Avilamycin A |
![]() Last updated: 15/09/2025 |
![]() |
(Also known as: flambamycin) |
|
![]() |
|
An oligosaccharide antibiotic drug active against gram-posive bacteria. | |
---|---|---|
|
Mainly used for pig and poultry growth promotion and to control bacterial enteric infections such as stress-induced post-weaning diarrhea in piglets, caused by Escherichia coli | |
|
Pigs; Poultry; Rabbits |
Approval status |
|
Not approved | |
---|---|---|
|
Not approved |
Chemical structure |
|
Avilamycin A exhibits complex isomerism due to its intricate structure, which includes multiple chiral centres and glycosidic linkages. The molecule primarily shows stereoisomerism, with numerous asymmetric carbon atoms giving rise to optical isomers that influence its antibiotic activity. It also displays conformational isomerism, as its flexible sugar rings and linkages allow for different spatial arrangements that affect how it interacts with bacterial ribosomes. While geometric isomerism is less prominent, some side chains may exhibit restricted rotation. | |
---|---|---|
|
C₆₁H₈₈Cl₂O₃₂ | |
|
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 | |
|
C[C@@H]1[C@H]([C@@H](C[C@@H](O1)O[C@@H]2[C@H](OC3(C[C@H]2O)O[C@@H]4[C@H](O[C@H](C[C@]4(O3)C)O[C@@H]5[C@H]([C@@H](O[C@@H]([C@@H]5OC)C)O[C@@H]6[C@H](O[C@H]([C@H]([C@H]6O)OC)O[C@H]7[C@@H]([C@H]8[C@H](CO7)O[C@@]9(O8)[C@H]1[C@H]([C@@]([C@H](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 | |
|
XIRGHRXBGGPPKY-FCNCREMHSA-N | |
|
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/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 | |
|
Yes |
General status |
|
Antibiotic, Antibacterial, Medicinal drug, Growth promotor, Feed additive | |
---|---|---|
|
Oligosaccharide | |
|
- | |
|
- | |
|
Semi-synthetic | |
|
Inhibits the protein synthesis of susceptible micro-organisms, binds to the 50S ribosomal subunit | |
|
[50S rRNA, Antagonist] | |
|
69787-79-7 | |
|
11051-71-1 (avilamycin isomer mix) | |
|
- | |
|
- | |
|
- | |
|
20054845 | |
|
Alimentary tract and metabolism: Antibiotics | |
|
QA07AA95 | |
|
No | |
|
- | |
|
1404.2 | |
|
- | |
|
[(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'-acetyl-7'-hydroxy-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 | |
|
- | |
|
- | |
|
- | |
|
- | |
|
White crystalline solid with musky odour |
Commercial |
|
|
|||
---|---|---|---|---|
|
Current | |||
|
1987, global introduction | |||
|
|
|||
|
|
|||
|
Usually supplied as a medicated pre-mix feed | |||
|
Avilamycin A is produced through a fermentation-based process using Streptomyces viridochromogenes, a soil-dwelling actinomycete. The production begins with culturing spores on a nutrient-rich medium to generate a seed culture, which is then inoculated into a fermentation broth. During fermentation, the bacteria synthesise avilamycin A as a secondary metabolite, with production regulated by specific genes like aviC1 and aviC2 that activate the biosynthetic gene cluster. Optimisation strategies, such as mutagenesis, medium composition adjustments, and supplementation with precursors like L-valine and D-xylose, can significantly enhance yield. After fermentation, the broth is processed to isolate and purify avilamycin A, typically through crystallisation and solvent extraction techniques. | |||
|
As microbial-based products tend to use fermentation-based production processes rather than chemical synthesis, they typically have a lower fossil fuel input in formulation and active ingredient creation, and also have reduced downstream emissions due to biodegradability and minimal soil disruption, their life-cycle GHG emissions are expected to be low. Whilst hard and precise data is not available, broad estimates suggest that typically emissions are likely to be below 5 kg CO₂e/kg. |
|
![]() |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
41.0 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data |
Moderate | ||||||||
|
4000 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Ethanol4 = Verified data |
- | ||||||||
5000 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Methanol4 = Verified data |
- | |||||||||
10000 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Ethyl acetate4 = Verified data |
- | |||||||||
50000 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Acetone4 = Verified data |
- | |||||||||
|
181 | E4 E = Manufacturers safety data sheets 4 = Verified data |
- | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
3.55 X 1002 | Calculated | - | |||||||
|
2.55 | F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 3 = Unverified data of known source |
Low | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
- | |||||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
