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Avoparcin

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Avoparcin

α-Avoparcin (R=H)
β-Avoparcin (R=Cl)
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
ECHA InfoCard 100.048.588 Edit this at Wikidata
E number E715 (antibiotics)
KEGG
PubChem CID
UNII
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/s1Key: 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/s1Key: CASDGWYZIKZSQE-ZUWMJMDKSA-N
SMILES
  • (α) (α): CN(C(=O)N5(O1O(CO)(O)(O)1O)c2ccc(cc2)Oc%13cc7cc(Oc4cc(O3C(N)(O)(C)O3)c(cc4Cl)C%10NC(=O)(NC(=O)7NC(=O)(NC5=O)c6ccc(O)cc6)c8ccc(O)c(c8)c9c(O)cc(O)cc9(NC%10=O)C(=O)O)c%13O%12O(CO)(O)(O)%12O%11C(N)(O)(C)O%11)c%15ccc(O%14O(C)(O)(O)%14O)cc%15
  • (β) (β): CN(C(=O)N5(O1O(CO)(O)(O)1O)c2ccc(cc2)Oc%13cc7cc(Oc4cc(O3C(N)(O)(C)O3)c(cc4Cl)C%10NC(=O)(NC(=O)7NC(=O)(NC5=O)c6ccc(O)c(Cl)c6)c8ccc(O)c(c8)c9c(O)cc(O)cc9(NC%10=O)C(=O)O)c%13O%12O(CO)(O)(O)%12O%11C(N)(O)(C)O%11)c%15ccc(O%14O(C)(O)(O)%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 , 100 kPa). Infobox references
Chemical compound

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. 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.

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

Streptomyces candidus was found to produce avoparcin.

Legal status

Avoparcin is prohibited in the Euopean Union, 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. It was never approved for use in the United States.

References

  1. ^ "Avoparcin". Australian Pesticides and Veterinary Medicine Authority. Archived from the original on 2014-03-10. Retrieved 2012-09-19.
  2. Acar, J.; Casewell, M.; Freeman, J.; Friis, C.; Goossens, H. (2000). "Avoparcin and virginiamycin as animal growth promoters: A plea for science in decision-making". Clinical Microbiology and Infection. 6 (9): 477–82. doi:10.1046/j.1469-0691.2000.00128.x. PMID 11168181.
  3. Bager, F; Madsen, M; Christensen, J; Aarestrup, F.M (1997). "Avoparcin used as a growth promoter is associated with the occurrence of vancomycin-resistant Enterococcus faecium on Danish poultry and pig farms". Preventive Veterinary Medicine. 31 (1–2): 95–112. doi:10.1016/S0167-5877(96)01119-1. PMID 9234429. S2CID 4958557.
  4. Peter J Collignon (1999). "Vancomycin-resistant enterococci and use of avoparcin in animal feed: is there a link?". Med J Aust. 171 (3): 144–146. doi:10.5694/j.1326-5377.1999.tb123568.x. PMID 10474607. S2CID 24378463.
  5. Lauderdale, TL; Shiau, YR; Wang, HY; Lai, JF; Huang, IW; Chen, PC; Chen, HY; Lai, SS; Liu, YF (2007). "Effect of banning vancomycin analogue avoparcin on vancomycin-resistant enterococci in chicken farms in Taiwan". Environmental Microbiology. 9 (3): 819–23. Bibcode:2007EnvMi...9..819L. doi:10.1111/j.1462-2920.2006.01189.x. PMID 17298380.
  6. 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
  7. Sams, R. (15 June 2000). "Veterinary drugs". Ullmann's Encyclopedia of Industrial Chemistry. doi:10.1002/14356007.a27_387. ISBN 978-3-527-30385-4.
  8. Press corner
  9. Motarjemi, Yasmine (2014). Encyclopedia of Food Safety. Elsevier Inc. p. 201. ISBN 978-0-12-378613-5.
  10. Alex Koppelman (Nov 7, 2007). "Is the way we raise our food giving us MRSA?". Salon.com.
Antibacterials: others (J01X, D06AX)
Glycopeptides
Lipoglycopeptides
Polymyxins
Steroid antibacterials
Imidazole derivatives
Pleuromutilins
Nitrofuran derivatives
Other antibacterials
Category: