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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H17N5O7S2
Molecular Weight 455.465
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFOTAXIME

SMILES

CO\N=C(/C(=O)N[C@H]1[C@H]2SCC(COC(C)=O)=C(N2C1=O)C(O)=O)C3=CSC(N)=N3

InChI

InChIKey=GPRBEKHLDVQUJE-QSWIMTSFSA-N
InChI=1S/C16H17N5O7S2/c1-6(22)28-3-7-4-29-14-10(13(24)21(14)11(7)15(25)26)19-12(23)9(20-27-2)8-5-30-16(17)18-8/h5,10,14H,3-4H2,1-2H3,(H2,17,18)(H,19,23)(H,25,26)/b20-9-/t10-,14-/m1/s1

HIDE SMILES / InChI

Molecular Formula C16H17N5O7S2
Molecular Weight 455.465
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description

Cefotaxime sodium is a semisynthetic, broad spectrum cephalosporin antibiotic for parenteral administration. It’s a 3rd Generation Cephalosporin that is FDA approved for the treatment of lower respiratory tract infections, genitourinary infections, gynecologic infections, bacteremia/septicemia, skin and skin structure infections, intra-abdominal infections, bone and/or joint infections and central nervous system infections. The bactericidal activity of cefotaxime sodium results from inhibition of cell wall synthesis. Cefotaxime sodium has in vitro activity against a wide range of gram-positive and gram-negative organisms. Cefotaxime sodium has a high degree of stability in the presence of ß-lactamases, both penicillinases and cephalosporinases, of gram-negative and gram-positive bacteria. Increased nephrotoxicity has been reported following concomitant administration of cephalosporins and aminoglycoside antibiotics. Common adverse reactions include injection site pain, injection site phlebitis, rash, diarrhea, vomiting. Increased nephrotoxicity has been reported following concomitant administration of cephalosporins and aminoglycoside antibiotics.

CNS Activity

Approval Year

PubMed

PubMed

TitleDatePubMed
Treatment of gonorrhea: comparison of cefotaxime and penicillin.
1981 May
Third-generation cephalosporins for polymicrobial surgical sepsis.
1983 Feb
Cefotaxime compared with nafcillin plus tobramycin for serious bacterial infections. A randomized, double-blind trial.
1984 Oct
A comparison of ampicillin-cefotaxime and ampicillin-chloramphenicol in childhood bacterial meningitis: an experience in 55 patients.
1984 Sep
Bactericidal activity of cefotaxime and fosfomycin in cerebrospinal fluid during the treatment of rabbit meningitis experimentally induced by methicillin-resistant Staphylococcus aureus.
1985
Susceptibility of intra- and extracellular Mycobacterium avium-intracellulare to cephem antibiotics.
1985 Jan
Determination of in vitro susceptibility of Mycobacterium tuberculosis to cephalosporins by radiometric and conventional methods.
1985 Jan
Role of piperacillin in surgical prophylaxis of genitourinary infections.
1985 Jul
Cefotaxime is more effective than is ampicillin-tobramycin in cirrhotics with severe infections.
1985 May-Jun
[Ciprofloxacin and cefotaxim: pharmacokinetic and therapeutic effectiveness in E. coli pyelonephritis in rats].
1986 Jul
Focal motor status epilepticus following treatment with azlocillin and cefotaxime.
1987 May-Jun
Broth microdilution testing of susceptibilities to 30 antimicrobial agents of Mycobacterium avium strains from patients with acquired immune deficiency syndrome.
1987 Oct
In vitro activity of antimicrobial agents against mycobacteria.
1988
Excessive serum concentrations of acyclovir and neurotoxicity.
1988 Feb
Meningitis due to beta-lactamase producing chloramphenicol resistant Haemophilus influenzae type b in Kuwait.
1988 Jul
In vitro susceptibilities of Mycobacterium tuberculosis to 10 antimicrobial agents.
1988 Sep
Seizure propensity with imipenem.
1989 Aug
[Purulent meningitis in childhood caused by Haemophilus influenzae with ampicillin and chloramphenicol resistance].
1989 Jun
Meningitis due to Haemophilus influenzae type b resistant to ampicillin and chloramphenicol.
1989 Mar-Apr
Comparison of in vitro antimicrobial susceptibilities of Mycobacterium avium-M. intracellulare strains from patients with acquired immunodeficiency syndrome (AIDS), patients without AIDS, and animal sources.
1990 Jul
Cefotaxime-induced immune hemolytic anemia due to antibodies reacting in vitro by more than one mechanism.
1990 Mar-Apr
Treatment of meningitis and other infections due to ampicillin-resistant Haemophilus influenzae type b in children.
1991 Mar-Apr
Animal models as predictors of outcome of therapy with broad spectrum cephalosporins.
1992 Apr
Ceftazidime encephalopathy: absence status and toxic hallucinations.
1992 Apr
[Bacteriostatic activity and killing curves of eight antibiotics against seven strains of penicillin G-resistant pneumococci].
1992 May
The in vitro activity of beta-lactamase inhibitors in combination with cephalosporins against M. tuberculosis.
1995 Apr
Randomized comparison of meropenem with cefotaxime for treatment of bacterial meningitis. Meropenem Meningitis Study Group.
1995 May
Acute interstitial nephritis due to cefotaxime.
1996
Second attack of acute tubulointerstitionephritis induced by cefataxim and pregnancy.
1996
Treatment of experimental endocarditis due to ampicillin-susceptible or ampicillin-resistant Salmonella enteritidis.
1996 Jul
Microplate alamar blue assay versus BACTEC 460 system for high-throughput screening of compounds against Mycobacterium tuberculosis and Mycobacterium avium.
1997 May
Fatal acute hepatic necrosis due to dose-dependent fluconazole hepatotoxicity.
1997 Nov
Antibiotic prophylaxis--Hobson's choice in burns management.
1998 Dec
Pharmacokinetic/pharmacodynamic parameters: rationale for antibacterial dosing of mice and men.
1998 Jan
[Basic and clinical studies on tazobactam/piperacillin in pediatric field].
1998 Jun
Contribution of beta-lactamases to beta-lactam susceptibilities of susceptible and multidrug-resistant Mycobacterium tuberculosis clinical isolates.
1998 Jun
Prospective comparison of ceftriaxone and cefotaxime for the short-term treatment of bacterial meningitis in children.
1998 Mar-Apr
Photodistributed telangiectasia following use of cefotaxime.
2000 Sep
Albumin: a look at the evidence.
2001 Mar
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
[An unusual case of a side effect. Cefotaxime-induced confusion in a patient with renal failure].
2003 Jul 10
Antibiotics induce apoptosis of human peritoneal mesothelial cells.
2003 Jun
Aminoglycoside-induced reversible tubular dysfunction.
2003 Mar
The vitro efficacy of beta-lactam and beta-lactamase inhibitors against multidrug resistant clinical strains of Mycobacterium tuberculosis.
2004 Apr
Effects of some antibiotics on human erythrocyte 6-phosphogluconate dehydrogenase: an in vitro and in vivo study.
2004 Aug
Antibiotics modulate the stimulated cytokine response to endotoxin in a human ex vivo, in vitro model.
2006 Oct
Bilateral acetabular fractures secondary to a seizure attack caused by antibiotic medicine.
2007 May
Inspissated bile syndrome in a neonate treated with cefotaxime: sonographic aid to diagnosis, management, and follow-up.
2009 Apr
In vitro and in vivo efficacy of β-lactams against replicating and slowly growing/nonreplicating Mycobacterium tuberculosis.
2013 Jun
Systems pharmacological analysis of drugs inducing stevens-johnson syndrome and toxic epidermal necrolysis.
2015 May 18
Patents

