Cloxacillin |
![]() Last updated: 07/09/2025 |
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(Not known by any other names) |
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An antibiotic drug that is a chlorinated detivative of oxacillin | |
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Mainly used to treat many different types of infections caused by staphylococcus bacteria | |
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Cattle; Dogs; Cats; Horses; Sheep |
Approval status |
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Approved - usually available as a prescription only medicine to be authorised by a veterinarian (POM-V) | |
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Approved |
Chemical structure |
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Cloxacillin exhibits stereoisomerism, specifically diastereomerism, due to its multiple chiral centres. As a semisynthetic beta-lactam antibiotic derived from oxacillin, cloxacillin contains a penam ring system with three key stereocentres at positions 2, 5, and 6 of the bicyclic structure. The biologically active form is the (2S,5R,6R) isomer, which is crucial for its ability to bind to bacterial penicillin-binding proteins (PBPs) and inhibit cell wall synthesis. Additionally, cloxacillin includes a chlorinated isoxazole side chain which can also give rise to positional isomers depending on the placement of the chlorine atom on the aromatic ring. However, in pharmaceutical formulations, the compound is standardised to a specific isomer to ensure consistent antibacterial activity and pharmacokinetics. | |
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C₁₉H₁₈ClN₃O₅S | |
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CC1=C(C(=NO1)C2=CC=CC=C2Cl)C(=O)NC3C4N(C3=O)C(C(S4)(C)C)C(=O)O | |
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CC1=C(C(=NO1)C2=CC=CC=C2Cl)C(=O)N[C@H]3[C@@H]4N(C3=O)[C@H](C(S4)(C)C)C(=O)O | |
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LQOLIRLGBULYKD-JKIFEVAISA-N | |
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InChI=1S/C19H18ClN3O5S/c1-8-11(12(22-28-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)29-17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1 | |
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Yes |
General status |
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Antibiotic, Antibacterial, Medicinal drug | |
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Isoxazolyl-penicillin | |
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Semi-synthetic | |
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Interferes with the last stage of bacterial cell wall synthesis | |
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[Penicillin-binding proteins 1A/1B, Antagonist], [Beta-lactamase, Agonist], [Penicillin-binding protein 2a, Antagonist], [Penicillin-binding protein 2B, Antagonist], [Penicillin-binding protein 3, Antagonist], [Penicillin-binding protein 5, Antagonist] | |
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61-72-3 | |
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200-514-7 | |
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6098 | |
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Antiinfectants for systemic use: Antibacterials for intramammary use; Sensory organs: Ophthalmologicals | |
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QJ51CF02; QS01AA90 | |
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No | |
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Allowed substance (Table 1: All food producing species) | |
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435.88 | |
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(2S,5R,6R)-6-[[3-(2-chlorophenyl)-5-methyl-1,2-oxazole-4-carbonyl]amino]-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid | |
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6-(3-(o-Chlorophenyl)-5-methyl-4-isoxazolecarboxamido)penicillanic acid | |
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White crystalline powder |
Commercial |
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Current | |||
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Early 1960s, first synthesised; 1966, first US approvals; Circa 1969, first UK approvals | |||
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Available in a variety of formulations including intramammary suspensions and infusions | |||
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Cloxacillin is produced through a semi-synthetic process starting with 6-aminopenicillanic acid (6-APA). First, 6-APA is reacted with sodium hydroxide to form its sodium salt. This intermediate then undergoes acylation with a chlorinated isoxazole derivative, specifically, o-chlorobenzoyl chloride, to introduce the bulky side chain that confers beta-lactamase resistance. The reaction mixture is then acidified with dilute sulphuric acid, followed by the addition of a salt-forming agent like sodium isooctanoate to yield cloxacillin sodium. | |||
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Published GHG data is not available for most pharmaceuticals. However, according to industry, global averages suggest producing 1 kg of a typical active pharmaceutical ingredient can range from 10 to 100 kg CO₂e for small molecule drugs and potentially up to 1000 kg CO₂e for complex biologicals such as vaccines, depending on the drug type, its formulation, complexity of synthesis, solvent recovery, and energy sources used. |
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13.9 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
Moderate | ||||||||
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173 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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3.02 X 1002 | Calculated | - | |||||||
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2.48 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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2.78 | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) 3 = Unverified data of known source |
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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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Fate indices |
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Known metabolites |
None
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Terrestrial ecotoxicology |
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> 5000 | 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 ) Rat as sodium salt4 = Verified data |
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Aquatic ecotoxicology |
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23.4 | R3 R = Peer reviewed scientific publications Raphidocelis subcapitata3 = Unverified data of known source |
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General |
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High (class III) | - | - | ||||||||
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> 5000 | 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 ) Rat as sodium salt4 = Verified data |
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Intravenous LDLo = 1680 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Human3 = Unverified data of known source |
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Intracerebral LD₅₀ = 8.1 mg kg⁻¹ | V3 V = ChemID Online Databases; Chemspider; PubChem. (ChemID ) Mouse3 = Unverified data of known source |
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Around 50% of administered dose is rapidly (<6hrs) excreted in urine with additional losses via bile and faeces | 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 cause diarrhoea and abdominal cramps May cause allergic reaction May cause skin rashes and contact dermatitis |
Handling issues |
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No information available | |||
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Not listed (Not listed) | |||
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cloxacillin | ||
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cloxacilline | ||
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cloxacilina | ||
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Record last updated: | 07/09/2025 |
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 |