User:Mr. Ibrahem/Flucloxacillin

Mr. Ibrahem/Flucloxacillin
Clinical data
Trade names	Floxapen, others
AHFS/Drugs.com	International Drug Names
Pregnancy; category	AU: B1; ;
Routes of; administration	By mouth, IM, IV, intrapleural, intraarticular
Legal status
Legal status	AU: S4 (Prescription only); UK: POM (Prescription only);
Pharmacokinetic data
Bioavailability	50–70%
Metabolism	Liver
Elimination half-life	0.75–1 hour
Excretion	Kidney
Identifiers
	IUPAC name (2S,5R,6R)-6-({[3-(2-chloro-5-fluorophenyl)-5-methylisoxazol-4-yl]carbonyl}amino)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylic acid;
Chemical and physical data
Formula	C19H17ClFN3O5S
Molar mass	453.87 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(O)[C@@H]3N4C(=O)[C@@H](NC(=O)c2c(onc2c1c(F)cccc1Cl)C)[C@H]4SC3(C)C;
	InChI InChI=1S/C19H17ClFN3O5S/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)/t13-,14+,17-/m1/s1 ; Key:UIOFUWFRIANQPC-JKIFEVAISA-N ;
	(verify)

Flucloxacillin, also known as floxacillin, is an antibiotic used to treat skin infections, external ear infections, infections of leg ulcers, diabetic foot infections, and infection of bone.^[3] It may be used together with other medications to treat pneumonia, and endocarditis.^[3] It may also be used prior to surgery to prevent Staphylococcus infections.^[3] It is not effective against methicillin-resistant Staphylococcus aureus (MRSA).^[4] It is taken by mouth or given by injection into a vein or muscle.^[3]

Common side effects include an upset stomach.^[3] Other side effects may include muscle or joint pains, shortness of breath, and liver problems.^[3]^[5] It appears to be safe during pregnancy and breastfeeding.^[3] It should not be used in those who are allergic to penicillin.^[3] It is a narrow-spectrum beta-lactam antibiotic of the penicillin class.^[5] It is similar in effect to cloxacillin and dicloxacillin, being active against penicillinase forming bacteria.^[6]

Flucloxacillin was patented in 1961.^[7] It is available as a generic medication.^[3] In the United Kingdom 100 capsules of 250 mg costs the NHS less than 20 pounds.^[3] It is not commonly used in the United States or Canada as of 2011.^[5]

References[edit]

^ "Flucloxacillin". Drugs.com. Archived from the original on 6 June 2016. Retrieved 11 December 2020.
^ ^a ^b Hitchings, Andrew; Lonsdale, Dagan; Burrage, Daniel; Baker, Emma (2019). The Top 100 Drugs: Clinical Pharmacology and Practical Prescribing (2nd ed.). Elsevier. pp. 188–189. ISBN 978-0-7020-7442-4. Archived from the original on 2021-05-22. Retrieved 2021-11-09.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j BNF (80 ed.). BMJ Group and the Pharmaceutical Press. September 2020 – March 2021. p. 582-587. ISBN 978-0-85711-369-6.{{cite book}}: CS1 maint: date format (link)
^ "Methicillin-resistant Staphylococcus aureus (MRSA)" (PDF). NHS. 2005. p. 3. Archived (PDF) from the original on 12 December 2020. Retrieved 11 December 2020.
^ ^a ^b ^c Wu, Alan H. B.; Yeo, Kiang-Teck J. (2011). Pharmacogenomic Testing in Current Clinical Practice: Implementation in the Clinical Laboratory. Springer Science & Business Media. ISBN 978-1-60761-283-4. Archived from the original on 2021-05-16. Retrieved 2020-12-14.
^ Weller, Richard B.; Hunter, Hamish J. A.; Mann, Margaret W. (2014). Clinical Dermatology. John Wiley & Sons. p. 411. ISBN 978-1-118-85097-8. Archived from the original on 2021-05-25. Retrieved 2020-12-18.
^ Alapi, Erika M.; Fischer, Jánus (2006). "Part III. Table of Selected Analogue Classes". In Fischer, János; Ganellin, C. Robin (eds.). Analogue-based Drug Discovery. Wiley-VCH. p. 491. ISBN 978-3-527-31257-3. Archived from the original on 2021-05-20. Retrieved 2020-09-19.

[Drugs.com-1] "Flucloxacillin". Drugs.com. Archived from the original on 6 June 2016. Retrieved 11 December 2020.

[Hitchings2019-2] Hitchings, Andrew; Lonsdale, Dagan; Burrage, Daniel; Baker, Emma (2019). The Top 100 Drugs: Clinical Pharmacology and Practical Prescribing (2nd ed.). Elsevier. pp. 188–189. ISBN 978-0-7020-7442-4. Archived from the original on 2021-05-22. Retrieved 2021-11-09.

[BNF80-3] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j BNF (80 ed.). BMJ Group and the Pharmaceutical Press. September 2020 – March 2021. p. 582-587. ISBN 978-0-85711-369-6.{{cite book}}: CS1 maint: date format (link)

[4] "Methicillin-resistant Staphylococcus aureus (MRSA)" (PDF). NHS. 2005. p. 3. Archived (PDF) from the original on 12 December 2020. Retrieved 11 December 2020.

[Wu2011-5] Wu, Alan H. B.; Yeo, Kiang-Teck J. (2011). Pharmacogenomic Testing in Current Clinical Practice: Implementation in the Clinical Laboratory. Springer Science & Business Media. ISBN 978-1-60761-283-4. Archived from the original on 2021-05-16. Retrieved 2020-12-14.

[Weller2014-6] Weller, Richard B.; Hunter, Hamish J. A.; Mann, Margaret W. (2014). Clinical Dermatology. John Wiley & Sons. p. 411. ISBN 978-1-118-85097-8. Archived from the original on 2021-05-25. Retrieved 2020-12-18.

[Alapi2006-7] Alapi, Erika M.; Fischer, Jánus (2006). "Part III. Table of Selected Analogue Classes". In Fischer, János; Ganellin, C. Robin (eds.). Analogue-based Drug Discovery. Wiley-VCH. p. 491. ISBN 978-3-527-31257-3. Archived from the original on 2021-05-20. Retrieved 2020-09-19.

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