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
[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
Molecular Formula | C19H17N3O4S2 |
Molecular Weight | 415.486 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: Description was created based on several sources. including http://www.drugbank.ca/drugs/DB09008 and http://onlinelibrary.wiley.com/doi/10.1002/cpt196896819/abstract
Curator's Comment: Description was created based on several sources. including http://www.drugbank.ca/drugs/DB09008 and http://onlinelibrary.wiley.com/doi/10.1002/cpt196896819/abstract
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
Sources: http://www.ncbi.nlm.nih.gov/pubmed/1239674
Curator's Comment: CNS penetrant in humans
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P39844 Gene ID: 939990.0 Gene Symbol: dacC Target Organism: Bacillus subtilis (strain 168) Sources: http://www.ncbi.nlm.nih.gov/pubmed/11160090 |
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Target ID: Rabbit proximal tubules Sources: http://www.ncbi.nlm.nih.gov/pubmed/2068729 |
1.1 mM [EC50] | ||
Target ID: CHEMBL2073693 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10636865 |
0.23 mM [IC50] | ||
Target ID: CHEMBL1641347 Sources: http://www.ncbi.nlm.nih.gov/pubmed/10929807 |
1250.0 µM [IC50] | ||
Target ID: CHEMBL1955711 Sources: http://www.ncbi.nlm.nih.gov/pubmed/12650826 |
4.48 mM [IC50] | ||
Target ID: Escherichia coli growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/18765691 |
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Target ID: map00550 Sources: http://www.kegg.jp/entry/D01075 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | Ceporan Approved UseRespiratory tract infections, Septicemia, Skin & Soft tissue infections, Urinary tract & genital tract infections, Surgical prophylaxis |
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Curative | Ceporan Approved UseRespiratory tract infections, Septicemia, Skin & Soft tissue infections, Urinary tract & genital tract infections, Surgical prophylaxis |
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Curative | Ceporan Approved UseRespiratory tract infections, Septicemia, Skin & Soft tissue infections, Urinary tract & genital tract infections, Surgical prophylaxis |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
38 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/278145/ |
1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEPHALORIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
40 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/278145/ |
1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEPHALORIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/278145/ |
1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEPHALORIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
69% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/278145/ |
1 g single, intramuscular dose: 1 g route of administration: Intramuscular experiment type: SINGLE co-administered: |
CEPHALORIDINE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 230 uM] | ||||
yes [IC50 4480 uM] | ||||
yes [Ki 2460 uM] | ||||
yes [Ki 3630 uM] | ||||
yes [Ki 740 uM] | ||||
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes | ||||
yes | ||||
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Nephrotoxicity and acute renal failure associated with cephalothin and cephaloridine. | 1971 Nov |
|
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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Cephaloridine, cephalothin and the kidney. | 1975 |
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Molecular basis for several drug-induced nephropathies. | 1977 Apr |
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Renal tubular necrosis following cephalothin. | 1979 |
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Nephrotoxicity of cefotiam (CGP 14221/E) in rats and rabbits. | 1981 Sep |
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Relieving effect of saline on cephaloridine nephrotoxicity in rats. | 1989 Mar |
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[Studies on the mechanisms of renal damages induced by nephrotoxic compounds]. | 1995 Dec |
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Magnesium lithospermate B ameliorates cephaloridine-induced renal injury. | 1997 Dec |
|
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
In Vitro Use Guide
Sources: http://www.ncbi.nlm.nih.gov/pubmed/1259406
Against meningococci cephaloridine inactivated all strains at concentrations
below 0.5 ug/ml
Substance Class |
Chemical
Created
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Record UNII |
LVZ1VC61HB
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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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573
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5773
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1910
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SUB06169MIG
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2233
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PRIMARY | RxNorm | ||
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CEPHALORIDINE
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D002509
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C76594
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DB09008
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3023
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50-59-9
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M1065
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200-052-6
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3537
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LVZ1VC61HB
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DTXSID9022782
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CHEMBL316157
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