Avoparcin

{{Chembox

| ImageFile = avoparcins.svg

| ImageSize = 250px

| ImageCaption = α-Avoparcin (R=H)
β-Avoparcin (R=Cl)

| IUPACName =

| OtherNames =

|Section1={{Chembox Identifiers

| index_label = mix

| index1_label = (α)

| index2_label = (β)

| index3_label = (ε)

| CASNo = 37332-99-3

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo1 = 73957-86-5

| CASNo1_Ref = {{cascite|correct|CAS}}

| CASNo2 = 73957-87-6

| CASNo2_Ref = {{cascite|correct|CAS}}

| CASNo3 = 88899-52-9

| ChemSpiderID1 = 16736403

| ChemSpiderID1_Comment = (α)

| ChemSpiderID2 = 16736404

| ChemSpiderID2_Comment = (β)

| PubChem1 = 20055225

| PubChem2 = 20055226

| PubChem5 = 101586590

| KEGG = D03016

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII1_Ref = {{fdacite|correct|FDA}}

| UNII2_Ref = {{fdacite|correct|FDA}}

| UNII = WJ13O9MNTI

| UNII1 = I4J49AU691

| UNII2 = W47D7146JL

| ChEMBL = 2108224

| SMILES1 = 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

| SMILES1_Comment = (α)

| StdInChI = 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

| StdInChI_Comment = (α)

| StdInChIKey = JWFVWARSGMYXRN-HTQQBIQNSA-N

| SMILES2 = 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

| SMILES2_Comment = (β)

| InChI2 = 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

| InChI2_Comment = (β)

| InChIKey2 = CASDGWYZIKZSQE-ZUWMJMDKSA-N

}}

|Section2={{Chembox Properties

| Formula = C₈₉H₁₀₂ClN₉O₃₆ (α)
C₈₉H₁₀₁Cl₂N₉O₃₆ (β)

| MolarMass = 1909.254 (α)
1943.699 (β)

| Appearance =

| Density =

| MeltingPt =

| BoilingPt =

| Solubility =

}}

|Section3={{Chembox Hazards

| MainHazards =

| FlashPt =

| AutoignitionPt =

}}

}}

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.{{cite web | url = http://www.apvma.gov.au/products/review/completed/avoparcin.php | title = Avoparcin | publisher = Australian Pesticides and Veterinary Medicine Authority | access-date = 2012-09-19 | archive-url = https://web.archive.org/web/20140310180955/http://apvma.gov.au/products/review/completed/avoparcin.php | archive-date = 2014-03-10 | url-status = dead }} It is also used as an aid in the prevention of necrotic enteritis in poultry.

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.{{cite journal | doi = 10.1046/j.1469-0691.2000.00128.x | title = Avoparcin and virginiamycin as animal growth promoters: A plea for science in decision-making | year = 2000 | last1 = Acar | first1 = J. | last2 = Casewell | first2 = M. | last3 = Freeman | first3 = J. | last4 = Friis | first4 = C. | last5 = Goossens | first5 = H. | journal = Clinical Microbiology and Infection | volume = 6 | issue = 9 | pages = 477–82 | pmid = 11168181| doi-access = free }}{{Cite journal | doi = 10.1016/S0167-5877(96)01119-1 | title = Avoparcin used as a growth promoter is associated with the occurrence of vancomycin-resistant Enterococcus faecium on Danish poultry and pig farms | year = 1997 | last1 = Bager | first1 = F | last2 = Madsen | first2 = M | last3 = Christensen | first3 = J | last4 = Aarestrup | first4 = F.M | journal = Preventive Veterinary Medicine | volume = 31 | pages = 95–112 | pmid = 9234429 | issue = 1–2| s2cid = 4958557 }}{{cite journal | title = Vancomycin-resistant enterococci and use of avoparcin in animal feed: is there a link? | author = Peter J Collignon | journal = Med J Aust | year = 1999 | volume = 171 | issue = 3 | pages = 144–146 | pmid = 10474607| author-link = Peter Collignon | doi = 10.5694/j.1326-5377.1999.tb123568.x | s2cid = 24378463 }}{{Cite journal | pmid = 17298380 | year = 2007 | last1 = Lauderdale | first1 = TL | last2 = Shiau | first2 = YR | last3 = Wang | first3 = HY | last4 = Lai | first4 = JF | last5 = Huang | first5 = IW | last6 = Chen | first6 = PC | last7 = Chen | first7 = HY | last8 = Lai | first8 = SS | last9 = Liu | first9 = YF | title = Effect of banning vancomycin analogue avoparcin on vancomycin-resistant enterococci in chicken farms in Taiwan | volume = 9 | issue = 3 | pages = 819–23 | doi = 10.1111/j.1462-2920.2006.01189.x | journal = Environmental Microbiology | bibcode = 2007EnvMi...9..819L }}

Avoparcin was once widely used in Australia and the European Union, but it is currently not permitted in either.[http://eur-lex.europa.eu/LexUriServ/LexUriServ.do?uri=CELEX:31997L0006:EN:HTML Commission Directive 97/6/EC of 30 January 1997 amending Council Directive 70/524/EEC concerning additives in feedingstuffs], Official Journal L 035 , 05/02/1997 P. 0011-0013

Streptomyces candidus was found to produce avoparcin.{{cite journal | vauthors=((Sams, R.)) | journal=Ullmann's Encyclopedia of Industrial Chemistry | title=Veterinary drugs | date=15 June 2000 | url=https://doi.org/10.1002/14356007.a27_387 | doi=10.1002/14356007.a27_387| isbn=978-3-527-30385-4 | url-access=subscription }}