Amoxicillin	Last updated: 20/03/2024
(Also known as: amoxycillin; amopen; amoxycillin trihydrate; p-hydroxyampicillin; AMC)

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GENERAL INFORMATION

Description	A broad spectrum semisynthetic a beta-lactam antibiotic / antimicrobial with applications in veterinary medicine
Availability status	Current
Introduction & key dates	1958, discovered; 1972, first medical use
Examples of veterinary uses	Mainly used to treat skin, respiratory, and urinary tract infections.
Examples of species treated	Birds; Domestic fowl; Cats; Dogs; Pigs

Approval status

VMR 2013/2033 approval status (GB/UK)	Approved
EU Regulatory approval status	Approved

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
Therapeutic Class	Antiinfectants for systemic use: Antibacterials for systemic use; Genito urinary system & sex hormones: Antiinfectants & antiseptics for intrautarine use
ATCvet Code	QJ01CR02; QG51AX01
Controlled Drug?	No
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	Legal Class (GB/UK)
Example products (past and present) 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)
	Amoxypen Suspension for injection	MSD Animal Health UK Ltd	UK National authorisation	Prescription only medicine to be authorised by a veterinarian (POM-V)
	Cladaxxa Chewable tablets	Zoetis UK Ltd	UK National authorisation	Prescription only medicine to be authorised by a veterinarian (POM-V)
	Betamox suspension for injection	Norbook Labs Ld	UK National authorisation	Prescription only medicine to be authorised by a veterinarian (POM-V)
Formulation and application details	Usually formulated as tablets or soluble powders to add to drinking water or feed

ENVIRONMENTAL FATE

Property		Value	Source; quality score; and other information	Interpretation
Solubility - In water at 20 °C (mg l⁻¹)		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 ) 4 = Verified data	High
Solubility - In organic solvents at 20 °C (mg l⁻¹)		7500	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Methanol	-
		3400	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source Ethanol	-
Melting point (°C)		202.7	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	-
Boiling point (°C)		-	-	-
Degradation point (°C)		-	-	-
Flashpoint (°C)		-	-	-
Octanol-water partition coefficient at pH 7, 20 °C	P	7.41 X 1000	Calculated	-
	Log P	0.87	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	Low
Fat solubility of residues	Solubility	-	-	-
	Data type	-	-	-
Density (g ml⁻¹)		1.401	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	-
Dissociation constant pKa) at 25 °C		-	-	-
		-
Vapour pressure at 20 °C (mPa)		1.58 X 10-13	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	Low volatility
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		In ethanol: 230nm = 10850, 274nm = 1400 In acid: 229nm = 9500, 272nm = 1080	L3 L = Pesticide manuals and hard copy reference books / other sources 3 = Unverified data of known source	-
Surface tension (mN m⁻¹)		-	-	-
Refractive Index		-	-	-
Environmental release		Substance may enter the environment via the urine of treated animals or by spilt product

Degradation

Property		Value	Source; quality score; and other information	Interpretation
Soil degradation (days) (aerobic)	DT₅₀ (typical)	1.74	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
	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; ECHA data 1.74 days
Manure DT₅₀ (days)		4	R4 R = Peer reviewed scientific publications 4 = Verified data 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)		-	-	-
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	Kd	-	R4 R = Peer reviewed scientific publications 4 = Verified data	Slightly mobile
	Koc	866
	Notes and range	Other data: EPI Suite 108.4 L/kg
Freundlich	Kf	-	-	-
	Kfoc	-
	1/n	-
	Notes and range	-
pH sensitivity		-

Fate indices

Property		Value	Source; quality score; and other information	Interpretation
GUS leaching potential index		0.26	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	V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source 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
Temperate Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		> 300	R4 R = Peer reviewed scientific publications 4 = Verified data Oncorhynchus mykiss	Low
Temperate Freshwater Fish - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
Tropical Freshwater Fish - Acute 96 hour LC₅₀ (mg l⁻¹)		132.4	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 Danio rerio Embryo 2 day	Low
Temperate Freshwater Aquatic invertebrates - Acute 48 hour EC₅₀ (mg l⁻¹)		101.6	R4 R = Peer reviewed scientific publications 4 = Verified data Daphnia magna	Low
Temperate Freshwater Aquatic invertebrates - Chronic 21 day NOEC (mg l⁻¹)		-	-	-
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)		> 1000	R3 R = Peer reviewed scientific publications 3 = Unverified data of known source Lemna gibba LOEC	Low
Algae - Acute 72 hour EC₅₀, growth (mg l⁻¹)		0.037	R3 R = Peer reviewed scientific publications 3 = Unverified data of known source Microcystis aeruginosa	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l⁻¹)		250	R3 R = Peer reviewed scientific publications 3 = Unverified data of known source Selenastrum capricornutum	Low
Mesocosm study data	NOEAEC mg l⁻¹	-	-	-
	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	V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source 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	V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source rat	-
		Subcutaneous LD₅₀ > 8000 mg kg⁻¹	V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source 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	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	-

Health issues

Specific human health issues		Carcinogen Genotoxic Endocrine disruptor XNo, known not to cause a problem A0 A = Chromosome aberration (EFSA database) 0 = No data ; B0 B = DNA damage/repair (EFSA database) 0 = No data ; C0 C = Gene mutation (EFSA database) 0 = No data ; D0 D = Genome mutation (EFSA database) 0 = No data ; E0 E = Unspecified genotoxicity type (miscellaneous data source) 0 = No data No data found Reproduction / development effects Acetyl cholinesterase inhibitor Neurotoxicant ✓Yes, known to cause a problem No data found No data found Respiratory tract irritant Skin irritant Skin sensitiser ?Possibly, status not identified ✓Yes, known to cause a problem No data found Eye irritant Phototoxicant   XNo, known not to cause a problem 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	Health: H317, H334
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	-

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Record last updated:	20/03/2024
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