Cefotaxime
![Cefotaxime Structure](CAS/GIF/63527-52-6.gif)
- CAS No.
- 63527-52-6
- Chemical Name:
- Cefotaxime
- Synonyms
- (6R,7R)-3-[(Acetyl-oxy)methyl]-7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)-acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid;635227-52-6;ACA-JW;Zariviz;Cefabol;Cefotaxime;Cephotaxime;Cefotaxima acid;Cefotaxime Acid L;Cefotaxime acid CRS
- CBNumber:
- CB6511698
- Molecular Formula:
- C16H17N5O7S2
- Molecular Weight:
- 455.47
- MOL File:
- 63527-52-6.mol
- Modify Date:
- 2024/7/26 15:15:06
Melting point | >158°C (dec.) |
---|---|
Density | 1.80±0.1 g/cm3(Predicted) |
storage temp. | Hygroscopic, -20°C Freezer, Under inert atmosphere |
solubility | DMSO (Slightly), Methanol (Slightly) |
pka | pKa 2.1 (H2O t=20.0 I<0.005 ) (Uncertain);3.4(H2O t=20.0 I<0.005 ) (Uncertain);10.9(H2O t=20.0 I<0.005 ) (Uncertain) |
form | Solid |
color | White to Off-White |
Stability | Hygroscopic |
LogP | 1.2 |
CAS DataBase Reference | 63527-52-6(CAS DataBase Reference) |
EPA Substance Registry System | 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[[(2Z)-2-(2-amino-4-thiazolyl)-2-(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)- (63527-52-6) |
SAFETY
Risk and Safety Statements
Symbol(GHS) | ![]() GHS08 |
---|---|
Signal word | Danger |
Hazard statements | H317-H334 |
Precautionary statements | P261-P280-P284-P304+P340-P342+P311 |
RTECS | XI0240000 |
HS Code | 29419000 |
Cefotaxime Chemical Properties,Uses,Production
Description
Like other third-generation cephalosporins, it has excellent anti-Gram-negative activity and is useful institutionally. It has a metabolically vulnerable acetoxy group attached to C-3 and loses approximately 90% of its activity when this is hydrolyzed. This metabolic feature also complicates the pharmacokinetic data, because both active forms are present and have different properties. Cefotaxime should be protected from heat and light and may color slightly without significant loss of potency. Like other third-generation cephalosporins, cefotaxime has less activity against staphylococci but has greater activity against Gram-negative organisms.
Uses
Cefotaxime has a broad spectrum of antibicrobial use. It acts bactericidally. It is highly
active with respect to Gram-negative microorganisms (E. coli, Citrobacter, Proteus
mirabilis, P. indole, Providencia, Klebsiella, Serratia), and a few strains of Pseudomonas,
H. influenzae that are resistant to other antibiotics. Cefotaxime is less active with respect
to streptococci, pneumococci, meningococci, gonococci, and bacteroides. It is resistant to
the majority of beta-lacatamases of Gram-positive and Gram-negative microorganisms.
This drug is used for severe bacterial infections caused by microorganisms that are sensitive to the drug such as peritonitis, sepsis, abdominal infections, infections of the pelvis
minor, infections of the lower respiratory tract, urinary tract, bones, joints, skin, soft tissues,
and infected wounds and burns. Synonyms of this drug are claforan, zarivis, and others.
Antimicrobial activity
The aminothiazoyl and methoximino groups at the 7-amino position confer, respectively, potent activity against many Gram-negative rods and cocci and stability to most β-lactamases. Ps. aeruginosa, Sten. maltophilia and other pseudomonads are often resistant. Brucella melitensis and some strains of Nocardia asteroides are susceptible. Activity against L. monocytogenes and B. fragilis is poor.
Acquired resistance
Many enterobacteria resistant to other b-lactam agents are susceptible, but selection of resistant strains with derepressed chromosomal molecular class C cephalosporinases may occur. Gram-negative bacilli producing variants of the TEM enzymes (pp. 230–231) are resistant.
