Mr. Ibrahem/Ceftriaxone
Clinical data
Pronunciation/ˌsɛftrˈæksn/
Trade namesRocephin, Epicephin, Wintriaxone, others
AHFS/Drugs.comMonograph
MedlinePlusa685032
License data
Pregnancy
category
Routes of
administration
Intravenous, intramuscular
Drug classAntibiotic (3rd-generation cephalosporin)
Legal status
Legal status
Pharmacokinetic data
Bioavailabilityn/a
MetabolismNegligible
Elimination half-life5.8–8.7 hours
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
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 an antibiotic used for the treatment of a number of bacterial infections.[2] 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.[2] It is also sometimes used before surgery and following a bite wound to try to prevent infection.[2] Ceftriaxone can be given by injection into a vein or into a muscle.[2]

Common side effects include pain at the site of injection and allergic reactions.[2] Other possible side effects include C. difficile associated diarrhea, hemolytic anemia, gall bladder disease, and seizures.[2] It is not recommended in those who have had anaphylaxis to penicillin but may be used in those who have had milder reactions.[2] The intravenous form should not be given with intravenous calcium.[2] 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.[2] It can cross the blood-brain barrier.[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.[2] In the developing world the wholesale cost per one-gram vial is about US$0.20 to US$5.80 as of 2015.[7] In the United States a course of treatment is typically less than US$25.[8]

References

edit
  1. ^ a b c "Ceftriaxone (Rocephin) Use During Pregnancy". Drugs.com. 12 December 2019. Archived from the original on 23 August 2016. Retrieved 24 December 2019.
  2. ^ a b c d e f g h i j k l "Ceftriaxone Sodium Monograph for Professionals". Drugs.com. Archived from the original on 2016-05-31. Retrieved 2016-08-27.
  3. ^ Cite error: The named reference WHO2020DDD was invoked but never defined (see the help page).
  4. ^ Ritter, James M.; Flower, Rod; Henderson, Graeme; Loke, Yoon Kong; Rang, Humphrey P. (2020). "52. Antibacterial drugs". Rang & Dale's Pharmacology (9th ed.). Elsevier. pp. 665–666. ISBN 978-0-7020-7448-6. Archived from the original on 28 August 2021. Retrieved 1 December 2021.
  5. ^ Fischer, Jnos; Ganellin, C. Robin (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 495. ISBN 9783527607495. Archived from the original on 20 December 2016. Retrieved 5 June 2020.
  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.
  7. ^ "Single Drug Information – International Medical Products Price Guide". Archived from the original on 28 August 2021. Retrieved 28 May 2020.
  8. ^ Facep, Hamilton (2013). Tarascon Pocket Pharmacopoeia 2014 Deluxe Lab-Coat Edition. Jones & Bartlett Publishers. p. 75. ISBN 9781284053999. Archived from the original on 2017-09-08.