File:Ceftriaxone_skeletal_formula_from_xtal_2018.svg · Wikimedia Commons · See Wikimedia Commons
ceftriaxone
Sign in to saveAlso known as (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)sulfanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Ceftriaxone, sold under the brand name Rocephin, is a third-generation cephalosporin antibiotic used for the treatment of a number of bacterial infections. 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. 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.
Chemical data
- Formula
- C18H18N8O7S3
- Molecular weight
- 554.6 g/mol
- IUPAC name
- (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-3-[(2-methyl-5,6-dioxo-1H-1,2,4-triazin-3-yl)sulfanylmethyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
- SMILES
- CN1C(=NC(=O)C(=O)N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)O
- InChIKey
- VAAUVRVFOQPIGI-SPQHTLEESA-N
- XLogP
- -1.3
- Polar surface area
- 288 Ų
- H-bond donors
- 4
- H-bond acceptors
- 13
- Formal charge
- 0
via PubChem
Research
18,541 papers- Efficacy of Ceftriaxone 1 g daily Versus 2 g daily for The Treatment of Community-Acquired Pneumonia: A Systematic Review with Meta-Analysis.Expert review of anti-infective therapy · 2019
- Ceftriaxone and methicillin-susceptible staphylococcus aureus: a perspective from pharmacokinetics/pharmacodynamics studies.Expert opinion on drug metabolism & toxicology · 2021
- Ceftriaxone treatment of spondylodiscitis and other serious infections with Cutibacterium acnes.The Journal of antimicrobial chemotherapy · 2020
- Ceftriaxone.Indian pediatrics · 1990
- Ceftriaxone use for acute otitis media: Associated factors in a large U.S. primary care population.International journal of pediatric otorhinolaryngology · 2022
via PubMed
Wikidata facts
- Mass
- 554.046058
Show 7 more facts
- chemical formula
- C₁₈H₁₈N₈O₇S₃
- Commons category
- Ceftriaxone
- canonical SMILES
- CN1C(=NC(=O)C(=O)N1)SCC2=C(N3C(C(C3=O)NC(=O)C(=NOC)C4=CSC(=N4)N)SC2)C(=O)O
- isomeric SMILES
- CN1C(=NC(=O)C(=O)N1)SCC2=C(N3[C@@H]([C@@H](C3=O)NC(=O)/C(=N\OC)/C4=CSC(=N4)N)SC2)C(=O)O
- defined daily dose
- 2
- World Health Organisation international non-proprietary name
- ceftriaxone
- stylized name
- cefTRIAXone
Sources (8)
via Wikidata · CC0
~15 min read
Article
15 sectionsContents
- Medical use
- Spectrum of activity
- Available forms
- Specific populations
- Pregnancy
- Breastfeeding
- Newborns
- Elderly
- Adverse effects
- Contraindications
- Mechanism of action
- Pharmacokinetics
- Chemistry
- Research
- References
{{Drugbox | Watchedfields = changed | verifiedrevid = 460025108 | drug_name = | image = Ceftriaxone skeletal formula from xtal 2018.svg | width = 200px | image_class = skin-invert-image | alt = | image2 = Ceftriaxone ball-and-stick model from xtal 2018.png | image_class2 = bg-transparent | alt2 = | width2 = 250px
| pronounce = | tradename = Rocephin, Epicephin, Wintriaxone, others | Drugs.com = | MedlinePlus = a685032 | DailyMedID = Ceftriaxone | pregnancy_AU = B1 | pregnancy_AU_comment = | routes_of_administration = Intravenous, intramuscular | class = Third-generation cephalosporin | ATC_prefix = J01 | ATC_suffix = DD04