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Identification
NameCeftriaxone
Accession NumberDB01212  (APRD00395)
TypeSmall Molecule
GroupsApproved
Description

A broad-spectrum cephalosporin antibiotic with a very long half-life and high penetrability to meninges, eyes and inner ears. [PubChem]

Structure
Thumb
Synonyms
(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
Cefatriaxone
Ceftriaxona
Ceftriaxonum
Ceftriazone
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ceftriaxone and Dextroseinjection, solution1 g/50mLintravenousB. Braun Medical Inc.2005-04-20Not applicableUs
Ceftriaxone and Dextroseinjection, solution2 g/50mLintravenousB. Braun Medical Inc.2005-04-20Not applicableUs
Ceftriaxone for Injectionpowder for solution100 gintravenousFresenius Kabi Canada Ltd2014-06-05Not applicableCanada
Ceftriaxone for Injectionpowder for solution10.0 gintramuscular; intravenousFresenius Kabi Canada LtdNot applicableNot applicableCanada
Ceftriaxone for Injectionpowder for solution2.0 gintramuscular; intravenousFresenius Kabi Canada LtdNot applicableNot applicableCanada
Ceftriaxone for Injectionpowder for solution0.50 gintramuscular; intravenousFresenius Kabi Canada LtdNot applicableNot applicableCanada
Ceftriaxone for Injectionpowder for solution1 gintramuscular; intravenousFresenius Kabi Canada LtdNot applicableNot applicableCanada
Ceftriaxone for Injectionpowder for solution0.25 gintramuscular; intravenousFresenius Kabi Canada LtdNot applicableNot applicableCanada
Ceftriaxone for Injection USPpowder for solution2.0 gintramuscular; intravenousSandoz Canada Incorporated2007-02-23Not applicableCanada
Ceftriaxone for Injection USPpowder for solution1 gintramuscular; intravenousSandoz Canada Incorporated2007-02-23Not applicableCanada
Ceftriaxone for Injection USPpowder for solution0.25 gintramuscular; intravenousSandoz Canada Incorporated2007-02-23Not applicableCanada
Ceftriaxone for Injection USPpowder for solution10.0 gintramuscular; intravenousHospira Healthcare Corporation2007-11-30Not applicableCanada
Ceftriaxone for Injection USPpowder for solution2.0 gintramuscular; intravenousHospira Healthcare Corporation2007-11-30Not applicableCanada
Ceftriaxone for Injection USPpowder for solution250 mgintramuscular; intravenousHospira Healthcare Corporation2008-04-10Not applicableCanada
Ceftriaxone for Injection USPpowder for solution10.0 gintramuscular; intravenousSandoz Canada Incorporated2007-02-23Not applicableCanada
Ceftriaxone for Injection USPpowder for solution1 gintramuscular; intravenousHospira Healthcare Corporation2007-11-30Not applicableCanada
Ceftriaxone Sodium for Injectionpowder for solution2 gintramuscular; intravenousNovopharm LimitedNot applicableNot applicableCanada
Ceftriaxone Sodium for Injectionpowder for solution10 gintramuscular; intravenousTeva Canada Limited2007-09-14Not applicableCanada
Ceftriaxone Sodium for Injectionpowder for solution0.25 gintramuscular; intravenousNovopharm LimitedNot applicableNot applicableCanada
Ceftriaxone Sodium for Injectionpowder for solution1 gintramuscular; intravenousTeva Canada Limited2007-09-14Not applicableCanada
Ceftriaxone Sodium for Injection BPpowder for solution2 gintramuscular; intravenousSterimax Inc2011-01-31Not applicableCanada
Ceftriaxone Sodium for Injection BPpowder for solution10 gintravenousSterimax Inc2011-03-21Not applicableCanada
Ceftriaxone Sodium for Injection BPpowder for solution1 gintramuscular; intravenousSterimax Inc2011-03-21Not applicableCanada
Ceftriaxone Sodium for Injection BPpowder for solution250 mgintramuscular; intravenousSterimax Inc2011-04-23Not applicableCanada
Ceftriaxone Sodium for Injection BPpowder for solution500 mgintramuscular; intravenousSterimax IncNot applicableNot applicableCanada
