Synonym
Cloxacillin; Syntarpen; BRL 1621; BRL1621; BRL-1621; Methocillin S; HSDB3042; HSDB-3042; HSDB 3042;
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-, (2S-(2alpha,5alpha,6beta))-
InChi Key
LQOLIRLGBULYKD-JKIFEVAISA-N
InChi Code
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
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)N1C2=O)O
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
435.88
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.
| 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: Lotric S, Lejko-Zupanc T, Jereb M. Cloxacillin-induced cholestasis. Clin Infect Dis. 1994 Nov;19(5):981-2. doi: 10.1093/clinids/19.5.981. PMID: 7893901.
2: Bru JP, Garraffo R. Role of intravenous cloxacillin for inpatient infections. Med Mal Infect. 2012 Jun;42(6):241-6. doi: 10.1016/j.medmal.2011.10.015. Epub 2012 Apr 27. PMID: 22542764.
3: Uwaydah MM, Faris BM, Samara IN, Shammas HF, To'Mey KF. Cloxacillin penetration. Am J Ophthalmol. 1976 Jul;82(1):114-6. doi: 10.1016/0002-9394(76)90675-9. PMID: 937445.
4: Morales-Cartagena A, Lalueza A, San Juan R, Aguado JM. Staphylococcus aureus sensible a cloxacilina con CMI elevada a glucopéptidos. ¿Ponemos siempre cloxacilina? [Cloxacillin-susceptible Staphylococcus aureus with high MIC to glycopeptides. Ever we use cloxacillin?]. Rev Esp Quimioter. 2015 Sep;28 Suppl 1:25-9. Spanish. PMID: 26365730.
5: Gatell JM, Rello J, Miro JM, Martinez JA, Soriano E, SanMiguel Garcia J. Cloxacillin-induced neutropenia. J Infect Dis. 1986 Aug;154(2):372. doi: 10.1093/infdis/154.2.372. PMID: 3722871.
6: Rodríguez-Jiménez B, Domínguez-Ortega J, Santos-Magadán S, González-García JM, Kindelan-Recarte C. Cloxacillin-induced skin eruption. Clin Exp Dermatol. 2009 Oct;34(7):e330-1. doi: 10.1111/j.1365-2230.2009.03281.x. Epub 2009 May 18. PMID: 19456773.
7: Srinivasaraghavan R, Dhandapany G. Non availability of Cloxacillin, A Deterrent for Rational Antimicrobial Practice. Indian Pediatr. 2016 Nov 15;53(11):1032-1033. PMID: 27889744.
8: Garrigós C, Murillo O, Lora-Tamayo J, Verdaguer R, Tubau F, Cabellos C, Cabo J, Ariza J. Efficacy of daptomycin-cloxacillin combination in experimental foreign-body infection due to methicillin-resistant Staphylococcus aureus. Antimicrob Agents Chemother. 2012 Jul;56(7):3806-11. doi: 10.1128/AAC.00127-12. Epub 2012 May 14. PMID: 22585211; PMCID: PMC3393403.
9: Domínguez-Ortega J, Martínez-Alonso JC, Marcos-Pérez MC, Kindelan C, Frades A. Allergy to cloxacillin with normal tolerance to amoxicillin and cefuroxime. Allergol Immunopathol (Madr). 2006 Jan-Feb;34(1):37-8. doi: 10.1157/13084226. PMID: 16540070.
10: Mani SSR, Iyyadurai R. Cloxacillin induced agranulocytosis: A rare adverse event of a commonly used antibiotic. Int J Immunopathol Pharmacol. 2017 Sep;30(3):297-301. doi: 10.1177/0394632017724320. Epub 2017 Aug 8. PMID: 28786715; PMCID: PMC5815267.
