Flavomycin

Flavomycin	Last updated: 23/02/2024
(Also known as: flavomicin; bambermycins; flavophospholipol; moenomycin A; BAM)

GENERAL INFORMATION

Description

An antibiotic drug effective against gram-positive and some gram-negative bacteria and used as a performance enhancing substance

Availability status

Introduction & key dates

circa 1970, first registered in USA

Examples of veterinary uses

Used to promote increased weight gain and improved feed efficiency in a range of farmed animals

Examples of species treated

Pigs; Poultry; Cattle; Rabbits; Aquatic species

Approval status

VMR 2013/2033 approval status (GB/UK)

Not approved

EU Regulatory approval status

Not approved

Chemical structure

Isomerism

Isomeric

Chemical formula

C₆₉H₁₀₇N₄O₃₅P

Canonical SMILES

CC1C(C(C(C(O1)OC2C(OC(C(C2O)NC(=O)C)OC3C(C(C(OC3OP(=O)(O)OCC(C(=O)OCCC=C(C)CCC=CC(C)(C)CCC(=C)CC=C(C)CCC=C(C)C)O)C(=O)O)(C)O)OC(=O)N)COC4C(C(C(C(O4)CO)O)O)O)NC(=O)C)O)OC5C(C(C(C(O5)C(=O)NC6=C(CCC6=O)O)O)O)O

Isomeric SMILES

C[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)O[C@@H]2[C@H](O[C@H]([C@@H]([C@H]2O)NC(=O)C)O[C@@H]3[C@H]([C@]([C@H](O[C@@H]3OP(=O)(O)OC[C@H](C(=O)OCC/C=C(\C)/CC/C=C/C(C)(C)CCC(=C)C/C=C(\C)/CCC=C(C)C)O)C(=O)O)(C)O)OC(=O)N)CO[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)NC(=O)C)O)O[C@H]5[C@@H]([C@H]([C@H]([C@H](O5)C(=O)NC6=C(CCC6=O)O)O)O)O

International Chemical Identifier key (InChIKey)

FUIOWSNNCWZETH-NAMXWVJMSA-N

International Chemical Identifier (InChI)

InChI=1S/C70H109N4O35P/c1-31(2)16-14-18-33(4)20-21-34(5)24-26-69(9,10)25-13-12-17-32(3)19-15-27-97-62(92)40(80)29-99-110(95,96)109-67-57(58(108-68(71)93)70(11,94)59(107-67)61(90)91)106-64-45(73-37(8)77)48(83)55(42(102-64)30-98-65-52(87)49(84)46(81)41(28-75)101-65)104-63-44(72-36(7)76)47(82)54(35(6)100-63)103-66-53(88)50(85)51(86)56(105-66)60(89)74-43-38(78)22-23-39(43)79/h13,16,19-20,25,35,40-42,44-59,63-67,75,78,80-88,94H,5,12,14-15,17-18,21-24,26-30H2,1-4,6-11H3,(H2,71,93)(H,72,76)(H,73,77)(H,74,89)(H,90,91)(H,95,96)/b25-13+,32-19+,33-20+/t35-,40-,41-,42-,44-,45-,46-,47-,48-,49+,50+,51-,52-,53-,54-,55-,56+,57-,58-,59-,63+,64+,65-,66-,67-,70+/m1/s1

2D structure diagram/image available?

Yes

General status

Veterinary substance type

Antibiotic, Antibacterial, Antimicrobial, Performance enhancer, Feed additive

Substance groups

Phosphoglycolipid

Minimum active substance purity

Known relevant impurities

Substance origin

Natural

Mode of action

Broad spectrum, inhibits microorganism reproduction by intervening in the biosynthesis of murein, the structural substance of their cell walls.

Molecular targets

[Peptidoglycan synthetase ftsI, Antagonist]

CAS RN

11015-37-5

EC number

234-246-7

CIPAC number

US EPA chemical code

PubChem CID

Therapeutic Class

ATCvet Code

None allocated

Controlled Drug?

Regulation 37/2010 MRL Classification

Molecular mass

1583.57

PIN (Preferred Identification Name)

IUPAC name

(2S,3S,4R,5R,6R)-5-[(2S,3R,4R,5S,6R)-3-acetamido-5-[(2S,3R,4R,5S,6R)-3-acetamido-4-hydroxy-6-methyl-5-[(2R,3R,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-hydroxy-5-oxocyclopenten-1-yl)carbamoyl]oxan-2-yl]oxyoxan-2-yl]oxy-4-hydroxy-6-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]oxan-2-yl]oxy-4-carbamoyloxy-3-hydroxy-6-[hydroxy-[(2R)-2-hydroxy-3-oxo-3-[(3E,7E,14E)-4,9,9,15,19-pentamethyl-12-methylideneicosa-3,7,14,18-tetraenoxy]propoxy]phosphoryl]oxy-3-methyloxane-2-carboxylic acid

CAS name

Other status information

Evidence of use in third world countries

Relevant Environmental Water Quality Standards

Physical state

White to light brown coloured powder

Formulations

Property

Product

Manufacturer

Authorisation Route

Legal Class (GB/UK)

