U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H18N8O7S3
Molecular Weight 554.58
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFTRIAXONE

SMILES

CO\N=C(/C(=O)N[C@H]1[C@H]2SCC(CSC3=NC(=O)C(=O)NN3C)=C(N2C1=O)C(O)=O)C4=CSC(N)=N4

InChI

InChIKey=VAAUVRVFOQPIGI-SPQHTLEESA-N
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

HIDE SMILES / InChI

Description

Ceftriaxone is a broad-spectrum cephalosporin antibiotic with a very long half-life. Ceftriaxone is a bactericidal agent that acts by inhibition of bacterial cell wall synthesis. Ceftriaxone has activity in the presence of some beta-lactamases, both penicillinases and cephalosporinases, of Gram-negative and Gram-positive bacteria. It is approved for the treatment of lower respiratory tract infections, acute bacterial otitis media, skin infections, urinary tract infections, pelvic inflammatory disease, bacterial septicemia, bone and joint infections, intraabdominal infection, meningitis, and surgical prophylaxis. Common adverse reactions include erythema multiforme, Stevens-Johnson syndrome, toxic epidermal necrolysis, pseudomembranous enterocolitis, hemolytic anemia, hypersensitivity reaction, kernicterus, renal failure, and lung injury. Vancomycin, amsacrine, aminoglycosides, and fluconazole are incompatible with Ceftriaxone in admixtures. Precipitation of Ceftriaxone-calcium can occur when Ceftriaxone for Injection is mixed with calcium-containing solutions in the same intravenous administration line.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Ceftriaxone-associated nephrolithiasis.
1990
Ceftriaxone-induced cholelithiasis.
1991 Nov 1
Reversible symptomatic biliary obstruction associated with ceftriaxone pseudolithiasis.
1991 Sep
Disappearing "gallstones": biliary pseudolithiasis complicating ceftriaxone therapy.
1992 Aug
Ceftriaxone-associated gallbladder pseudolithiasis: report of one case.
2004 Sep-Oct
Ultrasonographic findings in ceftriaxone: associated biliary sludge and pseudolithiasis in children.
2005 Feb
[Pseudotumor cerebri probably due to ceftriaxone].
2005 Mar
Ceftriaxone-induced hemolytic anemia and hepatitis in an adolescent with hemoglobin SC disease.
2005 May
Ceftriaxone-induced symptomatic pseudolithiasis mimicking ICP elevation.
2005 May
[Cholelithiasis associated with the use of ceftriaxone].
2005 Nov-Dec
Nephrolithiasis in a child with acute pyelonephritis. Ceftriaxone-induced nephrolithiasis and biliary pseudolithiasis.
2005 Oct
Ceftriaxone-associated biliary pseudolithiasis in children.
2006 Jun
Acute necrotizing cholecystitis: a rare complication of ceftriaxone-associated pseudolithiasis.
2006 Jun
Ceftriaxone-related hemolysis and acute renal failure.
2006 May
Delirium induced by clarithromycin in a patient with community-acquired pneumonia.
2006 Sep
One center's experience: the serology and drugs associated with drug-induced immune hemolytic anemia--a new paradigm.
2007 Apr
Minocycline delays but does not attenuate the course of experimental autoimmune encephalomyelitis in Streptococcus pneumoniae-infected mice.
2007 Jan
[Serious side effects of frequently used antibiotics in childhood: biliary sludge or stones induced by ceftriaxone and thrombocytopenia induced by co-trimoxazole].
2007 Jun 9
Ceftriaxone associated nephrolithiasis: a prospective study in 284 children.
2007 May
Acute interstitial nephritis associated with coadministration of vancomycin and ceftriaxone: case series and review of the literature.
2007 Oct
Biliary precipitation during ceftriaxone therapy: frequency and risk factors.
2007 Oct-Dec
Success of ampicillin plus ceftriaxone rescue therapy for a relapse of Enterococcus faecalis native-valve endocarditis and in vitro data on double beta-lactam activity.
2008
Effects of prior effective therapy on the efficacy of daptomycin and ceftriaxone for the treatment of community-acquired pneumonia.
2008 Apr 15
The beta-lactam antibiotic ceftriaxone inhibits physical dependence and abstinence-induced withdrawal from cocaine, amphetamine, methamphetamine, and clorazepate in planarians.
2008 Apr 28
Ceftriaxone induced hemolysis complicated by acute renal failure.
2008 Jan
Intravascular haemolysis in a patient on ceftriaxone with demonstration of anticeftriaxone antibodies.
2008 Jun
Hemolytic anemia from ceftriaxone in an elderly patient: a case report.
2008 Oct
Randomised trial of oral versus sequential intravenous/oral cephalosporins in children with pyelonephritis.
2008 Sep
Acute cholecystitis caused by ceftriaxone stones in an adult.
2009
Normal pressure hydrocephalus or neuroborreliosis?
2009
[Acute pancreatitis associated with the administration of ceftriaxone in an adult patient].
2009 Apr
Intravenous ceftriaxone and calcium in the neonate: assessing the risk for cardiopulmonary adverse events.
2009 Apr
Ceftriaxone-induced acute reversible encephalopathy in a patient treated for a urinary tract infection.
2009 Feb
Fever, pain, and a limp: a case of a psoas and spinal epidural abscess caused by methicillin-resistant Staphylococcus aureus in a diabetic patient.
2009 Jan
[When an antibiotic becomes toxic].
2009 Jan
Short-term rifampicin pretreatment reduces inflammation and neuronal cell death in a rabbit model of bacterial meningitis.
2009 Jul
Adverse drug reactions in medical intensive care unit of a tertiary care hospital.
2009 Jul
Upregulation of GLT1 attenuates cue-induced reinstatement of cocaine-seeking behavior in rats.
2009 Jul 22
Ceftriaxone-induced toxic hepatitis.
2009 Jun 7
Ceftriaxone-vancomycin drug toxicity reduction by VRP 1020 in Mus musculus mice.
2009 May
Severe ceftriaxone-induced hemolysis complicated by diffuse cerebral ischemia in a child with sickle cell disease.
2009 Nov
Sonographic assessment of ceftriaxone-associated biliary pseudolithiasis in Chinese children.
2010
Transfusion med illustrated: Ceftriaxone-induced acute hemolytic anemia.
2010 Aug
Ceftriaxone-associated cholelithiasis: 30 min drip infusion versus bolus injection.
2010 Dec
Accidental induced seizures in three cynomologus macaques following administration of ceftriaxone dissolved in 1% lidocaine diluent.
2010 Jan
Ceftriaxone restores glutamate homeostasis and prevents relapse to cocaine seeking.
2010 Jan 1
[Reversible ceftriaxone-associated biliary pseudolithiasis in three children with renal diseases].
2010 Mar
Antistaphylococcal activities of telavancin tested alone and in combination by time-kill assay.
2010 May
Reversible choreoathetosis after the administration of ceftriaxone sodium in patients with end-stage renal disease.
2010 Nov
Epidural abscess caused by community-associated methicillin-resistant Staphylococcus aureus strain USA300 in Japan.
2010 Oct
Patents

