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
SMILES
[O-]C(=O)C1=C(C[N+]2=CC=CC=C2)CS[C@@H]3[C@H](NC(=O)CC4=CC=CS4)C(=O)N13
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
Molecular Formula | C19H17N3O4S2 |
Molecular Weight | 415.486 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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
PubMed
Title | Date | PubMed |
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Nephrotoxicity associated with the use of cephaloridine. | 1967 May 22 |
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Penicillin-induced haemolytic anaemia. | 1968 Jul 6 |
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Renal damage associated with prolonged administration of ampicillin, cephaloridine, and cephalothin. | 1969 |
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[Nephrotoxicity of cephaloridine. 3 cases of acute renal failure with anuria]. | 1969 Oct 18 |
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The nephrotoxicity of cephaloridine. | 1970 Oct |
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Reversible encephalopathy and acute renal failure after cephaloridine. | 1970 Oct 31 |
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Parkinsonism syndrome due to cephaloridine. | 1971 May 17 |
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Nephrotoxicity and acute renal failure associated with cephalothin and cephaloridine. | 1971 Nov |
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Nephrotoxicity of cephaloridine. | 1971 Oct 9 |
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Relative nephrotoxicity of cephalosporin antibiotics in an animal model. | 1972 Sep 9 |
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[Acute renal failure following combined cephaloridine-gentamycin therapy (author's transl)]. | 1973 Dec 21 |
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Molecular basis for several drug-induced nephropathies. | 1977 Apr |
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Renal and hepatic necrosis after metabolic activation of 2-substituted furans and thiophenes, including furosemide and cephaloridine. | 1977 Nov |
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Drug-induced lysosomal changes and nephrotoxicity in rats. | 1978 Nov |
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Renal tubular necrosis following cephalothin. | 1979 |
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Cephaloridine encephalopathy. | 1981 Aug 8 |
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IgE antibodies for penicillins and cephalosporins in rats. III. Antigenic specificity of rat anti-cephalosporin-OvA IgE sera. | 1981 Jan |
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Nephrotoxicity of cefotiam (CGP 14221/E) in rats and rabbits. | 1981 Sep |
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Renal tolerance of ceftazidime in animals. | 1981 Sep |
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In vitro and in vivo susceptibility of atypical mycobacteria to various drugs. | 1981 Sep-Oct |
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[Studies on the nephrotoxicity of cephaloridine in the mouse (author's transl)]. | 1982 |
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Lipid peroxidation: a possible mechanism of cephaloridine-induced nephrotoxicity. | 1983 Jan |
|
Ceftazidime nephrotoxicity in rats. | 1984 Apr |
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Vasopressin-resistant polyuria induced by cephaloridine administration in rats. | 1986 |
|
Biochemical mechanisms of cephaloridine nephrotoxicity. | 1988 |
|
Neurotoxicity of beta-lactam antibiotics. Experimental kinetic and neurophysiological studies. | 1988 |
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The use of renal cortical slices from the Fischer 344 rat as an in vitro model to evaluate nephrotoxicity. | 1988 Jul |
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Protective effect of piperacillin against nephrotoxicity of cephaloridine and gentamicin in animals. | 1988 Jun |
|
[Nephrotoxicity of cefodizime sodium in rats--single and 14-day repeated intravenous administration]. | 1988 Jun |
|
Relieving effect of saline on cephaloridine nephrotoxicity in rats. | 1989 Mar |
|
[Acute renal failure caused by ceporin, kanamycin and gentamicin]. | 1989 Mar-Apr |
|
Safety evaluation of meropenem in animals: studies on the kidney. | 1989 Sep |
|
Drugs as allergens: an immunoassay for detecting IgE antibodies to cephalosporins. | 1990 |
|
Methimazole protection of rats against chemically induced kidney damage in vivo. | 1992 Jan |
|
[Study on gamma-GTP activity in urine and renal tissue of drug-induced nephrotoxicity in rats]. | 1993 Jul |
|
Effects of KW-3902, a novel adenosine A1-receptor antagonist, on cephaloridine-induced acute renal failure in rats. | 1994 Jan |
|
Preventive effect of betamipron on nephrotoxicity and uptake of carbapenems in rabbit renal cortex. | 1994 Sep |
|
Can penicillins and other beta-lactam antibiotics be used to treat tuberculosis? | 1995 Dec |
|
[Studies on the mechanisms of renal damages induced by nephrotoxic compounds]. | 1995 Dec |
|
Glucocorticoid amelioration of nephrotoxicity: a study of cephaloridine-methylprednisolone interaction in the rat. | 1995 Jul |
|
Cephaloridine nephrotoxicity in diabetic rats: modulation by insulin treatment. | 1995 Jun 26 |
|
Suppressed expression of calcium-binding protein regucalcin mRNA in the renal cortex of rats with chemically induced kidney damage. | 1995 Oct 4 |
|
Magnesium lithospermate B ameliorates cephaloridine-induced renal injury. | 1997 Dec |
|
Effect of ginsenoside-Rd in cephaloridine-induced renal disorder. | 1999 Feb |
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Protective effect of serum thymic factor, FTS, on cephaloridine-induced nephrotoxicity in rats. | 2005 Nov |
|
Serum thymic factor, FTS, attenuates cisplatin nephrotoxicity by suppressing cisplatin-induced ERK activation. | 2005 Nov 1 |
|
Transcriptomic analysis of nephrotoxicity induced by cephaloridine, a representative cephalosporin antibiotic. | 2008 Jun |
|
In vitro gene expression analysis of nephrotoxic drugs in rat primary renal cortical tubular cells. | 2008 Mar |
|
Kidney injury molecule-1 expression in rat proximal tubule after treatment with segment-specific nephrotoxicants: a tool for early screening of potential kidney toxicity. | 2010 Apr |
|
In vitro and in vivo efficacy of β-lactams against replicating and slowly growing/nonreplicating Mycobacterium tuberculosis. | 2013 Jun |
Sample Use Guides
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Oct 21 19:50:08 UTC 2019
by
admin
on
Mon Oct 21 19:50:08 UTC 2019
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Record UNII |
LVZ1VC61HB
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Record Status |
Validated (UNII)
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WHO-VATC |
QJ01DB02
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NCI_THESAURUS |
C357
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WHO-ATC |
J01DB02
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5773
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1910
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SUB06169MIG
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2233
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CEPHALORIDINE
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D002509
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C76594
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DB09008
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50-59-9
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M1065
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200-052-6
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CHEMBL316157
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