Ceftriaxone

Ceftriaxone
Clinical data
Pronunciation/ˌsɛftraɪˈæksoʊn/
Trade namesRocephin, Epicephin, Wintriaxone, others
AHFS/Drugs.comMonograph
MedlinePlusa685032
License data
Pregnancy
category
Routes of
administration		Intravenous, intramuscular
Drug classThird-generation cephalosporin
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityn/a
MetabolismNegligible
Elimination half-life5.8–8.7 hours[3]
Excretion33–67% kidney, 35–45% biliary
Identifiers
  • (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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.070.347 Edit this at Wikidata
Chemical and physical data
FormulaC18H18N8O7S3
Molar mass554.57 g·mol−1
3D model (JSmol)
  • 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=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 checkY
  • Key:VAAUVRVFOQPIGI-SPQHTLEESA-N checkY
  (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]

  1. ^ a b "Ceftriaxone (Rocephin) Use During Pregnancy". Drugs.com. 12 December 2019. Archived from the original on 23 August 2016. Retrieved 24 December 2019.
  2. ^ "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.
  3. ^ 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.
  4. ^ 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.
  5. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 495. ISBN 978-3-527-60749-5.
  6. ^ 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.