Ceftriaxone Sodium for Injection, BPpowder for solution500 mgintramuscular; intravenousHospira Healthcare CorporationNot applicableNot applicableCanada
Ceftriaxone Sodium for Injection, BPpowder for solution2 gintramuscular; intravenousHospira Healthcare Corporation2007-04-04Not applicableCanada
Ceftriaxone Sodium for Injection, BPpowder for solution1 gintramuscular; intravenousHospira Healthcare Corporation2007-04-04Not applicableCanada
Ceftriaxone Sodium for Injection, BPpowder for solution10 gintramuscular; intravenousHospira Healthcare Corporation2007-04-30Not applicableCanada
Ceftriaxone Sodium for Injection, BPpowder for solution250 mgintramuscular; intravenousHospira Healthcare Corporation2007-04-30Not applicableCanada
Rocephin Inj 10gm/vialpowder for solution10 gintravenousHoffmann La Roche Limited1990-12-312009-07-29Canada
Rocephin Pws 1gm/vialpowder for solution1 gintramuscular; intravenousHoffmann La Roche Limited1987-12-312011-10-17Canada
Rocephin Pws 2gm/vialpowder for solution2 gintramuscular; intravenousHoffmann La Roche Limited1987-12-312009-07-29Canada
Rocephin Pws Inj 0.25gm/vialpowder for solution250 mgintramuscular; intravenousHoffmann La Roche Limited1987-12-312012-06-20Canada
Rocephin Pws Inj 1gm/vialpowder for solution1 gintravenousHoffmann La Roche Limited1991-12-312003-07-30Canada
Sandoz Ceftriaxonepowder for solution2 gintramuscular; intravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Sandoz Ceftriaxonepowder for solution1 gintramuscular; intravenousSandoz Canada IncorporatedNot applicableNot applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ceftriaxoneinjection, powder, for solution250 mg/1intramuscularREMEDYREPACK INC.2013-12-17Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intramuscular; intravenousWG Critical Care, LLC2008-07-24Not applicableUs
Ceftriaxoneinjection, powder, for solution500 mg/1intramuscular; intravenousWG Critical Care, LLC2008-07-24Not applicableUs
Ceftriaxoneinjection, powder, for solution250 mg/1intramuscular; intravenousApotex Corporation2005-08-02Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intramuscular; intravenousWockhardt Limited2006-05-12Not applicableUs
Ceftriaxoneinjection, powder, for solution500 mg/1intramuscular; intravenousLupin Pharmaceuticals, Inc.2009-06-01Not applicableUs
Ceftriaxoneinjection, powder, for solution2 g/1intramuscular; intravenousAPP Pharmaceuticals , LLC2011-06-20Not applicableUs
Ceftriaxoneinjection, powder, for solution250 mg/1intramuscularREMEDYREPACK INC.2014-09-15Not applicableUs
Ceftriaxoneinjection, powder, for solution2 g/1intramuscular; intravenousCephazone Pharma LLC2008-07-15Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intramuscular; intravenousLupin Pharmaceuticals, Inc.2009-06-01Not applicableUs
Ceftriaxoneinjection, powder, for solution250 mg/1intramuscularREMEDYREPACK INC.2013-10-15Not applicableUs
Ceftriaxoneinjection, solution2 g/50mLintravenousBaxter Healthcare Corporation2005-08-23Not applicableUs
Ceftriaxoneinjection, powder, for solution250 mg/1intramuscular; intravenousRebel Distributors Corp2007-04-12Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intramuscular; intravenousBaxter Healthcare Corporation2003-09-30Not applicableUs
Ceftriaxoneinjection, powder, for solution2 g/1intramuscular; intravenousApotex Corporation2005-08-02Not applicableUs
Ceftriaxoneinjection, powder, for solution2 g/1intramuscular; intravenousWockhardt Limited2007-04-12Not applicableUs
Ceftriaxoneinjection, powder, for solution250 mg/1intramuscular; intravenousLupin Pharmaceuticals, Inc.2009-06-01Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intramuscular; intravenousAPP Pharmaceuticals , LLC2011-06-20Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intramuscular; intravenousCephazone Pharma LLC2008-07-15Not applicableUs
