Cefixime

Bezeichnung:Cefixime

CAS-Nr79350-37-1

Englisch Name:Cefixime

CBNumberCB4210362

SummenformelC16H15N5O7S2

Molgewicht453.45

MOL-Datei79350-37-1.mol

Cefixime physikalisch-chemischer Eigenschaften

Schmelzpunkt	218-225°C
Dichte	1.85±0.1 g/cm3(Predicted)
storage temp.	Keep in dark place,Inert atmosphere,2-8°C
Löslichkeit	Slightly soluble in water, soluble in methanol, sparingly soluble in anhydrous ethanol, practically insoluble in ethyl acetate.
pka	pKa 2.10 (Uncertain)
Aggregatzustand	Solid
Farbe	Off-White to Pale Yellow
Wasserlöslichkeit	55.11 mg/L
BCS Class	4
Stabilität	Hygroscopic
CAS Datenbank	79350-37-1(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	42/43
S-Sätze:	22-36/37-45
WGK Germany	3
F	10-23
HS Code	38210000
Toxizität	LD50 oral in rat: > 10gm/kg

Gefahreninformationscode (GHS)

Cefixime Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Beschreibung
Cefixime is the first orally active third-generation cephalosponn with a true broad spectrum of activity. It is reportedly more effective against Gram-negative bacteria than conventional oral cephems such as cephalexin and cefaclor.
Chemische Eigenschaften
Pale Yellow Solid
Chemische Eigenschaften
Cefixime is an oral third generation cephalosporin antibiotic. It was sold under the trade name Suprax in the United States until 2003. The oral suspension form of “Suprax” was re-launched. Cefixime is prescribed for bacterial infections of the chest, ears, urinary tract, and throat (tonsilitis and pharyngitis), and for uncomplicated gonorrhea, upper and lower respiratory tract infections, acute otitis media, and gonococcal urethritis.
Originator
Fujisawa (Japan)
Verwenden
Orally active, third generation cephalosporin antibiotic.
Verwenden
Cephalosporin antibacterial
Definition
ChEBI: A third-generation cephalosporin antibiotic bearing vinyl and (2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido groups at positions 3 and 7, respectively, of the cephem skeleton. It is used in the treatment of gonorrhoea tonsilitis, pharyngitis, bronchitis, and urinary tract infections.
Manufacturing Process
To a suspension of 7-amino-3-vinyl-3-cephem-4-carboxylic acid (11.25 g), 2- (aminothiazol-4-yl)-2-(tert-butoxycarbonylmethoxyimino)acetic acid S-mercaptobenzothiazole ester (23.88 g) in ethylacetate (266 ml) and water (9 ml) at 2°C is added triethylamine. After completion of the reaction, water is added and pH is adjusted to 2.1 with diluted sulfuric acid. The phases are separated and the aqueous phase is extracted with ethylacetate. The organic extracts are combined and concentrated to a volume of 120 ml, then acetonitrile (100 ml) and formic acid (22 ml) are added. The mixture is stirred at 30-35°C for 1 hour. The mixture is cooled to 2°C, the precipitate is filtered, washed with acetonitrile and dried to obtain 20.86 g of 5-thia-1- azabicyclo(4.2.0)oct-2-ene-2-carboxylic acid, 7-(((2Z)-(2-amino-4- thiazolyl)(carboxymethoxy)imino)acetylamino)-3-ethenyl-8-oxo-, (6R,7R)- (Cefixime).
Trademarks
Suprax(Lupin);Cefspan.
Therapeutic Function
Antibiotic
Antimicrobial activity
It is active against N. gonorrhoeae, M. catarrhalis, H. influenzae and a wide range of enterobacteria, including most strains of Citrobacter, Enterobacter and Serratia spp. Its antistaphylococcal activity is poor. It is not active against Acinetobacter spp., Ps. aeruginosa or B. fragilis. It is resistant to hydrolysis by common β-lactamases.
Health Hazard
Exposures to cefi xime may cause side effects that include, but are not limited to, stomach and abdominal pain, diarrhea, vomiting, mild skin rash, headache, fever, urticaria, pruritis, eosinophilia, leucopenia, anaphylaxis, superinfection, hemolytic anemia, dyspepsia, and fl atulence. Also, cefi xime may cause transient elevation of SGOT, SGPT, alkaline phosphatase, BUN, and creatinine. Reports have indicated that cefi xime is mainly excreted unchanged in the bile and urine
Pharmakokinetik
Oral absorption: c. 50%
C_max 400 mg oral: 4–5.5 mg/L after 4 h
Plasma half-life: 3-ndash;4 h
Volume of distribution: 0.1 L/kg
Plasma protein binding: 60-ndash;70%
Absorption and distribution
Oral absorption is slow and incomplete, but is unaffected by aluminum magnesium hydroxide. Penetration into cantharides blister fluid was very slow but exceeded the plasma level. CSF concentrations are poor even in the presence of meningeal inflammation, reaching an average of around 0.22 mg/L in children with meningitis.
Metabolism and excretion
It is not metabolized and is excreted unchanged in urine (mainly by glomerular filtration) and in bile, in which concentrations exceeding 100 mg/L have been found. Less than 20% of an oral dose is recovered from the urine over 24 h, falling to less than 5% in patients with severe renal impairment, with a corresponding increase in plasma concentration. It is not removed by peritoneal or hemodialysis.
