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1. 2-bromo-2-nitro-1,3-propanediol
2. Bronosol
1. 2-bromo-2-nitro-1,3-propanediol
2. 52-51-7
3. 2-bromo-2-nitropropane-1,3-diol
4. Bronosol
5. Bronocot
6. Bronidiol
7. Bronopolu
8. Bronotak
9. 1,3-propanediol, 2-bromo-2-nitro-
10. Onyxide 500
11. Lexgard Bronopol
12. 2-nitro-2-bromo-1,3-propanediol
13. Bnpd
14. Mfcd00007390
15. Beta-bromo-beta-nitrotrimethyleneglycol
16. Nsc 141021
17. Chebi:31306
18. Nsc-141021
19. 6pu1e16c9w
20. Ncgc00164057-01
21. Bronopolum
22. Dsstox_cid_4652
23. Dsstox_rid_77484
24. Dsstox_gsid_24652
25. Bronopolu [polish]
26. Caswell No. 116a
27. Bioban
28. Bronopolum [inn-latin]
29. Myacide As Plus
30. Myacide Bt
31. Cas-52-51-7
32. Bronopol [inn:ban:jan]
33. Myacide Pharma Bp
34. Canguard 409
35. Bnpk
36. Hsdb 7195
37. Einecs 200-143-0
38. Un3241
39. Epa Pesticide Chemical Code 216400
40. Brn 1705868
41. Unii-6pu1e16c9w
42. Ai3-61639
43. 2-bromo-2-nitropropan-1,3-diol
44. 2-bromo-2-nitro-propane-1,3-diol
45. Bronopol (jan/inn)
46. Bronopol [hsdb]
47. Bronopol [inn]
48. Bronopol [jan]
49. Bronopol [mi]
50. Bronopol [vandf]
51. Bronopol [mart.]
52. Wln: Wnxe1q1q
53. 1, 2-bromo-2-nitro-
54. 2-bromo-2-nitropropane-1,3-diol (bronopol)
55. Bronopol [who-dd]
56. Ec 200-143-0
57. Schembl23260
58. Bioban Bnpd-40 (salt/mix)
59. Chembl1408862
60. Dtxsid8024652
61. Schembl16556987
62. Lvdkznitiuwner-uhfffaoysa-
63. 2-bromo-2nitro-1,3-propanediol
64. Amy8948
65. 2-bromo-2-nitro-1,3-propandiol
66. 2-bromo-2-nitropropane-1,3-diol [un3241] [flammable Solid]
67. Albb-031641
68. Hy-b1217
69. Zinc1088216
70. Tox21_112079
71. Tox21_300126
72. Bdbm50248122
73. Nsc141021
74. S4553
75. 2-bromanyl-2-nitro-propane-1,3-diol
76. Akos003606838
77. Ccg-213823
78. Cs-4699
79. Db13960
80. Bronopol 100 Microg/ml In Acetonitrile
81. Ncgc00164057-02
82. Ncgc00164057-03
83. Ncgc00253984-01
84. As-11889
85. 2-bromo-2-nitro-1,3-propanediol, 98%
86. .beta.-bromo-.beta.-nitrotrimethyleneglycol
87. Db-027831
88. B1247
89. Bronopol, Pestanal(r), Analytical Standard
90. Ft-0611399
91. 52b517
92. D01577
93. E85247
94. Ab01563195_01
95. 2-bromo-2-nitropropane-1,3-diol [inci]
96. A829125
97. Sr-01000944249
98. Q-200765
99. Q2462902
100. Sr-01000944249-1
| Molecular Weight | 199.99 g/mol |
|---|---|
| Molecular Formula | C3H6BrNO4 |
| XLogP3 | -0.6 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 4 |
| Rotatable Bond Count | 2 |
| Exact Mass | 198.94802 g/mol |
| Monoisotopic Mass | 198.94802 g/mol |
| Topological Polar Surface Area | 86.3 Ų |
| Heavy Atom Count | 9 |
| Formal Charge | 0 |
| Complexity | 107 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
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. In addition, preservative uses include household products (e.g., dishwashing liquids, laundry products), latex emulsions, polymer lattices, pigments, leather and milk samples for analysis. Bronopol is also formulated into granular domestic end-use products in the form of cat litter.
At concentrations of 12.5 to 50 g/mL, bronopol mediated an inhibitory activity against various strains of Gram negative and positive bacteria _in vitro_. The bactericidal activity is reported to be greater against Gram-negative bacteria than against Gram-positive cocci. 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. The inhibitory activity of bronopol decreases with increasing pH of the media. Bronopol also elicits an anti-protozoal activity, as demonstrated with _Ichthyophthirius multifiliis_ _in vitro_ and _in vivo_. It is proposed that bronopol affects the survival of all free-living stages of _I. multifiliis_.
Anti-Infective Agents
Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)
Anti-Infective Agents, Local
Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)
Indicators and Reagents
Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant and Hackh's Chemical Dictionary, 5th ed, p301, p499) (See all compounds classified as Indicators and Reagents.)
Absorption
Bronopol was rapidly absorbed in animal studies. It may be absorbed via aerosol inhalation, dermal contact, and ingestion. In rats, approximately 40% of the topically applied dose of bronopol was absorbed through the skin within 24 hr. Following oral administration of 1 mg/kg in rats, the peak plasma concentrations of bronopol were reached up to 2 hours post-dosing.
Route of Elimination
Metabolism studies indicate that bronopol is primarily excreted in the urine. In rats, about 19% of dermally-applied bronopol was excreted in the urine, feces and expired air. 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. Following intravenous administration in rat, the recoveries in the urine and expired air were 74% and 9% of the dose, respectively.
Volume of Distribution
The highest concentrations of bronopol were detected in the excretory organs of rat such as kidney, liver, and lung. The lowest concentration was in the fat.
