Ceftriaxone

drugbox

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width=200
IUPAC_name = (6"R",7"R","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
CAS_number = 73384-59-5
ATC_prefix=J01
ATC_suffix=DD01
PubChem=5479530
DrugBank=APRD00395
C = 18 | H = 18 | N = 8 | O = 7 | S = 3
molecular_weight = 554.58 g/mol
bioavailability = n/a
metabolism = Negligible
elimination_half-life = 5.8–8.7 hours
excretion = 33–67% renal, 35–45% biliary
pregnancy_AU = B1
pregnancy_US = B
legal_AU = S4
routes_of_administration = Intravenous, intramuscular

Ceftriaxone (INN) (pronEng|ˌsɛftraɪˈæksoʊn/, /ˌkɛf-) 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.

Clinical use

Ceftriaxone is often used (in combination, but not direct, with macrolide and/or aminoglycoside antibiotics) for the treatment of community-acquired or mild to moderate health care-associated 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,Typhoid Fever and gonorrhea.

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 gonorrhoea a single intramuscular injection is usually given, and the patients generally also treated for chlamydia, often with azithromycin.fact|date=August 2008

It must not be mixed or administered simultaneously (within 48 hours) with calcium-containing solutions or products, even via different infusion lines (rare fatal cases of calcium-ceftriaxone precipitates in lung and kidneys in neonates have been described).

Ceftriaxone may be reconstituted with 1% Lidocaine for injection when dose is to be given intramuscularly to prevent painful injection.

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.

References

[http://www.rocheusa.com/products/rocephin/pi.pdf 1. Ceftriaxone package insert]

External links

* [http://www.nlm.nih.gov/medlineplus/druginfo/uspdi/202119.html MedlinePlus Drug Information: Cephalosporins (systemic)] – information from USP DI Advice for the Patient
* [http://www.rocheusa.com/products/rocephin/ Rocephin U.S. Prescribing Information]