Avilamycin | CAS# 11051-71-1 | Antimicrobial Agent

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

MedKoo CAT#: 574447

CAS#: 11051-71-1

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

Chemical Structure

Avilamycin

CAS# 11051-71-1

Instruction

Theoretical Analysis

MedKoo Cat#: 574447
Name: Avilamycin
CAS#: 11051-71-1
Chemical Formula: C61H88Cl2O32
Exact Mass: 1,402.46
Molecular Weight: 1,404.240
Elemental Analysis: C, 52.18; H, 6.32; Cl, 5.05; O, 36.46

Price and Availability

Size	Price	Availability
50mg	USD 260	2 Weeks
250mg	USD 600	2 Weeks
1g	USD 1475	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

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

Instruction:

View handling instruction

Biological target:
In vitro activity:
In vivo activity:

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.

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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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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.

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