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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

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
Drug-induced gallbladder disease. Incidence, aetiology and management.
1992 Jan-Feb
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Efficacy of the combination ampicillin plus ceftriaxone in the treatment of a case of enterococcal endocarditis due to Enterococcus faecalis highly resistant to gentamicin: efficacy of the "ex vivo" synergism method.
2004 Aug
Nephrolithiasis associated with ceftriaxone therapy: a prospective study in 51 children.
2004 Nov
Delayed diagnosis of penicillin-resistant Streptococcus mitis endocarditis following single-dose amoxicillin prophylaxis in a child.
2004 Oct
Treatment of urinary tract infections among febrile young children with daily intravenous antibiotic therapy at a day treatment center.
2004 Oct
Pediatric ceftriaxone nephrolithiasis.
2005 Feb
QTc prolongation associated with combination therapy of levofloxacin, imipramine, and fluoxetine.
2005 Mar
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 Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
WHO-ATC J01DD54
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
LIVERTOX 174
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
WHO-VATC QJ01DD54
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
WHO-ESSENTIAL MEDICINES LIST 6.2.1
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
NDF-RT N0000175488
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
WHO-ATC J01DD04
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
NDF-RT N0000011161
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
Code System Code Type Description
PUBCHEM
5479530
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY SWITZERF
WIKIPEDIA
CEFTRIAXONE
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY
NCI_THESAURUS
C62020
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY
DRUG BANK
DB01212
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY
RXCUI
2193
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY RxNorm
MERCK INDEX
M3225
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY Merck Index
ECHA (EC/EINECS)
277-405-6
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY
IUPHAR
5326
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY
CAS
73384-59-5
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY
EVMPD
SUB07431MIG
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY
EPA CompTox
73384-59-5
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY
MESH
D002443
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY
INN
4923
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY
ChEMBL
CHEMBL161
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY
LactMed
73384-59-5
Created by admin on Tue Mar 06 10:26:59 UTC 2018 , Edited by admin on Tue Mar 06 10:26:59 UTC 2018
PRIMARY