Ceftriaxone (CHEM002094)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesTargets (5)XML
Record Information
Version1.0
Creation Date2009-07-05 03:20:59 UTC
Update Date2026-05-14 16:58:47 UTC
Accession NumberCHEM002094
Identification
Common NameCeftriaxone
ClassSmall Molecule
DescriptionCeftriaxone is only found in individuals that have used or taken this drug. It is a broad-spectrum cephalosporin antibiotic with a very long half-life and high penetrability to meninges, eyes and inner ears. [PubChem]Ceftriaxone works by inhibiting the mucopeptide synthesis in the bacterial cell wall. The beta-lactam moiety of Ceftriaxone binds to carboxypeptidases, endopeptidases, and transpeptidases in the bacterial cytoplasmic membrane. These enzymes are involved in cell-wall synthesis and cell division. By binding to these enzymes, Ceftriaxone results in the formation of of defective cell walls and cell death.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • T3DB toxins
Contaminant Type
  • Amide
  • Amine
  • Anti-Bacterial Agent
  • Cephalosporin
  • Drug
  • Ester
  • Ether
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(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 acidChEBI
CeftriaxonaChEBI
CeftriaxonumChEBI
RocephinChEBI
CTRXKegg
(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-carboxylateGenerator
(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)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylateGenerator
(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)sulphanyl]methyl}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acidGenerator
CefatriaxoneHMDB
CeftriazoneHMDB
BenaxonaHMDB
Irex brand OF ceftriaxoneHMDB
LongacefHMDB
LongacephHMDB
Pisa brand OF ceftriaxone sodiumHMDB
TerbacHMDB
CeftrexHMDB
Ceftriaxon hexalHMDB
Ceftriaxone sodium, anhydrousHMDB
Ceftriaxone, disodium salt, hemiheptahydrateHMDB
Columbia brand OF ceftriaxoneHMDB
Hexal brand OF ceftriaxone sodiumHMDB
Hoffman-la roche brand OF ceftriaxone sodiumHMDB
RocefalinHMDB
Syntex brand OF ceftriaxone sodiumHMDB
CeftriaxonHMDB
Ceftriaxon curamedHMDB
Ceftriaxona LDP torlanHMDB
Ceftriaxone sodiumHMDB
Ceftriaxone, disodium saltHMDB
Anhydrous ceftriaxone sodiumHMDB
Boehringer mannheim brand OF ceftriaxone sodiumHMDB
CefaxonaHMDB
Ceftriaxona andreuHMDB
Ceftriaxone irexHMDB
Curamed brand OF ceftriaxone sodiumHMDB
Fustery brand OF ceftriaxone sodiumHMDB
Galen brand OF ceftriaxone sodiumHMDB
Inibsa brand OF ceftriaxone sodiumHMDB
LendacinHMDB
Roche brand OF ceftriaxone sodiumHMDB
Hoffman la roche brand OF ceftriaxone sodiumHMDB
RocefinHMDB
RocephineHMDB
Sodium, ceftriaxoneHMDB
TacexHMDB
Chemical FormulaC18H18N8O7S3
Average Molecular Mass554.580 g/mol
Monoisotopic Mass554.046 g/mol
CAS Registry Number73384-59-5
IUPAC Name(6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetamido]-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
Traditional Nameceftriaxone
SMILES[H][C@]12SCC(CSC3=NC(=O)C(=O)NN3C)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O
InChI IdentifierInChI=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
InChI KeyVAAUVRVFOQPIGI-SPQHTLEESA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aminoglycosides. These are molecules or a portion of a molecule composed of amino-modified sugars.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbohydrates and carbohydrate conjugates
Direct ParentAminoglycosides
Alternative Parents
Substituents
  • Aminoglycoside core
  • Macrolide
  • Glycosyl compound
  • O-glycosyl compound
  • Oxane
  • Monosaccharide
  • Tertiary alcohol
  • 1,2-aminoalcohol
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Ketone
  • Cyclic ketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Secondary alcohol
  • Lactone
  • Acetal
  • Carboxylic acid derivative
  • Dialkyl ether
  • Ether
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Alcohol
  • Amine
  • Organopnictogen compound
  • Organonitrogen compound
  • Organic oxide
  • Aliphatic heteromonocyclic compound
Molecular FrameworkAliphatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical Roles
Physical Properties
StateSolid
AppearanceSolid (MSDS, A308).
