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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
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Treatment of urinary tract infections among febrile young children with daily intravenous antibiotic therapy at a day treatment center.
2004 Oct
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
[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.
Substance Class Chemical
Created
by admin
on Tue Mar 06 10:26:59 UTC 2018
Edited
by admin
on Tue Mar 06 10:26:59 UTC 2018
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 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
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
BINDER -> LIGAND
BINDING
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC