Avilamycin C

Avilamycin C

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Avilamycin C
Category Antibiotics
Catalog number BBF-00616
CAS 69787-80-0
Molecular Weight 1406.25
Molecular Formula C61H90Cl2O32
Purity 95%

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Description

Avilamycin C is produced by the strain of Streptomyces viridochromogenes NRRL 2860. It inhibits the binding of amino acid-based tRNA to the bacterial ribosome for 30S subunit and has anti-gram-positive bacterial activity. It has been tried as feed additive in animal feeding.

Specification

Synonyms SCHEMBL6753731
IUPAC Name [(2R,3S,4R,6S)-6-[(2'R,3'S,3aR,4R,4'R,6S,7aR)-6-[(2S,3R,4R,5S,6R)-2-[(2R,3S,4S,5S,6S)-6-[(2R,3aS,3'aR,6S,6'R,7R,7'S,7aR,7'aR)-7'-hydroxy-7'-(1-hydroxyethyl)-6'-methyl-7-(2-methylpropanoyloxy)spiro[4,6,7,7a-tetrahydro-3aH-[1,3]dioxolo[4,5-c]pyran-2,4'-6,7a-dihydro-3aH-[1,3]dioxolo[4,5-c]pyran]-6-yl]oxy-4-hydroxy-5-methoxy-2-(methoxymethyl)oxan-3-yl]oxy-3-hydroxy-5-methoxy-6-methyloxan-4-yl]oxy-4'-hydroxy-2',4,7a-trimethylspiro[3a,4,6,7-tetrahydro-[1,3]dioxolo[4,5-c]pyran-2,6'-oxane]-3'-yl]oxy-4-hydroxy-2-methyloxan-3-yl] 3,5-dichloro-4-hydroxy-2-methoxy-6-methylbenzoate
Canonical SMILES 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(C)O)O)OCO1)OC(=O)C(C)C)COC)O)C)C)O)OC(=O)C1=C(C(=C(C(=C1OC)Cl)O)Cl)C
InChI InChI=1S/C61H90Cl2O32/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/h21,23-34,39-45,47-52,55-57,64-69,72H,15-20H2,1-14H3/t23-,24-,25-,26-,27?,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
InChI Key AEIFATUAVHHRBC-GYPCSUJESA-N

Properties

Appearance Achromatic Flake Crystalline
Antibiotic Activity Spectrum gram-positive bacterial
Melting Point 188-189 °C

