Ceftriaxone

Systematic (IUPAC) name
(6R,7R)-7-{[(2Z)-2-(2-amino-1,3-thiazol-4-yl)->2-(methoxyimino)acetyl]amino}-3-{[(2-methyl-5,6-dioxo-1,2,5,6-tetrahydro-1,2,4-triazin-3-yl)thio]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Identifiers
CAS number	73384-59-5
ATC code	J01DD04
PubChem	CID 5479530
DrugBank	APRD00395
ChemSpider	4586394
Chemical data
Formula	C18H18N8O7S3
Mol. mass	554.58 g/mol
SMILES	eMolecules & PubChem
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	Prescription Only (S4) (AU)
Routes	Intravenous, intramuscula

Ceftriaxone (INN) (pronounced /ˌsɛftraɪˈæksoʊn/) is a third-generation cephalosporinantibiotic. Like other third-generation cephalosporins, it has broad spectrum activity againstGram-positive and Gram-negative bacteria. In most cases, it is considered to be equivalent tocefotaxime in terms of safety and efficacy. Ceftriaxone sodium is marketed by Hoffman-La Roche under the trade name Rocephin, Rocetrax by Star Laboratories in Pakistan, as well as under various other names in several countries. Gepach International markets Ceftraixone Injections under the brand name Cefatrin®

Contents  [hide] 1 Clinical use 2 Chemistry 3 References 4 External links

[edit]Clinical use

Main article: Cephalosporin

Ceftriaxone is often used (in combination, but not direct, with macrolide and/or aminoglycosideantibiotics) for the treatment of community-acquired or mild to moderate health care-associatedpneumonia. 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. The dosage for acute ear infection in the very young is 50 mg/kg IM, one dose only. It has also been used in the treatment of Lyme disease, typhoid fever andgonorrhea.^{[citation needed]}

Intravenous dosages may be adjusted for body mass in younger patients and is administered every 12–24 hours, at a dose that depends on the type and severity of the infection.

For the treatment of gonorrhea, a single intramuscular injection is usually given. Treatment forchlamydia infection is also recommended (usually with azithromycin) unless it is specifically ruled out.^[1]

It must not be mixed or administered simultaneously (within 48 hours) with calcium-containing solutions or products for patients younger than 28 days old^[2], even via different infusion lines (rare fatal cases of calcium-ceftriaxone precipitates in lung and kidneys in neonates have been described).^[3]

To reduce the pain of intramuscular injection, ceftriaxone may be reconstituted with 1% lidocaine.^[4]

Ceftriaxone has also been investigated for efficacy in preventing relapse to cocaine addiction.^[5]

[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 easilyhydrolysed acetyl group of cefotaxime, ceftriaxone has a metabolically stable thiotriazinedione moiety.