Ceftriaxone
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| 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 | |
| Clinical data | |
| Trade names | Rocephin |
| AHFS/Drugs.com | monograph |
| Pregnancy cat. | B1 (AU) B (US) |
| Legal status | Prescription Only (S4) (AU) |
| Routes | Intravenous, intramuscular |
| Pharmacokinetic data | |
| Bioavailability | n/a |
| Metabolism | Negligible |
| Half-life | 5.8–8.7 hours |
| Excretion | 33–67% renal, 35–45% biliary |
| Identifiers | |
| CAS number | 73384-59-5  |
| ATC code | J01DD04 |
| PubChem | CID 5479530 |
| DrugBank | APRD00395 |
| ChemSpider | 4586394 |
| UNII | 75J73V1629 |
| KEGG | D07659 |
| ChEBI | CHEBI:29007 |
| ChEMBL | CHEMBL161 |
| Chemical data | |
| Formula | C18H18N8O7S3 |
| Mol. mass | 554.58 g/mol |
| SMILES | eMolecules & PubChem |
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Ceftriaxone (INN) (
/ˌsɛftraɪˈæksoʊn/) 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.
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[edit] 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. 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 and gonorrhea.[1]
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. According to the Journal of Family Practice, Volume 60, NO 12, December 2011; the intramuscular dose of ceftriaxone (Rocephin) has been increased from 125mg IM to 250mg IM due to increasing resistance of the gonococcal bacteria. It is also recommended that 1000mg of azithromycin be given orally at the same time for dual treatment. This also takes care of treatment of underlying chlamydia since treatment for chlamydia infection is also recommended. 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]
Ceftriaxone seems to increase EAAT2 pump expression in central nervous system and has therefore a potential to reduce glutamatergic toxicity.[6] Despite earlier negative results in 1990s, new, large clinical trials are underway to test its effacy in Amyotrophic lateral sclerosis (ALS) patients.
[edit] Chemistry
Ceftriaxone is a white 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] Adverse Effect
Hypoprothrombinaemia and bleeding are specific side effects. Haemolysis is reported. Biliary sludging is another known though rare adverse effect which occurs primarily in neonates.[7]
[edit] References
- ^ Gladwin, Mark (2007). Clinical Microbiology Made Ridiculously Simple 4th ed.. Miami, FL: MedMaster, Inc.. pp. 67. ISBN 0-940780-81-X.
- ^ "FDA Updates warning on Ceftriaxone-Calcium injection". http://healthcare.utah.edu/pharmacy/alerts/243.htm.
- ^ Bradley JS, Wassel RT, Lee L, Nambiar S (April 2009). "Intravenous ceftriaxone and calcium in the neonate: assessing the risk for cardiopulmonary adverse events". Pediatrics 123 (4): e609–13. doi:10.1542/peds.2008-3080. PMID 19289450.
- ^ Schichor A, Bernstein B, Weinerman H, Fitzgerald J, Yordan E, Schechter N (January 1994). "Lidocaine as a diluent for ceftriaxone in the treatment of gonorrhea. Does it reduce the pain of the injection?". Arch Pediatr Adolesc Med 148 (1): 72–5. PMID 8143016.
- ^ Knackstedt LA, Melendez RI, Kalivas PW (August 2009). "Ceftriaxone restores glutamate homeostasis and prevents relapse to cocaine-seeking". Biol Psychiatry 67 (1): 81–4. doi:10.1016/j.biopsych.2009.07.018. PMC 2795043. PMID 19717140. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2795043.
- ^ Lee SG, Su ZZ, Emdad L, Gupta P, Sarkar D, Borjabad A, Volsky DJ, Fisher PB (2008). "Mechanism of Ceftriaxone Induction of Excitatory Amino Acid Transporter-2 Expression and Glutamate Uptake in Primary Human Astrocytes". The Journal of Biological Chemistry 283 (19): 13116–13123. doi:10.1074/jbc.M707697200. PMC 2442320. PMID 18326497. http://www.pubmedcentral.nih.gov/articlerender.fcgi?tool=pmcentrez&artid=2442320.
- ^ Shiffman ML, Keith FB, Moore EW (December 1990). "Pathogenesis of ceftriaxone-associated biliary sludge. In vitro studies of calcium-ceftriaxone binding and solubility". Gastroenterology 99 (6): 1772–8. PMID 2227290.
[edit] External links
- MedlinePlus Drug Information: Ceftriaxone Injection
- Rocephin U.S. Prescribing Information
- Side Effects of Rocephin
- U.S. National Library of Medicine: Drug Information Portal - Ceftriaxone
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