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MedKoo Cat#: 317877 | Name: Flucloxacillin sodium
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Description:

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

Flucloxacillin is a narrow-spectrum beta-lactam antibiotic of the penicillin class. It is used to treat infections caused by susceptible Gram-positive bacteria. Unlike other penicillins, flucloxacillin has activity against beta-lactamase-producing organisms such as Staphylococcus aureus as it is beta-lactamase stable. However, it is ineffective against methicillin-resistant Staphylococcus aureus (MRSA). It is very similar to dicloxacillin and they are considered interchangeable.

Chemical Structure

Flucloxacillin sodium
Flucloxacillin sodium
CAS#1847-24-1 (sodium)

Theoretical Analysis

MedKoo Cat#: 317877

Name: Flucloxacillin sodium

CAS#: 1847-24-1 (sodium)

Chemical Formula: C19H16ClFN3NaO5S

Exact Mass: 0.0000

Molecular Weight: 475.85

Elemental Analysis: C, 47.96; H, 3.39; Cl, 7.45; F, 3.99; N, 8.83; Na, 4.83; O, 16.81; S, 6.74

Price and Availability

Size Price Availability Quantity
250mg USD 350.00 2 Weeks
500mg USD 550.00 2 Weeks
1g USD 950.00 2 Weeks
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Related CAS #
5250-39-5 (free acid) 40182-54-5 (magnesium) 1847-24-1 (sodium) 34214-51-2 (sodium hydrate)
Synonym
Flucloxacillin sodium; Floxacillin sodium;Floxapen sodium; Fluorochloroxacillin; NSC 277175; NSC277175; NSC-277175
IUPAC/Chemical Name
Sodium (2S-(2alpha,5alpha,6beta))-6-(((3-(2-chloro-6-fluorophenyl)-5-methylisoxazol-4-yl)carbonyl)amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo(3.2.0)heptane-2-carboxylate
InChi Key
OTEANHMVDHZOPB-SLINCCQESA-M
InChi Code
InChI=1S/C19H17ClFN3O5S.Na/c1-7-10(12(23-29-7)11-8(20)5-4-6-9(11)21)15(25)22-13-16(26)24-14(18(27)28)19(2,3)30-17(13)24;/h4-6,13-14,17H,1-3H3,(H,22,25)(H,27,28);/q;+1/p-1/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=C(F)C=CC=C4Cl)=O)N1C2=O)[O-].[Na+]
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, 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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 475.85 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: Andrews E, Daly AK. Flucloxacillin-induced liver injury. Toxicology. 2008 Dec 30;254(3):158-63. doi: 10.1016/j.tox.2008.08.009. Epub 2008 Aug 29. PMID: 18793693. 2: Koek GH, Stricker BH, Blok AP, Schalm SW, Desmet VJ. Flucloxacillin- associated hepatic injury. Liver. 1994 Oct;14(5):225-9. doi: 10.1111/j.1600-0676.1994.tb00079.x. PMID: 7997079. 3: Menezes MN, de Marco BA, Fiorentino FAM, Zimmermann A, Kogawa AC, Salgado HRN. Flucloxacillin: A Review of Characteristics, Properties and Analytical Methods. Crit Rev Anal Chem. 2019;49(1):67-77. doi: 10.1080/10408347.2018.1468728. Epub 2018 May 30. PMID: 29846080. 4: Mastroviti S, Cassarino G. La flucloxacillina [Flucloxacillin]. G Batteriol Virol Immunol. 1975 Jul-Dec;68(7-12):279-88. Italian. PMID: 1234594. 5: van Daele PLA. Therapeutic drug monitoring of flucloxacillin. Neth J Med. 2019 Sep;77(7):233. PMID: 31582583. 6: McKean AR, Aggarwal D, Torres-Grau J, Welman T, Moore LSP, Jones I. Is flucloxacillin monotherapy sufficient for the treatment of skin and soft tissue infections in plastic surgery? J Plast Reconstr Aesthet Surg. 2018 Jun;71(6):919-920. doi: 10.1016/j.bjps.2018.01.034. Epub 2018 Feb 7. PMID: 29477266. 