4-Hydroxy-3-lodo-5-NitrobenOnitrile
nitroxinil
CAS: 1689-89-0
Molecular Formula: C7H3IN2O3
4-Hydroxy-3-lodo-5-NitrobenOnitrile - Names and Identifiers
| Name | nitroxinil |
| Synonyms | dovenix NITROXINIL NITROXYNIL NITROXINYL Nitroxynil nitroxinil Fluconix-340 4-CYANO-2-IODO-6-NITROPHENOL 4-Hydroxy-3-lodo-5-NitrobenOnitrile 4-hydroxy-3-iodo-5-nitro benzonitril 4-hydroxy-3-iodo-5-nitro-benzonitril 4-HYDROXY-3-IODO-5-NITROBENZONITRILE 4-Hydroxy-3-iodo-5-nitrobenzonitrile Benzonitrile, 4-hydroxy-3-iodo-5-nitro- |
| CAS | 1689-89-0 |
| EINECS | 216-884-8 |
| InChI | InChI=1/C7H3IN2O3/c8-5-1-4(3-9)2-6(7(5)11)10(12)13/h1-2,11H |
4-Hydroxy-3-lodo-5-NitrobenOnitrile - Physico-chemical Properties
| Molecular Formula | C7H3IN2O3 |
| Molar Mass | 290.01 |
| Density | 2.1385 (estimate) |
| Melting Point | 137-138° |
| Boling Point | 280.1±40.0 °C(Predicted) |
| Flash Point | 123.2°C |
| Vapor Presure | 0.00227mmHg at 25°C |
| Appearance | White to yellow powder |
| pKa | 3.00±0.38(Predicted) |
| Storage Condition | Keep in dark place,Sealed in dry,Room Temperature |
| Refractive Index | 1.735 |
4-Hydroxy-3-lodo-5-NitrobenOnitrile - Risk and Safety
| Hazard Symbols | T - Toxic |
| Risk Codes | R25 - Toxic if swallowed R36/37/38 - Irritating to eyes, respiratory system and skin. R43 - May cause sensitization by skin contact |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36/37 - Wear suitable protective clothing and gloves. S45 - In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) |
| UN IDs | UN2811 6.1/PG 3 |
| WGK Germany | 3 |
| RTECS | DI4600000 |
| HS Code | 29269090 |
4-Hydroxy-3-lodo-5-NitrobenOnitrile - Reference Information
| NIST chemical information | Information provided by: webbook.nist.gov (external link) |
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| background and overview | hepatosporiosis is one of the main parasitic diseases that harm cattle and sheep, especially ruminants such as cattle and sheep. Its pathogens belong to the family Fasciolidae, the genus schistosomiasis, and there are three types of schistosomiasis (Fasciolahepatica), giant schistosomiasis (F. gagantica) and large schistosomiasis (F. magna). There are two species of liver fluke and giant fluke found in my country. The former is more common, and the latter is mostly distributed in southern provinces such as Fujian, Jiangsu, and Guangxi. It is a regional epidemic in all provinces and regions of our country and is very common. The infection rate of cattle and sheep is the most serious. The infection rate of sheep is generally 30% ~ 50%, reaching 100% in some areas, 30% ~ 60% in cattle and more than 90% in some areas. In the process of chronic diseases, it will lead to lean animals and developmental disorders, which will reduce the production capacity of farm cattle, reduce the milk production of dairy cattle, reduce the yield or quality of wool meat, and cause huge losses to the animal husbandry economy. It is estimated that the economic loss of animal husbandry caused by the disease in China amounts to hundreds of millions of yuan every year. Nitrophenol nitrile is a new type of liver fluke medicine. It is an effective synthetic drug developed by the French Rhone Merrieu Institute to remove liver fluke. It is currently one of the clinically effective anti-liver fluke drugs. It has the advantages of small dose (10~20 mg/kg), convenient use, high efficiency and safety. Blocking the oxidative phosphorylation of the worm body, affecting energy metabolism and causing the worm body to die. In addition to having good effects on cattle, sheep, fluke, and large fluke, it is also effective on bovine pancreatic fluke, sheep front and back fluke, cattle and sheep twirling blood spear nematode, porcine fluke, and canine hookworm. The excretion is slow and cannot be slaughtered and eaten within 31 days after medication. It is forbidden for dairy cows. Although the drug has been imported into veterinary clinic in China since 987, it has still been dependent on import, which limits its wide application to a certain extent. |
| properties | nitrocophenol nitrile is light yellow powder, odorless or almost odorless, insoluble in water, soluble in organic solvent and sodium hydroxide solution, sensitive to light, should be stored away from light. |
| use | nitrocodophenol nitrile is a new type of liver-killing fluke. oral administration of this product is not as effective as injection. subcutaneous injection is similar to intramuscular injection, but subcutaneous injection is mostly used clinically. Its deworming mechanism is to block the oxidative phosphorylation process of the worm, reduce the concentration of ATP, reduce the energy supply of the worm and cause the death of the worm. It has good effects on cattle, sheep liver fluke, and anterior and posterior fluke adults, and it also has good effects on pig liver fluke, sheep blood spear nematode, and canine roundworm. A test on the effect of nitroodophenol nitrile on the mitochondrial function of rat hepatocytes proved that it is an uncoupling agent for oxidative phosphorylation. The peak concentration of plasma can be reached after 30 min by injecting nitroiodophenol under the skin of cattle and sheep, and the drug is quickly absorbed. When the adult parasite ingests the host's blood, it can uncouple the ATP reaction in the mitochondria of the insect's somatic cells, thereby reducing the ATP concentration, and eventually leading to the death of the worm and achieving the purpose of killing insects. Because the drug is highly bound to plasma protein in the blood (binding rate> 97%), it has a slow-release effect and lasts for a long time in the host body, so the worm body can be in a drug environment for a long time, and it can give full play to its inhibitory effect on larvae. |
