amoxicillin ** amoxycillin ** amopen ** amoxycillin trihydrate ** p-hydroxyampicillin ** AMC ** Translations

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GENERAL INFORMATION

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

Introduction: -

Examples of species treated: Birds, Domestic fowl, Cats, Dogs, Pigs

General status:

Veterinary substance type	Antibacterial, Antibiotic, Medicinal drug
Substance group	Penicillin
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	-
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?	No
Regulation 37/2010 MRL Classification	Allowed substance (Table 1: All food producing species)
Chemical formula	C16H19N3O5S
SMILES	N12[C@@H]([C@@H](NC([C@@H](c3ccc(O)cc3)N)=O)C2=O)SC([C@@H]1C(O)=O)(C)C
International Chemical Identifier (InChI)	InChI=1/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
Structure diagram/image available?	Yes
Molecular mass (g mol-1)	365.40
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	-
Physical state	White crystalline solid
Related substances & organisms	-

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/Other Information	Interpretation
Solubility - In water at 20oC (mg l-1)		3430	V3	High
Solubility - In organic solvents at 20oC (mg l-1)		7500	L3 - Methanol	-
		3400	L3 - Ethanol	-
Melting Point (oC)		194	F4	-
Boiling Point (oC)		-	-	-
Degradation point (oC)		-	-	-
Flashpoint (oC)		-	-	-
Octanol-water partition coefficient at pH 7, 20oC	P	7.41 X 1000	Calculated	-
	Log P	0.87	V3	Low
Bulk density (g ml-1)/Specific gravity		-	-	-
Dissociation constant (pKa) at 25oC		-	-	-
		Note:
Vapour pressure at 25oC (mPa)		6.24 X 10-12	V3	Non-volatile
Henry's law constant at 25oC (Pa m3 mol-1)		-	-	-
Henry's law constant at 20oC (dimensionless)		2.73 X 10-19	Calculated	Non-volatile
GUS leaching potential index		-0.68	Calculated	Low leachability
Maximum UV-vis absorption L mol-1 cm-1		In ethanol: 230nm = 10850, 274nm = 1400; [In acid: 229nm = 9500, 272nm = 1080	L3	-
Surface tension (mN m-1)		-	-	-
Refractive Index		-	-	-

Degradation:

Property		Value	Source/Quality Score/Other Information	Interpretation
Soil degradation (days) (aerobic)	DT50 (typical)	0.23	R4	Non-persistent
	DT50 (lab at 20oC)	-	-	-
	DT50 (field)	-	-	-
	DT90 (lab at 20oC)	-	-	-
	DT90 (field)	-	-	-
	Note	General literature gives DT50 0.16-0.29 days, very rapid
Manure DT50 (days)		4	R4 Manure	-
Aqueous photolysis DT50 (days) at pH 7	Value	-	-	-
	Note	-
Aqueous hydrolysis DT50 (days) at 20oC and pH 7	Value	-	-	-
	Note	-
Water-Sediment DT50 (days)		-	-	-
Water phase only DT50 (days)		-	-	-

Soil adsorption and mobility:

Property		Value	Source/Quality Score/Other Information	Interpretation
Linear	Kd	-	R4	Slightly mobile
	Koc	866
	Notes and range	-
Freundlich	Kf	-	-	-
	Kfoc	-
	1/n	-
	Notes and range	-
pH sensitivity		-

ECOTOXICOLOGY

Property		Value	Source/Quality Score/Other Information	Interpretation
Bio-concentration factor	BCF	-	-	-
	CT50 (days)	-		-
Bioaccumulation potential		-	Calculated	Low
Mammals - Acute oral LD50 (mg kg-1)		> 15000	V3 Rat	Low
Mammals - Short term dietary NOEL	(mg kg-1)	-	-	-
	(ppm diet)	-		-
Birds - Acute LD50 (mg kg-1)		-	-	-
Birds - Short term dietary (LC50/LD50)		-	-	-
Fish - Acute 96 hour LC50 (mg l-1)		> 300	R4 Oncorhynchus mykiss	Low
Fish - Chronic 21 day NOEC (mg l-1)		-	-	-
Aquatic invertebrates - Acute 48 hour EC50 (mg l-1)		101.6	R4 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	R3 LOEC	Low
Algae - Acute 72 hour EC50, growth (mg l-1)		0.037	R3 Microcystis aeruginosa	Moderate
Algae - Chronic 96 hour NOEC, growth (mg l-1)		250	R3 Selenastrum capricornutum	Low
Honeybees - Acute 48 hour LD50 (µg bee-1)		-	-	-
Earthworms - Acute 14 day LC50 (mg kg-1)		-	-	-
Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1)		-	-	-
Other soil macro-organisms - e.g. Collembola	LR50product ha EC50product ha NOECproduct ha % Effect	-	-	-
Other arthropod (1)	LR50 g ha-1	-	-	-
	% Effect	-	-	-
Other arthropod (2)	LR50 g ha-1	-	-	-
	% Effect	-	-	-
Soil micro-organisms		-	-	-
Mesocosm study data	NOEAEC mg l-1	-	-	-
	NOEAEC mg l-1	-	-	-

HUMAN HEALTH AND PROTECTION

General:

Property		Value	Source/Quality Score/Other Information	Interpretation
Mammals - Acute oral LD50 (mg kg-1)		> 15000	V3 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 rat	-
		Subcutaneous LD50 > 8000 mg kg-1	V3 Rat	-
ADI - Acceptable Daily Intake (mg kg-1bw day-1)		-	-	-
ARfD - Acute Reference Dose (mg kg-1bw day-1)		-	-	-
AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1)		-	-	-
Dermal penetration studies (%)		-	-	-
Dangerous Substances Directive 76/464		-	-	-
Exposure Limits		-	-	-
Exposure Routes	Public	-
	Occupational	-
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	-

Health issues:

Carcinogen	Mutagen	Endocrine disrupter	Reproduction / development effects	Acetyl cholinesterase inhibitor	Neurotoxicant	Respiratory tract irritant	Skin irritant	Eye irritant
	-	-		-	-
General human health issues		[May cause vomiting, rashes and antibiotic-associated colitis], [May cause allergic or asthmatic symptoms or breathing difficulties if inhaled]

: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data

Handling issues:

Property		Value	Source/Quality Score/Other Information	Interpretation
General		[Not regulated under IMDG]
EC Risk Classification		-
EC Safety Classification		-
WHO Classification		None - not a ppp	-	-
US EPA Classification (formulation)		-	-	-
UN Number		-
Waste disposal & packaging		-

TRANSLATIONS