Cefotaxime

Cefotaxime
Clinical data


Pronunciation	/ˌsɛfəˈtækˌsiːm/
Trade names	Claforan, others
AHFS/Drugs.com	Monograph
MedlinePlus	a682765
Pregnancy category	AU: B1 US: B (No risk in non-human studies)
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
Biological 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
Synonyms	cefotaxime sodium
CAS Number	63527-52-6^Y
PubChem CID	5479527
DrugBank	DB00493^Y
ChemSpider	4586392^Y
UNII	N2GI8B1GK7
KEGG	D07647^Y
ChEMBL	CHEMBL102^Y
ECHA InfoCard	100.058.436
Chemical and physical data
Formula	C₁₆H₁₇N₅O₇S₂
Molar mass	455.47 g/mol
3D model (Jmol)	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^Y Key:GPRBEKHLDVQUJE-VINNURBNSA-N^Y

Cefotaxime is an antibiotic used to treat a number of bacterial infections. Specifically it is used to treat joint infections, pelvic inflammatory disease, meningitis, pneumonia, urinary tract infections, sepsis, gonorrhea, and cellulitis. It is given either by injection into a vein or muscle.

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

Cefotaxime was discovered in 1976 and came into commercial use in 1980. It is on the World Health Organization's List of Essential Medicines, the most effective and safe medicines needed in a health system. It is available as a generic medication. The wholesale cost in the developing world is about 0.23 to 4.70 USD per dose. In the United States a course of treatment costs 100 to 200 USD.