220119-17-5

Basic information

• Product Name: Selamectin
• Synonyms: Selamectin;hypnocarpic acid;AverMectin A1a,25-cyclohexyl-4'-O-de(2,6-dideoxy-3-O-Methyl-a-L-arabino-hexopyranosyl)-5-deMethoxy-25-de(1-Methylpropyl)-22,23-dihydro-5-(hydroxyiMino)-,(5Z)-;(5Z)-25-Cyclohexyl-4'-O-de(2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranosyl)-5-demethoxy-25-de(1-methylpropyl)-22,23-dihydro-5-(hydroxyimino)-avermectin A1a;Revolution (antibiotic);Stronghold
• CAS NO: 220119-17-5
• Molecular Formula: C43H63NO11
• Molecular Weight: 769.967
• EINECS: 1592732-453-0
• Product Categories: Anthelmintic;ectoparasiticide
• Mol File: 220119-17-5.mol

Chemical Properties

• Boiling Point: 917 °C at 760 mmHg
• Flash Point: 508.4 °C
• Appearance: /
• Density: 1.35 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.618
• Storage Temp.: 2-8°C
• Solubility: Chloroform (Slightly), Dichloromethane (Slightly, Heated), DMSO (Slightly), Etha
• PKA: 10.34±0.70(Predicted)
• Stability: Hygroscopic
• CAS DataBase Reference: Selamectin(CAS DataBase Reference)
• NIST Chemistry Reference: Selamectin(220119-17-5)
• EPA Substance Registry System: Selamectin(220119-17-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 220119-17-5(Hazardous Substances Data)

Usage

Uses

Used in Veterinary Medicine:
Selamectin is used as a topical parasiticide for controlling fleas (Ctenocephalides spp.) and flea-allergy dermatitis in cats and dogs. It is also used to prevent heartworm disease and to control ear mites (Otodectes cynotes) in these animals.
Used in Veterinary Antihelminithic Applications:
Selamectin is used as a veterinary antihelminithic agent for the treatment and control of sarcoptic mange (Sarcoptes scabiei) in dogs and hookworms (Ancylostoma tubaeformis) and roundworms (Toxocara cati) in cats. It selectively binds to parasite glutamate-gated chloride ion channels and disrupts neurotransmission, leading to paralysis and death of the parasite.
Used in Parasite Control Research:
At 0.1 μg/ml, selamectin is reported to inhibit growth in an H. contortus larval development assay, making it a valuable compound for research purposes in the field of parasite control and treatment.

Veterinary Drugs and Treatments

Topical selamectin (Revolution?—Pfizer) is indicated for flea infestations (Ctenocephalides felis), prevention of heartworm disease (Dirofilaria immitis), and for ear mites (Otodectes cynotis) in both dogs and cats. Additionally in dogs, it is indicated for sarcoptic mange (Sarcoptes scabeii), and tick infestations (Dermacentor variabilis). In cats: hookworm (Ancylostoma tubaeforme) and roundworm (Toxocara cati). The product (Revolution?) is labeled as not effective against either adult heartworms or clearing circulating microfilaria, but it possibly may have some efficacy with prolonged, continuous administration (Atkins 2007b).

Toxicity evaluation

Acute oral LD50 for rats: >1,600 mg/kg

InChI:InChI=1/C43H63NO11/c1-24-11-10-14-30-23-50-40-36(44-48)27(4)19-33(43(30,40)47)41(46)52-32-20-31(16-15-25(2)38(24)53-35-21-34(49-6)37(45)28(5)51-35)54-42(22-32)18-17-26(3)39(55-42)29-12-8-7-9-13-29/h10-11,14-15,19,24,26,28-29,31-35,37-40,45,47-48H,7-9,12-13,16-18,20-23H2,1-6H3/b11-10+,25-15+,30-14+,44-36-/t24-,26-,28-,31+,32-,33-,34-,35?,37?,38-,39-,40+,42+,43+/m0/s1

Upstream product

• 142680-85-1 C₅₀H₇₆O₁₄ 
• 142680-85-1 doramectin 
• 117704-25-3 doramectin 

Relevant articles and documents

New Selamectin Intermediates, Preparation Method Thereof And Preparation Method For Selamectin Using The Same

The present invention relates to a novel intermediate of selamectin which is an antiparasitic drug, a manufacturing method thereof, and an improved method for manufacturing selamectin using the same. More particularly, the present invention relates to: the novel intermediate produced by a four-step synthesis process of a deglycosylation reaction, a hydrogenation reaction, an oxidation reaction, and an oximation reaction; and the improved method of selamectin using the same. The novel intermediate of selamectin according to the present invention has thermal and chemical stability and by using the novel method for manufacturing selamectin of the present invention, it is possible to manufacture selamectin having a higher synthesis yield and purity compared to existing technology.COPYRIGHT KIPO 2019

Preparation method of high-purity celecampin

The invention provides an improved selamectin preparation process. The process comprises the following steps: (1) performing hydrogen reduction on doramectin DL in the presence of a Wilson catalyst to obtain an intermediate SL1; (2) recrystallizing and purifying the intermediate SL1 obtained in the step (1) by use of methyl alcohol; (3) desugarizing the intermediate SL1 obtained in the step (2) by use of sulfuric acid to obtain an intermediate SL2; (4) oxidizing the intermediate SL2 obtained in the step (3) by use of manganese dioxide to obtain an intermediate SL3; (5) performing oximation on the intermediate SL3 obtained in the step (4) by use of hydroxylamine hydrochloride to obtain selamectin SL; (6) recrystallizing the crude product SL obtained in the step (5) for three times by use of methylbenzene, acetone and methyl alcohol to obtain purified SL.

Preparation method of selamectin

The invention provides an improved preparation technology of selamectin. The improved preparation technology comprises the following steps of (1) in the presence of a Wilson catalyst, reducing the selamectin DL by hydrogen, so as to obtain an intermediate SL1; (2) desugaring the intermediate SL1 obtained in step (1) by an organic solvent hydrochloric acid solution (by dissolving hydrochloric acid gas into an organic solvent), so as to obtain an intermediate SL2; (3) oxidizing the intermediate SL2 obtained in step (2) by manganese dioxide, so as to obtain an intermediate SL3; (4) oximating the intermediate SL3 obtained in step (3) by hydroxylamine hydrochloride, so as to obtain selamectin SL; (5) recrystallizing the crude product of selamectin SL obtained in step (4) by methylbenzene, acetone and methanol, so as to obtain the purified selamectin SL.

NEW SYNTHESIS PROCESS OF ANTIPARASITIC DRUG SELAMECTIN

Provided in the present invention are novel key intermediates of selamectin and the preparation method thereof. Also provided is a new synthesis process, using doramectin as a starting material, and obtaining selamectin via hydrogenation, oxidation, oximation and desugaring. The new process of the present invention has few steps, and is simple to operate, high in yield, low in cost and causes little pollution, and is more suitable for large scale industrial production.