Ceftriaxoneinjection, solution1 g/50mLintravenousBaxter Healthcare Corporation2005-08-23Not applicableUs
Ceftriaxoneinjection, powder, for solution500 mg/1intramuscular; intravenousRebel Distributors Corp2007-04-12Not applicableUs
Ceftriaxoneinjection, powder, for solution2 g/20mLintravenousApotex Corporation2005-08-02Not applicableUs
Ceftriaxoneinjection, powder, for solution500 mg/1intramuscular; intravenousWockhardt Limited2007-04-12Not applicableUs
Ceftriaxoneinjection, powder, for solution100 g/1intravenousSamson Medical Technologies, LLC2014-06-30Not applicableUs
Ceftriaxoneinjection, powder, for solution500 mg/1intramuscular; intravenousAPP Pharmaceuticals , LLC2011-06-20Not applicableUs
Ceftriaxoneinjection, powder, for solution2 g/1intramuscular; intravenousCephazone Pharma LLC2008-07-15Not applicableUs
Ceftriaxoneinjection, powder, for solution250 mg/1intramuscular; intravenousWest Ward Pharmaceuticals Corp2008-01-10Not applicableUs
Ceftriaxoneinjection, powder, for solution10 g/100mLintravenousSagent Pharmaceuticals2009-11-05Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/10mLintravenousApotex Corporation2005-08-02Not applicableUs
Ceftriaxoneinjection, powder, for solution250 mg/1intramuscular; intravenousWockhardt Limited2007-04-12Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intramuscular; intravenousWockhardt USA LLC.2006-05-12Not applicableUs
Ceftriaxoneinjection, powder, for solution250 mg/1intramuscular; intravenousAPP Pharmaceuticals, LLC2006-03-08Not applicableUs
Ceftriaxoneinjection, powder, for solution100 mg/mLintravenousApotex Corporation2005-08-02Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intramuscular; intravenousCephazone Pharma LLC2008-07-15Not applicableUs
Ceftriaxoneinjection, powder, for solution2 g/1intramuscular; intravenousSagent Pharmaceuticals2009-11-05Not applicableUs
Ceftriaxoneinjection, powder, for solution2 g/1intramuscular; intravenousApotex Corporation2005-08-02Not applicableUs
Ceftriaxoneinjection, powder, for solution2 g/1intramuscular; intravenousWockhardt USA LLC.2007-04-12Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intramuscular; intravenousProficient Rx LP2009-06-01Not applicableUs
Ceftriaxoneinjection, powder, for solution100 mg/mLintravenousApotex Corporation2005-08-02Not applicableUs
Ceftriaxoneinjection, powder, for solution500 mg/1intramuscular; intravenousCephazone Pharma LLC2008-07-15Not applicableUs
Ceftriaxoneinjection, powder, for solution500 mg/1intramuscular; intravenousCardinal Health2009-07-22Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/10mLintramuscularREMEDYREPACK INC.2013-06-102016-04-05Us
Ceftriaxoneinjection, powder, for solution500 mg/1intramuscular; intravenousWest Ward Pharmaceuticals Corp2008-01-10Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intramuscular; intravenousApotex Corporation2005-08-02Not applicableUs
Ceftriaxoneinjection, powder, for solution500 mg/1intramuscular; intravenousWockhardt USA LLC.2007-04-12Not applicableUs
Ceftriaxoneinjection, powder, for solution250 mg/1intramuscularREMEDYREPACK INC.2015-08-19Not applicableUs
Ceftriaxoneinjection, powder, for solution2 g/1intravenousHospira, Inc.2012-08-20Not applicableUs
Ceftriaxoneinjection, powder, for solution250 mg/1intramuscular; intravenousCephazone Pharma LLC2008-07-15Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intramuscularREMEDYREPACK INC.2013-06-13Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intramuscular; intravenousWest Ward Pharmaceuticals Corp2008-01-10Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intramuscular; intravenousSagent Pharmaceuticals2009-11-05Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intravenousHospira, Inc.2012-08-20Not applicableUs
