| Identification | More | [Name]
Cefazolin sodium salt | [CAS]
27164-46-1 | [Synonyms]
CEFAMEDIN
CEFAZOLINE SODIUM
CEFAZOLIN NA
CEFAZOLIN SODIUM
CEFAZOLIN SODIUM SALT
SKF-41558
(6r-trans
ancef
biazolina
cezsodium
firmacef
gramaxin
kefzol
lampocef
liviclina
monosodiumcefazolin
sodiumcefazolin
sodiumcephazolin
sodiumcez
totacef | [EINECS(EC#)]
248-278-4 | [Molecular Formula]
C14H13N8NaO4S3 | [MDL Number]
MFCD00056883 | [Molecular Weight]
476.49 | [MOL File]
27164-46-1.mol |
| Chemical Properties | Back Directory | [Appearance]
White to off-white powder | [Melting point ]
190 °C | [refractive index ]
20 ° (C=10, H2O) | [storage temp. ]
2-8°C
| [solubility ]
H2O: 50 mg/mL, clear, colorless
| [form ]
crystalline powder | [color ]
White to Off-White | [Stability:]
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. | [Sensitive ]
Light Sensitive | [Usage]
Semi-synthetic antibiotic derived from 7-amino-cepphalosporanic acid. An antibacterial | [Merck ]
1917 | [BRN ]
3585038 | [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 DataBase Reference]
27164-46-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn,Xi | [Risk Statements ]
R42/43:May cause sensitization by inhalation and skin contact .
R36/37/38:Irritating to eyes, respiratory system and skin .
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed . | [Safety Statements ]
S22:Do not breathe dust .
S36/37:Wear suitable protective clothing and gloves .
S36:Wear suitable protective clothing .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice . | [WGK Germany ]
2
| [RTECS ]
XI0390000
| [HS Code ]
29419090 | [Toxicity]
LD50 in mice, rats (mg/kg): 3.9, 3.18 i.v.; 6.2, 7.4 i.p. (Birkhead) |
| Hazard Information | Back Directory | [Chemical Properties]
White to off-white powder | [Originator]
Cefamedin,Fujisawa,Japan,1971 | [Uses]
enzyme inhibitor, Gaucher's disease therapy | [Uses]
Semi-synthetic antibiotic derived from 7-amino-cephalosporanic acid. An antibacterial. | [Uses]
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. | [Brand name]
Ancef (GlaxoSmithKline);
Kefzol (Lilly). | [Therapeutic Function]
Antibacterial | [Biological Activity]
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]. | [References]
[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. |
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