Avoparcin

Avoparcin is a glycopeptide antibiotic effective against Gram-positive bacteria. It has been used in agriculture as an additive to livestock feed to promote growth in chickens, pigs, and cattle.^[1] It is also used as an aid in the prevention of necrotic enteritis in poultry.^[1]

Avoparcin

α-Avoparcin (R=H) β-Avoparcin (R=Cl)
Identifiers
CAS Number	mix: 37332-99-3 Y (α): 73957-86-5 Y (β): 73957-87-6 Y (ε): 88899-52-9
3D model (JSmol)	(α) (α): Interactive image (β) (β): Interactive image
ChEMBL	mix: ChEMBL2108224
ChemSpider	(α): 16736403 (α) (β): 16736404 (β)
ECHA InfoCard	100.048.588
E number	E715 (antibiotics)
KEGG	mix: D03016
PubChem CID	(α): 20055225 (β): 20055226 101586590
UNII	mix: WJ13O9MNTI Y (α): I4J49AU691 Y (β): W47D7146JL Y
InChI InChI=1S/C89H102ClN9O36/c1-31-67(106)47(91)26-58(124-31)130-52-28-53-46(90)20-38(52)21-49-80(116)98-65(86(122)123)45-24-41(103)25-51(105)60(45)44-19-37(11-18-50(44)104)63(82(118)94-49)96-84(120)64-39-22-54(78(55(23-39)129-53)135-89-79(74(113)71(110)57(30-101)132-89)133-59-27-48(92)68(107)32(2)125-59)127-42-16-9-36(10-17-42)77(134-88-76(115)73(112)70(109)56(29-100)131-88)66(85(121)95-62(83(119)97-64)35-5-12-40(102)13-6-35)99-81(117)61(93-4)34-7-14-43(15-8-34)128-87-75(114)72(111)69(108)33(3)126-87/h5-20,22-25,28,31-33,47-49,56-59,61-77,79,87-89,93,100-115H,21,26-27,29-30,91-92H2,1-4H3,(H,94,118)(H,95,121)(H,96,120)(H,97,119)(H,98,116)(H,99,117)(H,122,123)/t31-,32-,33-,47+,48+,49-,56-,57+,58-,59-,61-,62-,63+,64+,65+,66+,67-,68-,69-,70-,71+,72+,73+,74-,75+,76+,77+,79+,87-,88-,89-/m0/s1 Key: JWFVWARSGMYXRN-HTQQBIQNSA-N (β) (β): InChI=1S/C89H101Cl2N9O36/c1-30-67(107)46(92)25-58(125-30)131-52-27-53-45(91)19-37(52)20-48-80(117)99-65(86(123)124)43-23-39(103)24-51(106)60(43)42-17-35(9-15-49(42)104)62(82(119)95-48)96-84(121)64-38-21-54(78(55(22-38)130-53)136-89-79(74(114)71(111)57(29-102)133-89)134-59-26-47(93)68(108)31(2)126-59)128-40-13-7-34(8-14-40)77(135-88-76(116)73(113)70(110)56(28-101)132-88)66(85(122)97-63(83(120)98-64)36-10-16-50(105)44(90)18-36)100-81(118)61(94-4)33-5-11-41(12-6-33)129-87-75(115)72(112)69(109)32(3)127-87/h5-19,21-24,27,30-32,46-48,56-59,61-77,79,87-89,94,101-116H,20,25-26,28-29,92-93H2,1-4H3,(H,95,119)(H,96,121)(H,97,122)(H,98,120)(H,99,117)(H,100,118)(H,123,124)/t30-,31-,32-,46+,47+,48-,56-,57+,58-,59-,61-,62+,63-,64+,65+,66+,67-,68-,69-,70-,71+,72+,73+,74-,75+,76+,77+,79+,87-,88-,89-/m0/s1 Key: CASDGWYZIKZSQE-ZUWMJMDKSA-N
SMILES (α) (α): CN[C@H](C(=O)N[C@@H]5[C@H](O[C@@H]1O[C@@H](CO)[C@H](O)[C@@H](O)[C@H]1O)c2ccc(cc2)Oc%13cc7cc(Oc4cc(O[C@H]3C[C@@H](N)[C@@H](O)[C@H](C)O3)c(cc4Cl)C[C@@H]%10NC(=O)[C@H](NC(=O)[C@@H]7NC(=O)[C@@H](NC5=O)c6ccc(O)cc6)c8ccc(O)c(c8)c9c(O)cc(O)cc9[C@@H](NC%10=O)C(=O)O)c%13O[C@@H]%12O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%12O[C@H]%11C[C@@H](N)[C@@H](O)[C@H](C)O%11)c%15ccc(O[C@@H]%14O[C@@H](C)[C@H](O)[C@@H](O)[C@H]%14O)cc%15 (β) (β): CN[C@H](C(=O)N[C@@H]5[C@H](O[C@@H]1O[C@@H](CO)[C@H](O)[C@@H](O)[C@H]1O)c2ccc(cc2)Oc%13cc7cc(Oc4cc(O[C@H]3C[C@@H](N)[C@@H](O)[C@H](C)O3)c(cc4Cl)C[C@@H]%10NC(=O)[C@H](NC(=O)[C@@H]7NC(=O)[C@@H](NC5=O)c6ccc(O)c(Cl)c6)c8ccc(O)c(c8)c9c(O)cc(O)cc9[C@@H](NC%10=O)C(=O)O)c%13O[C@@H]%12O[C@H](CO)[C@@H](O)[C@H](O)[C@H]%12O[C@H]%11C[C@@H](N)[C@@H](O)[C@H](C)O%11)c%15ccc(O[C@@H]%14O[C@@H](C)[C@H](O)[C@@H](O)[C@H]%14O)cc%15
Properties
Chemical formula	C89H102ClN9O36 (α) C89H101Cl2N9O36 (β)
Molar mass	1909.254 (α) 1943.699 (β)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Avoparcin is a mixture of two closely related chemical compounds, known as α-avoparcin and β-avoparcin, which differ by the presence of an additional chlorine atom in β-avoparcin. Avoparcin also shares a chemical similarity with vancomycin. Because of this similarity, concern exists that widespread use of avoparcin in animals may lead to an increased prevalence of vancomycin-resistant strains of bacteria.^[2][3][4][5]

Avoparcin was once widely used in Australia and the European Union, but it is currently not permitted in either.^[1][6]

Streptomyces candidus was found to produce avoparcin.^[7]

Legal status

Avoparcin is prohibited in the Euopean Union,^[8] Australia, and the United States. It was first banned in Denmark in 1995 as a feed additive, for its contributions to vancomycin-resistant Enterococcus (VRE), and later banned in several other European countries.^[9] It was never approved for use in the United States.^[10]