Name | DIMINAZENE ACETURATE |
Synonyms | CL218 ganaseg ganasag DIMINAZENE ACETURATE 4,4'-(diamino)dibenzamidediaceturate 4,4'-(Diazoamino)dibenzamidinediaceturate glycine,n-acetyl-,compd.with4,4'-(1-triazene-1,3-diyl)bis(benzenecarboxim glycine,n-acetyl-,compd.with4,4'-(1-triazene-1,3-diyl)bis[benzenecarboximid |
CAS | 908-54-3 |
EINECS | 212-999-2 |
Molecular Formula | C22H29N9O6 |
Molar Mass | 515.52 |
Melting Point | 202 °C |
Appearance | Morphological powder |
Storage Condition | Inert atmosphere,2-8°C |
Stability | Stable. Incompatible with strong oxidizing agents. |
Physical and Chemical Properties | Chemical properties yellow crystalline powder. Melting point 217 ℃ (decomposition). Soluble in 14 parts of 20 ℃ water, slightly soluble in ethanol, insoluble in chloroform, ether, acetone. No smell, bitter taste. |
Use | Uses veterinary drugs. For the treatment of everyone animal pyrophylla and trypanosomiasis. Usual dosage, horse: 3-4 mg/kg (body weight), cattle: 4-7 mg/kg (body weight), sheep: 3-5 mg/kg (body weight). With 5% aqueous solution, from the muscle or subcutaneous injection. |
WGK Germany | 3 |
RTECS | MB7605000 |
Raw Materials | Iron Sodium methanolate p-Nitrobenzoic acid p-Toluenesulfonamide Potassium iodide statch paper 4-Nitrobenzonitrile N-Acetylglycine triazene |
overview
diacetamide triazamidine is a new type of anti-blood protozoa drug commonly used at present. the main object of use is dairy cows during lactation. unreasonable use will cause veterinary drug residues in fresh milk, which has certain safety risks.
pharmacological action
diacetamide triazamidine has effects on trypanosomes, pyriformes and edge insects (invisible bodies) of domestic animals. After medication, the blood concentration is high, but the duration is short, so it is mainly used for treatment and the preventive effect is poor. Its mechanism of action is to selectively block the DNA synthesis or replication of the trypanosome's motor matrix, and produce irreversible binding with the nucleus, so that the trypanosome's motor matrix disappears and cannot divide and reproduce.
biological activity
Diminazene is a diamidine, also known as 4,4-(1-triazene-1, 3-disubstituent) bis (benzamidine), used as an effective trypanosicide.
in vitro study
Diminazene can inhibit the activity of P2 transporter, which is lost in Diminazene-adapted trypanosomes. this does not prove TbAT1 transport Diminazene, nor does it determine whether the addition of carrier protein to P2 can participate in Diminazene uptake. Diminazene acts on Trypanosoma brucei and accumulates rapidly by 427 single transport, with a value of K m of 0.45 μM. [
in vivo studies
Diminazene aceturate (3.5 mg/kg) has a significant effect on the initial treatment of horses and T. evansi-infected mules. The parasites were removed from the peripheral blood of horses and mules from 1-7 days and 1-14 days respectively. Diminazene aceturate (DA) (7 mg/kg, I. m.) to treat infected dogs is effective in removing parasites from the blood.
production method
using p-nitrobenzoic acid as raw material, it reacts with p-toluenesulfonamide at high temperature to generate p-nitrobenzonitrile (C7H4N2O2[619-72-7]. Then it is obtained by the addition, amination, reduction, diazotization, coupling, and salt of p-nitrobenzonitrile. 1. Addition and amination Add p-nitrobenzonitrile, methanol and sodium methoxide to the reaction pot, stir and dissolve, and react at 25-30 ℃ for 3 hours. Ammonium chloride was added and stirred at 10-15 ℃ for 5h. Recover methanol to dryness, add dilute hydrochloric acid to boil, filter to obtain p-nitrobenzamidine hydrochloride solution. 2. Reduction Heat the above solution to 50°C, add glacial acetic acid, and slowly add iron powder at 60°C. After addition, the temperature is raised to 105 ℃ for 5h. Filtration, the filtrate is alkalized with sodium hydroxide solution to pH 12. Filtration, with hydrochloric acid to re-acidify the filtrate to pH 1-2. Concentrate, cool and crystallize, and filter to obtain p-aminobenzidine hydrochloride. 3. Diazotization and coupling First, add half of the p-aminobenzidine hydrochloride to water, add hydrochloric acid to dissolve, add 10% sodium nitrite solution dropwise at -5~0 ℃, use potassium iodide starch test paper Check the end point, mix the other half of p-aminobenzidine hydrochloride with a small amount of water, then add saturated sodium acetate, and precipitate yellow precipitate. Filter, dissolve the filter cake in water, adjust the pH to 9-10 with 10% sodium hydroxide solution, and precipitate crystallization. Filtration, the filter cake is washed with cold water and methanol to obtain 1, 3-bis (p-amidinobenzene)-triazene. 4. Salt The triazene, acetylglycine and methanol are stirred for 0.5h, then the pH is adjusted to 7 with ammonia water, and the temperature is raised and dissolved back. Add activated carbon, filter, and the filtrate is cooled and crystallized. Filter, dry, get the diaminaqin.