Reference Reading

1. Performance, gut morphology and microbiology effects of a Bacillus probiotic, avilamycin and their combination in mixed grain broiler diets
A L Wealleans, M Sirukhi, I A Egorov Br Poult Sci. 2017 Oct;58(5):523-529. doi: 10.1080/00071668.2017.1349298. Epub 2017 Jul 10.
1. This study aimed to determine the effect of avilamycin (AGP) and a multi-strain Bacillus probiotic (DFM) on the performance, gut histology and microbiology of broilers fed on a mixed grain diet. 2. A total of 800 chicks were allocated to four treatments: a control diet, control+AGP, control+DFM, or control+AGP+DFM. Bodyweight, feed intake and FCR were measured at d 0, 21 and 42. Samples were taken at d42 to determine villus height (VH), crypt depth (CD) and ratio (VH:CD). Mucosal E. coli and Lactobacilli counts were measured at d42. 3. At d42, DFM and AGP+DFM significantly increased weight over the control, with AGP returning an intermediate value. FCR followed a similar pattern. DFM and AGP+DFM significantly increased VH and CD in all gut sections compared to the control. 4. DFM and AGP+DFM reduced E. coli counts compared to control, with AGP reducing caecal counts only, while Lactobacilli counts were increased. 5. Divergent histology and microbiology between treatments highlight the different modes of action of AGP and DFM for improving broiler growth and feed efficiency.
2. Optimal Regimens and Clinical Breakpoint of Avilamycin Against Clostridium perfringens in Swine Based on PK-PD Study
Anxiong Huang, Xun Luo, Zihui Xu, Lingli Huang, Xu Wang, Shuyu Xie, Yuanhu Pan, Shiwei Fang, Zhenli Liu, Zonghui Yuan, Haihong Hao Front Pharmacol. 2022 Feb 24;13:769539. doi: 10.3389/fphar.2022.769539. eCollection 2022.
Clostridium perfringens causes significant morbidity and mortality in swine worldwide. Avilamycin showed no cross resistance and good activity for treatment of C. perfringens. The aim of this study was to formulate optimal regimens of avilamycin treatment for C. perfringens infection based on the clinical breakpoint (CBP). The wild-type cutoff value (COWT) was defined as 0.25 μg/ml, which was developed based on the minimum inhibitory concentration (MIC) distributions of 120 C. perfringens isolates and calculated using ECOFFinder. Pharmacokinetics-pharmacodynamics (PK-PD) of avilamycin in ileal content were analyzed based on the high-performance liquid chromatography method and WinNonlin software to set up the target of PK/PD index (AUC0-24h/MIC)ex based on sigmoid Emax modeling. The PK parameters of AUC0-24h, Cmax, and Tmax in the intestinal tract were 428.62 ± 14.23 h μg/mL, 146.30 ± 13.41 μg/ml,, and 4 h, respectively. The target of (AUC0-24h/MIC)ex for bactericidal activity in intestinal content was 36.15 h. The PK-PD cutoff value (COPD) was defined as 8 μg/ml and calculated by Monte Carlo simulation. The dose regimen designed from the PK-PD study was 5.2 mg/kg mixed feeding and administrated for the treatment of C. perfringens infection. Five respective strains with different MICs were selected as the infection pathogens, and the clinical cutoff value was defined as 0.125 μg/ml based on the relationship between MIC and the possibility of cure (POC) following nonlinear regression analysis, CART, and "Window" approach. The CBP was set to be 0.25 μg/ml and selected by the integrated decision tree recommended by the Clinical Laboratory of Standard Institute. The formulation of the optimal regimens and CBP is good for clinical treatment and to control drug resistance.
3. Prevalence and antimicrobial susceptibility of Clostridium perfringens in chickens and pigs from Beijing and Shanxi, China
Jiyun Li, Yuqing Zhou, Dawei Yang, Shan Zhang, Zhiliang Sun, Yang Wang, Shaolin Wang, Congming Wu Vet Microbiol. 2020 Nov 24;252:108932. doi: 10.1016/j.vetmic.2020.108932. Online ahead of print.
The prevalence and antimicrobial susceptibility of Clostridium perfringens (C. perfringens) in chickens and pigs were investigated in Beijing and Shanxi, China. In total, 322 C. perfringens (chicken n = 60 and pig n = 262) were obtained from 620 feces of chickens (n = 256) and pigs (n = 364). Multiplex PCR for toxin typing of C. perfringens revealed that all the isolates belong to type A, with 45.7 % (147/322) isolates carrying beta-2 toxin-encoding gene cpb2. Minimum inhibitory concentrations of 27 antimicrobial agents showed that 91.0 % of the tested C. perfringens isolates were resistant to gentamicin and sulfonamides (sulfisoxazole and trimethoprim-sulfamethoxazole), and little resistance was showed to amoxicillin-clavulanate, ceftiofur, doxycycline, vancomycin and linezolid. Additionally, nosiheptide, avilamycin, virginiamycin and bacitracin exhibited good activity against the tested C. perfringens with low MIC50 (0.06 to ≤4 μg/mL) and MIC90 values (0.25-8 μg/mL). Whole genome sequencing (WGS) of 48 representative isolates from each farm indicated that the C. perfringens contained diverse antimicrobial resistance genes [tetA(P), ant(6)-Ib, erm(Q), etc.] and toxin genes (cpb2, colA, cloSI, pfoA, etc.). By comparative analysis, four C. perfringens isolates from three different pig farms harboured cpb2-carrying plasmid p1 with 100 % nucleotide sequence identity, suggesting horizontal gene transfer among these microorganisms. The further phylogenomic reconstruction, based on the core-genome single nucleotide polymorphisms (SNPs) of the representatives, demonstrating that C. perfringens from the same farms and regions were closely related. These findings expanded our knowledge of C. perfringens isolated from animals in China, which provided scientific basis for efficient intervention or prevention measures of antimicrobial resistance in animal husbandry in China.

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