Clinical Use
Cefixime (Suprax) is the first orally active, third-generationcephalosporin that is not an ester prodrug to be approved fortherapy in the United States. Oral bioavailability is surprisinglyhigh, ranging from 40% to 50%. Facilitated transportof cefixime across intestinal brush border membranes involvingthe carrier system for dipeptides may explain itssurprisingly good oral absorption. This result was not expectedbecause cefixime lacks the ionizable α-amino grouppresent in dipeptides and β-lactams previously known to betransported by the carrier system.Cefixime is a broad-spectrum cephalosporin that is resistantto many β-lactamases. It is particularly effective againstGram-negative bacilli, including E. coli, Klebsiella spp., P.mirabilis, indole-positive Proteus, Providencia, and someCitrobacter spp. Most Pseudomonas, Enterobacter, andBacteroides spp. are resistant. It also has useful activityagainst streptococci, gonococci, H. influenzae, and M. catarrhalis.It is much less active against S. aureus. Cefixime isused for the treatment of various respiratory tract infections(e.g., acute bronchitis, pharyngitis, and tonsillitis) and otitismedia. It is also used to treat uncomplicated urinary tract infectionsand gonorrhea caused by β-lactamase–producingbacterial strains.
The comparatively long half-life of cefixime (t_1/2 is3–4 hours) allows it to be administered on a twice-a-dayschedule. Renal tubular reabsorption and a relatively high fraction of plasma protein binding (～65%) contribute to thelong half-life. It is provided in two-oral dosage forms: 200-or 400-mg tablets and a powder for the preparation of anaqueous suspension.
Clinical Use
Cefixime has been used successfully in uncomplicated cystitis, upper and lower respiratory tract infections and various other infections. Its failure to provide adequate cover for staphylococci should be noted.
Nebenwirkungen
It is well tolerated, but diarrhea is fairly common and pseudomembranous colitis has been reported. Other side effects common to cephalosporins are occasionally seen.
Veterinary Drugs and Treatments
Uses for cefixime are limited in veterinary medicine. Its use should be reserved for those times when infections (systemic or urinary tract) are caused by susceptible gram-negative organisms where oral treatment is indicated or when approved fluoroquinolones or other 3rd generation cephalosporins (e.g., cefpodoxime) are either contraindicated or ineffective.
in vitro
previous study found that cefixime was more active than cephalexin, cefaclor, and amoxicillin against various gram-negative bacteria. cefixime was also significantly more active than tested reference drugs against clinical isolates of klebsiella pneumoniae, escherichia coli, indole-positive and -negative proteus species, providencia species, and neisseria gonorrhoeae. moreover, cefixime was active against strains of k. pneumoniae, e. coli, as well as proteus mirabilis resistant to the reference agents [1].
in vivo
the therapeutic activities of cefixime in mice infected with gram-negative bacilli were found to be far superior to the activities of cephalexin, cefaclor, and amoxicillin, but they were inferior to the activities against infection with staphylococcus aureus [1].
Arzneimittelwechselwirkung
Potentially hazardous interactions with other drugs
Anticoagulants: effects of coumarins may be enhanced.
Stoffwechsel
About 20% of an oral dose (or 50% of an absorbed dose) is excreted unchanged in the urine via glomerular filtration within 24 hours. Up to 60% may be eliminated by non-renal mechanisms; there is no evidence of metabolism but some drug is probably excreted into the faeces from bile.
Vorsichtsmaßnahmen
Users of cefi xime should be careful in health conditions such as neonates, pregnancy, lactation, and renal failure. Users should follow suitable and appropriate health care measures to control superinfection (if it happens during therapy). It is contraindicated in patients with a known allergy to penicillin or any other ingredients of Taximax. Taxim-O is contraindicated in patients with a known allergy to the cephalosporin group of antibiotics.
Einzelnachweise
[1] kamimura, t. ,kojo, h.,matsumoto, y., et al. in vitro and in vivo antibacterial properties of fk 027, a new orally active cephem antibiotic. antimicrobial agents and chemotherapy 25(1), 98-104 (1984).
[2] quintiliani r. cefixime in the treatment of patients with lower respiratory tract infections: results of us

Cefixime Upstream-Materialien And Downstream Produkte

Cefixime Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

79350-37-1, Cefixime Verwandte Suche:

Send Inquriy