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Cefotaxime Acid

Alias: Cephotaxime RU-24662 RU24662
Cat No.:V6149 Purity: ≥98%
Cefotaxime is a third-generation cephalosporin antibiotic and lactamase-resistant cephalosporin with broad activity against Gram-positive (Gram+) and Gram-negative (Gram-) bacteria.
Cefotaxime Acid
Cefotaxime Acid Chemical Structure CAS No.: 63527-52-6
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
100mg
250mg
500mg
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Other Forms of Cefotaxime Acid:

  • Cefotaxime Sodium
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Cefotaxime is a third-generation cephalosporin antibiotic and lactamase-resistant cephalosporin with broad activity against Gram-positive (Gram+) and Gram-negative (Gram-) bacteria.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
Cefotaxime's minimum inhibitory concentration (MIC) for Vibrio vulnificus CMCP6 is 0.0625 mg/L [4].
ln Vivo
Compared to earlier regimens, the combination of ciprofloxacin and cefotaxime is more successful in removing V. vulnificus from the body [4].
Animal Protocol
Animal/Disease Models: Female, specific pathogen-free, 8weeks old balb/c (Bagg ALBino) mouse [4].
Doses: 30 mg/kg. Management: IP every 6 hrs (hrs (hours)).
Experimental Results: The number of viable bacteria in the liver of mice in the cefotaxime + ciprofloxacin treatment group was lower than that in the cefotaxime alone group (P<0.001 at 24 hrs (hrs (hours)) and 48 hrs (hrs (hours))).
ADME/Pharmacokinetics
Absorption, Distribution and Excretion
Rapidly absorbed following intramuscular injection.
Approximately 20-36% of an intravenously administered dose of 14C-cefotaxime is excreted by the kidney as unchanged cefotaxime and 15-25% as the desacetyl derivative, the major metabolite.
Metabolism / Metabolites
Approximately 20-36% of an intravenously administered dose of 14C-cefotaxime is excreted by the kidney as unchanged cefotaxime and 15-25% as the desacetyl derivative, the major metabolite. The desacetyl metabolite has been shown to contribute to the bactericidal activity. Two other urinary metabolites (M2 and M3) account for about 20-25%. They lack bactericidal activity.
Biological Half-Life
Approximately 1 hour.
Toxicity/Toxicokinetics
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
Cefotaxime is no longer marketed in the United States. Limited information indicates that cefotaxime produces low levels in milk that are not expected to cause adverse effects in breastfed infants. Occasionally disruption of the infant's gastrointestinal flora, resulting in diarrhea or thrush have been reported with cephalosporins, but these effects have not been adequately evaluated. Cefotaxime is acceptable in nursing mothers.
◉ Effects in Breastfed Infants
Relevant published information was not found as of the revision date.
◉ Effects on Lactation and Breastmilk
Relevant published information was not found as of the revision date.
References

[1]. In vivo efficacy of the combination of ciprofloxacin and cefotaxime against Vibrio vulnificus sepsis. PLoS One. 2014 Jun 30;9(6):e101118.

[2]. A comparison of the prophylactic efficacy of ceftriaxone and cefotaxime in abdominal surgery. Am J Surg. 2003 Jan;185(1):45-9.

[3]. Prospective comparison of ceftriaxone and cefotaxime for the short-term treatment of bacterial meningitis in children. Chemotherapy. 1998 Mar-Apr;44(2):142-7.

[4]. Differences between ceftriaxone and cefotaxime: microbiological inconsistencies. Ann Pharmacother. 2008 Jan;42(1):71-9.

[5]. Use of cefotaxime, a beta-lactamase stable cephalosporin, in the therapy of serious infections, including those due to multiresistant organisms. Am J Med. 1981 Sep;71(3):435-42.

Additional Infomation
Cefotaxime is a cephalosporin compound having acetoxymethyl and [2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetyl]amino side groups. It has a role as a drug allergen and an antibacterial drug. It is a member of 1,3-thiazoles, an oxime O-ether and a cephalosporin. It is a conjugate acid of a cefotaxime(1-).
Cefotaxime is a third-generation cephalosporin antibiotic. Like other third-generation cephalosporins, it has broad spectrum activity against Gram positive and Gram negative bacteria. In most cases, it is considered to be equivalent to ceftriaxone in terms of safety and efficacy. Cefotaxime sodium is marketed under various trade names including Claforan (Sanofi-Aventis).
Cefotaxime is a Cephalosporin Antibacterial.
Cefotaxime has been reported in Melodinus cochinchinensis with data available.
Cefotaxime is a third generation semisynthetic cephalosporin antibiotic with bactericidal activity. Cefotaxime inhibits mucopeptide synthesis by binding to and inactivating penicillin binding proteins thereby interfering with the final transpeptidation step required for cross-linking of peptidoglycan units which are a component of bacterial cell walls. This results in a reduction of cell wall stability and causes cell lysis.
Semisynthetic broad-spectrum cephalosporin.
See also: Cefotaxime Sodium (has salt form).
Drug Indication
Used to treat gonorrhoea, meningitis, and severe infections including infections of the kidney (pyelonephritis) and urinary system. Also used before an operation to prevent infection after surgery.
FDA Label
Mechanism of Action
The bactericidal activity of cefotaxime results from the inhibition of cell wall synthesis via affinity for penicillin-binding proteins (PBPs). Cefotaxime shows high affinity for penicillin-binding proteins in the cell wall including PBP Ib and PBP III.
Pharmacodynamics
Cefotaxime is a third generation intravenous cephalosporin antibiotic. It has broad spectrum activity against Gram positive and Gram negative bacteria. It does not have activity against Pseudomonas aeruginosa. Cefotaxime works by inhibiting bacterial cell wall biosynthesis. A positive feature of cefotaxime is that it display a resistance to penicillinases and is useful to treat infections that are resistant to penicillin derivatives.
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Exact Mass
455.056
CAS #
63527-52-6
Related CAS #
Cefotaxime sodium;64485-93-4
PubChem CID
5742673
Appearance
White to off-white solid powder
Density
1.8±0.1 g/cm3
Melting Point
162-163℃
Index of Refraction
1.779
LogP
1.2
Hydrogen Bond Donor Count
3
Hydrogen Bond Acceptor Count
12
Rotatable Bond Count
8
Heavy Atom Count
30
Complexity
833
Defined Atom Stereocenter Count
2
SMILES
CC(OCC1=C(N2C([C@@H](NC(/C(/C3=CSC(N3)=N)=N\OC)=O)[C@H]2SC1)=O)C(O)=O)=O
InChi Key
GPRBEKHLDVQUJE-QSWIMTSFSA-N
InChi Code
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
Chemical Name
(6R,7R)-3-(acetyloxymethyl)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-methoxyiminoacetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
Synonyms
Cephotaxime RU-24662 RU24662
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO : ~250 mg/mL (~548.88 mM)
Solubility (In Vivo)
Solubility in Formulation 1: ≥ 2.08 mg/mL (4.57 mM) (saturation unknown) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL.
Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution.

