Amoxicillin

Amoxicillin	Last updated: 30/08/2023
(Also known as: amoxycillin; amopen; amoxycillin trihydrate; p-hydroxyampicillin; AMC)

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 Moderate alert: Drainflow: Slightly mobile Warning: Significant data are missing	Ecotoxicity Low alert: Fish acute ecotoxicity: Low; Daphnia acute ecotoxicity: Low Warning: Significant data are missing	Human health High alert: Reproduction/development effects Warning: Significant data are missing

GENERAL INFORMATION

Description

A broad spectrum semisynthetic a beta-lactam antibiotic / antimicrobial with applications in veterinary medicine

Availability status

Current

Introduction & key dates

Examples of species treated

Birds, Domestic fowl, Cats, Dogs, Pigs

Chemical structure

Isomerism

Isomeric

Chemical formula

C₁₆H₁₉N₃O₅S

Canonical SMILES

CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=C(C=C3)O)N)C(=O)O)C

Isomeric SMILES

CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=C(C=C3)O)N)C(=O)O)C

International Chemical Identifier key (InChIKey)

LSQZJLSUYDQPKJ-NJBDSQKTSA-N

International Chemical Identifier (InChI)

InChI=1S/C16H19N3O5S/c1-16(2)11(15(23)24)19-13(22)10(14(19)25-16)18-12(21)9(17)7-3-5-8(20)6-4-7/h3-6,9-11,14,20H,17H2,1-2H3,(H,18,21)(H,23,24)/t9-,10-,11+,14-/m1/s1

2D structure diagram/image available?

Yes

Cambridge Crystallographic Data Centre diagrams

Common Name	Relationship	Link
Sodium salt	Variant

General status

Veterinary substance type

Antibacterial, Antibiotic, Medicinal drug

Substance groups

Penicillin related

Minimum active substance purity

Known relevant impurities

Substance origin

Semi-synthetic

Mode of action

Inhibits the synthesis of bacterial cell walls

Molecular targets

[Penicillin-binding proteins 1A/1B, antagonist]

CAS RN

26787-78-0

EC number

248-003-8

CIPAC number

US EPA chemical code

PubChem CID

33613

ATCvet Code

QJ01CR02; QG51AX01

Therapeutic Class

Antiinfectants for systemic use: Antibacterials for systemic use; Genito urinary system & sex hormones: Antiinfectants & antiseptics for intrautarine use

Controlled Drug?

Regulation 37/2010 MRL Classification

Allowed substance (Table 1: All food producing species)

Molecular mass

365.40

PIN (Preferred Identification Name)

IUPAC name

(2S,5R,6R)- 6-([(2R)-2-amino-2-(4-hydroxyphenyl)-acetyl]amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid

CAS name

D-(-)-6-(2-amino-2-phenylacetamido)-3,3-dimethyl-7 -oxo-4-thia-1-azabicyclo [3.2.0] heptane-2-carboxylic acid

Other status information

Relevant Environmental Water Quality Standards

Physical state

White crystalline solid

Formulations

Property

Product

Manufacturer

Authorisation Route

UK Legal Class

Example products using this active

Amoxicure 30% powder for oral solution

Oropharma N.V.

UK National authorisation

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

Amoxival Vet Tablets

Sogeval S.A.

EU Mutually recognised procedure

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

Synulox Palatable Tablets 50mg

Pfizer ltd

UK National authorisation

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

Betamox 200mg Palatable Tablets

Norbook Labs

UK National authorisation

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

Formulation and application details

Ingested, available as capsules, tablets, chewable tablets and powders/tablets for aqueous suspension

ENVIRONMENTAL FATE

Property

Value

Source; quality score; and other information

Interpretation

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

3430

High

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

7500

Methanol

3400

Ethanol

Melting point (°C)

194

Boiling point (°C)

Degradation point (°C)

Flashpoint (°C)

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

7.41 X 10⁰⁰

Calculated

Log P

0.87

Low

Fat solubility of residues

Solubility

Data type

Density (g ml⁻¹)

Dissociation constant pKa) at 25 °C

Vapour pressure at 20 °C (mPa)

6.24 X 10^-12

Low volatility

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

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

In ethanol: 230nm = 10850, 274nm = 1400
In acid: 229nm = 9500, 272nm = 1080

Surface tension (mN m⁻¹)

Refractive Index

Degradation

Property

Value

Source; quality score; and other information

Interpretation

Soil degradation (days) (aerobic)

DT₅₀ (typical)

0.23

Non-persistent

DT₅₀ (lab at 20 °C)

DT₅₀ (field)

DT₉₀ (lab at 20 °C)

DT₉₀ (field)

Note

General literature gives DT₅₀ 0.16-0.29 days, very rapid

Manure DT₅₀ (days)

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

Slightly mobile

K_oc

866

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

-0.68

Calculated

Low leachability

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)

> 15000

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)

> 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)

> 1000

Lemna gibba LOEC

Low

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

0.037

Microcystis aeruginosa

Moderate

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

250

Selenastrum capricornutum

Low

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)

> 15000

Rat

Low

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

Mammals - Inhalation LC₅₀ (mg l⁻¹)

Other Mammal toxicity endpoints

Intraperitoneal LD₅₀ = 2870 mg kg⁻¹

rat

Subcutaneous LD₅₀ > 8000 mg kg⁻¹

Rat

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

Rapidly absorbed by the gastrointestinal tract after oral administration, whilst some is metabolised, it is rapidly mostly unchanged in the urine

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

May cause vomiting, rashes and antibiotic-associated colitis
May cause allergic or asthmatic symptoms or breathing difficulties if inhaled

Handling issues

Property

Value and interpretation

General

Not regulated under IMDG

CLP classification 2013

WHO Classification

Not listed (Not listed)

UN Number

Waste disposal & packaging

Shelf-life, storage, stability and reactivity

TRANSLATIONS

Language

Name

English

amoxicillin

French

amoxicilline

German

Danish

Italian

Spanish

amoxicilina

Greek

Polish

Swedish

Hungarian

Dutch

Norwegian

Record last updated:	30/08/2023
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