Ceftriaxoneinjection, powder, for solution10 g/1intravenousLupin Pharmaceuticals, Inc.2006-09-12Not applicableUs
Ceftriaxoneinjection, powder, for solution10 g/100mLintravenousWG Critical Care, LLC2008-07-24Not applicableUs
Ceftriaxoneinjection, powder, for solution2 g/1intramuscular; intravenousWest Ward Pharmaceuticals Corp2008-01-10Not applicableUs
Ceftriaxoneinjection, powder, for solution500 mg/1intramuscular; intravenousSagent Pharmaceuticals2009-11-05Not applicableUs
Ceftriaxoneinjection, powder, for solution500 mg/1intramuscular; intravenousApotex Corporation2005-08-02Not applicableUs
Ceftriaxoneinjection, powder, for solution250 mg/1intramuscular; intravenousWockhardt USA LLC.2007-04-12Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intramuscularREMEDYREPACK INC.2015-07-22Not applicableUs
Ceftriaxoneinjection, powder, for solution2 g/1intramuscular; intravenousWG Critical Care, LLC2008-07-24Not applicableUs
Ceftriaxoneinjection, powder, for solution10 g/100mLintravenousWest ward Pharmaceutical Corp2009-08-06Not applicableUs
Ceftriaxoneinjection, powder, for solution250 mg/1intramuscular; intravenousApotex Corporation2005-08-02Not applicableUs
Ceftriaxoneinjection, powder, for solution10 g/1intravenousAPP Pharmaceuticals , LLC2011-06-20Not applicableUs
Ceftriaxoneinjection, powder, for solution1 g/1intravenousREMEDYREPACK INC.2015-06-01Not applicableUs
Ceftriaxoneinjection, powder, for solution10 g/100mLintravenousAGILA SPECIALTIES PRIVATE LIMITED2013-01-07Not applicableUs
Ceftriaxoneinjection, powder, for solution2 g/1intramuscular; intravenousLupin Pharmaceuticals, Inc.2009-06-01Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution250 mg/1intramuscular; intravenousCardinal Health2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution500 mg/1intramuscular; intravenousSandoz Inc2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution1 g/1intramuscular; intravenousHospira, Inc2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution500 mg/1intramuscular; intravenousRebel Distributors Corp2005-08-02Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution1 g/1intramuscular; intravenousSandoz Inc2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution2 g/1intravenousCardinal Health2005-05-03Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution1 g/1intramuscular; intravenousCardinal Health2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution250 mg/1intramuscular; intravenousSandoz Inc2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution250 mg/1intramuscular; intravenousCardinal Health2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution1 g/1intravenousREMEDYREPACK INC.2013-08-21Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution500 mg/1intramuscular; intravenousHospira, Inc2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution2 g/1intramuscular; intravenousSandoz Inc2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution250 mg/1intramuscular; intravenousHospira, Inc2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution1 g/1intramuscular; intravenousSandoz Inc2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution1 g/1intramuscular; intravenousCardinal Health2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution500 mg/1intravenousREMEDYREPACK INC.2013-05-06Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution500 mg/1intramuscular; intravenousSandoz Inc2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution250 mg/1intramuscular; intravenousCardinal Health2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution2 g/1intravenousHospira, Inc2005-05-03Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution1 g/1intramuscular; intravenousCardinal Health2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution250 mg/1intramuscular; intravenousPhysicians