11051-71-1

Basic information

• Product Name: Avilamycin
• Synonyms: Avilomycin
• CAS NO: 11051-71-1
• Molecular Formula: C61H88Cl2O32
• Molecular Weight: 1404.23822
• Mol File: 11051-71-1.mol
• Article Data: 0

Chemical Properties

• Melting Point: 188-189℃
• Appearance: /
• Density: 1.5 g/cm³
• Refractive Index: 1.6
• CAS DataBase Reference: Avilamycin(CAS DataBase Reference)
• NIST Chemistry Reference: Avilamycin(11051-71-1)
• EPA Substance Registry System: Avilamycin(11051-71-1)

Safety Data

• Hazardous Substances Data: 11051-71-1(Hazardous Substances Data)

Usage

Originator

Maxus,Eli Lilly

Uses

Antibacterial.

Manufacturing Process

Avilamycin is produced from Streptomyces viridochromogenes NRRL 2860: A nutrient solution is prepared which contains 20.0 g of meat meal, 20.0 g of salt extract, 10.0 g of calcium carbonate and 1 L of tap water and adjusted to pH=7. This solution, or a multiple thereof, is charged into conical flasks of 500 ml capacity (100 ml of nutrient solution each) or into fermenters of 500 L capacity (300 L of nutrient solution each) and sterilized for 20-30 min under a pressure of 1 atm. The contents of the flasks are then inoculated with up to 10% of a partially sporulating vegetative culture of Streptomyces viridochromogenes NRRL 2860 and incubated at 27°C with thorough shaking or stirring, and in the fermenters with aerating with about 1 volume of sterile air per volume of nutrient solution per minute. The cultures are allowed to grow for 24-48 h, mixed with about 1.5% of a filtration assistant and then filtered depending on the volume, through a suction filter or a filter press or a rotary filter to free the antibiotically active aqueous solution from the mycelium and other solid constituents. The medium described above is replaced the nutrient media: 10.0 g of crude glucose, 5.0 g of peptone, 3.0 g of meat extract (Oxo Lab- Lemco), 5.0 g of sodium chloride, 10.0 g of calcium carbonate and 1 L of tap water, pH - prior to sterilization: 7.5, analogous sterilization, inoculation with Streptomnyces viridochromogenes NRRL 2860, incubation at 27°C and filtration likewise yield aqueous antibiotically active solutions. 90 L of culture filtrate are extracted with 20 L of ethyl acetate, and the extract is concentrated to 400 ml. When the concentrate is kept for 20 h at 2°C, avilamycin precipitates in the form of a dense floccular substance which is filtered off. After having been dried in an exsiccator, the practically colorless crystal cake consisting of strongly felted small needles weighs 3.07 g. The mother liquors are concentrated to about 200 ml and mixed with twice the amount of ether. When the concentrate is kept for 4 days at 0°C, a further 3.28 g of avilamycin crystallize out. 3.0 g of the crystallizate are dissolved in 50 ml of acetone, and a small amount of insoluble sludge is filtered off. The clear filtrate is mixed with ether and concentrated. On cooling, 2.0 g of colorless fine needles crystallize out. Concentration of the mother liquors to about one quarter their volume produces a further 0.48 g of crystals. For analysis a test portion of these crystals is recrystallized 4 times from acetone+ether and dried for 20 h in a high vacuum at 70°C. The analytically pure antibiotic avilamycin have a melting point 188°-189.5°C. Optical rotation [α]D 20=+0.8° (c=1.165 in absolute ethanol).

Brand name

Surmax (Lilly).

Therapeutic Function

Antibiotic

InChI:InChI=1/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/t23-,24-,25-,26-,28-,29-,30-,31-,32+,33+,34+,39+,40-,41-,42-,43+,44-,45-,47-,48+,49-,50-,51-,52-,55+,56?,57+,58-,59?,60+,61-/m1/s1

Related news

Research ArticleGenes Encoding Enzymes Responsible for Biosynthesis of L-Lyxose and Attachment of Eurekanate during Avilamycin (cas 11051-71-1) Biosynthesis08/21/2019

SummaryThe oligosaccharide antibiotic avilamycin A is composed of a polyketide-derived dichloroisoeverninic acid moiety attached to a heptasaccharide chain consisting of six hexoses and one unusual pentose moiety. We describe the generation of mutant strains of the avilamycin producer defective ...detailed

Research PaperBiosynthesis of the orthosomycin antibiotic Avilamycin (cas 11051-71-1) A: deductions from the molecular analysis of the avi biosynthetic gene cluster of Streptomyces viridochromogenes Tü57 and production of new antibiotics08/20/2019

Background: Streptomyces viridochromogenes Tü57 is the producer of avilamycin A. The antibiotic consists of a heptasaccharide side chain and a polyketide-derived dichloroisoeverninic acid as aglycone. Molecular cloning and characterization of the genes governing the avilamycin A biosynthesis is...detailed

Short communicationDetermination of Avilamycin (cas 11051-71-1) A and B in pig faeces by solid phase extraction and reverse-phase HPLC assay08/19/2019

A HPLC method is described for the simultaneous determination of avilamycin A and B in pig faeces, following extraction using acetonitrile and normal-phase solid phase extraction. The HPLC stationary phase was Kromosil 5 μ C-18 with a mobile phase of 48% acetonitrile and 52% 0.01N ammonium acet...detailed

ArticleNovel Avilamycin (cas 11051-71-1) Derivatives with Improved Polarity Generated by Targeted Gene Disruption08/18/2019

The oligosaccharide antibiotics avilamycin A and C are produced by Streptomyces viridochromogenes Tü57. Both consist of a heptasaccharide chain, which is attached to a polyketide-derived dichloroisoeverninic acid moiety. They show excellent antibiotic activity against Gram-positive bacteria. Bo...detailed

Use of Avilamycin (cas 11051-71-1) for growth promotion and Avilamycin (cas 11051-71-1)-resistance among Enterococcus faecium from broilers in a matched case–control study in France08/17/2019

We assessed the putative link between avilamycin-resistant Enterococcus faecium carriage and avilamycin consumption in broilers. As part of the French programme of monitoring for antimicrobial resistance, broilers sampled at slaughterhouse in 1999 and 2000 and carrying avilamycin-resistant E. fa...detailed

Analytical MethodsDetermination of total Avilamycin (cas 11051-71-1) residues as dichloroisoeverninic acid in porcine muscle, fat, and liver by LC-MS/MS08/16/2019

A sensitive and reliable method for determining the total avilamycin residues was developed using LC–MS/MS. Avilamycin (consisting of avilamycin A and 15 other minor factors) and its metabolites in porcine muscle, fat, and liver were analysed as the marker residue dichloroisoeverninic acid (DIA...detailed