Absorption, Distribution and Excretion
The absorption, distribution, metabolism and excretion of [14C]tecnazene has been studied in the rat. Earlier metabolism studies with unlabelled tecnazene were also carried out on the rat, rabbit, guinea pig and pigeon. Tecnazene is extensively metabolized in all species. In animals the nitro group is reduced, yielding 2,3,5,6-tetrachloroaniline and 4-amino-2,3,5,6- tetrachlorophenol. These metabolites are excreted in the urine as such or, in the case of the phenol, after the formation of ethereal glucuronide or sulfate conjugates. The nitro group can be replaced by glutathione, leading to the formation of another major metabolite, S-(2,3,5,6-tetrachlorophenyl)-Nacetylcysteine, which is also excreted in the urine.
... the disposition of [14C]tecnazene and its metabolites was followed in male and female rats dosed at 1 mg/kg bw. After 24 hours the highest tissue concentrations of 14C were in the kidneys, liver and nasal passages of both sexes. After seven days 14C residues were low but generally slightly higher in males where the highest concentrations were found in the abdominal fat (0.032 mg/kg, expressed as tecnazene), kidneys (0.016 mg/kg), lungs (0.016), blood (0.014) and heart (0.013 mg/kg). In females, the highest concentration was 0.011 mg/kg in the abdominal fat, blood and ovaries. After seven days the total proportion of the dose present in the tissues was 0.13% and 0.05% in male and female rats respectively. The concentrations of 14C in the tissues appeared to decrease as a function of time on the evidence of autoradiograms at 24 and 48 hours and liquid scintillation counting at 7 days.
Rabbits receiving a single oral dose of 0.1-3.0 g/animal eliminated 60-78% in the feces within 3 days, while the urine accounted for 35-38% (primarily as conjugated products). At 0.01 g/animal, 22-30% was recovered in the feces.

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Metabolism / Metabolites
The metabolic fate of [U-14C]-2,3,5,6-tetrachloronitrobenzene (tecnazene) has been determined in the male and female rat following a single dose of 1 mg/kg and in surgically prepared, bile-duct-cannulated rats following a single oral dose of 135 mg/kg. Radioactivity in the female rat was excreted mainly in urine (82%). The male rat, however, excreted approximately equal amounts of radioactivity in urine and feces (the latter via bile). The principal metabolic pathway was conjugation with glutathione (GSH) and concomitant nitro-displacement. The GSH-conjugate and related metabolites were excreted in the bile and ultimately in the urine as the mercapturic acid conjugate. The cysteine conjugate underwent beta-lyase-mediated metabolism to yield a thiol that underwent subsequent methylation to the thioanisole followed by S-oxidation. 4. A novel tetrachloromethyldisulphide metabolite was also formed.
Some redn of nitro group took place in gut after admin of 2,3,5,6-tetrachloro- nitrobenzene to rabbits. Very small amt of tetrachloroaniline, mercapturic acid, free 4-amino-2,3,5,6-tetrachlorophenol, a sulfate, and a glucuronide were excreted in urine.
Yields S-(2,3,5,6-tetrachlorophenyl)glutathione in rat. /From table/
Mercapturic acid conjugate was excreted at a rate of 11% within 48 hr of the administration of 1-3 g of tecnazene to rabbits. Other metabolites excreted included an ether glucuronide (12%), 2,3,5,6-tetrachloroaniline (10%), unconjugated 4-amino-2,3,5,6-tetrachlorophenol (2%) and an etheral sulfate (1%).
For more Metabolism/Metabolites (Complete) data for TECNAZENE (7 total), please visit the HSDB record page.

Non-Human Toxicity Values
LD50 Rat ip 3500 mg/kg
LD50 Rat oral 250 mg/kg
LD50 Rat oral 7500 mg/kg bw

2,3,5,6-tetrachloronitrobenzene appears as pale yellow crystals. (NTP, 1992)
Tecnazene is a C-nitro compound that is nitrobenzene in which the four hydrogens located ortho- and para- to the nitro group have been replaced by chlorines. A fungicide used to control dry rot, it is no longer approved for use within the European Union. It has a role as an antifungal agrochemical. It is a C-nitro compound, a tetrachlorobenzene and an aromatic fungicide. It is functionally related to a 1,2,4,5-tetrachlorobenzene.

C6HCL4NO2

260.88

258.876

117-18-0

8330

Colorless crystals

1.8±0.1 g/cm3

304.0±0.0 °C at 760 mmHg

98-101 °C(lit.)

143.1±26.5 °C

0.0±0.6 mmHg at 25°C

1.620

3.73

0

2

0

13

195

0

C1=C(C(=C(C(=C1Cl)Cl)[N+](=O)[O-])Cl)Cl

XQTLDIFVVHJORV-UHFFFAOYSA-N

InChI=1S/C6HCl4NO2/c7-2-1-3(8)5(10)6(4(2)9)11(12)13/h1H

1,2,4,5-tetrachloro-3-nitrobenzene

NSC-10235; NSC 10235; Tecnazene

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.)