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Cephaloridine

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Cephaloridine Basic information

Product Name:
Cephaloridine
CAS:
50-59-9
MF:
C19H17N3O4S2
MW:
0
EINECS:
200-052-6
Mol File:
50-59-9.mol
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Cephaloridine Chemical Properties

Melting point:
184°C
alpha 
D +47.7° (c = 1.25 in water)
Density 
1.3230 (rough estimate)
refractive index 
1.6390 (estimate)
storage temp. 
2-8°C
pka
3.2(at 25℃)
Water Solubility 
>20g/L(21 ºC)
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Safety Information

Hazard Codes 
Xn
Risk Statements 
42/43
Safety Statements 
22-36/37-45
Toxicity
LD50 mice, rats (g/kg): >15, 2.5-4 orally; in monkeys (g/kg): >0.2 i.m. (Atkinson)
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Cephaloridine Usage And Synthesis

Originator

Ceporin,Glaxo,UK,1964

Uses

Antibacterial agent.

Definition

ChEBI: A cephalosporin compound having pyridinium-1-ylmethyl and 2-thienylacetamido side-groups. A first-generation semisynthetic derivative of cephalosporin C.

Manufacturing Process

7-Aminocephalosporanic acid (5.00 g) which passed through a 100-mesh sieve was suspended in boiling ethyl acetate (200 ml), and 2-thienylacetyl chloride (Cagniant, Bull. Soc. Chim. France, 1949, 847) (4.42 g, 1.5 equiv.) was added in ethyl acetate (20 ml). The mixture was boiled under reflux for 40 minutes, cooled, and filtered. Aniline (5.03 ml) was added, and after 1 hour the mixture was extracted with 3% sodium hydrogen carbonate solution (1 x 150 ml, 2 x 100 ml, 1 x 50 ml) and the alkaline extracts washed with ethyl acetate (3 x 100 ml). The aqueous solution was acidified to pH 1.2, and extracted with ethyl acetate (2 x 150 ml). The ethyl acetate extract was washed with water (4 x 40 ml), dried (MgSO4), and concentrated in vacuo to low volume. The crude 7-2'-thienylacetamidocephalosporanic acid (2.5 g) which separated was collected by filtration. Evaporation of the filtrate gave a further 2.68 g (71%) of the product, which was purified by crystallization from ethyl acetate, then aqueous acetone, MP 150°C to 157°C (decomp.).
7-2'-Thienylacetamidocephalosporanic acid (7.0 g) was suspended in water (60 ml) and stirred with pyridine (7 ml) until the acid dissolved. The resulting solution (pH 5.9) was kept at 35°C for 3 days, then filtered and extracted with methylene chloride (4 x 60 ml). The methylene chloride extract was back-extracted with a little water and the total aqueous solutions were then percolated through a column of Dowex 1 x 8 resin, (100 to 200 mesh, 150 g) in the acetate form at pH 4.3. The column was washed with water until the optical rotation of the eluate fell to zero and the eluate (500 ml) was freeze-dried. The residual white solid was dissolved in the minimum volume of methanol and after a few minutes the pyridine derivative crystallized; this is the cephaloridine product.

brand name

Kefloridin (Lilly); Loridine (Lilly);Cepalorin;Faredina;Latorex;Lauridin.

Therapeutic Function

Antibacterial

World Health Organization (WHO)

Cefaloridine, a semi-synthetic cephalosporin antibiotic, was introduced into medicine in 1964 for the treatment of bacterial infections. It is considered to be the most toxic of the cephalosporins, and for this reason is now seldom used. Nevertheless, it still remains available in certain countries and the World Health Organization is not aware of restrictive actions taken elsewhere.

Hazard

Moderately to very toxic.

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CephaloridineSupplierMore

Beijing HuaMeiHuLiBiological Chemical
Tel:
010-56205725
Email:
waley188@sohu.com
Shanghai T&W Pharmaceutical Co., Ltd.
Tel:
+86 21 61551611
Email:
Kuer Chemical Technology (Beijing) Co., Ltd.
Tel:
13810511747 4008369963
Email:
kuer@kuerhuaxue.com
Aikon International Limited
Tel:
13611564524 025-58851090-
Email:
lwan@aikonchem.com
Hefei Bomei Biotechnology Co., Ltd.
Tel:
13739298932
Email:
531626407@qq.com
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