Ceftriaxone

Ceftriaxone
Clinical data


Pronunciation	/ˌsɛftraɪˈæksoʊn/
Trade names	Rocephin, Epicephin, others
AHFS/Drugs.com	Monograph
Pregnancy category	AU: B1 US: B (No risk in non-human studies)
Routes of administration	Intravenous, intramuscular
ATC code	J01DD04 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)
Pharmacokinetic data
Bioavailability	n/a
Metabolism	Negligible
Biological half-life	5.8–8.7 hours
Excretion	33–67% kidney, 35–45% biliary
Identifiers
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
CAS Number	73384-59-5^Y
PubChem CID	5479530
IUPHAR/BPS	5326
DrugBank	DB01212^Y
ChemSpider	4586394^Y
UNII	75J73V1629
KEGG	D07659^Y
ChEBI	CHEBI:29007^Y
ChEMBL	CHEMBL161^Y
ECHA InfoCard	100.070.347
Chemical and physical data
Formula	C₁₈H₁₈N₈O₇S₃
Molar mass	554.58 g/mol
3D model (Jmol)	Interactive image
SMILES O=C2N1/C(=C(\CS[C@@H]1[C@@H]2NC(=O)C(=N\OC)/c3nc(sc3)N)CS\C4=N\C(=O)C(=O)NN4C)C(=O)O
InChI 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

Ceftriaxone, sold under the trade name Rocephin, is an antibiotic useful for the treatment of a number of bacterial infections. This includes middle ear infections, endocarditis, meningitis, pneumonia, bone and joint infections, intra-abdominal infections, skin infections, urinary tract infections, gonorrhea, and pelvic inflammatory disease. It is also sometimes used before surgery and following a bite wound to try to prevent infection. Ceftriaxone can be given by injection into a vein or into a muscle.

Common side effects include pain at the site of injection and allergic reactions. Other possible side effects include C. difficile associated diarrhea, hemolytic anemia, gall bladder disease, and seizures. It is not recommended in those who have had anaphylaxis to penicillin but may be used in those who have had milder reactions. The intravenous form should not be given with intravenous calcium. There is tentative evidence that ceftriaxone is relatively safe during pregnancy and breastfeeding. It is a third-generation cephalosporin that works by preventing bacteria from making a cell wall.

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