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Amoxicillin
Last updated: 02/05/2024
(Also known as: amoxycillin; amopen; amoxycillin trihydrate; p-hydroxyampicillin; AMC)
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 substance
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)
- - -
Sediment 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.
Decay in stored produce DT₅₀
-
Soil adsorption and mobility
Property
Value
Source; quality score; and other information
Interpretation
Linear
Kd (mL g⁻¹)
-
R4 R = Peer reviewed scientific publications
4 = Verified data
 Slightly mobile
Koc (mL g⁻¹)
866
Notes and range
Other data: EPI Suite 108.4 L/kg
Freundlich
Kf (mL g⁻¹)
- - -
Kfoc (mL g⁻¹)
-
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
- - -
Notes
-
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
- - -
Marine bivalves
- - -
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
-
Record last updated: 02/05/2024
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