Eprinomectin CAS 123997-26-2

Introduction:Basic information about Eprinomectin CAS 123997-26-2, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Eprinomectin Basic information

Product Name:Eprinomectin
Synonyms:EPRINOMECTIN;(4''R)-4''-(ACETYLAMINO)-4''-DEOXY-AVERMECTIN B1;Emamectin B1 Benzoate;EPRINOMECTIN VETRANAL;EprinomectinB1;Avermectin B1, 4-(acetylamino)-4-deoxy-, (4R)-;(4''r)-4''-(acetylamino)-4''-deoxy-avermectin b1solution;eprinex
CAS:123997-26-2
MF:C50H75NO14
MW:914.1288
EINECS:602-966-4
Product Categories:Chiral Reagents;Heterocycles
Mol File:123997-26-2.mol

Eprinomectin Chemical Properties

Melting point 163-166°C
density 1.23
Fp 2 °C
storage temp. 2-8°C
solubility DMF: 30 mg/ml; DMSO: 30 mg/ml; Ethanol: 30 mg/ml
form Solid
color White to off-white
Stability:Hygroscopic
Major Applicationpharmaceutical (small molecule)
InChIKeyWPNHOHPRXXCPRA-TVXIRPTOSA-N

Safety Information

Hazard Codes F,Xn,N,T
Risk Statements 11-20/21/22-36-62-50/53-25-63
Safety Statements 26-36/37-16-61-60-45
RIDADR UN 2811
WGK Germany 3
HS Code 2941906000
Storage Class6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
Hazard ClassificationsAcute Tox. 3 Oral
Aquatic Acute 1
Aquatic Chronic 1
Repr. 2
ToxicityLD50 orally in mice: 24 mg/kg (Jones)

Eprinomectin Usage And Synthesis

DescriptionEprinomectin is a semisynthetic avermectin that consistsof a mixture of two homologues, eprinomectinB1a (4 epi-acetylamino-4 -deoxy-avermectin B1; 90%) andeprinomectin B1b (10%).Eprinomectin was developedas a topical endectocide for all categories of cattleincluding lactating dairy cattle, and the process bywhich eprinomectin was selected for further developmenthas been described (90). Briefly, several hundred avermectin/milbemycin analogues were screened in a sheepmodel for efficacy against a range of endoparasites andin lactating dairy cows for a low milk:plasma partitioningratio. Themilk:plasma ratio for eprinomectin is <0.2; ivermectin,by comparison, partitions equally between milkand plasma.
DescriptionEprinomectin is an avermectin with anthelmintic and insecticidal activities. It is comprised of eprinomectin B1a and eprinomectin B1b . Eprinomectin (≥0.08 mg/kg, applied topically) reduces worm burden by 99% or more in bovine models of adult H. placei, O. ostertagi, T. axei, Cooperia punctata, N. helvetianus, O. radiatum, or D. viviparus infection. It also reduces parasite burden in bovine models of horn fly (H. irritans) or mange mite (C. bovis) infestation, as well as in cows naturally infested with lice (L. vituli), when applied topically at doses ranging from 0.16 to 0.5 mg/kg. Formulations containing eprinomectin have been used in the treatment and control of a variety of endo- and ectoparasites in cattle.
Chemical PropertiesCrystalline Solid
UsesA mixture of semi-synthetic Avermectins; containing 90% or more of component B1a and 10% or less of component B1b. Antiparasitic
UsesEprinomectin is a mixture of eprinomectins B1a and B1b in a 9:1 ratio, produced from a mixture of avermectin B1a and B1b. Eprinomectin is used commercially as a topical endectocide (insecticide, miticide and nematocide) for cattle, including lactating dairy cows. Like all avermectins and milbemycins, eprinomectin acts by binding to parasite glutamate-gated chloride ion channels and disrupts neurotransmission leading to paralysis and death of the parasite, mite or insect.
UsesA mixture of Eprinomectin B1a and B1b showing anti-anthelintic activity
Brand nameEprinex [Veterinary](Merial).
Veterinary Drugs and TreatmentsIn cattle, eprinomectin is indicated for a variety gastrointestinalroundworms includingadult and L4 stages of Haemonchus placei,Ostertagia ostertagi, Trichostrongylus axei and colubriformis,Cooperia oncophora/punctata/surnabada, Nematodirus helvetianus,Oesophagostomum radiatum, Bunostomum phlebotomum, andTrichuris spp. (adults only); cattle grubs; lice; mange mites; hornflies (for 7 days after treatment), and lungworms (Dictyocaulusvivaparus—for 21 days after treatment).
Topical eprinomectin may be useful for the topical treatmentof ear mites (Psoroptes cuniculi) in rabbits. One small study (6 subjects)showed partial response when rabbits were dosed at 5 mg/kgtopically, twice at 14 day intervals. (Ulutas, Voyvoda et al. 2005)
Toxicity evaluationAcute oral LD50 for rats: 55mg/kg
References[1] W.L. SHOOP. Eprinomectin: A novel avermectin for use as a topical endectocide for cattle[J]. International journal for parasitology, 1996, 26 11: Pages 1237-1242. DOI: 10.1016/s0020-7519(96)00123-3
[2] XIAOMO JIANG. Inactivating mutations of RNF43 confer Wnt dependency in pancreatic ductal adenocarcinoma.[J]. Proceedings of the National Academy of Sciences of the United States of America, 2013, 110 31: 12649-12654. DOI: 10.1073/pnas.1307218110

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