Substance may enter the environment via the faeces of treated animals or by leaching from spilt medicated feed. |
Degradation |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
|
25 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data |
Non-persistent | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
Literature states DT₅₀ in soil 3 to 4 weeks | ||||||||||
|
28 | F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Manure3 = Unverified data of known source |
- | ||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
As this parameter is not normally measured directly, a surrogate measure is used: ‘Photochemical oxidative DT₅₀’. Where data is available, this can be found in the Fate Indices section below. | ||||||||||
|
- |
Soil adsorption and mobility |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
|
61 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) 4 = Verified data |
Slightly mobile | |||||||
|
2934 | ||||||||||
|
US data Kd range 23-109 mL g⁻¹, Koc range 1769-3633 mL g⁻¹, Soils = 3 Literature Koc values range 1802-3685 mL g⁻¹ | ||||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | ||||||||||
|
- | ||||||||||
|
- |
Fate indices |
|
|
|
|
||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
0.74 | Calculated | Low leachability | ||||||||||||||||||||||||||
|
|
- | - | - | |||||||||||||||||||||||||
|
- | - |
Known soil and groundwater metabolites |
None
Other known metabolites |
|
|
|
|
||||
---|---|---|---|---|---|---|---|
flambic acid | - | Rat (Liver); Livestock | - | ||||
flambalactone | - | - | - |
|
![]() |
Terrestrial ecotoxicology |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
> 4640 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Rat4 = Verified data |
Low | ||||||||
|
|
- | - | - | |||||||
|
- | - | |||||||||
|
- | - | - | ||||||||
|
> 372.5 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Colinus virginianus4 = Verified data |
Moderate | ||||||||
|
> 745 ppm | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Colinus virginianus4 = Verified data |
- | ||||||||
|
- | - | - | ||||||||
|
> 100 | F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Lumbricus terrestris3 = Unverified data of known source |
Moderate | ||||||||
|
> 330 | F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Lumbricus terrestris3 = Unverified data of known source |
Low | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
- | |||||||||||
|
- | - | - | ||||||||
- | |||||||||||
|
|
- | - | - | |||||||
|
- | - | - | ||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
|
- | - | - | |||||||
|
- | ||||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - |
Aquatic ecotoxicology |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
- | - | - | ||||||||
|
47.8 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Oncorhynchus mykiss4 = Verified data |
Low | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
23.8 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Daphnia magna4 = Verified data |
Low | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
> 10 | F3 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Synechococcus leopoliensis3 = Unverified data of known source |
Low | ||||||||
|
- | - | - | ||||||||
|
|
- | - | - |
|
- | - | - | |||
|
- | - | - |
|
![]() |
General |
|
|
|
|
||||||||
---|---|---|---|---|---|---|---|---|---|---|---|
|
High (class III) | - | - | ||||||||
|
> 4640 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Rat4 = Verified data |
Low | ||||||||
|
2000 | F4 F = U.S. EPA ECOTOX database / U.S. EPA pesticide fate database / Miscellaneous WHO documents / FAO data, IPCS INCHEM data (US EPA Databases Related to Pesticide Risk Assessment ) Rabbit4 = Verified data |
- | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
- | - | - | ||||||||
|
|
- | |||||||||
|
- | ||||||||||
|
Extensively metabolised and rapidly excreted in the faeces and urine | A5 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 5 = Verified data used for regulatory purposes |
- |
Health issues |
|
|
||||||||||||||||||||||||||||
---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|---|
|
Possible liver toxicant |
Handling issues |
|
|
|||
---|---|---|---|---|
|
No information available | |||
|
- | |||
|
Not listed (Not listed) | |||
|
- | |||
|
- | |||
|
- |
|
![]() |
|
|
||
---|---|---|---|
|
avilamycin A | ||
|
avilamycine A | ||
|
- | ||
|
- | ||
|
- | ||
|
avilamycina A | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- | ||
|
- |
Record last updated: | 15/09/2025 |
Contact: | aeru@herts.ac.uk |
Please cite as: | Lewis, K.A., Tzilivakis, J., Warner, D. and Green, A. (2016) An international database for pesticide risk assessments and management. Human and Ecological Risk Assessment: An International Journal, 22(4), 1050-1064. DOI: 10.1080/10807039.2015.1133242 |