Cefotaxime

Cefotaxime
Clinical data
Pronunciation	/ˌsɛfəˈtækˌsiːm/
Trade names	Claforan, others
Other names	cefotaxime sodium
AHFS/Drugs.com	Monograph
MedlinePlus	a682765
License data	US DailyMed: Cefotaxime;
Pregnancy; category	AU: B1;
Routes of; administration	Intravenous and intramuscular
ATC code	J01DD01 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only);
Pharmacokinetic data
Bioavailability	n/a
Metabolism	liver
Elimination half-life	0.8–1.4 hours
Excretion	50–85% kidney
Identifiers
	IUPAC name (6R,7R,Z)-3-(Acetoxymethyl)-7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;
CAS Number	63527-52-6 ;
PubChem CID	5479527;
DrugBank	DB00493 ;
ChemSpider	4586392 ;
UNII	N2GI8B1GK7;
KEGG	D07647 ;
ChEMBL	ChEMBL102 ;
CompTox Dashboard (EPA)	DTXSID6022761 ;
ECHA InfoCard	100.058.436
Chemical and physical data
Formula	C16H17N5O7S2
Molar mass	455.46 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)\c3nc(sc3)N)COC(=O)C)C(=O)O;
	InChI InChI=1S/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9+/t10-,14-/m1/s1 ; Key:GPRBEKHLDVQUJE-VINNURBNSA-N ;
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Cefotaxime is an antibiotic used to treat several bacterial infections in humans, other animals, and plant tissue culture.^[3] Specifically in humans it is used to treat joint infections, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, sepsis, gonorrhea, and cellulitis.^[3] It is given either by injection into a vein or muscle.^[3]

Common side effects include nausea, allergic reactions, and inflammation at the site of injection.^[3] Another side effect may include Clostridioides difficile diarrhea.^[3] It is not recommended in people who have had previous anaphylaxis to a penicillin.^[3] It is relatively safe for use during pregnancy and breastfeeding.^[3]^[4] It is in the third-generation cephalosporin family of medications and works by interfering with the bacteria's cell wall.^[3]

Cefotaxime was discovered in 1976 and came into commercial use in 1980.^[5]^[6] It is on the World Health Organization's List of Essential Medicines.^[7] It is available as a generic medication.^[3]

^ "Cefotaxime". Merriam-Webster.com Dictionary. Merriam-Webster. Retrieved 21 January 2016.
^ ^a ^b "Cefotaxime (Claforan) Use During Pregnancy". Drugs.com. 5 April 2019. Retrieved 24 December 2019.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ "Cefotaxime Sodium". The American Society of Health-System Pharmacists. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
^ Hamilton R (2015). Tarascon Pocket Pharmacopoeia 2015 Deluxe Lab-Coat Edition. Jones & Bartlett Learning. p. 87. ISBN 9781284057560.
^ Newbould BB (2012). "The Future of Drug Discovery". In Walker BC, Walker SR (eds.). Trends and Changes in Drug Research and Development. Springer Science & Business Media. p. 109. ISBN 9789400926592. Archived from the original on 14 September 2016.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 494. ISBN 9783527607495. Archived from the original on 20 December 2016.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.