| Size | Price | |
|---|---|---|
| 500mg | ||
| 1g | ||
| Other Sizes |
Furylfuramide is a novel and potent nitrofuran analogue
| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
After oral administration of 1.3 mg/kg body weight (14) C-AF-2 to rats, 83% of the radioactive material was excreted in feces and 21% in urine within 48 hours… Metabolism/Metabolites In the presence of electron donors, AF-2 can be reduced to the corresponding free radical anions by xanthine oxidase, acyl dehydrogenase, DT-dihydroflavinase, or liver microsomes. After oral administration of 3 mg/kg dose of 2-(2-furanyl)-3-(5-nitro-2-furanyl)acrylamide to rats, it was mainly metabolized. In the small intestine, the permeability of the metabolite was lower than that of the parent compound. Xanthine oxidase was involved in the metabolic process. After oral administration of AF-2 to rabbits, a metabolite, 2-(β-carboxypropionyl)-3-(5-methylthio-2-furanyl)acrylamide, was identified by mass spectrometry, infrared spectroscopy, and nuclear magnetic resonance spectroscopy. A second metabolite was identified based on its UV and mass spectrometry data and behavior on thin-layer chromatography, presumably a cis-trans isomer of the aforementioned metabolite. In the presence of rat liver microsomal fractions (S9 mixture), the genetic activity of AF-2 in bacteria and yeast rapidly disappeared. Even incubation with the S9 mixture at 37°C for 10 minutes was sufficient to completely inactivate it. Activation is clearly a necessary condition for the generation of genotoxicity. The activation step likely involves the reduction of nitrofurans to amino groups. This reduction is likely achievable in most cultured cell systems, such as bacteria, yeast, Neurospora, mammalian cells, and human lymphocytes. The rapid loss of AF-2 gene activity in the presence of rat liver homogenate suggests that rat liver microsomes may further metabolize the reduction product to an inactive form. For more complete metabolite/metabolite data on furfural (7 metabolites), please visit the HSDB record page. |
|---|---|
| Toxicity/Toxicokinetics |
Interactions
Adding 0.06% 4-(dimethylamino)azobenzene to the diet of 2-month-old rats induced histopathological changes in liver tissue, while the simultaneous addition of 0.2% 2-(2-furanyl)-3-(5-nitro-2-furanyl)acrylamide almost completely inhibited these changes. Mutant activity was significantly increased when ginger (Zingiber officinale) rhizome juice was added to AF2 solution. Component separation of ginger juice revealed that 6-gingerol is a potent mutagen. However, ginger juice also contains anti-6-gingerol anti-mutagenic components. Studies have shown that 6-gingerol components may be activated in the presence of AF2, thus exhibiting mutagenic activity. Anti-mutagenic effect of cinnamaldehyde against chemical mutagen-induced mutagenesis was investigated in Escherichia coli WP2 UVRA-TRPE-. Addition to agar medium reduced the number of furfural-induced TRP+ reversion mutants. Non-human toxicity values LD50 Fisher rat, oral, 340 mg/kg LD50 ICR/Jcl female mouse, oral, 475 mg/kg LD50 Donryu rat, oral, 1554 mg/kg |
| Additional Infomation |
According to an independent committee of scientific and health experts, furanylfuranamide may be carcinogenic. Af-2 is a bright orange crystalline solid. (NTP, 1992) (Z)-2-(2-furanyl)-3-(5-nitro-2-furanyl)acrylamide is a type of acrylamide compound in which the acrylamide molecule is substituted at the 2 and 3 positions with 2-furanyl and 5-nitro-2-furanyl groups, respectively (trans isomer). It was once used as a food preservative but was withdrawn from the market due to suspected carcinogenicity. It is a nitrofuran antibiotic, a C-nitro compound, a primary carboxamide, and also a type of acrylamide compound. It was once used as an antibacterial food additive. It can cause mutations in many cell cultures and may be carcinogenic.
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| Molecular Formula |
C11H8N2O5
|
|---|---|
| Molecular Weight |
248.19
|
| Exact Mass |
248.043
|
| CAS # |
3688-53-7
|
| PubChem CID |
5280707
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| Appearance |
Reddish-orange needles
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| Density |
1.453g/cm3
|
| Boiling Point |
459.6ºC at 760mmHg
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| Melting Point |
151-152ºC
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| Flash Point |
231.8ºC
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| LogP |
3.03
|
| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
5
|
| Rotatable Bond Count |
3
|
| Heavy Atom Count |
18
|
| Complexity |
376
|
| Defined Atom Stereocenter Count |
0
|
| SMILES |
O=[N+](C1=CC=C(/C=C(/C2=CC=CO2)\C(=O)N)O1)[O-]
|
| InChi Key |
LYAHJFZLDZDIOH-VURMDHGXSA-N
|
| InChi Code |
InChI=1S/C11H8N2O5/c12-11(14)8(9-2-1-5-17-9)6-7-3-4-10(18-7)13(15)16/h1-6H,(H2,12,14)/b8-6-
|
| Chemical Name |
(Z)-2-(furan-2-yl)-3-(5-nitrofuran-2-yl)prop-2-enamide
|
| Synonyms |
Furylfuramide NSC 44973 NSC 44973NSC 44973
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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)
|
| Solubility (In Vitro) |
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
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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 | 4.0292 mL | 20.1459 mL | 40.2917 mL | |
| 5 mM | 0.8058 mL | 4.0292 mL | 8.0583 mL | |
| 10 mM | 0.4029 mL | 2.0146 mL | 4.0292 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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