7: Jatzlauk G, Althaus K, Strobel U, Kiefel V, Wesche J, Muehlenberg K, Greinacher A, Bakchoul T. Flucloxacillin-induced immune thrombocytopenia. Transfusion. 2016 Jan;56(1):67-72. doi: 10.1111/trf.13284. Epub 2015 Sep 1. PMID: 26331798. 8: Van Daele R, Wauters J, Vandenbriele C, Lagrou K, Vos R, Debaveye Y, Spriet I. Interaction between flucloxacillin and azoles: Is isavuconazole next? Mycoses. 2021 Dec;64(12):1508-1511. doi: 10.1111/myc.13373. Epub 2021 Oct 9. PMID: 34553797. 9: Fairley CK, Boyd I, Purcell P, McNeil J. Flucloxacillin jaundice. Lancet. 1992 Mar 14;339(8794):679. doi: 10.1016/0140-6736(92)90837-s. PMID: 1347364. 10: Chaudhuri A, Wade SL. Flucloxacillin-warfarin interaction: an under- appreciated phenomenon. Intern Med J. 2018 Jul;48(7):860-863. doi: 10.1111/imj.13944. PMID: 29984514. 11: Angheleanu R, Swart JN. Flucloxacillin-induced liver injury in elderly patient. BMJ Case Rep. 2021 May 6;14(5):e241071. doi: 10.1136/bcr-2020-241071. PMID: 33958360; PMCID: PMC8103827. 12: Wallenburg E, Ter Heine R, de Lange DW, van Leeuwen H, Schouten JA, Ten Oever J, Kolwijck E, Burger DM, Pickkers P, Gieling EM, de Maat MM, Frenzel T, Brüggemann RJ. High unbound flucloxacillin fraction in critically ill patients. J Antimicrob Chemother. 2021 Nov 12;76(12):3220-3228. doi: 10.1093/jac/dkab314. PMID: 34463730; PMCID: PMC8598283. 13: Yagupsky P. FLUCLOXACILLIN AND ANTIBIOTIC THERAPY FOR KINGELLA KINGAE INFECTIONS. J Paediatr Child Health. 2021 Mar;57(3):460-461. doi: 10.1111/jpc.15397. Epub 2021 Feb 15. PMID: 33586821. 14: Unsworth PF, Heatley FW, Phillips I. Flucloxacillin in bone. J Clin Pathol. 1978 Aug;31(8):705-11. doi: 10.1136/jcp.31.8.705. PMID: 690233; PMCID: PMC1145392. 15: Devereaux BM, Crawford DH, Purcell P, Powell LW, Roeser HP. Flucloxacillin associated cholestatic hepatitis. An Australian and Swedish epidemic? Eur J Clin Pharmacol. 1995;49(1-2):81-5. doi: 10.1007/BF00192363. PMID: 8751026. 16: Rodrigues MA, Caetano M, Amorim I, Selores M. Dermo-Hipodermites Bacterianas Agudas Não Necrotizantes: Erisipela e Celulite Infeciosa [Non-Necrotizing Acute Dermo-Hypodermal Infections: Erysipela and Infectious Cellulitis]. Acta Med Port. 2021 Mar 1;34(3):217-228. Portuguese. doi: 10.20344/amp.12642. Epub 2021 Mar 1. PMID: 33971117. 17: Xu B, Murray M. Flucloxacillin induced acute renal failure. Aust Fam Physician. 2008 Dec;37(12):1009-11. PMID: 19142275. 18: Veenhof H, Schouw HM, Besouw MTP, Touw DJ, Gracchi V. Flucloxacillin decreases tacrolimus blood trough levels: a single-center retrospective cohort study. Eur J Clin Pharmacol. 2020 Dec;76(12):1667-1673. doi: 10.1007/s00228-020-02968-z. Epub 2020 Jul 25. PMID: 32712713; PMCID: PMC7661399. 19: Chew R, Woods ML. Flucloxacillin does not achieve therapeutic cerebrospinal fluid levels against meticillin-sensitive Staphylococcus aureus in adults: A case report and review of the literature. Int J Antimicrob Agents. 2016 Mar;47(3):229-31. doi: 10.1016/j.ijantimicag.2015.12.009. Epub 2016 Jan 15. PMID: 26915477. 20: Desmond PV. Flucloxacillin hepatitis--an Australian epidemic. Aust N Z J Med. 1995 Jun;25(3):195-6. doi: 10.1111/j.1445-5994.1995.tb01520.x. PMID: 7487684.

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