Sample Use Guides

In Vivo Use Guide
The usual adult daily dose is 1 to 2 grams given once a day (or in equally divided doses twice a day) depending on the type and severity of infection. The total daily dose should not exceed 4 grams. For the treatment of uncomplicated gonococcal infections, a single intramuscular dose of 250 mg is recommended.
Route of Administration: Intravenously; Intramuscularly
In Vitro Use Guide
ceftriaxone MIC cutoff of 8 μg/ml against E. coli, Klebsiella spp., and P. mirabilis is an excellent predictor of extended-spectrum β-lactamase (ESBL) production, with a positive predictive value and negative predictive value approaching 100% and 99.5%, respectively.
Name Type Language
CEFTRIAXONE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2-AMINO-4-THIAZOLYL)(METHOXYIMINO)ACETYL)AMINO)-8-OXO-3-(((1,2,5,6-TETRAHYDRO-2-METHYL-5,6-DIOXO-1,2,4-TRIAZIN-3-YL)THIO)METHYL)-, (6R-(6.ALPHA.,7.BETA.(Z)))-
Common Name English
CEFTRIAXON
Common Name English
CEFTRIAXONE [INN]
Common Name English
CEFTRIAXONE [MI]
Common Name English
CEFTRIAXONE [VANDF]
Common Name English
CEFTRIAXONE [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QJ01DD04
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
WHO-ATC J01DD54
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
LIVERTOX 174
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
WHO-VATC QJ01DD54
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
WHO-ATC J01DD63
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
NCI_THESAURUS C357
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 6.2.1
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
NDF-RT N0000175488
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
WHO-ATC J01DD04
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
EU-Orphan Drug EU/3/14/1425
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
Code System Code Type Description
PUBCHEM
5479530
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY
WIKIPEDIA
CEFTRIAXONE
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY
NCI_THESAURUS
C62020
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY
DRUG BANK
DB01212
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY
RXCUI
2193
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY RxNorm
MERCK INDEX
M3225
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY Merck Index
ECHA (EC/EINECS)
277-405-6
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY
IUPHAR
5326
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY
CAS
73384-59-5
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY
EVMPD
SUB07431MIG
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY
EPA CompTox
73384-59-5
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY
MESH
D002443
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY
INN
4923
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY
ChEMBL
CHEMBL161
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY
LactMed
73384-59-5
Created by admin on Mon Oct 21 19:50:10 UTC 2019 , Edited by admin on Mon Oct 21 19:50:10 UTC 2019
PRIMARY