oxyclozanide
oxyclozanide
CAS: 2277-92-1
Molecular Formula: C13H6Cl5NO3
oxyclozanide - Names and Identifiers
| Name | oxyclozanide |
| Synonyms | oxyclozanide Oxycloxanide OXYCLOZANIDE BPV OXYCLOZANIDE B.P BPV OXYCLOZANIDE BPV 3,3',5,5',6-pentachloro-2,2'-dihydroxybenzanilide 2,2'-dihydroxy-3,3',5,5',6-pentachlorobenzanilide 2,3,5-TRICHLORO-N-(3,5-DICHLORO-2-HYDROXYPHENYL)-6-HYDROXYBENZAMIDE 2,3,5-trichloro-n-(3,5-dichloro-2-hydroxyphenyl)-6-hydroxy-benzamid 2,3,5-trichloro-N-(3,5-dichloro-2-hydroxy-phenyl)-6-hydroxy-benzamide |
| CAS | 2277-92-1 |
| EINECS | 218-904-0 |
| InChI | InChI=1/C13H6Cl5NO3/c14-4-1-6(16)11(20)8(2-4)19-13(22)9-10(18)5(15)3-7(17)12(9)21/h1-3,20-21H,(H,19,22) |
| InChIKey | JYWIYHUXVMAGLG-UHFFFAOYSA-N |
oxyclozanide - Physico-chemical Properties
| Molecular Formula | C13H6Cl5NO3 |
| Molar Mass | 401.46 |
| Density | 1.6274 (rough estimate) |
| Melting Point | 77-81C |
| Boling Point | 215C |
| Flash Point | 223.5°C |
| Water Solubility | 29mg/L(25 ºC) |
| Vapor Presure | 1.43E-08mmHg at 25°C |
| Appearance | White to light yellow powder |
| pKa | 5.07±0.50(Predicted) |
| Storage Condition | Sealed in dry,Room Temperature |
| Refractive Index | 1.6200 (estimate) |
| Physical and Chemical Properties | As the preferred drug for clinical anti-helminth infection, it has broad-spectrum and low toxicity, excellent characteristics such as low residue. The chemical name is 2,3, 5-dichloro-n-(3, 5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide. As a chemical synthetic drug against helminth infection, pentachlorosamine has the excellent characteristics of broad spectrum, low toxicity and low residue, and has a significant effect in the treatment of worm infection such as trematode and Taenia. |
oxyclozanide - Risk and Safety
| Risk Codes | R22 - Harmful if swallowed R50/53 - Very toxic to aquatic organisms, may cause long-term adverse effects in the aquatic environment. R36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S60 - This material and its container must be disposed of as hazardous waste. S61 - Avoid release to the environment. Refer to special instructions / safety data sheets. S36 - Wear suitable protective clothing. S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. |
| UN IDs | UN 3077 |
| WGK Germany | 3 |
| RTECS | CV8576000 |
oxyclozanide - Reference Information
Open Data Unverified Data
| introduction | pentachlorosilamide (Oxyclozanide), also known as hydroxychlorosilamide, hydroxychlorosilamide and hydroxychlorizamide, as the first choice for clinical anti-worm infection drugs, has broad-spectrum, low toxicity, low residue and other excellent characteristics. The chemical name is 2,3, 5-dichloro-N-(3, 5-dichloro-2-hydroxyphenyl)-6-hydroxybenzamide. As a chemical synthetic drug against helminth infection, pentachlorosamide has excellent characteristics such as broad spectrum, low toxicity and low residue. It has significant effect in the treatment of helminth infection such as trematodes and tapeworms, and there is no report of relevant drug resistance so far. It is the first choice for clinical anti-helminth infection. |
| mechanism of action | in the middle and late 20th century, foreign research on the mechanism of pentachlorosamide has been carried out one after another, and it has been reported that pentachlorosamide, as an oxidative phosphoric acid dissolving coupling agent, has shown good therapeutic effect in the treatment of diseases caused by fluke infection in cattle and sheep. In addition, the drug also has a good repellent effect on tapeworms. Like other salicylanilides antiparasitic drugs, pentachlorosamide is an oxidative phosphorylation coupling agent. Its main mechanism of action is to block the oxidative phosphorylation process of the worm body and inhibit the mitochondria of the worm body. Adenosine triphosphate (ATP) is the production of energy, which leads to the death of insects due to energy metabolism disorders. |
