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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, E-

SMILES

[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)C(=N\OC)\C3=CSC(N)=N3)C(O)=O

InChI

InChIKey=GPRBEKHLDVQUJE-VINNURBNSA-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

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

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
CLAFORAN
Curative
CLAFORAN
Curative
CLAFORAN
Curative
CLAFORAN
Curative
CLAFORAN
Curative
CLAFORAN
Curative
CLAFORAN
Curative
CLAFORAN
Curative
CLAFORAN

Cmax

ValueDoseCo-administeredAnalytePopulation
40.8 μg/mL
0.5 g single, intravenous
CEFOTAXIME plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
104 μg × h/mL
0.5 g single, intravenous
CEFOTAXIME plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
0.72 h
0.5 g single, intravenous
CEFOTAXIME plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Drug as perpetrator​

Drug as victim

PubMed

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: Other
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).