Cloxacillin sodium

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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.

Chemical Structure

Cloxacillin sodium
CAS# 7081-44-9 (sodium)

Theoretical Analysis

MedKoo Cat#: 317560
Name: Cloxacillin sodium
CAS#: 7081-44-9 (sodium)
Chemical Formula: C19H17ClN3NaO5S
Exact Mass:
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

Price and Availability

Size Price Availability Quantity
1.0g USD 165.0 2 Weeks
2.0g USD 285.0 2 Weeks
5.0g USD 550.0 2 Weeks
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Related CAS #: 23736-58-5 (benzathine)   61-72-3 (free base)   7081-44-9 (sodium)   76788-83-5 (sulfone)  

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

Preparing Stock Solutions

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.

Recalculate based on batch purity %
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

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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.

3: Morales-Cartagena A, Lalueza A, San Juan R, Aguado JM. [Cloxacillin-susceptible Staphylococcus aureus with high MIC to glycopeptides. Ever we use cloxacillin?]. Rev Esp Quimioter. 2015 Sep;28 Suppl 1:25-9. Review. Spanish. PubMed PMID: 26365730.

4: Zezos P, Harel Z. Cloxacillin - A new cause of pill-induced esophagitis. Can J Gastroenterol Hepatol. 2015 Sep 11. pii: 17102. [Epub ahead of print] PubMed PMID: 26359625.

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.