User:Mr. Ibrahem/Oxacillin

Mr. Ibrahem/Oxacillin
Clinical data
Trade names	Bactocill
AHFS/Drugs.com	Monograph
MedlinePlus	a685020
Drug class	Antibiotic (penicillin)
Identifiers
	IUPAC name (2S,5R,6R)-3,3-dimethyl-6-[(5-methyl-3-phenyl-; 1,2-oxazole-4-carbonyl)amino]-7-oxo-4-thia-1-; azabicyclo[3.2.0]heptane-2-carboxylic acid;
Chemical and physical data
Formula	C19H19N3O5S
Molar mass	401.44 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.49 g/cm3
Boiling point	686.8 °C (1,268.2 °F)
	SMILES [H][C@]12SC(C)(C)[C@@H](N1C(=O)[C@H]2NC(=O)C1=C(C)ON=C1C1=CC=CC=C1)C(O)=O;
	InChI InChI=1S/C19H19N3O5S/c1-9-11(12(21-27-9)10-7-5-4-6-8-10)15(23)20-13-16(24)22-14(18(25)26)19(2,3)28-17(13)22/h4-8,13-14,17H,1-3H3,(H,20,23)(H,25,26)/t13-,14+,17-/m1/s1 ; Key:UWYHMGVUTGAWSP-JKIFEVAISA-N ;
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Oxacillin, sold under the brand name Bactocill among others, is an antibiotic used to treat and prevent straphylococcal infections.^[1] This includes includes of the skin, respiratory tract, urine, and blood.^[1] It is given by injection into a vein or muscle.^[1]

Common side effects include pain and inflammation at the site of injection.^[1] Other side effects may include anaphylaxis and Clostridioides difficile infection.^[1] There is no evidence of harm with use in pregnancy, though such use has not been well studied.^[2] It is a beta-lactam antibiotic of the penicillin class.^[1]

Oxacillin was patented in 1960 and approved for medical use in 1962.^[3] In the United States 10 doses of 2 grams costs about 45 USD as of 2021.^[4] In 39 countries it was only available in 6 as of 2017.^[5]

References[edit]

^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Oxacillin Monograph for Professionals". Drugs.com. Archived from the original on 12 August 2021. Retrieved 10 November 2021.
^ "Oxacillin (Bactocill) Use During Pregnancy". Drugs.com. Archived from the original on 5 December 2020. Retrieved 10 November 2021.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495. Archived from the original on 2017-09-08. Retrieved 2021-07-17.
^ "Oxacillin Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 18 January 2021. Retrieved 10 November 2021.
^ Pulcini, C; Mohrs, S; Beovic, B; Gyssens, I; Theuretzbacher, U; Cars, O; ESCMID Study Group for Antibiotic Policies (ESGAP), ReAct Working Group on Old, Antibiotics. (January 2017). "Forgotten antibiotics: a follow-up inventory study in Europe, the USA, Canada and Australia". International journal of antimicrobial agents. 49 (1): 98–101. doi:10.1016/j.ijantimicag.2016.09.029. PMID 27887966.

[AHFS2021-1] ^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Oxacillin Monograph for Professionals". Drugs.com. Archived from the original on 12 August 2021. Retrieved 10 November 2021.

[2] "Oxacillin (Bactocill) Use During Pregnancy". Drugs.com. Archived from the original on 5 December 2020. Retrieved 10 November 2021.

[Fis2006-3] Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 490. ISBN 9783527607495. Archived from the original on 2017-09-08. Retrieved 2021-07-17.

[4] "Oxacillin Prices, Coupons & Patient Assistance Programs". Drugs.com. Archived from the original on 18 January 2021. Retrieved 10 November 2021.

[5] Pulcini, C; Mohrs, S; Beovic, B; Gyssens, I; Theuretzbacher, U; Cars, O; ESCMID Study Group for Antibiotic Policies (ESGAP), ReAct Working Group on Old, Antibiotics. (January 2017). "Forgotten antibiotics: a follow-up inventory study in Europe, the USA, Canada and Australia". International journal of antimicrobial agents. 49 (1): 98–101. doi:10.1016/j.ijantimicag.2016.09.029. PMID 27887966.

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