTD. 2020-04-13 Not applicable US
Categories
- Drug Categories
- Alcohols
- Anti-Infective Agents
- Anti-Infective Agents, Local
- Cell-mediated Immunity
- Compounds used in a research, industrial, or household setting
- Drugs that are Mainly Renally Excreted
- Glycols
- Increased Histamine Release
- Indicators and Reagents
- Laboratory Chemicals
- Preservatives, Pharmaceutical
- Standardized Chemical Allergen
- Classification
- Not classified
- Affected organisms
- Yeast and other fungi
- Gram negative and gram positive bacteria
- Pseudomonas aeruginosa
- Streptococcus pyogenes
- Escherichia coli
- Staphylococcus aureus
- Proteus vulgaris
- Shigella
- Proteus mirabilis
- Klebsiella pneumoniae
- Enterobacter aerogenes
Chemical Identifiers
- UNII
- 6PU1E16C9W
- CAS number
- 52-51-7
- InChI Key
- LVDKZNITIUWNER-UHFFFAOYSA-N
- InChI
- InChI=1S/C3H6BrNO4/c4-3(1-6,2-7)5(8)9/h6-7H,1-2H2
- IUPAC Name
- 2-bromo-2-nitropropane-1,3-diol
- SMILES
- OCC(Br)(CO)[N+]([O-])=O
References
- General References
- Shepherd JA, Waigh RD, Gilbert P: Antibacterial action of 2-bromo-2-nitropropane-1,3-diol (bronopol). Antimicrob Agents Chemother. 1988 Nov;32(11):1693-8. [Article]
- Shinn AP, Picon-Camacho SM, Bron JE, Conway D, Yoon GH, Guo FC, Taylor NG: The anti-protozoal activity of bronopol on the key life-stages of Ichthyophthirius multifiliis Fouquet, 1876 (Ciliophora). Vet Parasitol. 2012 May 25;186(3-4):229-36. doi: 10.1016/j.vetpar.2011.11.025. Epub 2011 Nov 12. [Article]
- CROSHAW B, GROVES MJ, LESSEL B: SOME PROPERTIES OF BRONOPOL, A NEW ANTIMICROBIAL AGENT ACTIVE AGAINST PSEUDOMONAS AERUGINOSA. J Pharm Pharmacol. 1964 Dec;16:SUPPL:127-30T. [Article]
- Wang H, Provan GJ, Helliwell K: Determination of bronopol and its degradation products by HPLC. J Pharm Biomed Anal. 2002 Jun 20;29(1-2):387-92. [Article]
- Buttar HS, Downie RH: The biotransformation and disposition of bronopol following topical and intravenous administration to rats. Toxicol Lett. 1980 Jul;6(2):101-7. [Article]
- BRONOPOL - National Library of Medicine HSDB Database [Link]
- Health Canada Cosmetic Ingredient Hotlist of Prohibited and/or Restricted Ingredients [Link]
- Health Canada Drug and Health Products Chemical Substance: Bronopol Profile [Link]
- United States Environmental Protection Agency (EPA): Bronopol R.E.D. Facts Sheet [File]
- The activity and safety of the antimicrobial agent Bronopol (2-bromo-2-nitropropan-1, 3-diol) [File]
- Canadian Pest Management Regulatory Agency Re-evaluation of Bronopol [File]
- External Links
- KEGG Drug
- D01577
- KEGG Compound
- C13034
- ChemSpider
- 2356
- BindingDB
- 50248122
- 1114345
- ChEBI
- 31306
- ChEMBL
- CHEMBL1408862
- ZINC
- ZINC000001088216
- Wikipedia
- Bronopol
- MSDS
- Download (63.7 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Swab Topical Liquid Topical Cloth Topical Patch Topical Soap Topical Kit Cutaneous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 123-130 MSDS boiling point (°C) 130 MSDS water solubility 25-25g/100mL at 22°C MSDS logP -0.6 MSDS - Predicted Properties
Property Value Source Water Solubility 12.8 mg/mL ALOGPS logP -0.21 ALOGPS logP -0.19 Chemaxon logS -1.2 ALOGPS pKa (Strongest Acidic) 12.55 Chemaxon pKa (Strongest Basic) -3.7 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 83.6 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 31.66 m3·mol-1 Chemaxon Polarizability 13.17 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Mass Spectrum (Electron Ionization) MS splash10-057r-9800000000-96a2fa8203c140ebd484 1H NMR Spectrum 1D NMR Not Applicable 13C NMR Spectrum 1D NMR Not Applicable Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 123.9639346 predictedDarkChem Lite v0.1.0 [M-H]- 127.01364 predictedDeepCCS 1.0 (2019) [M+H]+ 125.7552346 predictedDarkChem Lite v0.1.0 [M+H]+ 130.0364 predictedDeepCCS 1.0 (2019) [M+Na]+ 123.6936346 predictedDarkChem Lite v0.1.0 [M+Na]+ 138.87654 predictedDeepCCS 1.0 (2019)
Targets
References
- Shepherd JA, Waigh RD, Gilbert P: Antibacterial action of 2-bromo-2-nitropropane-1,3-diol (bronopol). Antimicrob Agents Chemother. 1988 Nov;32(11):1693-8. [Article]
Drug created at January 17, 2018 17:10 / Updated at February 03, 2022 06:26