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| Other Sizes |
| ln Vivo |
Exposure of Silurana tropicalis tadpoles (stages 49–50 at start) to simetryn at 0.04 mg/L and 0.40 mg/L for 28 days caused significant retardation in growth and development. At both concentrations, total body length and wet body mass were significantly reduced, and hind limb length was significantly shortened from day 7 (0.40 mg/L) or day 21 (0.04 mg/L) onward. Developmental stage was significantly delayed from day 21 at both concentrations. The ratio of hind limb length/total body length was significantly reduced in the 0.40 mg/L group from day 7 and in the 0.04 mg/L group from day 21. Wet body mass at test termination was significantly smaller in both treatment groups compared to control (0.04 mg/L: T=7.937, P=1.324×10⁻⁶; 0.40 mg/L: T=10.60, P=1.324×10⁻⁶). These effects were concentration-dependent. No histopathological abnormalities were observed in the thyroid glands of tadpoles exposed to simetryn. Additionally, a significantly high incidence (7/30 = 23.3%, P=5.271×10⁻³, Fisher's exact test) of axial malformation (lateral spinal flexure near the tail base) was observed in the 0.40 mg/L group from day 21 onward. No mortality or abnormal behavior was noted in any treatment group [2].
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| Animal Protocol |
The chronic toxicity of simetryn was assessed using a 28-day semistatic amphibian metamorphosis assay under an individual-separated exposure system. Tadpoles of Silurana tropicalis at Nieuwkoop and Faber stages 49–50 (total body length approx. 20 mm) were used. Each tadpole was housed individually in a 500-ml glass beaker containing 330 ml of test solution, with 30 tadpoles per treatment group. Test concentrations were 0.04 mg/L and 0.40 mg/L (1/100 and 1/10 of the previously determined 96-h LC50 value of 3.70 mg/L). A diluent control (dechlorinated tap water) was included. The test solutions were renewed three times per week (Monday, Wednesday, Friday). Tadpoles were kept at 25±1°C under a 12-h light/12-h dark photoperiod. Feeding was performed daily: 0.5 ml/day/beaker of a 10% (w/v) Sera Micron solution for the first 7 days, then 1 ml/day/beaker thereafter. At seven-day intervals, each tadpole was inspected for developmental stage (according to Nieuwkoop and Faber), hind limb length, and total body length (measured to 0.1 mm) using an inverted digital microscope. Daily observations were made for mortality, abnormal behavior, and gross malformations. At test termination, all tadpoles were euthanized in a 200 mg/L tricaine methanesulfonate solution neutralized with 0.1% NaHCO₃, then fixed in 10% neutral buffered formalin. Each fixed tadpole was blotted dry and weighed to the nearest 1 mg. For thyroid histopathology, eight tadpoles were randomly selected from each group; thyroid tissues were processed and examined according to OECD guidance [2].
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| ADME/Pharmacokinetics |
In the used test solutions (allowed to stand static for three days), the concentration of simetryn decreased gradually but remained above 80% of nominal concentrations even on day 28 (86.1±6.68% at 0.04 mg/L nominal; 85.5±4.97% at 0.40 mg/L nominal). No other pharmacokinetic parameters (absorption, distribution, metabolism, excretion, half-life, oral bioavailability) are reported [2].
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| Toxicity/Toxicokinetics |
The 96-h LC50 value of simetryn for Silurana tropicalis tadpoles (stages 49–50) is 3.70 mg/L (as previously reported by Saka, 2010). In the 28-day chronic toxicity test at 0.04 and 0.40 mg/L, no weakened or dead tadpoles were observed in any treatment group. Exposure to 0.40 mg/L induced a significant incidence (23.3%) of axial malformation (scoliosis near the tail base) from day 21 onward. simetryn caused significant retardation in growth (shorter total body length, smaller wet body mass) and development (delayed developmental stage, reduced hind limb length/total body length ratio) at both test concentrations. No histopathological lesions (atrophy, hypertrophy, follicular cell hyperplasia) were observed in thyroid glands of exposed tadpoles. Reduced feeding (leftover food) was observed in the 0.40 mg/L group from day 21, suggesting that growth inhibition may result from decreased food consumption [2].
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| References |
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| Additional Infomation |
Cimetidine is a diamino-1,3,5-triazine compound with the structure N,N'-diethyl-1,3,5-triazine-2,4-diamine, substituted with a methyl thio group at the 6-position. It is a herbicide. It is both a diamino-1,3,5-triazine compound and a methyl thio-1,3,5-triazine compound.
simetryn is a triazine herbicide used in rice paddy fields in Japan. In paddy water, its concentration typically rises to 0.1–1 mg/L within a few days after application, then gradually decreases over 2–3 weeks, with a half-life of about 5 days. The chronic toxicity study shows that simetryn can induce sublethal effects (growth/development retardation and axial malformations) even at concentrations as low as 0.04 mg/L (1/100 of the 96-h LC50), which persist in paddy water for 2–4 weeks. These effects may reduce tadpole survival by impairing swimming performance (due to scoliosis) and delaying metamorphosis completion in ephemeral aquatic environments. The study suggests that risk assessments based solely on acute toxicity data may underestimate the ecological risk of simetryn to wild anuran tadpoles. No positive correlation was found between acute and chronic toxicity for the tested herbicides [2]. |
| Molecular Formula |
C8H15N5S
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|---|---|
| Molecular Weight |
213.3
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| Exact Mass |
213.104
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| CAS # |
1014-70-6
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| PubChem CID |
13905
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| Appearance |
White to off-white solid powder
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| Density |
1.3±0.1 g/cm3
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| Boiling Point |
302.5±25.0 °C at 760 mmHg
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| Melting Point |
82-83°C
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| Flash Point |
136.8±23.2 °C
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| Vapour Pressure |
0.0±0.6 mmHg at 25°C
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| Index of Refraction |
1.623
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| LogP |
1.21
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| Hydrogen Bond Donor Count |
2
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| Hydrogen Bond Acceptor Count |
6
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
14
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| Complexity |
143
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| Defined Atom Stereocenter Count |
0
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| SMILES |
CSC1=NC(NCC)=NC(NCC)=N1
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| InChi Key |
MGLWZSOBALDPEK-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C8H15N5S/c1-4-9-6-11-7(10-5-2)13-8(12-6)14-3/h4-5H2,1-3H3,(H2,9,10,11,12,13)
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| Chemical Name |
2-N,4-N-diethyl-6-methylsulfanyl-1,3,5-triazine-2,4-diamine
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
DMSO : ≥ 37 mg/mL (~173.46 mM)
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| Solubility (In Vivo) |
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.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *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). View More
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)] Oral Formulations
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). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.6882 mL | 23.4412 mL | 46.8823 mL | |
| 5 mM | 0.9376 mL | 4.6882 mL | 9.3765 mL | |
| 10 mM | 0.4688 mL | 2.3441 mL | 4.6882 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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