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Cephaloridine

CAS No.
50-59-9
Chemical Name:
Cephaloridine
Synonyms
Sefacin;Ceporin;Ceporan;Ceflorin;Keflodin;Keflordin;Sch 11527;Cephaloridine;Cephaloridine II;Cephaloridine USP/EP/BP
CBNumber:
CB4875354
Molecular Formula:
C19H17N3O4S2
Molecular Weight:
415.48
MDL Number:
MFCD00012127
MOL File:
50-59-9.mol
MSDS File:
SDS
TDS File:
TDS
Last updated:2026-05-28 01:29:24
Product description Number Pack Size Price
Cephaloridine AA00DCAP 10mg $513
Cephaloridine FC76417 1mg $50
Cephaloridine FC76417 2mg $80
Cephaloridine FC76417 5mg $150
Cephaloridine FC76417 10mg $250

Cephaloridine 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℃)
optical activity +47.720 (c 1.25, H2O)
Water Solubility >20g/L(21 ºC)
FDA UNII LVZ1VC61HB

SAFETY

Risk and Safety Statements

Symbol(GHS)  Exclamation Mark (GHS07)
GHS07
Signal word  Warning
Hazard statements  H317
Precautionary statements  P261-P272-P280-P302+P352-P333+P313-P321-P363-P501
Hazard Codes  Xn
Risk Statements  42/43
Safety Statements  22-36/37-45
Hazardous Substances Data 50-59-9(Hazardous Substances Data)
Toxicity LD50 mice, rats (g/kg): >15, 2.5-4 orally; in monkeys (g/kg): >0.2 i.m. (Atkinson)

Cephaloridine price

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
aablocks AA00DCAP Cephaloridine 50-59-9 10mg $513 2026-05-28 Buy
Biosynth FC76417 Cephaloridine 50-59-9 1mg $50 2021-12-16 Buy
Biosynth FC76417 Cephaloridine 50-59-9 2mg $80 2021-12-16 Buy
Biosynth FC76417 Cephaloridine 50-59-9 5mg $150 2021-12-16 Buy
Biosynth FC76417 Cephaloridine 50-59-9 10mg $250 2021-12-16 Buy
Product number Packaging Price Buy
AA00DCAP 10mg $513 Buy
FC76417 1mg $50 Buy
FC76417 2mg $80 Buy
FC76417 5mg $150 Buy
FC76417 10mg $250 Buy

Cephaloridine Chemical Properties,Uses,Production

Description

This 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.

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.

General Description

Cephaloridine, along with cephalothin, was the first member of the synthetic cephalosporin C class of antibiotic, to be introduced clinically. It was synthesized, starting with 7-aminocephalosporanic acid, by Glaxo Research Laboratories in 1962. This drug shows strong activity against gram-positive and gramnegative bacteria and Leptospira, including benzylpenicillin-resistant strains. It has been given widely by intravenous, intramuscular, and intraspinal injection to treat a variety of infections caused by Staphylococcus, Streptococcus, Neisseria, Klebsiella, Escherichia coli, and other pathogens. Because of its renal toxicity and the development of newer and more active synthetic cephalosporins, its use is declining.

Hazard

Moderately to very toxic.

110-86-1
50-59-9
Synthesis of Cephaloridine from Pyridine

Cephaloridine Preparation Products And Raw materials

Cephaloridine Suppliers

Global( 25)Suppliers
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Shaanxi DIDU pharmaceutical and Chemical Co., Ltd 029-029-029-81148696 18161915376 1040@dideu.com China 9999 58
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 Keflordin Sefacin (6R,7R)-8-oxo-3-(pyridin-1-ium-1-ylmethyl)-7-[(2-thiophen-2-ylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate Cephaloridine II (6R,7R)-8-Oxo-3-(1-pyridiniumylmethyl)-7-[(2-thienylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate PyridiniuM,1-[[(6R,7R)-2-carboxy-8-oxo-7-[[2-(2-thienyl)acetyl]aMino]-5-thia-1-azabicyclo[4.2.0]oct- N-(7-[2′-Thienylacetamidoceph-3-ylmethyl])pyridinium 2-carboxylate Cephaloridine USP/EP/BP CEFALORIDINE (ALPHA FORM) USP/EP/BP Sch 11527 Enavogliflozin Impurity 32 50-59-9 C19H17N3O4S4 C19H17N3O4S2 C19H18N3O4S2