Structure via PubChem · Public domain (PubChem)
cefotaxime
Sign in to saveAlso known as (6R,7R)-3-acetoxymethyl-7-{2-(2-amino-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R,Z)-3-(acetoxymethyl)-7-(2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid, (6R,7R)-3-(acetoxymethyl)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Cefotaxime is an antibiotic used to treat several bacterial infections in humans, other animals, and plant tissue culture. Specifically in humans 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.
Chemical data
- Formula
- C16H17N5O7S2
- Molecular weight
- 455.5 g/mol
- IUPAC name
- (6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- CC(=O)OCC1=C(N2[C@@H]([C@@H](C2=O)NC(=O)/C(=N\OC)/C3=CSC(=N3)N)SC1)C(=O)O
- InChIKey
- GPRBEKHLDVQUJE-QSWIMTSFSA-N
- XLogP
- -1.4
- Polar surface area
- 227 Ų
- H-bond donors
- 3
- H-bond acceptors
- 12
- Formal charge
- 0
via PubChem
Research
21,363 papers- Cefotaxime: microbiology, pharmacology, and clinical use.Clinical pharmacy · 1982
- Cefotaxime. A pharmacoeconomic review of its use in the treatment of infections.PharmacoEconomics · 1998
- Cefotaxime in urinary tract infections.Infection · 1989
- Cefotaxime. A reappraisal of its antibacterial activity and pharmacokinetic properties, and a review of its therapeutic efficacy when administered twice daily for the treatment of mild to moderate infections.Drugs · 1997
- Cefotaxime is extensively used for surgical prophylaxis.American journal of surgery · 1992
via PubMed
~7 min read
Encyclopedic overview
9 sectionsContents
- Medical uses
- Spectrum of activity
- Adverse reactions
- Mechanism of action
- Administration
- Plant tissue culture
- See also
- References
- External links
Cefotaxime is an antibiotic used to treat several bacterial infections in humans, other animals, and plant tissue culture. Specifically in humans 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. Another side effect may include Clostridioides 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.
Excerpted from Wikipedia’s “cefotaxime” article, available under the CC BY-SA 4.0 licence.