For research use only. Not for therapeutic Use.
Cloxacillin（Cat No.:I006171）is a semisynthetic β-lactam antibiotic belonging to the penicillin class, specifically designed to resist β-lactamase enzymes produced by certain bacteria. It is effective against Gram-positive organisms, particularly Staphylococcus aureus, including penicillinase-producing strains. Cloxacillin works by inhibiting bacterial cell wall synthesis through binding to penicillin-binding proteins (PBPs), leading to bacterial lysis. It is commonly used to treat infections such as skin and soft tissue infections, osteomyelitis, and septicemia. Its oral and injectable formulations make it versatile for various clinical applications in combating resistant staphylococcal infections.
| Catalog Number | I006171 |
| CAS Number | 61-72-3 |
| Synonyms | Cloxacilina; Cloxacilline; Cloxacillinum; Syntarpen; Tegopen;(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 |
| Molecular Formula | C19H18ClN3O5S |
| Purity | ≥95% |
| Target | Beta-lactamase |
| Solubility | Soluble in DMSO, not in water |
| Storage | -20°C |
| IUPAC Name | (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 |
| InChI | 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 |
| InChIKey | LQOLIRLGBULYKD-JKIFEVAISA-N |
| SMILES | 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 |
| Reference | </br>1:Higher risk of revision for infection using systemic clindamycin prophylaxis than with cloxacillin. Robertsson O, Thompson O, W-Dahl A, Sundberg M, Lidgren L, Stefánsdóttir A.Acta Orthop. 2017 May 11:1-6. doi: 10.1080/17453674.2017.1324677. [Epub ahead of print] PMID: 28492106 </br>2:Systematic overdosing of oxa- and cloxacillin in severe infections treated in ICU: risk factors and side effects. Neuville M, El-Helali N, Magalhaes E, Radjou A, Smonig R, Soubirou JF, Voiriot G, Le Monnier A, Ruckly S, Bouadma L, Sonneville R, Timsit JF, Mourvillier B.Ann Intensive Care. 2017 Dec;7(1):34. doi: 10.1186/s13613-017-0255-8. Epub 2017 Mar 22. PMID: 28332157 Free PMC Article</br>3:Determination of cloxacillin residues in dairy cows after intramammary administration. Burmańczuk A, Grabowski T, Osypiuk M, Polska B, Kowalski C.J Vet Pharmacol Ther. 2017 Jan 30. doi: 10.1111/jvp.12391. [Epub ahead of print] PMID: 28133845 </br>4:Non availability of Cloxacillin, A Deterrent for Rational Antimicrobial Practice. Srinivasaraghavan R, Dhandapany G.Indian Pediatr. 2016 Nov 15;53(11):1032-1033. No abstract available. PMID: 27889744 Free Article</br>5:Subcritical water oxidation of 6-aminopenicillanic acid and cloxacillin using H<sub>2</sub>O<sub>2</sub>, K<sub>2</sub>S<sub>2</sub>O<sub>8</sub>, and O<sub>2</sub>. Yabalak E, Döndaş HA, Gizir AM.J Environ Sci Health A Tox Hazard Subst Environ Eng. 2017 Feb 23;52(3):210-220. doi: 10.1080/10934529.2016.1246935. Epub 2016 Nov 11. PMID: 27835054 </br>6:Phenol-Rich Compounds Sweet Gel: A Statistically More Effective Antibiotic than Cloxacillin Against Pseudomonas Aeruginosa. Dashtdar M, Dashtdar MR, Dashtdar B, Khan GA, Kardi K.J Pharmacopuncture. 2016 Sep;19(3):246-252. PMID: 27695634 Free PMC Article</br>7:Cloxacillin: A New Cause of Pill-Induced Esophagitis. Zezos P, Harel Z, Saibil F.Can J Gastroenterol Hepatol. 2016;2016:2904256. doi: 10.1155/2016/2904256. Epub 2016 Apr 14. PMID: 27446834 Free PMC Article</br>8:Simultaneous Determination of Eight β-Lactam Antibiotics, Amoxicillin, Cefazolin, Cefepime, Cefotaxime, Ceftazidime, Cloxacillin, Oxacillin, and Piperacillin, in Human Plasma by Using Ultra-High-Performance Liquid Chromatography with Ultraviolet Detection. Legrand T, Vodovar D, Tournier N, Khoudour N, Hulin A.Antimicrob Agents Chemother. 2016 Jul 22;60(8):4734-42. doi: 10.1128/AAC.00176-16. Print 2016 Aug. PMID: 27216076 Free PMC Article</br>9:Significant Pharmacokinetic Interactions Between Quinine and Ampicillin-Cloxacillin Combination. Falade OB, Falusi AG, Olaniyi AA, Ezeasor C, Kwasi DA, Babalola CP.Drugs R D. 2016 Jun;16(2):193-203. doi: 10.1007/s40268-016-0128-x. PMID: 27020278 Free PMC Article</br>10:Enhanced chemiluminescence of carminic acid-permanganate by CdS quantum dots and its application for sensitive quenchometric flow injection assays of cloxacillin. Khataee A, Hasanzadeh A, Lotfi R, Joo SW.Talanta. 2016 May 15;152:171-8. doi: 10.1016/j.talanta.2016.01.055. Epub 2016 Jan 27. PMID: 26992508 |