Clearance
No data available.
The rat metabolism data for bronopol consist of four separate studies conducted with male and female Sprague-Dawley rats. Animals were treated by gavage with (14)C bronopol (radiochemical purity: >95-100%). In the first study animals received a single dose of 10 mg/kg. The second study employed a higher dose of 50 mg/kg. Doses higher the 50 mg/kg caused respiratory problems and death. The third study's dose was 10 mg/kg (14 daily doses of nonradioactive, 100% pure, bronopol, followed by one dose of (14)C-bronopol). Urine, feces and CO2 were collected for 7 days after dosing, at which time the rats were killed and the tissues examined for radioactivity. Because, irrespective of the dose, most of the administered (14)C was excreted in urine (64-78% in 24 hours and 68-83% in 7 days), urine was used for the identification of metabolites in the fourth study. Feces, CO2 and tissues represented minor routes of excretion of (14)C. Very little (14)C was also detected in the whole blood and plasma. From the results of these four studies... /it was/ concluded that bronopol administered orally was rapidly absorbed and rapidly excreted by the rats of both sexes, with urine being the major route of excretion.
USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Bronopol. Case 2770, September 1995. Available from, as of March 2, 2004: https://www.epa.gov/pesticides/reregistration/status.htm
Oral doses are rapidly absorbed and rapidly excreted, mainly in the urine /in animals/.
Tomlin CDS, ed. Bronopol (52-51-7). In: The e-Pesticide Manual, Version 2.2 (2002). Surrey UK, British Crop Protection Council.
The substance can be absorbed into the body by inhalation of its aerosol, through the skin and by ingestion.
IPCS, CEC; International Chemical Safety Card on 2-Bromo-2-nitro-1,3-propanediol. (October 1995). Available from, as of March 10, 2004: https://www.inchem.org/documents/icsc/icsc/eics0415.htm
Approximately 40% of the topically applied dose of antibacterial agent [(14)C] bronopol([(14)C]BP) was absorbed through the rat skin within 24 hr. Of the applied radioactivity, about 19% was excreted in the urine, feces and expired air. The 24 hr recoveries of (14)C in the urine and expired air were 15 and 2%, respectively, of the dose applied to the skin, and 74 and 9%, respectively, of the dose given intravenously.
PMID:7414618 Buttar HS et al; Toxicol Lett 6 (2): 101-7 (1980)
Bronopol undergoes degradation in aqueous medium to form bromonitroethanol from a retroaldol reaction with the liberation of an equimolar amount of formaldehyde. Formaldehyde is a degradation product of bronopol, which may cause sensitization. Bromonitroethanol further decomposes to formaldehyde and bromonitromethane. Bromonitroethanol may also break down to release a nitrite ion and 2-bromoethanol.
Approx. 40% of the topically applied dose of antibacterial agent [(14)C] bronopol([(14)C]BP) was absorbed through the rat skin within 24 hr. Of the applied radioactivity, about 19% was excreted in the urine, feces and expired air. The 24 hr recoveries of (14)C in the urine and expired air were 15 and 2%, respectively, of the dose applied to the skin, and 74 and 9%, respectively, of the dose given intravenously. The TLC of the urines showed three metabolites, but no unchanged [(14)C]BP in both groups. The results suggest that rat skin is quite permeable to bronopol.
Buttar HS and Downie RH. Toxicol Lett 6 (2): 101-7 (1980) 7414618
Transformation products usually differ in environmental behaviors and toxicological properties from the parent contaminants, and probably cause potential risks to the environment. Toxicity evolution of a labile preservative, bronopol, upon primary aquatic degradation processes was investigated. Bronopol rapidly hydrolyzed in natural waters, and primarily produced more stable 2-bromo-2-nitroethanol (BNE) and bromonitromethane (BNM). Light enhanced degradation of the targeted compounds with water site specific photoactivity. The bond order analysis theoretically revealed that the reversible retroaldol reactions were primary degradation routes for bronopol and BNE. Judging from toxicity assays and the relative pesticide toxicity index, these degradation products (i.e., BNE and BNM), more persistent and higher toxic than the parent, probably accumulated in natural waters and resulted in higher or prolonging adverse impacts. Therefore, these transformation products should be included into the assessment of ecological risks of non-persistent and low toxic chemicals such as the preservative bronopol.
PMID:21035931 Cui N et al; Environ Pollut 159 (2): 609-15 (2011)
The major metabolite /in animals/ has been identified as 2-nitropropane-1,3-diol.
Tomlin CDS, ed. Bronopol (52-51-7). In: The e-Pesticide Manual, Version 2.2 (2002). Surrey UK, British Crop Protection Council.
The only metabolite identified in urine was BTS 23 913 (2-nitropropane-1,3- diol or desbromo-bronopol), accounting for 45-50% of the radioactivity taken for analyses. The remaining radioactivity was not identified (one radioactive peak and radioactivity not resolved into peaks). Unchanged bronopol was not detected.
USEPA/Office of Pesticide Programs; Reregistration Eligibility Decision Document - Bronopol. Case 2770, September 1995. Available from, as of March 2, 2004: https://www.epa.gov/pesticides/reregistration/status.htm
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. The photolysis half-life is 24 hours in water but may be up to 2 days under natural sunlight.
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. 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. 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.
...Under aerobic conditions, bronopol catalytically oxidizes thiol-containing materials such as cysteine, with atmospheric oxygen as the final oxidant. By-products of this reaction are active oxygen species such as superoxide and peroxide, which are directly responsible for the bactericidal activity of the compound and for the reduced growth rate after the bacteriostatic period.
PMID:3075439 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC175953 Shepherd JA et al; Antimicrob Agents Chemother 32 (11): 1693-8 (1988)
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