Total Care, Inc.2006-05-12Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution2 g/1intramuscular; intravenousHospira, Inc2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution250 mg/1intramuscular; intravenousSandoz Inc2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution500 mg/1intramuscular; intravenousPhysicians Total Care, Inc.2008-01-15Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution10 g/100mLintravenousHospira, Inc2005-05-17Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution10 g/100mLintravenousSandoz Inc2005-05-17Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution2 g/1intravenousCardinal Health2005-05-03Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution1 g/1intravenousREMEDYREPACK INC.2014-02-20Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution1 g/1intravenousHospira, Inc2005-05-03Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution1 g/1intramuscular; intravenousRebel Distributors Corp2005-08-02Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution2 g/1intramuscular; intravenousSandoz Inc2005-05-09Not applicableUs
Ceftriaxone Sodiuminjection, powder, for solution1 g/1intravenousCardinal Health2005-05-03Not applicableUs
Rocephininjection, powder, for solution1 g/1intramuscular; intravenousGenentech, Inc.1993-08-132016-02-28Us
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AcantexRoche
BiotraksonBioton
RocephineRoche
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Ceftriaxone sodium
ThumbNot applicableDBSALT001213
Categories
UNII75J73V1629
CAS number73384-59-5
WeightAverage: 554.58
Monoisotopic: 554.04605704
Chemical FormulaC18H18N8O7S3
InChI KeyInChIKey=VAAUVRVFOQPIGI-SPQHTLEESA-N
InChI
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
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
SMILES
[H][C@]12SCC(CSC3=NC(=O)C(=O)NN3C)=C(N1C(=O)[[email protected]]2NC(=O)C(=N/OC)\C1=CSC(N)=N1)C(O)=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as cephalosporins. These are compounds containing a 1,2-thiazine fused to a 2-azetidinone to for a oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid moiety or a derivative thereof.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassLactams
Sub ClassBeta lactams
Direct ParentCephalosporins
Alternative Parents
Substituents
  • Cephalosporin
  • N-acyl-alpha amino acid or derivatives
  • Alpha-amino acid or derivatives
  • Alkylarylthioether
  • 2,4-disubstituted 1,3-thiazole
  • 1,2,4-triazine
  • Triazine
  • Primary aromatic amine
  • Meta-thiazine
  • Heteroaromatic compound
  • Thiazole
  • Tertiary carboxylic acid amide
  • Azole
  • Tertiary amine
  • Secondary carboxylic acid amide
  • Oxime ether
  • Carboxamide group
  • Azetidine
  • Azacycle
  • Dialkylthioether
  • Sulfenyl compound
  • Hemithioaminal
  • Thioether
  • Monocarboxylic acid or derivatives
  • Enamine
  • Carboxylic acid
  • Carboxylic acid derivative
  • Carboxylic acid amide
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Pharmacology
IndicationFor 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
PharmacodynamicsCeftriaxone is a cephalosporin/cephamycin beta-lactam antibiotic used in the treatment of bacterial infections caused by susceptible, usually gram-positive, organisms. Ceftriaxone has in vitro activity against gram-positive and gram-negative aerobic and anaerobic bacteria. The bactericidal activity of Ceftriaxone results from the inhibition of cell wall synthesis and is mediated through Ceftriaxone binding to penicillin binding proteins (PBPs). Ceftriaxone is stable against hydrolysis by a variety of beta-lactamases, including penicillinases, and cephalosporinases and extended spectrum beta-lactamases.
Mechanism of actionCeftriaxone 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.
