Ceftriaxone

Ceftriaxone
Clinical data
Pronunciation	/ˌsɛftraɪˈæksoʊn/
Trade names	Rocephin, Epicephin, Wintriaxone, others
AHFS/Drugs.com	Monograph
MedlinePlus	a685032
License data	US DailyMed: Ceftriaxone;
Pregnancy; category	AU: B1;
Routes of; administration	Intravenous, intramuscular
Drug class	Third-generation cephalosporin
ATC code	J01DD04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); US: ℞-only;
Pharmacokinetic data
Bioavailability	n/a
Metabolism	Negligible
Elimination 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 ;
PubChem CID	5479530;
IUPHAR/BPS	5326;
DrugBank	DB01212 ;
ChemSpider	4586394 ;
UNII	75J73V1629;
KEGG	D07659 ;
ChEBI	CHEBI:29007 ;
ChEMBL	ChEMBL161 ;
PDB ligand	9F2 (PDBe, RCSB PDB);
CompTox Dashboard (EPA)	DTXSID0022773 ;
ECHA InfoCard	100.070.347
Chemical and physical data
Formula	C18H18N8O7S3
Molar mass	554.57 g·mol−1
3D model (JSmol)	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 ; Key:VAAUVRVFOQPIGI-SPQHTLEESA-N ;
	(verify)

Ceftriaxone, sold under the brand name Rocephin, is a third-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections.^[4] These include middle ear infections, endocarditis, meningitis, pneumonia, bone and joint infections, intra-abdominal infections, skin infections, urinary tract infections, gonorrhea, and pelvic inflammatory disease.^[4] It is also sometimes used before surgery and following a bite wound to try to prevent infection.^[4] Ceftriaxone can be given by injection into a vein or into a muscle.^[4]

Common side effects include pain at the site of injection and allergic reactions.^[4] Other possible side effects include C. difficile-associated diarrhea, hemolytic anemia, gall bladder disease, and seizures.^[4] It is not recommended in those who have had anaphylaxis to penicillin but may be used in those who have had milder reactions.^[4] The intravenous form should not be given with intravenous calcium.^[4] There is tentative evidence that ceftriaxone is relatively safe during pregnancy and breastfeeding.^[1] It is a third-generation cephalosporin that works by preventing bacteria from making a cell wall.^[4]

Ceftriaxone was patented in 1978 and approved for medical use in 1982.^[5] It is on the World Health Organization's List of Essential Medicines.^[6] It is available as a generic medication.^[4]

^ ^a ^b "Ceftriaxone (Rocephin) Use During Pregnancy". Drugs.com. 12 December 2019. Archived from the original on 23 August 2016. Retrieved 24 December 2019.
^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Archived from the original on 6 July 2023. Retrieved 30 March 2024.
^ Beam TR (1985). "Ceftriaxone: a beta-lactamase-stable, broad-spectrum cephalosporin with an extended half-life". Pharmacotherapy. 5 (5): 237–253. doi:10.1002/j.1875-9114.1985.tb03423.x. PMID 3906584. S2CID 25559476.
^ ^a ^b ^c ^d ^e ^f ^g ^h ⁱ ^j "Ceftriaxone Sodium Monograph for Professionals". Drugs.com. Archived from the original on 31 May 2016. Retrieved 27 August 2016.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 495. ISBN 978-3-527-60749-5.
^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.