Absorption, Distribution and Excretion
This study investigated the absorption, distribution, excretion, and metabolism of bromobenzonitrile octanoate in male and female Sprague Dawley rats. Rats were administered a single dose of 14C-labeled bromobenzonitrile octanoate by gavage at a dose of 2 or 20 mg/kg; or, after 14 consecutive days of gavage administration of unlabeled bromobenzonitrile octanoate (2 mg/kg/day), a subsequent gavage administration of 14C-labeled bromobenzonitrile octanoate at a dose of 2 mg/kg. Results showed similar outcomes regardless of the administration regimen. Absorption rates were moderate in both male and female rats. Peak plasma radioactivity was reached 7–10 hours after administration. Radioactivity was widely distributed in most tissues. The highest concentrations were found in blood, plasma, liver, kidneys, and thyroid gland (especially in females). Radioactivity levels in tissues were generally higher in female rats than in male rats. Most radioactive material is excreted in urine (approximately 84-89% in males and 76-80% in females at 7 days), with a small amount excreted in feces (approximately 6-10% in both males and females at 7 days). Excretion is faster in males than in females. After 7 days, the residual amount of radioactive material in the tissues of male animals is approximately 2-3%, and in female animals, approximately 7-9%.
14C-bromobenzonitrile octanoate (as the active ingredient, at a content of 33.4%) was added to the final product Buctril and applied topically to the skin of male Sprague Dawley rats at doses of 0.08, 0.4, or 3.4 mg/rat for exposure times of 0.5, 1, 2, 4, 10, or 24 hours (4 rats per dose/exposure time). The absorption of radioactive material increased with increasing dose and exposure time. After 10 hours, the skin absorption rates for the 0.08, 0.4, and 3.4 mg/rat dose groups were 10.32%, 7.07%, and 4.51%, respectively. After washing with soap and water (10 hours later), 6.46%, 8.06%, and 6.13% of the drug remained on the skin in each dose group, respectively. After 24 hours, the skin absorption rates for 0.08, 0.4, and 3.4 mg/rat were 17.58%, 18.43%, and 10.88%, respectively. After washing with soap and water (24 hours later), 7.91%, 9.50%, and 4.97% of the drug remained on the skin in each dose group, respectively. A study of caprylate esters in rats showed that after oral administration, drug absorption is moderate. Peak plasma concentrations are reached 7 to 10 hours after administration. Most of the dose is eliminated within 7 days, primarily excreted in the urine.
Studies on skin absorption in rats showed that the absorption rate of octanoate within 24 hours was 11% to 18%, depending on the concentration…

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Metabolism/Metabolites
This study investigated the absorption, distribution, excretion, and metabolism of bromobenzonitrile octanoate in male and female Sprague Dawley rats. Rats were administered 14C-labeled bromobenzonitrile octanoate by gavage at a dose of 2 or 20 mg/kg, or by gavage of unlabeled bromobenzonitrile octanoate (2 mg/kg/day) for 14 consecutive days, followed by 14 gavage administrations of 2 mg/kg. Results were independent of the administration regimen. Bromobenzonitrile octanoate is rapidly and almost completely converted to bromobenzonitrile phenol via ester hydrolysis. In some specific studies, the only chemical detected in tissues was bromobenzonitrile phenol itself; bromobenzonitrile octanoate was not detected in tissues. The main substances in urine were free and bound bromobenzonitrile phenol; bromobenzonitrile octanoate was not detected. However, trace amounts of bromobenzonitrile octanoate were detected in feces. Octanoate is rapidly and completely converted to phenol and excreted in urine as phenol or its conjugates.

Toxicity Data
LC50 (Rat) = 720 mg/m3; Non-human Toxicity Values Mouse oral LD50: 245 mg/kg Rat oral LD50: 250 mg/kg Male rat oral LD50: 400 mg/kg /Technical Data/ /Data from Table/ Female rat oral LD50: 238 mg/kg /Technical Data/ /Data from Table/ For more complete non-human toxicity data for bromoxynil octanoate (8 items in total), please visit the HSDB record page.

[1]. Degradation of bromoxynil octanoate by strain Acinetobacter sp. XB2 isolated from contaminated soil. Curr Microbiol. 2011;63(2):218-225.

According to the U.S. Environmental Protection Agency (EPA), bromobenzonitrile octanoate may cause developmental toxicity. Bromobenzonitrile octanoate, [solid], is used as a selective contact herbicide. Mechanism of Action: The main action of benzonitrile compounds is uncoupling oxidative phosphorylation. Bromobenzonitrile octanoate is a fairly potent mitochondrial uncoupling agent in vitro, with a UC50 value of 3.2 to 5 μmol in rat liver mitochondria… The signs and symptoms of acute poisoning in vertebrates (including humans) are largely consistent with the uncoupling mechanism of its main toxicity.

C15H17BR2NO2

403.11

400.962

1689-99-2

15533

White to off-white solid powder

1.5±0.1 g/cm3

424.6±45.0 °C at 760 mmHg

45-46°C

210.6±28.7 °C

0.0±1.0 mmHg at 25°C

1.573

5.19

0

3

8

20

341

0

DQKWXTIYGWPGOO-UHFFFAOYSA-N

InChI=1S/C15H17Br2NO2/c1-2-3-4-5-6-7-14(19)20-15-12(16)8-11(10-18)9-13(15)17/h8-9H,2-7H2,1H3

(2,6-dibromo-4-cyanophenyl) octanoate

2934.99.9001

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.

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Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)
*Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution.
Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)
Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil)
Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals).

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Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)]
*Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.
Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline)
Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline)
Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline)
Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline
Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil)
Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline)

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Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium)
Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose
Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals).

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Oral Formulation 3: Dissolved in PEG400
Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose
Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose
Oral Formulation 6: Mixing with food powders

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Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.

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 (Please use freshly prepared in vivo formulations for optimal results.)