Ceftriaxone (CED0001152)

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
Description
Ceftriaxone belongs to the beta lactams, a subclass of lactams within the organic compounds. With an average molecular weight of 554.58 g/mol, Ceftriaxone is a heavy molecule. This exogenous organic compound, with the formula C18H18N8O7S3, exists as a solid at room temperature. It is classified as an organoheterocyclic compound. Ceftriaxone serves as an antibacterial drug, an antibacterial agent (PMC13079774), and a beta-lactamase (EC 3.5.2.6) inhibitor. It is used as a treatment for cholera (PMC6195322), endocarditis (PMC1492602), osteomyelitis (PMC5641666), and pneumonia (PMC11522587, PMC9987340). The compound acts as an inhibitor for five recorded protein targets, including Solute carrier family 22 member 6 (SLC22A6), Solute carrier family 22 member 11 (SLC22A11), Organic anion transporter 3 (SLC22A8), and Solute carrier family 15 member 1 (SLC15A1). The compound is found in seven recorded sources, including antibiotics, beta-lactam antibacterials, and healthcare, pharmaceuticals & veterinary products. It is also associated with household cleaning & consumer products such as tobacco pipes and non electric simulated smoking devices, as well as electrical & electronic equipment including antennas, amplifiers, and video games. Recorded exposure routes for Ceftriaxone include oral, intravenous, intramuscular, topical, and inhalation.
Contaminant Type
  • Amide
  • Amine
  • Anti-Bacterial Agent
  • Cephalosporin
  • Drug
  • Ester
  • Ether
  • Human Neurotoxin
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
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
Applications
Biological Roles
Chemical Roles
Organoleptic EffectsNot Available
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
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0a4i-0924040000-11c1c4ec5dc051494298Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-05fr-9774123000-c094d2c5681b0477a4aaNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0apl-3069470000-ea9533b06f6d727b78d9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-05mk-6139010000-862d2dcbf27819f7fdaaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-9043100000-fbf004668a64dff18475Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4r-5691220000-22e1520a7886282ef024Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4l-4940000000-3a6002666fe076cf5ad8Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9100000000-160408d1a7b4d7ae1995Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0013090000-bb4e8b82e0fb04e55aadNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0avi-0466190000-080d962933aef409d2d1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-056u-1944420000-18694b9d401854bf9e80Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0pb9-0910080000-bcb5ef0d6c356695310eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0900000000-803717215c9d04868fa4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-052f-9400000000-75fd909b2cc72f5d0010Not AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
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.
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Minimum Risk LevelNot Available
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).
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
10000.0mg/kg>10000RatLD50OralexperimentalNot Available
6265.0Log mg/kg[3500:11000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
pneumoniais_treatment_forNot AvailablePMC11522587 , PMC9987340
osteomyelitisis_treatment_forNot AvailablePMC5641666
cholerais_treatment_forNot AvailablePMC6195322
Endocarditisis_treatment_forNot AvailablePMC1492602
meningitisis_treatment_forNot AvailablePMC12519648
leptospirosisis_treatment_forNot AvailablePMC6195322
septic arthritisis_treatment_forNot AvailablePMC5641666
Urethritisis_treatment_forNot AvailablePMC10816374
appendicitisis_treatment_forNot AvailablePMC12070908
Exposure Sources
Source IDSourceSectorReference
306AntibioticsHealthcare, pharmaceuticals & veterinary productsNot Available
