Cefotaxime

Cefotaxime Struktur
63527-52-6
CAS-Nr.
63527-52-6
Englisch Name:
Cefotaxime
Synonyma:
(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;Zariviz;Cefabol;Cefotaxime;Cephotaxime;Cefotaxima acid;Cefotaxime Acid L;Cefotaxime acid CRS;1082579-72-3 (free acid)
CBNumber:
CB6511698
Summenformel:
C16H17N5O7S2
Molgewicht:
455.47
MOL-Datei:
63527-52-6.mol

Cefotaxime Eigenschaften

Schmelzpunkt:
>158°C (dec.)
Dichte
1.80±0.1 g/cm3(Predicted)
storage temp. 
Hygroscopic, -20°C Freezer, Under inert atmosphere
Löslichkeit
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)
Farbe
White to Off-White
Stabilität:
Hygroscopic
LogP
1.2
CAS Datenbank
63527-52-6(CAS DataBase Reference)
EPA chemische Informationen
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)
Sicherheit
  • Risiko- und Sicherheitserklärung
  • Gefahreninformationscode (GHS)
RTECS-Nr. XI0240000
HS Code  29419000
Bildanzeige (GHS) GHS hazard pictograms
Alarmwort Achtung
Gefahrenhinweise
Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code
H317 Kann allergische Hautreaktionen verursachen. Sensibilisierung der Haut Kategorie 1A Warnung P261, P272, P280, P302+P352,P333+P313, P321, P363, P501
H334 Kann bei Einatmen Allergie, asthmaartige Symptome oder Atembeschwerden verursachen. Sensibilisierung der Atemwege Kategorie 1 Achtung P261, P285, P304+P341, P342+P311,P501
Sicherheit
P261 Einatmen von Staub vermeiden.
P280 Schutzhandschuhe/Schutzkleidung/Augenschutz tragen.
P284 Atemschutz tragen.
P304+P340 BEI EINATMEN: Die Person an die frische Luft bringen und für ungehinderte Atmung sorgen.
P342+P311 Bei Symptomen der Atemwege: GIFTINFORMATIONSZENTRUM/Arzt/... (geeignete Stelle für medizinische Notfallversorgung vom Hersteller/Lieferanten anzugeben) anrufen.

Cefotaxime Chemische Eigenschaften,Einsatz,Produktion Methoden

Beschreibung

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.

Verwenden

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.

Pharmakokinetik

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.

Nebenwirkungen

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 Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte


Cefotaxime Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

Global( 279)Lieferanten
Firmenname Telefon E-Mail Land Produktkatalog Edge Rate
Henan Tengmao Chemical Technology Co. LTD
+8615238638457
salesvip2@hntmhg.com China 415 58
Shaanxi TNJONE Pharmaceutical Co., Ltd
+86-13474506593 +86-13474506593
sarah@tnjone.com China 713 58
Henan Tianfu Chemical Co.,Ltd.
+86-0371-55170693 +86-19937530512
info@tianfuchem.com China 21695 55
Hangzhou FandaChem Co.,Ltd.
008657128800458; +8615858145714
fandachem@gmail.com China 9353 55
career henan chemical co
+86-0371-86658258
sales@coreychem.com China 29914 58
HubeiwidelychemicaltechnologyCo.,Ltd
18627774460
faith@widelychemical.com CHINA 742 58
Chongqing Chemdad Co., Ltd
+86-023-61398051 +8613650506873
sales@chemdad.com China 39916 58
SIMAGCHEM CORP
+86-13806087780
sale@simagchem.com China 17367 58
Hefei TNJ Chemical Industry Co.,Ltd.
0551-65418671
sales@tnjchem.com China 34572 58
Shaanxi Dideu Medichem Co. Ltd
+86-029-89586680 +86-18192503167
1026@dideu.com China 9705 58

63527-52-6()Verwandte Suche:


  • Cefotaxime
  • Cefotaxima acid
  • 5-Thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-[(acetyloxy)methyl]-7-[[(2Z)-(2-amino-4-thiazolyl)(methoxyimino)acetyl]amino]-8-oxo-, (6R,7R)-
  • Cefabol
  • Cephotaxime
  • (((2-amino- 4-thiazolyl)methoxyimino)acetyl)amino)-8-oxo-, (6r-(6alpha,7beta(z) 3-[(Acetyloxy)methyl]-7-[[(2-amino-4-thiazoly)(methoxyimino)acethyl]amino]-8-oxo-5-thia-1-azabicyclo[4,2,0]oct-2-ene-2-carboxylic acid(sodium salt)
  • (6R)-3-(Acetoxymethyl)-7α-[[(2-amino-4-thiazolyl)[(Z)-methoxyimino]acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • (6R,7R)-7α-[2-(2-Amino-4-thiazolyl)-2-[(Z)-methoxyimino]acetylamino]-3-(acetoxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • Zariviz
  • (6R,7R)-3-[(acetyloxy)Methyl]-7-[(2E)-2-(2-aMino-1,3-thiazol-4-yl)-2-(MethoxyiMino)acetaMido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • (6R,7R)-3-(Acetoxymethyl)-7-((E)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-th
  • Cefotaxime Acid(Cefotaxime)
  • sodium 3-(acetyloxymethyl)-7-[[2-(2-amino-4-thiazolyl)-2-methoxyimino-1-oxoethyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
  • Cefotaxime Acid L
  • Cefotaxime acid CRS
  • 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)-
  • 1082579-72-3 (free acid)
  • (6S,7S)-3-(acetoxymethyl)-7-((Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • (6S,7R)-3-(acetoxymethyl)-7-((Z)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
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  • CefotaximeQ: What is Cefotaxime Q: What is the CAS Number of Cefotaxime Q: What is the storage condition of Cefotaxime Q: What are the applications of Cefotaxime
  • (6R,7R)-3-(acetoxymethyl)-7-((E)-2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
  • (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
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  • 63527-52-6
  • 24827-29-8
  • 635227-52-6
  • C16H17N5O7S
  • C16H17N6O7S2
  • Pharmaceutical intermediate
  • 63527-52-6
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