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MedKoo Cat#: 574447 | Name: Avilamycin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Avilamycin is an antimicrobial agent used against methicillin resistant Staphylococcus. Often used for broiler chickens.

Chemical Structure

Avilamycin
Avilamycin
CAS#11051-71-1

Theoretical Analysis

MedKoo Cat#: 574447

Name: Avilamycin

CAS#: 11051-71-1

Chemical Formula: C61H88Cl2O32

Exact Mass: 1402.4636

Molecular Weight: 1404.24

Elemental Analysis: C, 52.18; H, 6.32; Cl, 5.05; O, 36.46

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Synonym
Avilamycin; LY 048740; Maxus; Maxus 100; Maxus 200; Surmax
IUPAC/Chemical Name
6-((6'-((2-((6-((7'-acetyl-7'-hydroxy-7-(isobutyryloxy)-6'-methyloctahydro-4H-2,4'-spirobi[[1,3]dioxolo[4,5-c]pyran]-6-yl)oxy)-4-hydroxy-5-methoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl)oxy)-3-hydroxy-5-methoxy-6-methyltetrahydro-2H-pyran-4-yl)oxy)-4-hydroxy-4',6,7a'-trimethyloctahydro-4'H-spiro[pyran-2,2'-[1,3]dioxolo[4,5-c]pyran]-5-yl)oxy)-4-hydroxy-2-methyltetrahydro-2H-pyran-3-yl 3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoate
InChi Key
XIRGHRXBGGPPKY-UHFFFAOYSA-N
InChi Code
InChI=1S/C61H88Cl2O32/c1-21(2)53(70)87-49-45-32(92-61(93-45)52-51(78-20-79-52)60(72,27(8)64)28(9)91-61)19-77-56(49)89-57-48(76-14)39(68)44(31(83-57)18-73-11)88-55-40(69)47(43(74-12)24(5)82-55)85-34-17-58(10)50(26(7)81-34)94-59(95-58)16-30(66)42(25(6)90-59)84-33-15-29(65)41(23(4)80-33)86-54(71)35-22(3)36(62)38(67)37(63)46(35)75-13/h21,23-26,28-34,39-45,47-52,55-57,65-69,72H,15-20H2,1-14H3
SMILES Code
CC1C(C(CC(O1)OC2C(OC3(CC2O)OC4C(OC(CC4(O3)C)OC5C(C(OC(C5OC)C)OC6C(OC(C(C6O)OC)OC7C(C8C(CO7)OC9(O8)C1C(C(C(O9)C)(C(=O)C)O)OCO1)OC(=O)C(C)C)COC)O)C)C)O)OC(=O)C1=C(C(=C(C(=C1OC)Cl)O)Cl)C
Appearance
Light Beige to Beige Solid
Purity
>80% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Acetone (Slightly), DMSO (Slightly, Heated), Methanol (Slightly, Heated)
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Hygroscopic, -20°C Freezer, Under inert atmosphere