Example products (past and present) using this active

Flavomycin 40

Huvepharma

Not licensed

Formulation and application details

Often formulated as medicated pre-mix feed

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

Solubility - In water at 20 °C (mg l⁻¹)

250000

at 25 °C

High

Solubility - In organic solvents at 20 °C (mg l⁻¹)

64000

Methanol

500

Ethanol

100

Acetone

100

Benzene

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

Octanol-water partition coefficient at pH 7, 20 °C

1.91 X 10^-12

Calculated

Log P

-11.72

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

Henry's law constant at 25 °C (Pa m³ mol⁻¹)

Volatilisation as max % of applied dose lost

From plant surface

From soil surface

Maximum UV-vis absorption L mol⁻¹ cm⁻¹

Surface tension (mN m⁻¹)

Refractive Index

Environmental release

The primary manner in which flavomycin could be introduced into the environment is through cattle manure either directly deposited or via spreading to land

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

Non-persistent

DT₅₀ (lab at 20 °C)

Non-persistent

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

DT₅₀ range 13.3 to 28.0 days, n=4; Other data DT₅₀ <30 days (R4)

Manure DT₅₀ (days)

<30

Manure data for aminoglycosides generally; Other data <25 days soil & chicken manure (R3)

Aqueous photolysis DT₅₀ (days) at pH 7

Value

Note

Aqueous hydrolysis DT₅₀ (days) at 20 °C and pH 7

Value

Note

Water-sediment DT₅₀ (days)

Water phase only DT₅₀ (days)

Air degradation

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

Property

Value

Source; quality score; and other information

Interpretation

Linear

K_d

K_oc

Notes and range

Freundlich

K_f

K_foc

¹/_n

Notes and range

pH sensitivity

Fate indices

Property

Value

Source; quality score; and other information

Interpretation

GUS leaching potential index

Bio-concentration factor

BCF (l kg⁻¹)

CT₅₀ (days)

Known metabolites

None

ECOTOXICOLOGY

Terrestrial ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Short term dietary NOEL

(mg kg⁻¹)

(ppm diet)

Mammals - Chronic 21d NOAEL (mg kg⁻¹ bw d⁻¹)

Birds - Acute LD₅₀ (mg kg⁻¹)

Birds - Short term dietary (LC₅₀/LD₅₀)

Birds - Chronic 21d NOEL (mg kg⁻¹ bw d⁻¹)

Earthworms - Acute 14 day LC₅₀ (mg kg⁻¹)

> 25000

Eisenia foetida as product (8%)

Low

Earthworms - Chronic NOEC, reproduction (mg kg⁻¹)

Soil micro-organisms

Collembola

Acute LC₅₀ (mg kg⁻¹)

Chronic NOEC (mg kg⁻¹)

Non-target plants

Honeybees (Apis spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Unknown mode acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Chronic

Bumblebees (Bombus spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Mason bees (Osmia spp.)

Contact acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Oral acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg bee⁻¹)

Other bee species (1)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Other bee species (2)

Acute LD₅₀ (worst case from 24, 48 and 72 hour values - μg insect⁻¹)

Mode of exposure

Beneficial insects (Ladybirds)

Beneficial insects (Lacewings)

Beneficial insects (Parasitic wasps)

Beneficial insects (Predatory mites)

Beneficial insects (Ground beetles)

Aquatic ecotoxicology

Property

Value

Source; quality score; and other information

Interpretation

Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

598

Leuciscus idus as product (8%)

Low

Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)

250

Leuciscus idus as product (8%)

Low

Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

908

Daphnia magna as product (8%)

Low

Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)

433

Daphnia magna. as product (8%)

Low

Tropical Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)

Aquatic crustaceans - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Acute 96 hour LC₅₀ (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l⁻¹)

Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg⁻¹)

Aquatic plants - Acute 7 day EC₅₀, biomass (mg l⁻¹)

Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)

Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)

Mesocosm study data

NOEAEC mg l⁻¹

HUMAN HEALTH AND PROTECTION

General

Property

Value

Source; quality score; and other information

Interpretation

Threshold of Toxicological Concern (Cramer Class)

High (class III)

Mammals - Acute oral LD₅₀ (mg kg⁻¹)

> 2000

Rat

Low

Mammals - Dermal LD₅₀ (mg kg⁻¹ body weight)

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

Subcutaneous LD₅₀ = 500 mg kg⁻¹

Mouse

Intravenous LD₅₀ = 200 mg kg⁻¹

Mouse

ADI - Acceptable Daily Intake (mg kg⁻¹ bw day⁻¹)

ARfD - Acute Reference Dose (mg kg⁻¹ bw day⁻¹)

AAOEL - Acute Acceptable Operator Exposure Level (mg kg⁻¹ bw day⁻¹)

AOEL - Acceptable Operator Exposure Level - Systemic (mg kg⁻¹ bw day⁻¹)

Dermal penetration studies (%)

Dangerous Substances Directive 76/464

Exposure Routes

Public

Occupational

Mammalian dose elimination route and rate

Mostly unmetabolised and excreted unchanged in the faeces

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

No data found

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

No data found

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

No further information available

Handling issues

Property

Value and interpretation

General

Risk of dust explosions

CLP classification 2013

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

flavomycin

French

bambermycine

German

Danish

Italian

Spanish

bambermicina

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	23/02/2024
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