Eprinomectin

Eprinomectin B1b
Clinical data
Synonyms	4"-epi-acetylamino-4"-deoxy-avermectin B1b
ATC code	P54AA04 (WHO) ;
Identifiers
	IUPAC name (1'R,2S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-21',24'-Dihydroxy-6-isopropyl-5,11',13',22'-tetramethyl-2'-oxo-5,6-dihydrospiro[pyran-2,6'-[3,7,19]trioxatetracyclo[15.6.1.14,8.020,24]pentacosa[10,14,16,22]tetraen]-12'-yl 4-O-(4-acetamido-2,4,6-trideoxy-3-O-methyl-alpha-L-lyxo-hexopyranosyl)-2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranoside;
CAS Number	133305-89-2;
PubChem CID	20055319;
ChemSpider	16736608;
UNII	31OML2QZ0Q;
KEGG	D04037;
Chemical and physical data
Formula	C49H73NO14
Molar mass	900.12 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@H]1/C=C/C=C/2\CO[C@H]3[C@@]2([C@@H](C=C([C@H]3O)C)C(=O)O[C@H]4C[C@@H](C/C=C(/[C@H]1O[C@H]5C[C@@H]([C@H]([C@@H](O5)C)O[C@H]6C[C@@H]([C@@H]([C@@H](O6)C)NC(=O)C)OC)OC)\C)O[C@]7(C4)C=C[C@@H]([C@H](O7)C(C)C)C)O;
	InChI InChI=1S/C49H73NO14/c1-25(2)43-28(5)17-18-48(64-43)23-35-20-34(63-48)16-15-27(4)44(26(3)13-12-14-33-24-57-46-42(52)29(6)19-36(47(53)60-35)49(33,46)54)61-40-22-38(56-11)45(31(8)59-40)62-39-21-37(55-10)41(30(7)58-39)50-32(9)51/h12-15,17-19,25-26,28,30-31,34-46,52,54H,16,20-24H2,1-11H3,(H,50,51)/b13-12+,27-15+,33-14+/t26-,28-,30-,31-,34+,35-,36-,37-,38-,39-,40-,41+,42+,43+,44-,45-,46+,48+,49+/m0/s1; Key:WPNHOHPRXXCPRA-FZTOWWROSA-N;

Eprinomectin B1a
Clinical data
Synonyms	4"-epi-acetylamino-4"-deoxy-avermectin B1a
ATCvet code	QP54AA04 (WHO) ;
Identifiers
	IUPAC name (1'R,2S,4'S,5S,6R,8'R,10'E,12'S,13'S,14'E,16'E,20'R,21'R,24'S)-6-[(2S)-2-Butanyl]-21',24'-dihydroxy-5,11',13',22'-tetramethyl-2'-oxo-5,6-dihydrospiro[pyran-2,6'-[3,7,19]trioxatetracyclo[15.6.1.14,8.020,24]pentacosa[10,14,16,22]tetraen]-12'-yl 4-O-(4-acetamido-2,4,6-trideoxy-3-O-methyl-alpha-L-lyxo-hexopyranosyl)-2,6-dideoxy-3-O-methyl-alpha-L-arabino-hexopyranoside;
CAS Number	133305-88-1;
PubChem CID	6444397;
ChemSpider	16736607;
UNII	00OY54D31C;
KEGG	D04037;
Chemical and physical data
Formula	C50H75NO14
Molar mass	914.14 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC[C@H](C)[C@@H]1[C@H](C=C[C@@]2(O1)C[C@@H]3C[C@H](O2)C/C=C(/[C@H]([C@H](/C=C/C=C/4\CO[C@H]5[C@@]4([C@@H](C=C([C@H]5O)C)C(=O)O3)O)C)O[C@H]6C[C@@H]([C@H]([C@@H](O6)C)O[C@H]7C[C@@H]([C@@H]([C@@H](O7)C)NC(=O)C)OC)OC)\C)C;
	InChI 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; Key:ZKWQQXZUCOBISE-CRTGXIDZSA-N;

Eprinomectin (MK-397) is an avermectin used as a veterinary topical endectocide.^[1] It is a mixture of two chemical compounds, eprinomectin B1a and B1b.

References

↑ Shoop, W. L.; Egerton, J. R.; Eary, C. H.; Haines, H. W.; Michael, B. F.; Mrozik, H.; Eskola, P.; Fisher, M. H.; Slayton, L. (November 1996). "Eprinomectin: a novel avermectin for use as a topical endectocide for cattle". International Journal for Parasitology. 26 (11): 1237–1242. ISSN 0020-7519. PMID 9024867.

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[1] Shoop, W. L.; Egerton, J. R.; Eary, C. H.; Haines, H. W.; Michael, B. F.; Mrozik, H.; Eskola, P.; Fisher, M. H.; Slayton, L. (November 1996). "Eprinomectin: a novel avermectin for use as a topical endectocide for cattle". International Journal for Parasitology. 26 (11): 1237–1242. ISSN 0020-7519. PMID 9024867.