NAV

Bronopol

Identification

Summary

Bronopolis 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 preservatives9．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 products9．Compared to other aliphatic halogen-nitro compounds, bronopol is more stable to hydrolysis in aqueous media under normal conditions3．The inhibitory activity against various bacteria, includingPseudomonas aeruginosa是证明in vitro3．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 level11．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 products7和其他产品并不主要是be used in the role of a non-medicinal preservative antimicrobial8．

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

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 applications11．In addition, preservative uses include household products (e.g., dishwashing liquids, laundry products), latex emulsions, polymer lattices, pigments, leather and milk samples for analysis11．Bronopol is also formulated into granular domestic end-use products in the form of cat litter11．

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Associated Conditions
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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 bacteriain vitro3．The bactericidal activity is reported to be greater against Gram-negative bacteria than against Gram-positive cocci3．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 species3．The inhibitory activity of bronopol decreases with increasing pH of the media3,9．Bronopol also elicits an anti-protozoal activity, as demonstrated withIchthyophthirius multifiliisin vitroandin vivo2．It is proposed that bronopol affects the survival of all free-living stages ofI. multifiliis2．

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 cell1．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 period1．下一个noxic 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 occurs1．

Target Actions Organism
AThiol groups
oxidizer
 Humans
Absorption

Bronopol was rapidly absorbed in animal studies. It may be absorbed via aerosol inhalation, dermal contact, and ingestion6．In rats, approximately 40% of the topically applied dose of bronopol was absorbed through the skin within 24 hr6．Following oral administration of 1 mg/kg in rats, the peak plasma concentrations of bronopol were reached up to 2 hours post-dosing5．

Volume of distribution

The highest concentrations of bronopol were detected in the excretory organs of rat such as kidney, liver, and lung5．The lowest concentration was in the fat5．

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 formaldehyde4．Formaldehyde is a degradation product of bronopol, which may cause sensitization6．Bromonitroethanol further decomposes to formaldehyde and bromonitromethane. Bromonitroethanol may also break down to release a nitrite ion and 2-bromoethanol4．

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Route of elimination

Metabolism studies indicate that bronopol is primarily excreted in the urine9．In rats, about 19% of dermally-applied bronopol was excreted in the urine, feces and expired air6．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 hours5．Following intravenous administration in rat, the recoveries in the urine and expired air were 74% and 9% of the dose, respectively5．

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 days6．The photolysis half-life is 24 hours in water but may be up to 2 days under natural sunlight6．

Clearance

No data available.

Adverse Effects
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Toxicity

Oral LD50, dermal LD50, and inhalation LD50 in rat are 180 mg/kgMSDS, 64-160 mg/kg6, and > 5000 mg/m^3MSDS, respectively. In a 90-day dermal toxicity study in rabbits, the NOEL for systemic toxicity was 2 mg/kg/day9．In a rat 90-day oral toxicity study, bronopol was associated with a severe gastrointestinal irritation9．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 mice9．Bronopol was not mutagenic in four mutagenicity studies9．

Pathways
Not Available
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Not Available

Interactions

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

Products

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Mixture Products
Name 荷兰国际集团(Ing)redients 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 flag
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 flag
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 flag
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 flag
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 flag
Anti-Bacterial Multi-Purpose Cleaning Wipes Bronopol(50 mg/1001)+Benzalkonium chloride(150 mg/1001)+Ethanol(0.4 mL/1001)+Methylchloroisothiazolinone(0.9 mg/1001)+Methylisothiazolinone(0.3 mg/1001) Cloth Topical Publishers Clearing House LLC 2020-07-01 Not applicable US flag
Anti-Bacterial Multi-Purpose Cleaning Wipes Bronopol(50 mg/1001)+Benzalkonium chloride(150 mg/1001)+Ethanol(0.4 mL/1001)+Methylchloroisothiazolinone(0.9 mg/1001)+Methylisothiazolinone(0.3 mg/1001) Cloth Topical Wenzhou Guanshang Paper Co., Ltd 2020-07-01 Not applicable US flag
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 flag
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 flag
Antiseptic Hand Soap Bronopol(0.1 %)+Triclosan(0.6 %) Liquid Topical Dustbane Products Ltd 1983-12-31 Not applicable Canada flag
Unapproved/Other Products
Name 荷兰国际集团(Ing)redients 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 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

通用再保险公司ferences
  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
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Clinical Trials

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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
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
1H NMR Spectrum 1D NMR Not Applicable
13C NMR Spectrum 1D NMR Not Applicable

Targets

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Details 1.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