Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C50H75NO14 |
| Molecular Weight | 914.1288 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 20 / 20 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC[C@H](C)[C@H]1O[C@@]2(C[C@@H]3C[C@@H](C\C=C(C)\[C@@H](O[C@H]4C[C@H](OC)[C@@H](O[C@H]5C[C@H](OC)[C@H](NC(C)=O)[C@H](C)O5)[C@H](C)O4)[C@@H](C)\C=C\C=C6/CO[C@@H]7[C@H](O)C(C)=C[C@@H](C(=O)O3)[C@]67O)O2)C=C[C@@H]1C
InChI
InChIKey=ZKWQQXZUCOBISE-CRTGXIDZSA-N
InChI=1S/C50H75NO14/c1-12-26(2)45-29(5)18-19-49(65-45)24-36-21-35(64-49)17-16-28(4)44(27(3)14-13-15-34-25-58-47-43(53)30(6)20-37(48(54)61-36)50(34,47)55)62-41-23-39(57-11)46(32(8)60-41)63-40-22-38(56-10)42(31(7)59-40)51-33(9)52/h13-16,18-20,26-27,29,31-32,35-47,53,55H,12,17,21-25H2,1-11H3,(H,51,52)/b14-13+,28-16+,34-15+/t26-,27-,29-,31-,32-,35+,36-,37-,38-,39-,40-,41-,42+,43+,44-,45+,46-,47+,49+,50+/m0/s1
| Molecular Formula | C50H75NO14 |
| Molecular Weight | 914.1288 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 20 / 20 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.fda.gov/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm116813.htmCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24533275 |
http://www.inchem.org/documents/jecfa/jecmono/v041je02.htm
Sources: http://www.fda.gov/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm116813.htm
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/24533275 |
http://www.inchem.org/documents/jecfa/jecmono/v041je02.htm
Eprinomectin is 4"-deoxy-4"-epiacetylamino-avermectin B1. It is a semi-synthetic member of the avermectin family of macrocyclic lactones and consists of a mixture of two homologous components, B1a (not less than 90%) and B1b (not more than 10%), which differ by a single methylene group at C26. Eprinomectin is a member of the macrocyclic lactone class of endectocides which have a unique mode of action. Compounds of the class bind selectively and with high affinity to glutamate-gated chloride ion channels which occur in invertebrate nerve and muscle cells.
This leads to an increase in the permeability of the cell membrane to chloride ions with hyperpolarization of the nerve or muscle cell, resulting in paralysis and death of the parasite. Compounds of this class may also interact with other ligand-gated chloride channels, such as those gated by the neurotransmitter gamma-aminobutyric acid (GABA). Molecular studies indicate that these drugs interact strongly not only with ligand-gated ion channels, the mode-of action receptors of nematodes and arthropods, but also with efflux ABC transporters. The margin of safety for compounds of this class is attributable to the fact that mammals do not have glutamate-gated chloride channels, the macrocyclic lactones have a low affinity for other mammalian ligand-gated chloride channels and they do not readily cross the blood-brain barrier. IVOMEC EPRINEX (eprinomectin) Pour-On is indicated for the treatment and control of gastrointestinal roundworms (including inhibited Ostertagia ostertagi), lungworms, grubs, sucking and biting lice, chorioptic and sarcoptic mange mites, and horn flies in beef and dairy cattle of all ages, including lactating dairy cattle.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20089736
Curator's Comment: In wild-type mice the brain concentration of eprinomectin was very low, in accordance with the protective role of the blood-brain barrier.
No human data available.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9024866
Curator's Comment: Eprinomectin is the amino-avermectin derived from avermectin B1 with modified terminal oleandrose moiety called 4-epiacetylamino-4-deoxy-avermectin B1. It was found, from Ivermectin analogues synthesised by Merck, to have a favourable milk residue profile Reference retrieved from https://www.ncbi.nlm.nih.gov/pubmed/24533275 # Merck Research Laboratories
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: GO:0008068 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24533275 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Curative | EPRINEX Approved UseIVOMEC EPRINEX (eprinomectin, eprinomectin B1a is the major component >90%) Pour-On is indicated for the treatment and control of gastrointestinal roundworms (including inhibited Ostertagia ostertagi), lungworms, grubs, sucking and biting lice, chorioptic and sarcoptic mange mites, and horn flies in beef and dairy cattle of all ages, including lactating dairy cattle. Launch Date1997 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacokinetics and anthelmintic efficacy of topical eprinomectin in goats prevented from grooming. | 2014-11 |
|
| Pharmacokinetics and metabolism of eprinomectin in cats when administered in a novel topical combination of fipronil, (S)-methoprene, eprinomectin and praziquantel. | 2014-04-28 |
|
| Moxidectin and the avermectins: Consanguinity but not identity. | 2012-12 |
|
| Reevaluation of efficacy against nematode parasites and pharmacokinetics of topical eprinomectin in cattle. | 2012-09 |
|
| Efficacy in sheep and pharmacokinetics in cattle that led to the selection of eprinomectin as a topical endectocide for cattle. | 1996-11 |
Sample Use Guides
IVOMEC EPRINEX (eprinomectin, eprinomectin B1a is the major component >90%) Pour-On is indicated for the treatment and control of gastrointestinal roundworms (including inhibited Ostertagia ostertagi), lungworms, grubs, sucking and biting lice, chorioptic and sarcoptic mange mites, and horn flies in beef and dairy cattle of all ages, including lactating dairy cattle. Applied at the recommended dose volume of 1 mL/10 kg (22 lb) body weight, to achieve a dose level of 500 mcg eprinomectin/kg body weight
Route of Administration:
Transdermal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22493850
eprinomectin was lethal to An. arabiensis at low concentrations (LC50s 8.5 ppb)
| Substance Class |
Chemical
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