Cefquinome sulphate |
![]() Last updated: 16/09/2025 |
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(Also known as: cefquinome sulfate) |
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Used for the treatment of bacterial infections in animals caused by some gram-positive and gram-negative micro-organisms | |
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Used, generally as the sulphate, for the treatment of mastitis, respiratory disease, septicaemia, digital dermatitis. Also used for respiratory tract infections caused by Pasteurella multocida and Mannheimia haemolytica. | |
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Cattle; Pigs |
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Approved - usually supplied as a prescription only medicine to be authorised by a veterinarian (POM-V) | |
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Approved |
Chemical structure |
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Cefquinome sulphate exhibits chirality, due to the presence of two chiral centres in its cephalosporin core. These stereocentres are at the C6 and C7 positions of the beta-lactam ring, which are configured as (6R,7R) in the active pharmaceutical form. In addition, cefquinome contains a (2Z)-methoxyimino group in its acyl side chain, introducing geometric (cis-trans) isomerism. The Z (cis) configuration enhances resistance to beta-lactamase enzymes, making cefquinome more stable and effective against resistant bacteria. Only the (6R,7R)-(2Z) isomer is used in veterinary medicine, as other stereoisomers would have reduced efficacy or altered pharmacokinetics. | |
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C₂₃H₂₆N₆O₉S₃ | |
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CON=C(C1=CSC(=N1)N)C(=O)NC2C3N(C2=O)C(=C(CS3)C[N+]4=CC=CC5=C4CCCC5)C(=O)[O-].OS(=O)(=O)O | |
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CO/N=C(/C1=CSC(=N1)N)\C(=O)N[C@H]2[C@@H]3N(C2=O)C(=C(CS3)C[N+]4=CC=CC5=C4CCCC5)C(=O)[O-].OS(=O)(=O)O | |
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KYOHRXSGUROPGY-OFNLCGNNSA-N | |
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InChI=1S/C23H24N6O5S2.H2O4S/c1-34-27-16(14-11-36-23(24)25-14)19(30)26-17-20(31)29-18(22(32)33)13(10-35-21(17)29)9-28-8-4-6-12-5-2-3-7-15(12)28;1-5(2,3)4/h4,6,8,11,17,21H,2-3,5,7,9-10H2,1H3,(H3-,24,25,26,30,32,33);(H2,1,2,3,4)/b27-16-;/t17-,21-;/m1./s1 | |
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Yes |
General status |
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Antibacterial, Antibiotic, Medicinal drug | |
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Cephalosporin | |
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Synthetic | |
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Short lived, broad-spectrum drug that acts by inhibition of the cell wall synthesis | |
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[Beta-lactamase, Agonist] | |
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118443-89-3 | |
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690-053-1 | |
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9577261 | |
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Antiinfectants for Systemic use: Antibacterials for systemic use; Antibacterials for intramammary use | |
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QJ01DE90; QJ51DA92 | |
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No | |
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Allowed substance (Table 1: Bovine, Porcine, Equidae) | |
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626.7 | |
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(6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-3-(5,6,7,8-tetrahydroquinolin-1-ium-1-ylmethyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;sulfuric acid | |
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Pale yellow crystals | |
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Commercial |
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Current | |||
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1990s, developed; 2000s, wide spread vet use | |||
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Available in a variety of formulations including solutions & suspensions for injection and ointments for topical application | |||
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Cefquinome sulphate is synthesised through a multi-step chemical process starting from 7-aminocephalosporanic acid (7-ACA), the core structure of cephalosporins. In the first step, 7-ACA is reacted with a tetrahydroquinoline derivative under the influence of trimethyliodosilane, forming an intermediate known as 7-ACQ. This intermediate is then oxidised using hydrogen peroxide, introducing the methoxyimino group that enhances beta-lactamase resistance. Next, 7-ACQ undergoes acylation with an AE-active ester, which installs the quaternary ammonium side chain essential for cefquinome’s broad-spectrum activity and membrane penetration. The resulting cefquinome base is then converted into its sulphate salt form to improve water solubility and stability. Final steps include purification, crystallization, and drying. | |||
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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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3.24 X 10-02 | Calculated | - | |||||||
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-1.49 | Q3 Q = Miscellaneous data from online sources 3 = Unverified data of known source |
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Environmental exposure is mainly due to livestock excretion |
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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 |
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Terrestrial ecotoxicology |
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Aquatic ecotoxicology |
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General |
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Excreted predominately in the faeces, when intermammarily administered substance is excreted in breast milk | A5 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 ) 5 = Verified data used for regulatory purposes |
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Health issues |
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No further information available |
Handling issues |
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Will emit toxic gases when heated to decomposition IMDG Trnsport Hazard Class 9 |
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Health: H315, H319, H335 Environment: H400, H410 |
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Not listed (Not listed) | |||
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UN3077 | |||
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Packaging group III (minor danger) | |||
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cefquinome sulphate | ||
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cefquinoma | ||
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Record last updated: | 16/09/2025 |
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 |