NAV

Bronopol

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
3D
Similar Structures
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
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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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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Prevention ofBacterial infection••••••••••••
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Pharmacodynamics

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.

TargetActionsOrganism
AThiol groups
oxidizer
Humans
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.

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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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Toxicity

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
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
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interactions in your software
Tenofovir alafenamideThe serum concentration of Tenofovir alafenamide can be increased when it is combined with Bronopol.
Food Interactions
No interactions found.

Products

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Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
75% Alcohol WipesBronopol (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)ClothTopicalBaijieyuan Biotechnology (Shandong) Co., Ltd.2020-06-102020-06-16US flag
Aiweier Alcohol WipesBronopol (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)ClothTopicalBaijieyuan Biotechnology (Shandong) Co., Ltd.2020-06-10Not applicableUS flag
Aiweier Disinfecttant WipesBronopol (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)ClothTopicalBaijieyuan Biotechnology (Shandong) Co., Ltd.2020-06-10Not applicableUS flag
Aiweier Disinfecttant WipesBronopol (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)ClothTopicalBaijieyuan Biotechnology (Shandong) Co., Ltd.2020-06-10Not applicableUS flag
Alcohol wipesBronopol (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)ClothTopicalBaijieyuan Biotechnology (Shandong) Co., Ltd.2020-06-10Not applicableUS flag
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Antibacterial Wet WipesBronopol (0.061 g/100g) + Benzalkonium chloride (0.156 g/100g) + Didecyldimethylammonium chloride (0.012 g/100g) + Iodopropynyl butylcarbamate (0.077 g/100g)SwabTopicalSHANDONG PROVINCE RUNHE SANITARY MATERIALS CO.,LTD.2020-04-13Not applicableUS flag

Categories

Drug Categories
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
  1. 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]
  2. 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]
  3. 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]
  4. 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]
  5. 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]
  6. BRONOPOL - National Library of Medicine HSDB Database [Link]
  7. Health Canada Cosmetic Ingredient Hotlist of Prohibited and/or Restricted Ingredients [Link]
  8. Health Canada Drug and Health Products Chemical Substance: Bronopol Profile [Link]
  9. United States Environmental Protection Agency (EPA): Bronopol R.E.D. Facts Sheet [File]
  10. The activity and safety of the antimicrobial agent Bronopol (2-bromo-2-nitropropan-1, 3-diol) [File]
  11. Canadian Pest Management Regulatory Agency Re-evaluation of Bronopol [File]
KEGG Drug
D01577
KEGG Compound
C13034
ChemSpider
2356
BindingDB
50248122
RxNav
1114345
ChEBI
31306
ChEMBL
CHEMBL1408862
ZINC
ZINC000001088216
Wikipedia
Bronopol
MSDS
Download (63.7 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SwabTopical
LiquidTopical
ClothTopical
PatchTopical
SoapTopical
KitCutaneous
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)123-130MSDS
boiling point (°C)130MSDS
water solubility25-25g/100mL at 22°CMSDS
logP-0.6MSDS
Predicted Properties
PropertyValueSource
Water Solubility12.8 mg/mLALOGPS
logP-0.21ALOGPS
logP-0.19Chemaxon
logS-1.2ALOGPS
pKa (Strongest Acidic)12.55Chemaxon
pKa (Strongest Basic)-3.7Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area83.6 Å2Chemaxon
Rotatable Bond Count3Chemaxon
Refractivity31.66 m3·mol-1Chemaxon
Polarizability13.17 Å3Chemaxon
Number of Rings0Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Mass Spectrum (Electron Ionization)MSsplash10-057r-9800000000-96a2fa8203c140ebd484
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-123.9639346
predicted
DarkChem Lite v0.1.0
[M-H]-127.01364
predicted
DeepCCS 1.0 (2019)
[M+H]+125.7552346
predicted
DarkChem Lite v0.1.0
[M+H]+130.0364
predicted
DeepCCS 1.0 (2019)
[M+Na]+123.6936346
predicted
DarkChem Lite v0.1.0
[M+Na]+138.87654
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Thiol groups
Kind
Small molecule
Organism
Humans
Pharmacological action
Yes
Actions
Oxidizer
Thiol groups are encountered in biological systems in cysteine residues and in cofactors such as lipoamide and lipoic acid. They are also called sulfhydryl and mercapto groups.
References
  1. 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