Apramycin

Apramycin	Last updated: 31/08/2023
(Also known as: nebramycin II)

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
Environmental fate Low alert: Drainflow: Non-mobile Warning: Significant data are missing	Ecotoxicity Moderate alert: Birds acute ecotoxicity: Moderate	Human health Moderate alert: Reproduction/development effects

GENERAL INFORMATION

Description

An antibiotic and antibacterial compound used in veterinary medicine including the treatment of colibacillosis and salmonella in calves and bacterial enteritis in pigs and lambs

Availability status

Introduction & key dates

Examples of species treated

Pigs, Lambs, Cattle, Chickens

Chemical structure

Isomerism

Isomeric

Chemical formula

C₂₁H₄₁N₅O₁₁

Canonical SMILES

CNC1C(C2C(CC(C(O2)OC3C(CC(C(C3O)O)N)N)N)OC1OC4C(C(C(C(O4)CO)N)O)O)O

Isomeric SMILES

CN[C@H]1[C@H]([C@@H]2[C@H](C[C@H]([C@H](O2)O[C@@H]3[C@H](C[C@H]([C@@H]([C@H]3O)O)N)N)N)O[C@@H]1O[C@@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)N)O)O)O

International Chemical Identifier key (InChIKey)

XZNUGFQTQHRASN-XQENGBIVSA-N

International Chemical Identifier (InChI)

InChI=1S/C21H41N5O11/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31/h5-21,26-32H,2-4,22-25H2,1H3/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-/m1/s1

2D structure diagram/image available?

Yes

General status

Veterinary substance type

Antibiotic, Antimicrobial, Antibacterial

Substance groups

Aminoglycoside

Minimum active substance purity

Known relevant impurities

Substance origin

Synthetic

Mode of action

Inhibitor of protein synthesis in bacteria both in vivo and in vitro

Molecular targets

[16S rRNA]

CAS RN

37321-09-8

EC number

253-460-1

CIPAC number

US EPA chemical code

PubChem CID

3081545

ATCvet Code

QJ51GB90; QA07AA92; QJ01GB90

Therapeutic Class

Antiinfectants for systemic use: Antibacterials for intramammary use; Alimentary tract & metabolism: Intestinal antiinfectants; Antiinfectants for systemic use: Antibacterials for systemic use

Controlled Drug?

Regulation 37/2010 MRL Classification

Allowed substance (Table 1: Bovine, Ovine, Pocine, Chicken, Rabbit)

Molecular mass

539.58

PIN (Preferred Identification Name)

IUPAC name

(2R,3R,4S,5S,6S)-2-[[(2R,3S,4R,4αR,6S,7R,8αS)-7-amino-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2,3-dihydroxycyclohexyl]oxy-4-hydroxy-3-(methylamino)-2,3,4,4α,6,7,8,8α-octahydropyrano[3,2-β]pyran-2-yl]oxy]-5-amino-6-(hydroxymethyl)oxane-3,4-diol

CAS name

D-Streptamine,O-4-amino-4-deoxy-a-D-glucopyranosyl-(1®8)-O-(8R)-2-amino-2,3,7-trideoxy-7-(methylamino)-D-glycero-a-D-allo-octodialdo-1,5:8,4-dipyranosyl-(1®4)-2-deoxy-

Other status information

Relevant Environmental Water Quality Standards

Physical state

Colourless, needle-shaped crystals

Formulations

Property

Product

Manufacturer

Authorisation Route

UK Legal Class

Example products using this active

Apralan Soluble Powder for Oral Solution

Eli Lilly Company

UK National authorisation

Prescription only medicine to be authorised by a veterinarian (POM-V)

Apralan G200 Premix medicated feeding stuff

Eli Lilly Company

UK National authorisation (IC)

Prescription only medicine to be authorised by a veterinarian (POM-V)

Formulation and application details

Often supplied as a powder which is added to livestock's drinking water. Also available as premix and pour-on formulations

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

300000

High

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

Melting point (°C)

189

Boiling point (°C)

823

Degradation point (°C)

Flashpoint (°C)

451.6

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

5.01 X 10^-04

Calculated

Log P

-3.3

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

1.56

Dissociation constant pKa) at 25 °C

8.5

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)

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

Non-mobile

K_oc

500755

Notes and range

Literature values K_oc range 341900 - 659609 mL g⁻¹

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)

> 4160

Rat as the sulphate

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)

1669

Colinus virginianus

Moderate

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)

> 100

Eisenia foetida

Low

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)

300

Oncorhynchus mykiss

Low

Fish - Chronic 21 day NOEC (mg l⁻¹)

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

101.6

Daphnia magna

Low

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)

> 4160

Rat as the sulphate

Low

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

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

Intravenous LD₅₀ = 280 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

Apramycin is rapidly absorbed when administered orally and is excreted via the kidneys without metabolisation

Health issues

Specific human health issues

Carcinogen

Genotoxic

Endocrine disruptor

; ; ; ;

Reproduction / development effects

Acetyl cholinesterase inhibitor

Neurotoxicant

Respiratory tract irritant

Skin irritant

Skin sensitiser

No data found

Eye irritant

Phototoxicant

No data found

General human health issues

Possible kidney toxicant

Handling issues

Property

Value and interpretation

General

When heated to decomposition it emits acrid smoke and irritating fumes
Corrosive

CLP classification 2013

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

apramycin

French

apramycine

German

Danish

Italian

Spanish

apramicina

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