Related Articles
AbsorptionNot Available
Volume of distribution
  • 5.78 to 13.5 L
Protein binding95%
MetabolismNot Available
Route of eliminationThirty-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 life5.8-8.7 hours
Clearance
  • 0.58 – 1.45 L/h [healthy adults receiving 0.15-3 g of CEFTRIAXONE]
ToxicityNot Available
Affected organisms
  • Enteric bacteria and other eubacteria
  • Neisseria meningitidis
  • Haemophilus influenzae
  • Neisseria gonorrhoeae
  • Escherichia coli
  • Salmonella typhi
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption-0.952
Blood Brain Barrier-0.9748
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.726
P-glycoprotein inhibitor INon-inhibitor0.8942
P-glycoprotein inhibitor IIInhibitor0.5293
Renal organic cation transporterNon-inhibitor0.8024
CYP450 2C9 substrateNon-substrate0.7943
CYP450 2D6 substrateNon-substrate0.8172
CYP450 3A4 substrateSubstrate0.5374
CYP450 1A2 substrateNon-inhibitor0.7538
CYP450 2C9 inhibitorNon-inhibitor0.7088
CYP450 2D6 inhibitorNon-inhibitor0.8666
CYP450 2C19 inhibitorNon-inhibitor0.7034
CYP450 3A4 inhibitorInhibitor0.6432
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5509
Ames testNon AMES toxic0.7336
CarcinogenicityNon-carcinogens0.8392
BiodegradationNot ready biodegradable0.9968
Rat acute toxicity2.1681 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9865
hERG inhibition (predictor II)Non-inhibitor0.6145
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Injection, powder, for solutionintramuscular1 g/10mL
Injection, powder, for solutionintramuscular1 g/1
Injection, powder, for solutionintramuscular250 mg/1
Injection, powder, for solutionintramuscular; intravenous2 g/1
Injection, powder, for solutionintramuscular; intravenous250 mg/1
Injection, powder, for solutionintramuscular; intravenous500 mg/1
Injection, powder, for solutionintravenous1 g/10mL
Injection, powder, for solutionintravenous10 g/100mL
Injection, powder, for solutionintravenous10 g/1
Injection, powder, for solutionintravenous100 g/1
Injection, powder, for solutionintravenous100 mg/mL
Injection, powder, for solutionintravenous2 g/20mL
Injection, solutionintravenous1 g/50mL
Injection, solutionintravenous2 g/50mL
Powder for solutionintramuscular; intravenous0.50 g
Powder for solutionintravenous100 g
Powder for solutionintramuscular; intravenous0.25 g
Powder for solutionintramuscular; intravenous10.0 g
Powder for solutionintramuscular; intravenous2.0 g
Injection, powder, for solutionintravenous1 g/1
Injection, powder, for solutionintravenous2 g/1
Injection, powder, for solutionintravenous500 mg/1
Powder for solutionintramuscular; intravenous10 g
Powder for solutionintravenous10 g
Powder for solutionintramuscular; intravenous1 g
Powder for solutionintramuscular; intravenous2 g
Powder for solutionintramuscular; intravenous250 mg
Powder for solutionintramuscular; intravenous500 mg
Injection, powder, for solutionintramuscular; intravenous1 g/1
Powder for solutionintravenous1 g
Prices
Unit descriptionCostUnit
Rocephin 10 gm vial478.32USD vial
Rocephin 2 gm vial97.5USD vial
Ceftriaxone 2 gm piggyback94.17USD each
Rocephin 1 gm Solution Vial65.53USD vial
Rocephin 1 gm vial62.02USD vial
Ceftriaxone For Injection Usp 2 g/vial49.13USD vial
Ceftriaxone 1 gm piggyback47.91USD each
Rocephin 1 g/vial40.2USD vial
Ceftriaxone 10 gm vial36.25USD vial
Ceftriaxone 2 gm-d5w bag27.84USD each
Ceftriaxone For Injection Usp 1 g/vial24.93USD vial
Chloromycetin 1 g/vial20.33USD vial
Ceftriaxone 2 gm vial17.04USD vial
Ceftriaxone 1 gm-d5w bag13.92USD each
Rocephin 0.25 g/vial12.71USD vial
Ceftriaxone For Injection Usp 0.25 g/vial7.88USD vial
Ceftriaxone 1 gm vial7.56USD vial
Ceftriaxone sodium powder1.84USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point>155 °CNot Available
logP-1.7Not Available
Caco2 permeability-6.88ADME Research, USCD
Predicted Properties
PropertyValueSource
Water Solubility0.105 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity128.47 m3·mol-1ChemAxon
Polarizability51.47 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

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

US5026843
General ReferencesNot Available
External Links
ATC CodesJ01DD04J01DD54
AHFS Codes
  • 08:12.06.12
PDB EntriesNot Available
FDA labelDownload (211 KB)
MSDSDownload (53.3 KB)
Interactions
Drug Interactions
Drug
AcenocoumarolCeftriaxone may increase the anticoagulant activities of Acenocoumarol.