Sample Use Guides

In Vivo Use Guide
Daily dose depends on infection type and vary from 0,5 g to 12 g. The maximum daily dosage should not exceed 12 grams. Gonococcal urethritis/ cervicitis in males and females: 0.5 gram IM (single dose) Rectal gonorrhea in females: 0.5 gram IM (single dose) Rectal gonorrhea in males : 1 gram IM (single dose) Uncomplicated infections: 1 gram every 12 hours IM or IV Moderate to severe infections: 1-2 grams every 8 hours IM or IV Infections commonly needing antibiotics in higher dosage (e.g., septicemia): 2 grams every 6-8 hours IV Life-threatening infections: 2 grams every 4 hours IV
Route of Administration: Intramuscular; Intravenous
In Vitro Use Guide
For staphylococci and nonenterococcal streptococci, the mean values for the minimal inhibitory concentration50 (MIC50) of cefotaxime (i.e., the lowest concentration inhibiting growth of 50% of tested strains) are 1.1-1.9 microgram/ml and 0.01-0.05 microgram/ml, respectively. Cefotaxime is inactive against Streptococcus faecalis and most other serogroup D streptococci. It is moderately active against Pseudomonas aeruginosa (MIC50, 19 microgram/ml) and Acinetobacter calcoaceticus subspecies anitratus (MIC50, 18 microgram/ml).
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:49:05 UTC 2019
Edited
by admin
on Mon Oct 21 19:49:05 UTC 2019
Record UNII
N2GI8B1GK7
Record Status Validated (UNII)
Record Version
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Name Type Language
CEFOTAXIME
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
CEFOTAXIME [MI]
Common Name English
CEFOTAXIM HIKMA
Brand Name English
CEFOTAXIME [WHO-DD]
Common Name English
(6R,7R,Z)-3-(ACETOXYMETHYL)-7-(2-(2-AMINOTHIAZOL-4-YL)-2-(METHOXYIMINO)ACETAMIDO)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
Systematic Name English
CEFOTAXIME [INN]
Common Name English
CEFOTAXIME [VANDF]
Common Name English
CEFOTAXIME [JAN]
Common Name English
Classification Tree Code System Code
WHO-ESSENTIAL MEDICINES LIST 6.2.1
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
WHO-VATC QJ01DD01
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
WHO-ATC J01DD01
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
LIVERTOX 166
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
NCI_THESAURUS C357
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
NDF-RT N0000175488
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
WHO-ATC J01DD51
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
NDF-RT N0000011161
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
Code System Code Type Description
RXCUI
2186
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
PRIMARY RxNorm
MERCK INDEX
M3204
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
PRIMARY Merck Index
NCI_THESAURUS
C354
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
PRIMARY
INN
4504
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
PRIMARY
WIKIPEDIA
CEFOTAXIME
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
PRIMARY
CAS
63527-52-6
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
PRIMARY
LactMed
63527-52-6
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
PRIMARY
PUBCHEM
5742673
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
PRIMARY
DRUG BANK
DB00493
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
PRIMARY
ECHA (EC/EINECS)
264-299-1
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
PRIMARY
EVMPD
SUB07405MIG
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
PRIMARY
ChEMBL
CHEMBL1730
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
PRIMARY
EPA CompTox
63527-52-6
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
PRIMARY
MESH
D002439
Created by admin on Mon Oct 21 19:49:05 UTC 2019 , Edited by admin on Mon Oct 21 19:49:05 UTC 2019
PRIMARY
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BINDER->LIGAND
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Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC
Volume of Distribution PHARMACOKINETIC