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Cloxacillin

Cloxacillin

  • CAT Number: I006171
  • CAS Number: 61-72-3
  • Molecular Formula: C19H18ClN3O5S
  • Molecular Weight: 435.879
  • Purity: ≥95%
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Cloxacillin is an antibiotic useful for the treatment of a number of bacterial infections. It is semisynthetic and in the same class as penicillin. Cloxacillin is used against staphylococci that produce beta-lactamase, due to its large R chain, which does not allow the beta-lactamases to bind. This drug has a weaker antibacterial activity than benzylpenicillin, and is devoid of serious toxicity except for allergic reactions. Cloxacillin was discovered and developed by Beecham. It is sold under a number of trade names, including Cloxapen, Cloxacap, Tegopen and Orbenin. It is on the World Health Organization/’s List of Essential Medicines, the most important medication needed in a basic health system.

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%
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)NC3C4N(C3=O)C(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

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