Ceftriaxone

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 Y
UNII	75J73V1629 Y
KEGG	D07659 Y
ChEMBL	CHEMBL161 Y
Chemical data
Formula	C18H18N8O7S3
Mol. mass	554.58 g/mol
SMILES	eMolecules & PubChem
InChI[show] InChI=1S/C18H18N8O7S3/c1-25-18(22-12(28)13(29)23-25)36-4-6-3-34-15-9(14(30)26(15)10(6)16(31)32)21-11(27)8(24-33-2)7-5-35-17(19)20-7/h5,9,15H,3-4H2,1-2H3,(H2,19,20)(H,21,27)(H,23,29)(H,31,32)/b24-8-/t9-,15-/m1/s1 Y Key: VAAUVRVFOQPIGI-SPQHTLEESA-N Y
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, intramuscular
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Ceftriaxone (INN) (pronounced /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.

Contents 1 Clinical use 2 Chemistry

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 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.^{[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 for chlamydia 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]

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.