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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

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

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
Disappearing "gallstones": biliary pseudolithiasis complicating ceftriaxone therapy.
1992 Aug
Drug-induced gallbladder disease. Incidence, aetiology and management.
1992 Jan-Feb
[Renal gravel formation inducing renal insufficiency as a side-effect of ceftriaxon].
1999 Apr 4
Hepato-biliary abnormalities secondary to ceftriaxone use: a case report.
1999 Aug
Early biliary pseudolithiasis during ceftriaxone therapy for acute pyelonephritis in children: a prospective study in 34 children.
2000 Dec
Ceftriaxone-associated nephrolithiasis.
2000 Sep
Antibacterials for the prophylaxis and treatment of bacterial endocarditis in children.
2001
Breakthrough Streptococcus pneumoniae meningitis during clarithromycin therapy for acute otitis media.
2001 Feb
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Ceftriaxone-associated nephrolithiasis and biliary pseudolithiasis in a child.
2003 Sep
A case of acute hemolysis after ceftriaxone: immune complex mechanism demonstrated by flow cytometry.
2004 Aug
Cephalosporin-induced nonconvulsive status epilepticus in a uremic child.
2004 Feb
Ceftriaxone-associated biliary sludge and pseudocholelithiasis during childhood: a prospective study.
2004 Jun
Delayed diagnosis of penicillin-resistant Streptococcus mitis endocarditis following single-dose amoxicillin prophylaxis in a child.
2004 Oct
What is the safe dose of vitamin A in children with measles?
2005 Apr
Ultrasonographic findings in ceftriaxone: associated biliary sludge and pseudolithiasis in children.
2005 Feb
[Pseudotumor cerebri probably due to ceftriaxone].
2005 Mar
Ceftriaxone-associated biliary pseudolithiasis in paediatric surgical patients.
2005 Mar
Ceftriaxone-induced symptomatic pseudolithiasis mimicking ICP elevation.
2005 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
Acute interstitial nephritis associated with coadministration of vancomycin and ceftriaxone: case series and review of the literature.
2007 Oct
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
The beta-lactam antibiotic ceftriaxone inhibits physical dependence and abstinence-induced withdrawal from cocaine, amphetamine, methamphetamine, and clorazepate in planarians.
2008 Apr 28
Hemolytic anemia from ceftriaxone in an elderly patient: a case report.
2008 Oct
Normal pressure hydrocephalus or neuroborreliosis?
2009
[Acute pancreatitis associated with the administration of ceftriaxone in an adult patient].
2009 Apr
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
Ceftriaxone-induced toxic hepatitis.
2009 Jun 7
Severe ceftriaxone-induced hemolysis complicated by diffuse cerebral ischemia in a child with sickle cell disease.
2009 Nov
Transfusion med illustrated: Ceftriaxone-induced acute hemolytic anemia.
2010 Aug
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
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.
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:50:10 UTC 2019
Edited
by admin
on Mon Oct 21 19:50:10 UTC 2019
Record UNII
75J73V1629
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
BINDER->LIGAND
BINDING
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC