Avoparcin

Avoparcin	Last updated: 31/08/2023
(Also known as: avotan; CL 81588 ; compound 254)

Data alerts

The following alerts are based on the data in the tables below. An absence of an alert does not imply the substance has no implications for human health, biodiversity or the environment but just that we do not have the data to form a judgement.

Environmental fate	Ecotoxicity	Human health
		Human health Moderate alert: Reproduction/development effects

GENERAL INFORMATION

Description

A Gram-positive glycopeptide antibiotic used in livestock feed for growth promotion

Availability status

Introduction & key dates

Examples of species treated

Pigs, Meat poultry, Cattle

Chemical structure

Isomerism

Isomeric

Chemical formula

C₈₃H₉₂ClN₉O₃₁

Canonical SMILES

CC1C(C(CC(O1)OC2C(C(C(OC2OC3=C4C=C5C=C3OC6=C(C=C(C=C6)C(C7C(=O)NC(C8=CC(=CC(=C8C9=C(C=CC(=C9)C(C(=O)N7)NC(=O)C5NC(=O)C(NC(=O)C(C(C1=CC=C(O4)C=C1)O)NC(=O)C(C1=CC=C(C=C1)OC1C(C(C(C(O1)C)O)O)O)NC)C1=CC=C(C=C1)O)O)O)O)C(=O)O)OC1CC(C(C(O1)C)O)N)Cl)CO)O)O)N)O

Isomeric SMILES

C[C@H]1[C@@H]([C@@H](C[C@@H](O1)O[C@H]2[C@H]3C(=O)N[C@@H](C4=CC(=CC(=C4C5=C(C=CC(=C5)[C@H](C(=O)N3)NC(=O)[C@H]6C7=CC(=C(C(=C7)OC8=C(C=C2C=C8)Cl)O[C@H]9C([C@H]([C@@H]([C@H](O9)CO)O)O)O[C@H]1C[C@H]([C@H]([C@@H](O1)C)O)N)OC1=CC=C(C=C1)[C@H]([C@H](C(=O)N[C@H](C(=O)N6)C1=CC=C(C=C1)O)NC(=O)[C@@H](C1=CC=C(C=C1)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)NC)O)O)O)O)C(=O)O)N)O

International Chemical Identifier key (InChIKey)

OTKPPUXRIADSGD-PPRNARJGSA-N

International Chemical Identifier (InChI)

InChI=1S/C83H92ClN9O31/c1-30-64(99)46(85)27-54(115-30)122-72-37-12-20-50(45(84)22-37)120-52-24-38-23-51(73(52)124-83-74(70(105)68(103)53(29-94)121-83)123-55-28-47(86)65(100)31(2)116-55)118-41-17-9-35(10-18-41)67(102)62(92-75(107)57(87-4)33-7-15-42(16-8-33)119-82-71(106)69(104)66(101)32(3)117-82)79(111)88-58(34-5-13-39(95)14-6-34)76(108)90-60(38)78(110)89-59-36-11-19-48(97)43(21-36)56-44(25-40(96)26-49(56)98)61(81(113)114)91-80(112)63(72)93-77(59)109/h5-26,30-32,46-47,53-55,57-72,74,82-83,87,94-106H,27-29,85-86H2,1-4H3,(H,88,111)(H,89,110)(H,90,108)(H,91,112)(H,92,107)(H,93,109)(H,113,114)/t30-,31-,32-,46+,47+,53+,54-,55-,57+,58-,59+,60+,61-,62+,63-,64-,65-,66-,67+,68+,69+,70-,71+,72+,74?,82-,83-/m0/s1

2D structure diagram/image available?

Yes

General status

Veterinary substance type

Antibiotic, Antibacterial, Growth promotor, Feed additive

Substance groups

Glycopeptide

Minimum active substance purity

Known relevant impurities

Substance origin

Natural

Mode of action

Inhibition of bacterial cell wall synthesis

Molecular targets

CAS RN

37332-99-3

EC number

253-466-4

CIPAC number

US EPA chemical code

PubChem CID

16132294

ATCvet Code

QJ01XA

Therapeutic Class

Antiinfectives for systemic use: Antibacterials for systemic use

Controlled Drug?

Regulation 37/2010 MRL Classification

No data

Molecular mass

1741.12

PIN (Preferred Identification Name)

IUPAC name

(1S,2R,18R,19R,22S,25R,28R,40S)-2-[(2R,4R,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-48-[(2S,4S,5S,6R)-3-[(2R,4R,5R,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-5-chloro-18,32,35,37-tetrahydroxy-22-(4-hydroxyphenyl)-19-[[(2R)-2-(methylamino)-2-[4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyphenyl]acetyl]amino]-20,23,26,42,44-pentaoxo-7,13-dioxa-21,24,27,41,43-pentazaoctacyclopentaconta-

CAS name

Other status information

Banned as a growth promotor in EU since 1997; Not approved as feed additive in EU

Relevant Environmental Water Quality Standards

Physical state

White, amorphous solid

Related substances & organisms

virginiamycin

Formulations

Property

Product

Manufacturer

Authorisation Route

UK Legal Class

Example products using this active

None identified

No UK authorisation for use with animals

Not applicable

Formulation and application details

Supplied as a feed additive

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

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

Melting point (°C)

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

Log P

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)

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

Surface tension (mN m⁻¹)

Refractive Index

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

Manure DT₅₀ (days)

Beef cattle manure

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)

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)

> 10000

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)

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

Fish - Acute 96 hour LC₅₀ (mg l⁻¹)

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

Aquatic invertebrates - Chronic 21 day NOEC (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)

> 10000

Rat

Low

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

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

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

Mainly eliminated via 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

Linked to the emergence of Vancomycin Resistant Enterococci WRE

Handling issues

Property

Value and interpretation

General

No information available

CLP classification 2013

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

avoparcin

French

avoparcine

German

Danish

Italian

Spanish

avoparcina

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	31/08/2023
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