AmikacinCeftriaxone may increase the nephrotoxic activities of Amikacin.
ArbekacinCeftriaxone may increase the nephrotoxic activities of Arbekacin.
Calcium AcetateThe risk or severity of adverse effects can be increased when Calcium Acetate is combined with Ceftriaxone.
Calcium ChlorideThe risk or severity of adverse effects can be increased when Calcium Chloride is combined with Ceftriaxone.
Calcium gluconateThe risk or severity of adverse effects can be increased when Calcium gluconate is combined with Ceftriaxone.
DicoumarolCeftriaxone may increase the anticoagulant activities of Dicoumarol.
FramycetinCeftriaxone may increase the nephrotoxic activities of Framycetin.
GentamicinCeftriaxone may increase the nephrotoxic activities of Gentamicin.
KanamycinCeftriaxone may increase the nephrotoxic activities of Kanamycin.
NeomycinCeftriaxone may increase the nephrotoxic activities of Neomycin.
NetilmicinCeftriaxone may increase the nephrotoxic activities of Netilmicin.
Picosulfuric acidThe therapeutic efficacy of Sodium picosulfate can be decreased when used in combination with Ceftriaxone.
ProbenecidThe serum concentration of Ceftriaxone can be increased when it is combined with Probenecid.
RibostamycinCeftriaxone may increase the nephrotoxic activities of Ribostamycin.
SpectinomycinCeftriaxone may increase the nephrotoxic activities of Spectinomycin.
StreptomycinCeftriaxone may increase the nephrotoxic activities of Streptomycin.
TobramycinCeftriaxone may increase the nephrotoxic activities of Tobramycin.
WarfarinCeftriaxone may increase the anticoagulant activities of Warfarin.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Streptococcus pneumoniae (strain ATCC BAA-255 / R6)
Pharmacological action
yes
Actions
inhibitor
General Function:
Penicillin binding
Specific Function:
Not Available
Gene Name:
penA
Uniprot ID:
P0A3M6
Molecular Weight:
73872.305 Da
References
  1. Tomberg J, Unemo M, Davies C, Nicholas RA: Molecular and structural analysis of mosaic variants of penicillin-binding protein 2 conferring decreased susceptibility to expanded-spectrum cephalosporins in Neisseria gonorrhoeae: role of epistatic mutations. Biochemistry. 2010 Sep 21;49(37):8062-70. doi: 10.1021/bi101167x. [PubMed:20704258 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular Weight:
59970.945 Da
References
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
References
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inducer
General Function:
Manganese ion binding
Specific Function:
This enzyme has 2 functions: it catalyzes the production of glutamine and 4-aminobutanoate (gamma-aminobutyric acid, GABA), the latter in a pyridoxal phosphate-independent manner (By similarity). Essential for proliferation of fetal skin fibroblasts.