Preparing Stock Solutions

The following data is based on the product molecular weight 1,404.24 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: Yu G, Peng H, Cao J, Liao A, Long P, Huang J, Hui M. Avilamycin production enhancement by mutagenesis and fermentation optimization in Streptomyces viridochromogenes. World J Microbiol Biotechnol. 2022 Jan 31;38(3):50. doi: 10.1007/s11274-021-03191-3. PMID: 35098381. 2: Buzzetti F, Eisenberg F, Grant HN, Keller-Schierlein W, Voser W, Zähner H. Avilamycin [Avilamycin]. Experientia. 1968 Apr 15;24(4):320-3. German. doi: 10.1007/BF02140794. PMID: 5705169. 3: Simjee S, Gould G, Maduro L, Boulianne M, Pridmore A, Parent E. No change in avilamycin (Surmax® Premix) minimum inhibitory concentration for Clostridium perfringens isolates recovered from poultry up to 7 years post-approval in Canada. J Antimicrob Chemother. 2023 May 3;78(5):1278-1281. doi: 10.1093/jac/dkad089. PMID: 36995979. 4: Paradis MA, McMillan E, Bagg R, Vessie G, Zocche A, Thompson M. Efficacy of avilamycin for the prevention of necrotic enteritis caused by a pathogenic strain of Clostridium perfringens in broiler chickens. Avian Pathol. 2016 Jun;45(3):365-9. doi: 10.1080/03079457.2016.1165793. PMID: 26981841. 5: Choi JH, Lee K, Kim DW, Kil DY, Kim GB, Cha CJ. Influence of dietary avilamycin on ileal and cecal microbiota in broiler chickens. Poult Sci. 2018 Mar 1;97(3):970-979. doi: 10.3382/ps/pex360. PMID: 29253227. 6: Jones DJ, Mowrey DH, Anderson DB, Wellenreiter RH. Effect of various levels of avilamycin on the performance of growing-finishing swine. J Anim Sci. 1987 Oct;65(4):881-5. doi: 10.2527/jas1987.654881x. PMID: 3667460. 7: Burnett TJ. Avilamycin is poorly absorbed, is extensively metabolized by swine and is not persistent in the environment. J Mass Spectrom. 2005 Nov;40(11):1505. doi: 10.1002/jms.920. PMID: 16255060. 8: Aarestrup FM, Bager F, Andersen JS. Association between the use of avilamycin for growth promotion and the occurrence of resistance among Enterococcus faecium from broilers: epidemiological study and changes over time. Microb Drug Resist. 2000 Spring;6(1):71-5. doi: 10.1089/mdr.2000.6.71. PMID: 10868810. 9: Huang A, Luo X, Xu Z, Huang L, Wang X, Xie S, Pan Y, Fang S, Liu Z, Yuan Z, Hao H. Optimal Regimens and Clinical Breakpoint of Avilamycin Against Clostridium perfringens in Swine Based on PK-PD Study. Front Pharmacol. 2022 Feb 24;13:769539. doi: 10.3389/fphar.2022.769539. PMID: 35281904; PMCID: PMC8908370. 10: Kyriakis SC. The effect of avilamycin in the control of stress-induced post- weaning diarrhoea in piglets. J Vet Pharmacol Ther. 1989 Sep;12(3):296-301. doi: 10.1111/j.1365-2885.1989.tb00674.x. PMID: 2810479. 11: Boll R, Hofmann C, Heitmann B, Hauser G, Glaser S, Koslowski T, Friedrich T, Bechthold A. The active conformation of avilamycin A is conferred by AviX12, a radical AdoMet enzyme. J Biol Chem. 2006 May 26;281(21):14756-63. doi: 10.1074/jbc.M601508200. Epub 2006 Mar 14. PMID: 16537546. 12: Krupkin M, Wekselman I, Matzov D, Eyal Z, Diskin Posner Y, Rozenberg H, Zimmerman E, Bashan A, Yonath A. Avilamycin and evernimicin induce structural changes in rProteins uL16 and CTC that enhance the inhibition of A-site tRNA binding. Proc Natl Acad Sci U S A. 2016 Nov 1;113(44):E6796-E6805. doi: 10.1073/pnas.1614297113. Epub 2016 Oct 19. PMID: 27791159; PMCID: PMC5098648. 13: Weitnauer G, Hauser G, Hofmann C, Linder U, Boll R, Pelz K, Glaser SJ, Bechthold A. Novel avilamycin derivatives with improved polarity generated by targeted gene disruption. Chem Biol. 2004 Oct;11(10):1403-11. doi: 10.1016/j.chembiol.2004.08.016. PMID: 15489167. 14: Chauvin C, Gicquel-Bruneau M, Perrin-Guyomard A, Humbert F, Salvat G, Guillemot D, Sanders P. Use of avilamycin for growth promotion and avilamycin- resistance among Enterococcus faecium from broilers in a matched case-control study in France. Prev Vet Med. 2005 Sep 12;70(3-4):155-63. doi: 10.1016/j.prevetmed.2005.03.004. Epub 2005 Apr 25. PMID: 16023523. 15: Zhu CH, Lu FP, He YN, Han ZL, Du LX. Regulation of avilamycin biosynthesis in Streptomyces viridochromogenes: effects of glucose, ammonium ion, and inorganic phosphate. Appl Microbiol Biotechnol. 2007 Jan;73(5):1031-8. doi: 10.1007/s00253-006-0572-6. Epub 2006 Aug 29. PMID: 16941176. 16: Zhu CH, Lu FP, He YN, Zhang JK, Du LX. Statistical optimization of medium components for avilamycin production by Streptomyces viridochromogenes Tü57-1 using response surface methodology. J Ind Microbiol Biotechnol. 2007 Apr;34(4):271-8. doi: 10.1007/s10295-006-0195-z. Epub 2006 Dec 21. PMID: 17186208. 17: Lv XA, Jin YY, Li YD, Zhang H, Liang XL. Genome shuffling of Streptomyces viridochromogenes for improved production of avilamycin. Appl Microbiol Biotechnol. 2013 Jan;97(2):641-8. doi: 10.1007/s00253-012-4322-7. Epub 2012 Aug 22. PMID: 22911092. 18: Wolf H. Avilamycin, an inhibitor of the 30 S ribosomal subunits function. FEBS Lett. 1973 Oct 15;36(2):181-6. doi: 10.1016/0014-5793(73)80364-3. PMID: 4585189. 19: Chowdhury R, Islam KM, Khan MJ, Karim MR, Haque MN, Khatun M, Pesti GM. Effect of citric acid, avilamycin, and their combination on the performance, tibia ash, and immune status of broilers. Poult Sci. 2009 Aug;88(8):1616-22. doi: 10.3382/ps.2009-00119. PMID: 19590076. 20: Belanger AE, Shryock TR. Avilamycin did not play a role in the discontinuation of evernimicin as a clinical drug candidate. J Mass Spectrom. 2005 Aug;40(8):1109. doi: 10.1002/jms.889. PMID: 16041736.