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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17N3O4S2
Molecular Weight 415.486
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEPHALORIDINE

SMILES

[H][C@]12SCC(C[N+]3=CC=CC=C3)=C(N1C(=O)[C@H]2NC(=O)CC4=CC=CS4)C([O-])=O

InChI

InChIKey=CZTQZXZIADLWOZ-CRAIPNDOSA-N
InChI=1S/C19H17N3O4S2/c23-14(9-13-5-4-8-27-13)20-15-17(24)22-16(19(25)26)12(11-28-18(15)22)10-21-6-2-1-3-7-21/h1-8,15,18H,9-11H2,(H-,20,23,25,26)/t15-,18-/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H17N3O4S2
Molecular Weight 415.486
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Cephaloridine (or cefaloridine) is a first generation semisynthetic derivative of cephalosporin C. It is unique among cephalosporins in that it exists as a zwitterion. It is of semi synthetic origin and belongs to cephem carboxylate. It belongs to Peptidoglycan synthesis inhibitor pharmacological group on the basis of mechanism of action. Since the discovery of cephalosporins P, N and C in 1948 there have been many studies describing the antibiotic action of cephalosporins and the possibility to synthesize derivatives. Hydrolysis of cephalosporin C, isolation of 7-aminocephalosporanic acid and the addition of side chains opened the possibility to produce various semi-synthetic cephalosporins. In 1962, cephalothin and cephaloridine were introduced. Cephaloridine is very active against gram positive cocci and used in a large variety of bacterial infections, such as respiratory tract, skin and urinary tract infections. Cephaloridine is primarily indicated in conditions like Bacterial infections, Bronchitis, Gonorrhoea, and can also be given in adjunctive therapy as an alternative drug of choice in Corneal ulcers, Intraocular infections. Cephaloridine was temporarily popular because it was better tolerated intramuscularly and attained in higher and more sustained levels in blood than cephalothin. Because it is also poorly absorbed after oral administration the use of this drug for humans declined rapidly, especially since the second generation of cephalosporins was introduced in the 1970s. Today it is more commonly used in veterinary practice to treat mild to severe bacterial infections caused by penicillin resistant and penicillin sensitive Staphylococcus aureus, Escherichia coli, Streptococcus pyogenes, Streptococcus pneumoniae, Bacillus sutbtilis, Klebsiella, Clostridium diptheriae, Salmonella and Shigella. Before the 1970s, cephaloridine was used to treat patients with urinary tract infections. Besides the drug has been used successfully in the treatment of various lower respiratory tract infections. Cephaloridine was very effective to cure pneumococcal pneumonia. It has a high clinical and bacteriological rate of success in staphylococcal and streptococcal infections.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
1.1 mM [EC50]
0.23 mM [IC50]
1250.0 µM [IC50]
4.48 mM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Ceporan
Curative
Ceporan
Curative
Ceporan

Cmax

ValueDoseCo-administeredAnalytePopulation
38 μg/mL
1 g single, intramuscular
CEPHALORIDINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
40 μg × h/mL
1 g single, intramuscular
CEPHALORIDINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.5 h
1 g single, intramuscular
CEPHALORIDINE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
69%
1 g single, intramuscular
CEPHALORIDINE plasma
Homo sapiens

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer









Drug as perpetrator​

Drug as victim

PubMed

Sample Use Guides

In Vivo Use Guide
1gm to1.5gm daily in two or three divided doses I.M. or I.V. In severe infections: 1.5 gm 8 hourly or 12 hourly. Children: 15 to 30 mg/kg/d.
Route of Administration: Intramuscular
In Vitro Use Guide
Against meningococci cephaloridine inactivated all strains at concentrations below 0.5 ug/ml
Substance Class Chemical
Record UNII
LVZ1VC61HB
Record Status Validated (UNII)
Record Version