Gene Name:
GLUL
Uniprot ID:
P15104
Molecular Weight:
42064.15 Da
References
  1. Tumani H, Smirnov A, Barchfeld S, Olgemoller U, Maier K, Lange P, Bruck W, Nau R: Inhibition of glutamine synthetase in rabbit pneumococcal meningitis is associated with neuronal apoptosis in the dentate gyrus. Glia. 2000 Mar;30(1):11-8. [PubMed:10696140 ]
  2. Verma R, Mishra V, Sasmal D, Raghubir R: Pharmacological evaluation of glutamate transporter 1 (GLT-1) mediated neuroprotection following cerebral ischemia/reperfusion injury. Eur J Pharmacol. 2010 Jul 25;638(1-3):65-71. doi: 10.1016/j.ejphar.2010.04.021. Epub 2010 Apr 24. [PubMed:20423712 ]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
no
Actions
other/unknown
General Function:
Toxic substance binding
Specific Function:
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
References
  1. Gulian JM, Dalmasso C, Gonard V: Interaction of beta-lactam antibiotics on bilirubin-albumin complex: comparison by three methods, total bilirubin, unbound bilirubin and erythrocyte-bound bilirubin. Chemotherapy. 1990;36(2):91-7. [PubMed:2311445 ]
  2. Nerli B, Farruggia B, Pico G: A comparative study of the binding characteristics of ceftriaxone, cefoperazone and cefsulodin to human serum albumin. Biochem Mol Biol Int. 1996 Nov;40(4):823-31. [PubMed:8950041 ]
  3. Robertson A, Fink S, Karp W: Effect of cephalosporins on bilirubin-albumin binding. J Pediatr. 1988 Feb;112(2):291-4. [PubMed:3339510 ]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Proton-dependent oligopeptide secondary active transmembrane transporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides. May constitute a major route for the absorption of protein digestion end-products.
Gene Name:
SLC15A1
Uniprot ID:
P46059
Molecular Weight:
78805.265 Da
References
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Peptide:proton symporter activity
Specific Function:
Proton-coupled intake of oligopeptides of 2 to 4 amino acids with a preference for dipeptides.
Gene Name:
SLC15A2
Uniprot ID:
Q16348
Molecular Weight:
81782.77 Da
References
  1. Luckner P, Brandsch M: Interaction of 31 beta-lactam antibiotics with the H+/peptide symporter PEPT2: analysis of affinity constants and comparison with PEPT1. Eur J Pharm Biopharm. 2005 Jan;59(1):17-24. [PubMed:15567297 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS) (By similarity). Mediates the sodium-in...
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular Weight:
61815.78 Da
References
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604 ]
  2. Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [PubMed:12005172 ]
  3. Jariyawat S, Sekine T, Takeda M, Apiwattanakul N, Kanai Y, Sophasan S, Endou H: The interaction and transport of beta-lactam antibiotics with the cloned rat renal organic anion transporter 1. J Pharmacol Exp Ther. 1999 Aug;290(2):672-7. [PubMed:10411577 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
Molecular Weight:
59855.585 Da
References
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604 ]
  2. Jung KY, Takeda M, Shimoda M, Narikawa S, Tojo A, Kim DK, Chairoungdua A, Choi BK, Kusuhara H, Sugiyama Y, Sekine T, Endou H: Involvement of rat organic anion transporter 3 (rOAT3) in cephaloridine-induced nephrotoxicity: in comparison with rOAT1. Life Sci. 2002 Mar 8;70(16):1861-74. [PubMed:12005172 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Sodium-independent organic anion transmembrane transporter activity
Specific Function:
Mediates saturable uptake of estrone sulfate, dehydroepiandrosterone sulfate and related compounds.
Gene Name:
SLC22A11
Uniprot ID:
Q9NSA0
Molecular Weight:
59970.945 Da
References
  1. Takeda M, Babu E, Narikawa S, Endou H: Interaction of human organic anion transporters with various cephalosporin antibiotics. Eur J Pharmacol. 2002 Mar 8;438(3):137-42. [PubMed:11909604 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13