| toxicity test | research shows that when 10 mg/kg and 20 mg/kg doses are injected subcutaneously, cattle and sheep have no abnormal reaction, and even pregnant ewes have normal performance. The maximum tolerable dose of the drug for cattle and sheep is 40 mg/kg. At this time, cattle and sheep will have temporary rapid breathing and high body temperature. Typical symptoms of oxidative phosphorylation uncoupling. Tests on sheep showed that no abnormality was seen when 20 mg/k g was injected subcutaneously. When the dose was increased to 40 mg/kg, 3 of the 4 sheep began to shake their heads 20min after injection, walked and shook their heads, shortness of breath, 2 of them returned to normal after 5 hours, and 1 died after 6 hours. Postmortem autopsy found that in addition to obvious drug (yellow) staining of the connective tissue at the injection site, the visceral serosa and omentum tissues also showed mild yellow staining, and no abnormal changes were found in other tissues and organs. Qian Dexing et al. After intramuscular injection of nitrocophenol nitrile at a dose of 40 mg/kg, it was found that 1.5h after injection, the tested sheep showed depressed spirit, dull eyes, slow response and loss of appetite. After 3.5 h, shortness of breath occurred and a small amount of transparent nasal discharge occurred. After 5 h, the symptoms disappeared naturally and returned to normal. |
| synthesis route | using p-hydroxybenzaldehyde as raw material, first react with hydroxylamine hydrochloride and sodium formate in formic acid to synthesize p-hydroxybenzonitrile with a yield of 88.6%, and then react with concentrated nitric acid in glacial acetic acid to synthesize 3-nitro-4-hydroxybenzonitrile with a yield of 92.9%, and the latter reacts with iodine and hydrogen peroxide in acidic ethanol solution to synthesize nitroiodophenolonitrile, the yield was 93.9% and the total yield was 77.3%. The structures of intermediates and target products were confirmed by means of elemental analysis, IR and MS. The method is easy to obtain raw materials, easy to operate, and high in yield. The specific reaction process is as follows: |
| determination of content | the content of nitrocophenol nitrile was determined by reversed-phase high performance liquid chromatography (RP -HPLC). Using acetonitrile -0.01 mol/L phosphate pH 6.5(20 ∶ 80,V/V) as mobile phase, Zorbax SB-C18 chromatographic column (4.6mm × 250mm,5 μm) was Agilent at a flow rate of 1.0 mL/min, column temperature of 25 ℃, and detection wavelength of 273 nm. The results showed that there was a good linear relationship (r = 0.9995) between the concentration of nitrophenol nitrile and the peak area in the range of 0.050~1.20 mg/mL, the lowest detected concentration was 2.5 ng/mL, and the lowest quantitative concentration was 5.0 ng/mL. The recoveries of low, medium and high concentrations were 100. 21%, 99.07% and 101.90%,RSD = 0.48%(n = 9). The method is specific, accurate, simple, sensitive and stable, and can be used for the determination of nitrophenolonitrile. |
| indications | mainly used for liver fluke disease and gastrointestinal nematode disease in cattle, sheep, pigs and dogs. |
| specification | injection: 50 ml 12.5g, 250 ml 62.5g. |
| usage and dosage | subcutaneous injection: one dose, 10 mg per kilogram of body weight, cattle, sheep, pigs and dogs. |
| precautions | 1. the safety range of this product is narrow. when 40 mg per kilogram of body weight is taken orally by cattle and sheep, it will cause a significant increase in heart rate and respiratory rate. Injection has strong irritation to body tissues, especially to dogs. 2. drug withdrawal period: 30 days for sheep and 5 days for milk abandonment. 3. The injection is irritating to local tissues, and the reaction of dogs is the most serious. In addition to more than half of the severe local reactions, it is also easy to cause abscess. 4. When excreting, milk and urine can be yellow dyed. Attention should be paid to the timely replacement of padding. When injecting, liquid medicine should be prevented from leaking to prevent yellow hair. 5. the elimination in livestock is slow, and the primary dosage requires an excretion period of more than 31 d, during which it cannot be slaughtered for consumption. 6. Domestic animals during lactation should not be used. 7. The maximum tolerance of cattle and sheep is 40 mg/kg. 8. Repeated medication should be more than 4 weeks apart. |
| contraindications | other drugs cannot be mixed with nitrocophenol nitrile injection to avoid incompatibility. |
| Main reference materials | [1] Editor-in-Chief Kong Fanyao. Veterinary dictionary. Beijing: China Agriculture Press. 1999. Page 444. [2] Zhao Haishuang et al. Study on Synthesis of Nitrophenolonitrile, an anti-liver fluke drug. The chemical world. 2003,8:428-431. [3] Zhao Haishuang et al. Research and application of nitroiodophenol nitrile, an anti-liver fluster drug. Advances in animal medicine. 2001,(22) 4: 95-96. [4] Hu Gongzheng, edited by Cui Yaoming. Reasonable compatibility of veterinary drugs. Zhengzhou: Henan Science and Technology Press. 2009. [5] Ge Xiuwen et al. Determination of Nitrophenolonitrile by Reversed Phase High Performance Liquid Chromatography. Chinese Journal of Veterinary Medicine. 2010, 44( 8): 31~32, 41. [6] Hu Gongzheng, Li Honor, Xu Lanju Editor-in-Chief. New Handbook of Practical Veterinary Drugs. Zhengzhou: Henan Science and Technology Press. |
Last Update：2024-04-09 21:11:58
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