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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
Structure of EPRINOMECTIN B1A

SMILES

[H][C@@]12OC\C3=C/C=C/[C@H](C)[C@H](O[C@@]4([H])C[C@H](OC)[C@@]([H])(O[C@@]5([H])C[C@H](OC)[C@H](NC(C)=O)[C@H](C)O5)[C@H](C)O4)\C(C)=C\C[C@]6([H])C[C@@]([H])(C[C@]7(O6)O[C@]([H])([C@@H](C)CC)[C@@H](C)C=C7)OC(=O)[C@]([H])(C=C(C)[C@H]1O)[C@@]23O

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

HIDE SMILES / InChI

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

Description
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

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

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

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
EPRINEX

Approved Use

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.

Launch Date

1997
PubMed

PubMed

TitleDatePubMed
Pharmacokinetics and anthelmintic efficacy of topical eprinomectin in goats prevented from grooming.
2014 Nov
Patents

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
eprinomectin was lethal to An. arabiensis at low concentrations (LC50s 8.5 ppb)
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:41:06 GMT 2023
Edited
by admin
on Fri Dec 15 15:41:06 GMT 2023
Record UNII
00OY54D31C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPRINOMECTIN B1A
Common Name English
AVERMECTIN A1A, 4 SUP(2)-(ACETYLAMINO)-5-O-DEMETHYL-4 SUP(2)-DEOXY-, (4 SUP(2)R)-
Common Name English
AVERMECTIN A1A, 4''-(ACETYLAMINO)-5-O-DEMETHYL-4''-DEOXY-, (4''R)-
Common Name English
EPRINOMECTIN COMPONENT B1A
MI  
Common Name English
EPRINOMECTIN COMPONENT B1A [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Fri Dec 15 15:41:06 GMT 2023 , Edited by admin on Fri Dec 15 15:41:06 GMT 2023
Code System Code Type Description
CAS
133305-88-1
Created by admin on Fri Dec 15 15:41:06 GMT 2023 , Edited by admin on Fri Dec 15 15:41:06 GMT 2023
PRIMARY
FDA UNII
00OY54D31C
Created by admin on Fri Dec 15 15:41:06 GMT 2023 , Edited by admin on Fri Dec 15 15:41:06 GMT 2023
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PUBCHEM
6444397
Created by admin on Fri Dec 15 15:41:06 GMT 2023 , Edited by admin on Fri Dec 15 15:41:06 GMT 2023
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CHEBI
82597
Created by admin on Fri Dec 15 15:41:06 GMT 2023 , Edited by admin on Fri Dec 15 15:41:06 GMT 2023
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SMS_ID
300000023856
Created by admin on Fri Dec 15 15:41:06 GMT 2023 , Edited by admin on Fri Dec 15 15:41:06 GMT 2023
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EPA CompTox
DTXSID0048977
Created by admin on Fri Dec 15 15:41:06 GMT 2023 , Edited by admin on Fri Dec 15 15:41:06 GMT 2023
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NCI_THESAURUS
C83695
Created by admin on Fri Dec 15 15:41:06 GMT 2023 , Edited by admin on Fri Dec 15 15:41:06 GMT 2023
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MERCK INDEX
m4959
Created by admin on Fri Dec 15 15:41:06 GMT 2023 , Edited by admin on Fri Dec 15 15:41:06 GMT 2023
PRIMARY Merck Index