Ampicillin |
Last updated: 20/01/2024 |
(Also known as: alpha-aminobenzylpenicillin) |
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A common and extensively used antibiotic for a broad range of both gram-positive and gram-negative bacterial infections | |
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Current | |
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1961, introduced | |
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Used to treat upper respiratory infections like pneumonia, urinary tract infections, skin infections, soft tissue infections, gastroenteritis, tonsillitis, salmonella, canine parvovirosis, and leptospirosis | |
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Dogs; Cats; Rabbits; Cattle; Sheep; Pigs |
Approval status |
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Approved | |
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Approved |
Chemical structure |
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Isomeric | |
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C₁₆H₁₉N₃O₄S | |
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CC1(C(N2C(S1)C(C2=O)NC(=O)C(C3=CC=CC=C3)N)C(=O)O)C | |
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CC1([C@@H](N2[C@H](S1)[C@@H](C2=O)NC(=O)[C@@H](C3=CC=CC=C3)N)C(=O)O)C | |
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AVKUERGKIZMTKX-NJBDSQKTSA-N | |
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InChI=1S/C16H19N3O4S/c1-16(2)11(15(22)23)19-13(21)10(14(19)24-16)18-12(20)9(17)8-6-4-3-5-7-8/h3-7,9-11,14H,17H2,1-2H3,(H,18,20)(H,22,23)/t9-,10-,11+,14-/m1/s1 | |
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Yes |
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Common Name | Relationship | Link |
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ampicillin | - |
General status |
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Antibacterial, Antibiotic | |
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Aminopenicillin | |
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Semi-synthetic | |
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Broad-spectrum, inhibts bacterial cell-wall synthesis | |
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[Penicillin-binding protein 2a, Antagonist], [Penicillin-binding protein 1b, Antagonist], [Penicillin-binding protein 3, Antagonist], [Penicillin-binding protein 1A, Antagonist], [Penicillin-binding protein 2B, Antagonist] | |
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69-53-4 | |
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200-709-7 | |
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6249 | |
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Antiinfectants for systemic use: Antibacterials for intramammary | |
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QJ51CA01 | |
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No | |
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Allowed substance (Table 1: All food producing species) | |
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349.41 | |
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(2S,5R,6R)-6-([(2R)-2-amino-2-phenylacetyl]amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | |
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6-(D(-)-α-aminophenylacetamido)penicillanic acid | |
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- | |
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White to off-white powder |
Formulations |
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Amfipen LA, 100 mg/ml suspension for injection | MSD Animal Health UK Ltd | UK National authorisation (IC) | Prescription only medicine to be authorised by a veterinarian (POM-V) | ||||||
Bovaclox DC Xtra Intramammary Suspension | Norbrook Laboratories Ltd | UK National authorisation | Prescription only medicine to be authorised by a veterinarian (POM-V) | |||||||
Lactaclox Intramammary Infusion | Norbrook Laboratories Ltd | UK National authorisation | Prescription only medicine to be authorised by a veterinarian (POM-V) | |||||||
Kloxerate Gold Intrammary Infusion | Zoetis UK Ltd | UK National authorisation (IC) | Prescription only medicine to be authorised by a veterinarian (POM-V) | |||||||
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Supplied in a variety of formulations including intramammary suspensions & infustions, capsules and solutions for injection |
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10100 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
High | ||||||||
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50000 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Methanol3 = Unverified data of known source |
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4000 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Ethanol3 = Unverified data of known source |
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77000 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Dimethylacetamide3 = Unverified data of known source |
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208 | 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 |
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200 | A4 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 4 = Verified data |
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7.41 X 10-02 | Calculated | - | |||||||
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-1.13 | A4 A = EU regulatory and evaluation data as published by EC, EFSA (RAR, DAR & Conclusion dossiers), EMA (e.g. EU Annex III PIC DGD) (EU - Pesticides database; EFSA Scientific Publications ) 4 = Verified data |
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2.61 | R4 R = Peer reviewed scientific publications 4 = Verified data |
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1.61 X 10-14 | R4 R = Peer reviewed scientific publications 4 = Verified data |
Low volatility | ||||||||
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Degradation |
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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. | ||||||||||
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Soil adsorption and mobility |
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Fate indices |
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Known soil and groundwater metabolites |
None
Other known metabolites |
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5R,6R-penicilloic acid | - | Animal (Urine) | - | ||||
5S,6R-penicilloic acid | - | Animal (Urine) | - | ||||
piperazine-2,5-dione | - | Animal (Urine) | - |
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Terrestrial ecotoxicology |
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> 5000 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Aquatic ecotoxicology |
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> 1000 | R4 R = Peer reviewed scientific publications Selenastrum capricornutum4 = Verified data |
Low | ||||||||
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> 1000 | R4 R = Peer reviewed scientific publications Selanstrum capricornutum4 = Verified data |
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General |
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High (class III) | - | - | ||||||||
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> 5000 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
Low | ||||||||
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Subcutaneous LD₅₀ > 5000 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Intraperitoneal LD₅₀ = 4500 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Rat3 = Unverified data of known source |
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Excreted, largely unchanged, in the urine and to a lesser extent in faeces and bile | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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Health issues |
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May induce asthma, diarrhoea, nausea, vomiting, epigastric and abdominal pain May cause skin rashes and sensitisation |
Handling issues |
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No information available | |||
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Health: H317, H334 | |||
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Not listed (Not listed) | |||
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ampicillin | ||
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ampicilline | ||
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ampicilina | ||
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Record last updated: | 20/01/2024 |
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 |