WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 317560
CAS#: 7081-44-9 (sodium)
Description: 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.
MedKoo Cat#: 317560
Name: Cloxacillin sodium
CAS#: 7081-44-9 (sodium)
Chemical Formula: C19H17ClN3NaO5S
Molecular Weight: 457.86
Elemental Analysis: C, 49.84; H, 3.74; Cl, 7.74; N, 9.18; Na, 5.02; O, 17.47; S, 7.00
Synonym: Cloxacilina; Cloxacilline; Cloxacillinum; Syntarpen; Tegopen, Cloxacillin sodium.
IUPAC/Chemical Name: sodium (2S,5R,6R)-6-(3-(2-chlorophenyl)-5-methylisoxazole-4-carboxamido)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate
InChi Key: InChI=1S/C19H18ClN3O5S.Na/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);/q;+1/p-1/t13-,14+,17-;/m1./s1
InChi Code: InChI=1S/C19H18ClN3O5S.Na/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);/q;+1/p-1/t13-,14+,17-;/m1./s1
SMILES Code: CC1=C(C(N[C@H]2[C@@H]3N([C@@H](C(O[Na])=O)C(C)(C)S3)C2=O)=O)C(C4=CC=CC=C4Cl)=NO1
Appearance: White to light yellow solid powder.
Purity: >98% (or refer to the Certificate of Analysis)
Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility: Soluble in DMSO, not in water
Shelf Life: >2 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 457.86 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
1: Du K, Luo Z, Guo P, Tang W, Wu N, Zheng P, Du W, Zeng A, Jing W, Chang C, Fu Q. Preparation and evaluation of a molecularly imprinted sol-gel material as the solid-phase extraction adsorbents for the specific recognition of cloxacilloic acid in cloxacillin. J Sep Sci. 2015 Nov 23. doi: 10.1002/jssc.201500961. [Epub ahead of print] PubMed PMID: 26592970.
2: Sullivan T, Forest JM, Leclair G. Compatibility of Cloxacillin Sodium with Selected Intravenous Drugs During Simulated Y-Site Administration. Hosp Pharm. 2015 Mar;50(3):214-20. doi: 10.1310/hpj5003-214. PubMed PMID: 26405311; PubMed Central PMCID: PMC4567191.
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5: Hasselmann J, Kühme T, Acosta S. Antibiotic Prophylaxis With Trimethoprim/Sulfamethoxazole Instead of Cloxacillin Fails to Improve Inguinal Surgical Site Infection Rate After Vascular Surgery. Vasc Endovascular Surg. 2015 Jul-Aug;49(5-6):129-34. doi: 10.1177/1538574415600531. Epub 2015 Aug 30. PubMed PMID: 26323968.
6: Datta S, Chatterjee S, Mitra S, Basu S. A reliable phenotypic assay for detection of ESBLs and AmpCs in MBL-producing gram-negative bacteria with the use of aminophenylboronic acid, dipicolinic acid and cloxacillin. J Microbiol Methods. 2015 Aug;115:100-3. doi: 10.1016/j.mimet.2015.05.028. Epub 2015 Jun 3. PubMed PMID: 26048656.
7: Takayama Y, Adachi Y, Nihonyanagi S, Okamoto R. Modified Hodge test using Mueller-Hinton agar supplemented with cloxacillin improves screening for carbapenemase-producing clinical isolates of Enterobacteriaceae. J Med Microbiol. 2015 Jul;64(7):774-7. doi: 10.1099/jmm.0.000068. Epub 2015 May 1. PubMed PMID: 25934552.
8: Bai AD, Showler A, Burry L, Steinberg M, Ricciuto DR, Fernandes T, Chiu A, Raybardhan S, Science M, Fernando E, Tomlinson G, Bell CM, Morris AM. Comparative effectiveness of cefazolin versus cloxacillin as definitive antibiotic therapy for MSSA bacteraemia: results from a large multicentre cohort study. J Antimicrob Chemother. 2015 May;70(5):1539-46. doi: 10.1093/jac/dku560. Epub 2015 Jan 21. PubMed PMID: 25614044.
9: El Nekidy W, Dziamarski N, Soong D, Donaldson C, Ibrahim M, Kadri A. Cloxacillin-induced seizure in a hemodialysis patient. Hemodial Int. 2015 Oct;19(4):E33-6. doi: 10.1111/hdi.12262. Epub 2015 Jan 12. PubMed PMID: 25582344.
10: Eze FI, Ajali U, Ukoha PO. Synthesis, Physicochemical Properties, and Antimicrobial Studies of Iron (III) Complexes of Ciprofloxacin, Cloxacillin, and Amoxicillin. Int J Med Chem. 2014;2014:735602. doi: 10.1155/2014/735602. Epub 2014 Nov 19. PubMed PMID: 25505991; PubMed Central PMCID: PMC4258349.