Avoparcin

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Avoparcin
Avoparcins.svg
α-Avoparcin (R=H)
β-Avoparcin (R=Cl)
Identifiers
CAS number 37332-99-3 (α/β mix) YesY, 73957-86-5 (α) YesY, 73957-87-6 (β) YesY
ChemSpider 16736403 (α), 16736404 (β)
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C89H102ClN9O36 (α)
C89H101Cl2N9O36 (β)
Molar mass 1909.254 (α)
1943.699 (β)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

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 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] It was never approved for use in the United States.[7]

References[edit]

  1. ^ a b c "Avoparcin". Australian Pesticides and Veterinary Medicine Authority. 
  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. 
  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. PMID 10474607. 
  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. 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. ^ Alex Koppelman (Nov 7, 2007). "Is the way we raise our food giving us MRSA?". Salon.com.