Cephaloridine

Cephaloridine Basic information
Product Name:Cephaloridine
Synonyms:Cephaloridine;Ceflorin;Ceporan;N-[7-[2'-Thienyl-acetamidoceph-3-ylmethyl]] pyridinium-4-carboxylate;pyridinium, 1-((2-carboxy-8-oxo-7-(2-(2-thienyl)acetamido)-5-thia-1-azabicyclo( 4.2.0)o ct- 2-en-3-yl)methyl)-, hydroxide, inner salt 1-[(7'-beta-[2-(2-thienyl)acetamido]-8'-oxo-1'-aza-5'-t hiabicyclo[4.2.0]-oct-2 '-en-3'-yl)methyl]pyridinium-2'-carboxylate 40602 7-((2-thienyl)acetamido)-3-(1-pyridylmethyl)cephalosporanic acid 7-(alpha-(2-thienyl)acetamido)-3-(1-pyridylmethyl)-3-cephem-4-carboxylic acid 7-(alpha-(2-thienyl)acetamido)-3-(1-pyridylmethyl)-3-cephem-4-carboxylic acid b etaine;(6R,7R)-8-oxo-3-(pyridin-1-ylmethyl)-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate;Ceporin;Keflodin
CAS:50-59-9
MF:C19H17N3O4S2
MW:415.48
EINECS:200-052-6
Product Categories:
Mol File:50-59-9.mol
Cephaloridine Structure
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
pka3.2(at 25℃)
Water Solubility >20g/L(21 ºC)
Safety Information
Hazard Codes Xn
Risk Statements 42/43
Safety Statements 22-36/37-45
Hazardous Substances Data50-59-9(Hazardous Substances Data)
ToxicityLD50 mice, rats (g/kg): >15, 2.5-4 orally; in monkeys (g/kg): >0.2 i.m. (Atkinson)
MSDS Information
Cephaloridine Usage And Synthesis
DescriptionThis was derived by adding two side chains to the nucleus of cephalothin, and has the formula 7-(2-thienyl acetamido)-3-(1-pyridylmethyl)-3-cephem-4-carboxylic acid betaine (Muggleton et al., 1964). Cephaloridine was initially widely used, but it had two main disadvantages. It was an unreliable antistaphylococcal drug, as it was relatively easily hydrolyzed by Staphylococcus aureus beta-lactamase (Laverdiere et al., 1978; Sabath, 1989). Second, cephaloridine was nephrotoxic (Foord, 1975; Appel and Neu, 1977). Marketing of the drug was discontinued in the USA in December 1980. Nowadays, this drug is used very rarely, if at all.
OriginatorCeporin,Glaxo,UK,1964
UsesAntibacterial agent.
DefinitionChEBI: A cephalosporin compound having pyridinium-1-ylmethyl and 2-thienylacetamido side-groups. A first-generation semisynthetic derivative of cephalosporin C.
Manufacturing Process7-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 nameKefloridin (Lilly); Loridine (Lilly);Cepalorin;Faredina;Latorex;Lauridin.
Therapeutic FunctionAntibacterial
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.
HazardModerately to very toxic.
Cephaloridine Preparation Products And Raw materials
Raw materialsPyridine-->7-Aminocephalosporanic acid-->2-Thiopheneacetyl chloride-->2-Thiopheneacetic acid
Preparation Products4-Epoxypropanoxycarbazole-->Propylamine
ALLYL N-PROPYL SULFIDE METHALLYL MERCAPTAN H-ALA-GLY-OH glycyldehydroalanine 7-Amino-3-cephem-4-carboxylic acid N-(2-aminoethyl)propanamide Propanamide, 3-mercapto-N-methyl- DL-ALANYL-GLYCINE AC-ALA-NHME N-(2-MERCAPTOETHYL)ACETAMIDE N-ME-GLY-NME2 ALANINE-NH2 ACETATE SALT CYS-GLY 3-AMINOAZETIDINE N-Methyl-N-vinylacetamide Pyridinium acetate METHYL-(2-THIOPHEN-2-YL-ETHYL)-AMINE AC-ALA-NH2

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