Experimental Properties
PropertyValue
Melting Point>155°C
Boiling PointNot Available
Solubility1.05e-01 g/L
Predicted Properties
PropertyValueSource
Water Solubility0.1 g/LALOGPS
logP-0.01ALOGPS
logP-1.8ChemAxon
logS-3.7ALOGPS
pKa (Strongest Acidic)3.19ChemAxon
pKa (Strongest Basic)4.17ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area208.98 ŲChemAxon
Rotatable Bond Count8ChemAxon
Refractivity128.47 m³·mol⁻¹ChemAxon
Polarizability51.47 ųChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-0924040000-11c1c4ec5dc051494298Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05fr-9774123000-c094d2c5681b0477a4aaSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS ("Ceftriaxone,1TMS,#1" TMS) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_4) - 70eV, PositiveNot AvailableSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0apl-3069470000-ea9533b06f6d727b78d9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05mk-6139010000-862d2dcbf27819f7fdaaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-9043100000-fbf004668a64dff18475Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4r-5691220000-22e1520a7886282ef024Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4l-4940000000-3a6002666fe076cf5ad8Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-160408d1a7b4d7ae1995Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0013090000-bb4e8b82e0fb04e55aadSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0avi-0466190000-080d962933aef409d2d1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056u-1944420000-18694b9d401854bf9e80Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0pb9-0910080000-bcb5ef0d6c356695310eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0900000000-803717215c9d04868fa4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9400000000-75fd909b2cc72f5d0010Spectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
Toxicity Profile
Route of ExposureInhalation; dermal or skin contact; ingestion; intravenous (MSDS, A308).
Mechanism of ToxicityCeftriaxone works by inhibiting the mucopeptide synthesis in the bacterial cell wall. The beta-lactam moiety of Ceftriaxone binds to carboxypeptidases, endopeptidases, and transpeptidases in the bacterial cytoplasmic membrane. These enzymes are involved in cell-wall synthesis and cell division. By binding to these enzymes, Ceftriaxone results in the formation of of defective cell walls and cell death.
MetabolismCeftriaxone is eliminated unchanged in the urine by glomerular filtration (60%) and bile (40%) (2). Route of Elimination: Thirty-three percent to 67% of a ceftriaxone dose was excreted in the urine as unchanged drug and the remainder was secreted in the bile and ultimately found in the feces as microbiologically inactive compounds. Half Life: 5.8-8.7 hours
Toxicity ValuesLD50: >10 000 mg/kg (Oral, Rat)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor the treatment of the infections (respiratory, skin, soft tissue, UTI, ENT) caused by S. pneumoniae, H. influenzae, staphylococci, S. pyogenes (group A beta-hemolytic streptococci), E. coli, P. mirabilis, Klebsiella sp, coagulase-negative staph (1).
Minimum Risk LevelNot Available
Health EffectsSome observed adverse reactions ( < 0.1%) include abdominal pain, agranulocytosis, allergic pneumonitis, anaphylaxis, basophilia, biliary lithiasis, bronchospasm, colitis, dyspepsia, epistaxis, flatulence, gallbladder sludge, glycosuria, hematuria, jaundice, leukocytosis, lymphocytosis, monocytosis, nephrolithiasis, palpitations, a decrease in the prothrombin time, renal precipitations, seizures, and serum sickness (RxList, A308).
SymptomsAbdominal pain.
TreatmentIn the case of overdosage, drug concentration would not be reduced by hemodialysis or peritoneal dialysis. There is no specific antidote. Treatment of overdosage should be symptomatic (RxList, A308).
Concentrations
Not Available
DrugBank IDDB01212
HMDB IDHMDB0015343
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDCPD-12294
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkCeftriaxone
Chemspider ID4586394
ChEBI ID29007
PubChem Compound ID5479530
Kegg Compound IDC06683
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis Reference

Monguzzi Riccardo, Menaspace Silvano, Anzaghi Piergiorgio, “Process for the preparation of ceftriaxone.” U.S. Patent US5026843, issued November, 1984.

MSDSLink
General References
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