Natrium-(6R-trans)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-(1H-tetrazol-1-ylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylat

Bezeichnung:Natrium-(6R-trans)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-(1H-tetrazol-1-ylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylat

CAS-Nr27164-46-1

Englisch Name:Cefazolin sodium salt

CBNumberCB7403213

SummenformelC14H15N8NaO4S3

Molgewicht478.5

MOL-Datei27164-46-1.mol

Synonyma

Natrium-(6R-trans)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-(1H-tetrazol-1-ylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylat

Natrium-(6R-trans)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-(1H-tetrazol-1-ylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylat physikalisch-chemischer Eigenschaften

Schmelzpunkt	190 °C
Brechungsindex	20 ° (C=10, H2O)
storage temp.	Keep in dark place,Inert atmosphere,2-8°C
Löslichkeit	H₂O: 50 mg/mL, clear, colorless
Aggregatzustand	crystalline powder
Farbe	White to Off-White
Sensitive	Light Sensitive
Merck	14,1917
BRN	3585038
Stabilität	Stable, but may be heat sensitive - store in cool conditions. May discolour upon exposure to light - store in the dark. Incompatible with strong oxidizing agents.
InChIKey	LJIOGPYKTPCRAP-MVOALHSDNA-N
SMILES	C(C1=C(CS[C@]2([H])[C@H](NC(=O)CN3N=NN=C3)C(=O)N12)CSC1=NN=C(C)S1)(=O)O.[NaH] \|&1:5,7,r\|
LogP	1.133 (est)
CAS Datenbank	27164-46-1(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	Xn,Xi
R-Sätze:	42/43-36/37/38-20/21/22
S-Sätze:	22-36/37-36-26
WGK Germany	2
RTECS-Nr.	XI0390000
HS Code	29349990
Toxizität	LD50 in mice, rats (mg/kg): 3.9, 3.18 i.v.; 6.2, 7.4 i.p. (Birkhead)

Gefahreninformationscode (GHS)

Cefazolin sodium salt Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R42/43:Sensibilisierung durch Einatmen und Hautkontakt möglich.
R36/37/38:Reizt die Augen, die Atmungsorgane und die Haut.
R20/21/22:Gesundheitsschädlich beim Einatmen,Verschlucken und Berührung mit der Haut.
S-Sätze Betriebsanweisung:
S22:Staub nicht einatmen.
S36/37:Bei der Arbeit geeignete Schutzhandschuhe und Schutzkleidung tragen.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
Beschreibung
Cefazolin was synthesized by Fujisawa Pharmaceutical Co. in 1969. It was the first of the cephem antibiotics to introduce a thiadiazolylthiomethyl group at the 3 position and a tetrazole group at the 7 position in the side chain. Cefazolin is a parenteral cephem antibiotic showing better activity against gramnegative bacteria than cephalothin or cephaloridine. Its bactericidal activity, tissue distribution, and urinary excretion are excellent and it has wide clinical use.
Chemische Eigenschaften
White to off-white powder
Originator
Cefamedin,Fujisawa,Japan,1971
Verwenden
Semi-synthetic antibiotic derived from 7-amino-cephalosporanic acid. An antibacterial.
Verwenden
enzyme inhibitor, Gaucher's disease therapy
Verwenden
Semi-synthetic antibiotic derived from 7-amino-cepphalosporanic acid. An antibacterial
Definition
ChEBI: A cephalosporin organic sodium salt having [(5-methyl-1,3,4-thiadiazol-2-yl)sulfanyl]methyl and (1H-tetrazol-1-ylacetyl)amino side-groups.
Manufacturing Process
7-Aminocephalosporanic acid is converted to its sodium salt and acylated with 1H-tetrazole-1-acetyl chloride. The acetoxy group is then displaced by reaction with 5-methyl-1,3,4-thiadiazole-2-thiol in buffer solution. The product acid is converted to the sodium salt by NaHCO3.
Trademarks
Ancef (GlaxoSmithKline); Kefzol (Lilly).
Therapeutic Function
Antibacterial
Biologische Aktivität
cefazolin is a semisynthetic antibiotic with a broad spectrum of antibacterial activity. cefazolin has exhibited high activity against gram-positive bacteria and gram-negative bacteria [1].
Clinical Use
Cefazolin (Ancef, Kefzol) is one of a series of semisyntheticcephalosporins in which the C-3 acetoxy function has beenreplaced by a thiol-containing heterocycle—here, 5-methyl-2-thio-1,3,4-thiadiazole. It also contains the somewhatunusual tetrazolylacetyl acylating group. Cefazolin wasreleased in 1973 as a water-soluble sodium salt. It is activeonly by parenteral administration.
Cefazolin provides higher serum levels, slower renalclearance, and a longer half-life than other first-generationcephalosporins. It is approximately 75% protein bound inplasma, a higher value than for most other cephalosporins.Early in vitro and clinical studies suggest that cefazolin ismore active against Gram-negative bacilli but less activeagainst Gram-positive cocci than either cephalothin orcephaloridine. Occurrence rates of thrombophlebitis followingintravenous injection and pain at the site of intramuscularinjection appear to be the lowest of the parenteralcephalosporins.
Veterinary Drugs and Treatments
In the United States, there are no cefazolin products approved for veterinary species but it has been used clinically in several species when an injectable, first generation cephalosporin is indicated. It is used for surgical prophylaxis, and for variety of systemic infections (including orthopedic, soft tissue, sepsis) caused by susceptible bacteria. Most commonly given every 6 – 8 hours via parenteral routes, cefazolin constant rate intravenous infusion protocols are being developed as cefazolin is a time (above MIC)-dependent antibiotic, and serum/tissue concentrations can remain above MIC.
in vitro
in cultured mg-63 human osteosarcoma cell line, cefazolin (100 μg/ml) showed little or no effect on osteoblast replication. cefazolin (200μg/ml) significantly decreased cell replication, and 10,000 μg/ml caused cell death [2].
in vivo
in patients with normal and various degrees of compromised renal function, administration of cefazolin significantly decreased the urinary concentration and percentage of the dose excreted in the urine [3]. the half-life of cefazolin in serum of normal persons was 1.9 hr and as long as 35 hr in severely uremic patients. in uremic patients, cefazolin was well tolerated [4].
Einzelnachweise
[1] kariyone k, harada h, kurita m, et al. cefazolin, a new semisynthetic cephalosporin antibiotic. i[j]. the journal of antibiotics, 1970, 23(3): 131-136.
[2] edin m l, miclau t, lester g e, et al. effect of cefazolin and vancomycin on osteoblasts in vitro[j]. clinical orthopaedics and related research, 1996, 333: 245-251.
[3] levison m e, levison s p, ries k, et al. pharmacology of cefazolin in patients with normal and abnormal renal function[j]. journal of infectious diseases, 1973, 128(supplement 2): s354-s357.
[4] craig w a, welling p g, jackson t c, et al. pharmacology of cefazolin and other cephalosporins in patients with renal insufficiency[j]. journal of infectious diseases, 1973, 128(supplement 2): s347-s353.

Cefazolin sodium salt Upstream-Materialien And Downstream Produkte

Natrium-(6R-trans)-3-[[(5-methyl-1,3,4-thiadiazol-2-yl)thio]methyl]-8-oxo-7-(1H-tetrazol-1-ylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-en-2-carboxylat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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