Pharmacokinetics
Cmax 500 mg intramuscular: 10–15 mg/L after 0.5–1 h
1 g intravenous (15-min infusion): 90 mg/L end infusion
Plasma half-life: c.1 h
Volume of distribution: 32–37 L
Plasma protein binding: c. 40%
Distribution
It is widely distributed, achieving therapeutic concentrations
in sputum, lung tissue, pleural fluid, peritoneal fluid, prostatic
tissue and cortical bone. In patients receiving 2 g every
8 h, mean CSF concentrations in aseptic meningitis were 0.8 mg/L. Levels of 2–15 mg/L can be found in the CSF
in the presence of inflammation after doses of 50 mg/kg by
intravenous infusion over 30 min. A single intraventricular
dose of 40 mg/kg produced levels at 2, 4 and 6 h of 6.4, 5.7
and 4.5 mg/L, respectively.
Metabolism
About 15–25% of a dose is metabolized by hepatic esterases to
the desacetyl form, which may have some clinical importance
because of its concentration in bile and accumulation in renal
failure. Desacetylcefotaxime has about 10% of the activity of
the parent against enterobacteria, less against Staph. aureus.
Its half-life in normal subjects is around 1.5 h.
Excretion
Elimination is predominantly by the renal route, more than
half the dose being recovered in the urine over the first 24 h,
about 25% as the desacetyl derivative. Excretion is depressed
by probenecid and declines in renal failure with accumulation
of the metabolite. In patients with creatinine clearances in the
range 3–10 mL/min, the plasma half-life rose to 2.6 h while
that of the metabolite rose to 10 h.
Clinical Use
Cefotaxime is widely used in neutropenic patients, respiratory infection, meningitis, intra-abdominal sepsis, osteomyelitis, typhoid fever, urinary tract infection, neonatal sepsis and gonorrhea.
Side effects
Minor hematological and dermatological side effects common to group 4 cephalosporins have been described. Superinfection with Ps. aeruginosa in the course of treatment has occurred. Occasional cases of pseudomembranous colitis have been reported.
Cefotaxime Preparation Products And Raw materials
Raw materials
Preparation Products
Supplier | Tel | Country | ProdList | Advantage | Inquiry |
---|---|---|---|---|---|
SG Pharma Pvt Ltd | +91-2227622000 +91-2227622000 | Maharashtra, India | 6 | 58 | Inquiry |
Nectar Lifesciences Ltd | +91-9357244445 +91-9357244445 | Punjab, India | 29 | 58 | Inquiry |
KPS Chemicals & Pharmaceuticals | 91--8469484608 | Gujarat, India | 240 | 58 | Inquiry |
Medilink Pharmachem | +91 (79) 3007-0133 | New Delhi, India | 424 | 50 | Inquiry |
Pharmaffiliates Analytics and Synthetics P. Ltd | +91-172-5066494 | Haryana, India | 6773 | 58 | Inquiry |
Wockhardt | 09881062557 | Mumbai, India | 10 | 58 | Inquiry |
CLEARSYNTH LABS LTD. | +91-22-45045900 | Hyderabad, India | 6351 | 58 | Inquiry |
Pharma Affiliates | 172-5066494 | Haryana, India | 6761 | 58 | Inquiry |
Novorix Pharma Pvt. Ltd. | 91--9849201334 | Hyderabad, India | 47 | 58 | Inquiry |
Del Trade International | 91-11-29967331 | Delhi, India | 35 | 58 | Inquiry |
Supplier | Advantage |
---|---|
SG Pharma Pvt Ltd | 58 |
Nectar Lifesciences Ltd | 58 |
KPS Chemicals & Pharmaceuticals | 58 |
Medilink Pharmachem | 50 |
Pharmaffiliates Analytics and Synthetics P. Ltd | 58 |
Wockhardt | 58 |
CLEARSYNTH LABS LTD. | 58 |
Pharma Affiliates | 58 |
Novorix Pharma Pvt. Ltd. | 58 |
Del Trade International | 58 |
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