Solubility in Formulation 2: ≥ 2.08 mg/mL (4.57 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly.
Preparation of 20% SBE-β-CD in Saline (4°C,1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution.

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Solubility in Formulation 3: ≥ 2.08 mg/mL (4.57 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.


 (Please use freshly prepared in vivo formulations for optimal results.)
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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
             (2) Be sure to add the solvent(s) in order.

Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT02443285 UNKNOWN STATUS Drug: Cefotaxime
Drug: ceftriaxone
Primary Bacterial Peritonitis Tanta University 2015-01 Phase 3
NCT01820026 UNKNOWN STATUS Drug: Imipenem
Drug: Vancomycin
Drug: azithromycin
Cirrhosis University of Roma La Sapienza 2012-12 Phase 4
NCT01559753 COMPLETED Drug: Augmentin, Ceftriaxone, Cefotaxime, netilmycin, tobramycin
Drug: compare 8 to15 days of antibiotic treatment
Pneumonia Ventilator Associated Centre Hospitalier Universitaire de Besancon 1998-01 Phase 4
NCT01261546 COMPLETED Drug: Dexamethasone
Drug: Placebo
Empyema
Parapneumonic Pleural Effusion
Hospital Infanta Sofia 2010-12 Phase 2
NCT02123628 COMPLETED Drug: duration of the antibiotic therapy Diabetes Mellitus Tourcoing Hospital 2007-06 Phase 4
Biological Data
  • Time-kill curves for V. vulnificus CMCP6 after incubation with 3/4 MICs of cefotaxime alone, minocycline alone, ciprofloxacin alone, cefotaxime-plus-ciprofloxacin or cefotaxime-plus-minocycline.CFU, colony-forming unit; MIC, minimum inhibitory concentration.[1].Hee-Chang Jang, et al. In vivo efficacy of the combination of ciprofloxacin and cefotaxime against Vibrio vulnificus sepsis. PLoS One. 2014 Jun 30;9(6):e101118.
  • Survival rates of mice in each treatment group inoculated with 1×108 cfu V. vulnificus.The 96-h survival rate of the cefotaxime-plus-ciprofloxacin group (85%, 17/20) was significantly higher than that of the cefotaxime (0%, 0/20) or the cefotaxime-plus-minocycline groups (35%, 7/20) (P<0.001 and P = 0.003, respectively; log-rank test).[1].Hee-Chang Jang, et al. In vivo efficacy of the combination of ciprofloxacin and cefotaxime against Vibrio vulnificus sepsis. PLoS One. 2014 Jun 30;9(6):e101118.
  • The effects of sub-inhibitory concentrations of antibiotics on V. vulnificus cytotoxicity and rtxA1 transcription. A. Cytotoxicity assay. The impaired cytotoxicity of ΔrtxA1 compared with that of the WT strain shows that cytotoxicity at 120 min is due principally to RtxA1. V. vulnificus cytotoxicity is inhibited more markedly by 1/4 MIC of ciprofloxacin than by 1/4 MICs of cefotaxime or minocycline (n = 12 per group). B. Transcriptional reporter assay. The transcription of rtxA1 is more efficiently inhibited by 1/4 MIC of ciprofloxacin than by 1/4 MICs of cefotaxime or minocycline (n = 4 per group). WT, MO6-24/O; ΔrtxA1, CMM770 (MO6-24/O background with a deletion mutation in the rtxA1 gene); CTX, cefotaxime; CIP, ciprofloxacin; MCL, minocycline. *P<0.05 compared to the values for ciprofloxacin (Student’s t-test).[1].Hee-Chang Jang, et al. In vivo efficacy of the combination of ciprofloxacin and cefotaxime against Vibrio vulnificus sepsis. PLoS One. 2014 Jun 30;9(6):e101118.
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