Ceftriaxone

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Ceftriaxone chemical structure
Ceftriaxone
Systematic (IUPAC) name
(6R,7R,Z)-7-(2-(2-aminothiazol-4-yl)-
2-(methoxyimino)acetamido)-3-((6-hydroxy-2-methyl-5-oxo-
2,5-dihydro-1,2,4-triazin-3-ylthio)methyl)-8-oxo-5-thia-
1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Identifiers
CAS number 63527-52-6
ATC code J01DD01
PubChem 456256
DrugBank APRD00854
Chemical data
Formula C18H18N8O7S3 
Mol. weight 554.58 g/mol
Pharmacokinetic data
Bioavailability n/a
Metabolism Negligible
Half life 5.8–8.7 hours
Excretion 33–67% renal, 35–45% biliary
Therapeutic considerations
Pregnancy cat.

B1(AU) B(US)
Legal status

S4(AU)
Routes Intravenous, intramuscular

Ceftriaxone (INN) (IPA: [kɛfˈtraɪækson, sɛf-]) is a third-generation cephalosporin antibiotic. Like other third-generation cephalosporins, it has broad spectrum activity against Gram positive and Gram negative bacteria. In most cases, it is considered to be equivalent to cefotaxime in terms of safety and efficacy. Ceftriaxone sodium is marketed by Hoffman-La Roche under the trade name Rocephin.

[edit] Clinical use

Main article: Cephalosporin

Ceftriaxone is often used (in combination, but not direct, with macrolide and/or aminoglycoside antibiotics) for the treatment of community-acquired pneumonia. It is also a choice drug for treatment of bacterial meningitis. In pediatrics, it is commonly used in febrile infants between 4 and 8 weeks of age who are admitted to the hospital to exclude sepsis. It has also been used in the treatment of Lyme disease and gonorrhoea.

The usual starting dose is 1 gram IV daily. Doses range from 1–2 grams IV or IM every 12–24 hours, depending on the type and severity or the infection, up to 4 grams daily. For gonorrhoea the usual adult dose is a single intramuscular injection of 250 mg. Patients treated for gonorrhoea are usually also treated for chlamydia, often with azithromycin.

Ceftriaxone is contraindicated in patients with known hypersensitivity to cephalosporins, penicillins and/or carbapenems.

[edit] Chemistry

Ceftriaxone is a yellowish-orange crystalline powder which is readily-soluble in water, sparingly soluble in methanol and very slightly soluble in ethanol. The pH of a 1% aqueous solution is approximately 6.7.

The syn-configuration of the methoxyimino moiety confers stability to β-lactamase enzymes produced by many Gram-negative bacteria. Such stability to β-lactamases increases the activity of ceftriaxone against otherwise resistant Gram-negative bacteria. In place of the easily hydrolysed acetyl group of cefotaxime, ceftriaxone has a metabolically-stable thiotriazinedione moiety.

[edit] External links


Cephalosporin Antibiotics (J01D) edit
First Generation:

Cefacetrile, Cefadroxil, Cefalexin, Cefaloglycin, Cefalonium, Cefaloridine, Cefalotin, Cefapirin, Cefatrizine, Cefazaflur, Cefazedone, Cefazolin, Cefradine, Cefroxadine, Ceftezole
Second Generation:

Cefaclor, Cefamandole, Cefonicid, Ceforanide, Cefotiam, Cefprozil, Cefuroxime, Cefuzonam
Third Generation:

Cefcapene , Cefdaloxime, Cefdinir, Cefditoren, Cefetamet, Cefixime, Cefmenoxime, Cefodizime, Cefoperazone, Cefotaxime, Cefpimizole, Cefpiramide, Cefpodoxime, Cefsulodin, Ceftazidime, Cefteram, Ceftibuten, Ceftiofur, Ceftiolene, Ceftizoxime, Ceftriaxone, Latamoxef
Fourth Generation:

Cefclidine, Cefepime, Cefetecol, Cefluprenam, Cefoselis, Cefozopran, Cefpirome, Cefquinome
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