MedKoo Cat#: 413197 | Name: Cloxacillin sulfone

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Cloxacillin sulfone 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 sulfone
Cloxacillin sulfone
CAS#76788-83-5 (sulfone)

Theoretical Analysis

MedKoo Cat#: 413197

Name: Cloxacillin sulfone

CAS#: 76788-83-5 (sulfone)

Chemical Formula: C19H18ClN3O7S

Exact Mass: 467.0554

Molecular Weight: 467.88

Elemental Analysis: C, 48.78; H, 3.88; Cl, 7.58; N, 8.98; O, 23.94; S, 6.85

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Synonym
Cloxacillin sulfone;
IUPAC/Chemical Name
4-Thia-1-azabicyclo(3.2.0)heptane-2-carboxylic acid, 6-(((3-(2-chlorophenyl)-5-methyl-4-isoxazolyl)carbonyl)amino)-3,3-dimethyl-7-oxo-, 4,4-dioxide, (2S-(2alpha,5alpha,6beta))-
InChi Key
NVNVYZJTNPZRPA-JKIFEVAISA-N
InChi Code
InChI=1S/C19H18ClN3O7S/c1-8-11(12(22-30-8)9-6-4-5-7-10(9)20)15(24)21-13-16(25)23-14(18(26)27)19(2,3)31(28,29)17(13)23/h4-7,13-14,17H,1-3H3,(H,21,24)(H,26,27)/t13-,14+,17-/m1/s1
SMILES Code
O=C([C@@H](C(C)(C)S([C@]1([H])[C@@H]2NC(C3=C(C)ON=C3C4=CC=CC=C4Cl)=O)(=O)=O)N1C2=O)O
Appearance
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
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 467.88 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
1: Yamaguchi A, Adachi A, Hirata T, Adachi H, Sawai T. Conversion of cloxacillin into a progressive inhibitor of beta-lactamases by sulfonation and its activity against various types of these enzymes. J Antibiot (Tokyo). 1985 Jan;38(1):83-93. doi: 10.7164/antibiotics.38.83. PMID: 3871761. 2: Yamaguchi A, Inaba T, Sawai T. Isolation of a cephalosporinase inhibitor derived from cloxacillin sulfone in the presence of phosphate anions. J Antibiot (Tokyo). 1988 May;41(5):690-3. doi: 10.7164/antibiotics.41.690. PMID: 3260231. 3: Sawai T, Yamaguchi A. Mechanism of beta-lactamase inhibition: differences between sulbactam and other inhibitors. Diagn Microbiol Infect Dis. 1989 Jul- Aug;12(4 Suppl):121S-129S. doi: 10.1016/0732-8893(89)90124-7. PMID: 2591172. 4: Yamaguchi A, Nemoto M, Adachi A, Inaba T, Sawai T. Delayed inactivation of Citrobacter freundii cephalosporinase by 6 beta-[3-(2-chlorophenyl)-5-methyl-4-isoxazolyl]penicillin sulfone. J Antibiot (Tokyo). 1986 Dec;39(12):1744-53. doi: 10.7164/antibiotics.39.1744. PMID: 3493233. 5: Sawai T, Yamaguchi A, Tsukamoto K. Amino acid sequence, active-site residue, and effect of suicide inhibitors on cephalosporinase of Citrobacter freundii GN346. Rev Infect Dis. 1988 Jul-Aug;10(4):721-5. doi: 10.1093/clinids/10.4.721. PMID: 3263684.