| preparation | 1) synthesis of 2,4 dichloro -6-nitrophenol (3). 48.9g(0.3 mo1) of 2,4-dichlorophenol is injected into a clean 250mL beaker, 60g of methanol is added, and the glass rod is stirred until dissolved. In a 500mL four-mouth flask of 15% nitric acid 280g(1.0 mo1), start stirring, 25 DEG C dropwise addition of the above 2,4 dichlorophenol methanol solution, about 4 hours. After dropping, heat preservation reaction, reaction is over, distillation to evaporate methanol. The remaining reaction solution was cooled and crystallized for 30min. Suction filtration, filter cake water 100mL washing. 59.7g of yellow solid was obtained after drying for 5 hours with 95.7% yield and 99.9% purity (GC). 2) Synthesis of 2-amino -4,6-dichlorophenol (4) 2,4-12-chlorine -6-nitrophenol 41.6g(0.2 too1), methanol 185g ferric chloride 2.1g and activated carbon 5.8g are injected into a dry 500mL four-mouth flask. Start stirring, heat up to reflux, and reflux 10rain to stable. Slowly drop 29.5g(0.5mol) of 85% hydrazine hydrate for about 2 hours. After dropping, continue to return for 1h. Cooling to 5 ℃ IC, filtering to remove activated carbon. Distillation of mother liquor. About 140g of solvent methanol was evaporated. Steam finished. Slowly add water 300mI crystallization, the process of yellow-gray flocculent solid precipitation, about 2 hours. Cool down and keep warm and stir for 30min. Suction filtration, filter cake water 200mL washing. The yellow-gray flocculent homolog 32.5g was obtained after drying at 45cC for 8 hours with 91.3% yield and 99.3% purity (HPLC). 3) Synthesis of Chlorosilamide (Chlorosilamide) Crude Product (1) 380g of chlorobenzene, 36.6g of 3,5,6-trichlorosalicylic acid (0.152 mo1) and 26.7g of 2-amino -4,6-dichlorophenol (0.15 too1) are put into a dry 500mL four-mouth flask. Start stirring and heat until the material is completely dissolved. In the reflux state, 18.9g(0.159 mo1) of thionyl chloride is slowly added dropwise for about 3 hours, and the tail gas generated in the process is absorbed by liquid alkali. After dropping, continue the reflux reaction for 2 hours. Slowly cool to 10 ℃, filter for about 2 hours, and wash with 250mL of filter cake toluene. 58.4g of brown solid was obtained by drying at 55 ℃ for 6h, and the yield was 97.0%. 4) Synthesis of Chlorosalamide (Chlorosalamide) Finished Product (1) Add 256g of methanol, 40.0g of Chlorosalamide (Chlorosalamide) crude product and activated carbon into a dry 500mL four-mouth flask 2.0 to start stirring, heat to reflux, and heat preservation and reflux for 30rain. Cool to 50 ℃ and filter to remove activated carbon. The mother liquor is distilled until yellow solid is precipitated, the solvent methanol is distilled to be reduced to about 180go, and the temperature is kept for 2 hours. Suction filtration, filter cake rinse with a small amount of methanol. 25.9g of light yellow powder was obtained by drying at 55 ℃ for 4h, with 64.7% yield, 99.7% purity (HPLC, the same method as above), and melting point 207~209 ℃. |
| biological activity | Oxyclozanide (Oxiclozanidum, Zanil, Oxyclozanid, Zanilox) is an N-salicylanilide insect repellent and also a mitochondrial uncoupling insect repellent. For veterinary use. |
| target | Parasite |
Last Update：2024-04-09 19:43:38
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