341Beta-lactam antibacterialsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
566Tobacco PipesHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
597ChemosterilantsAgriculture & land managementNot Available
616Face Mask CosmeticsPersonal care & cosmeticsNot Available
Pathways
1 pathway
Ceftriaxone Drug Metabolism Action Pathway
Ceftriaxone Drug Metabolism Action Pathway
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansPredicted (SEA)0.0778492
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansPredicted (SEA)0.0778492
Solute carrier family 22 member 11 structureClick to view 3D structureSolute carrier family 22 member 11Q9NSA0HumansPredicted (SEA)0.0778492
Click to view 3D structureBeta-lactamaseB2ZTR6Acinetobacter baumanniiPredicted (SEA)0.155698
Click to view 3D structureADC-11D6NSM8Acinetobacter baumanniiPredicted (SEA)0.155698
Peptidoglycan D,D-transpeptidase FtsI structureClick to view 3D structurePeptidoglycan D,D-transpeptidase FtsIQ51504Pseudomonas aeruginosaPredicted (SEA)0.311397
Click to view 3D structureStreptokinase AP10520Streptococcus pyogenes serotype M1Predicted (SEA)34.5651
Click to view 3D structureAmpCQ83TT7Escherichia coliPredicted (SEA)0.311397
Penicillin-binding protein 1A structureClick to view 3D structurePenicillin-binding protein 1AQ07806Pseudomonas aeruginosa (strain ATCC 15692 / PAO1 / 1C / PRS 101 / LMG 12228)Predicted (SEA)0.311397
Click to view 3D structureSHV-5 extended spectrum beta-lactamaseQ6REX6Escherichia coliPredicted (SEA)0.311397
Apoptotic protease-activating factor 1 structureClick to view 3D structureApoptotic protease-activating factor 1O14727HumansPredicted (SEA)13.0787
72 kDa type IV collagenase structureClick to view 3D structure72 kDa type IV collagenaseP08253HumansPredicted (SEA)506.02
Speckle-type POZ protein structureClick to view 3D structureSpeckle-type POZ proteinO43791HumansPredicted (SEA)1.55698
Click to view 3D structureBeta-lactamase ACC-4A4ZYU9Escherichia coliPredicted (SEA)0.778492
26S proteasome non-ATPase regulatory subunit 14 structureClick to view 3D structure26S proteasome non-ATPase regulatory subunit 14O00487HumansPredicted (SEA)14.7914
Excitatory amino acid transporter 2 structureClick to view 3D structureExcitatory amino acid transporter 2P43004HumansPredicted (SEA)18.9174
Carboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1 structureClick to view 3D structureCarboxy-terminal domain RNA polymerase II polypeptide A small phosphatase 1Q9GZU7HumansPredicted (SEA)283.371
D-amino-acid oxidase structureClick to view 3D structureD-amino-acid oxidaseP14920HumansPredicted (SEA)29.5049
Alpha-synuclein structureClick to view 3D structureAlpha-synucleinP37840HumansPredicted (SEA)47.488
Click to view 3D structurePER-2 beta-lactamaseA2RP81Citrobacter freundiiPredicted (SEA)0.856341
Small ubiquitin-related modifier 1 structureClick to view 3D structureSmall ubiquitin-related modifier 1P63165HumansPredicted (SEA)832.208
Click to view 3D structureProbable nicotinate-nucleotide adenylyltransferaseP65502Staphylococcus aureus (strain N315)Predicted (SEA)438.135
DNA (cytosine-5)-methyltransferase 1 structureClick to view 3D structureDNA (cytosine-5)-methyltransferase 1P26358HumansPredicted (SEA)1207.52
Click to view 3D structureEfflux transporterQ3S5C3Salmonella newportPredicted (SEA)1.01204
Click to view 3D structureClass C beta-lactamase CMY-36Q48435Klebsiella pneumoniaePredicted (SEA)1.01204
Solute carrier family 15 member 1 structureClick to view 3D structureSolute carrier family 15 member 1P46059HumansKnownNot Available
Solute carrier family 22 member 11 structureClick to view 3D structureSolute carrier family 22 member 11Q9NSA0HumansKnownNot Available
Click to view 3D structureSolute carrier family 22 member 6Q4U2R8HumansKnownNot Available
Click to view 3D structureOrganic anion transporter 3Q8TCC7HumansKnownNot Available
Concentrations
Not Available
External Links
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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