Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C16H16N2O6S2 |
Molecular Weight | 396.438 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CC3=CC=CS3)C(O)=O
InChI
InChIKey=XIURVHNZVLADCM-IUODEOHRSA-N
InChI=1S/C16H16N2O6S2/c1-8(19)24-6-9-7-26-15-12(14(21)18(15)13(9)16(22)23)17-11(20)5-10-3-2-4-25-10/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23)/t12-,15-/m1/s1
Molecular Formula | C16H16N2O6S2 |
Molecular Weight | 396.438 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdfCurator's Comment: description was created based on several sources, including:
http://www.druginfosys.com/drug.aspx?drugcode=150 | http://cdn-1.consultaremedios.com.br/bulas/2/14787.pdf
Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf
Curator's Comment: description was created based on several sources, including:
http://www.druginfosys.com/drug.aspx?drugcode=150 | http://cdn-1.consultaremedios.com.br/bulas/2/14787.pdf
Cephalothin is a first generation, semisynthetic analogue of natural cephalosporin antibiotic. The in-vitro bactericidal action of Cephalothin results from inhibition of cell-wall synthesis. In general, Cephalothin has higher activity against Gram positive than Gram negative organisms. Cephalothin is primarily indicated in conditions like bone and joint infection, genitourinary tract infections, respiratory tract infections, soft tissue and skin infections and others. The severe or irreversible adverse effects of Cephalothin, which give rise to further complications, include nephrotoxicity, hemolytic anemia. Cephalothin produces potentially life-threatening effects, which include anaphylaxis, serum sickness syndrome. The symptomatic adverse reactions produced by Cephalothin are: rashes, urticaria, allergic reactions, thrombophlebitis, pain at injection site. Co-administration of diuretics, such as furanthril, ethacrynic acid and nephrotoxic antibiotics may increase the risk of renal damage. Reciprocal inactivation could be observed during in vitro mixing of Cephalothin with aminoglycosides.
Originator
Sources: https://www.google.com/patents/US3218318
Curator's Comment: # Eli Lilly Co
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421 |
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Target ID: P15555 Gene ID: NA Gene Symbol: NA Target Organism: Streptomyces sp. (strain R61) |
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Target ID: Q9Y694 Gene ID: 10864.0 Gene Symbol: SLC22A7 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12650826 |
1.41 mM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | KEFLIN Approved UseCephalothin is indicated in the treatment of serious infections caused by susceptible strains of the designated microorganisms in the respiratory tract infections, skin and soft-tissue infections, genito-urinary tract infections, septicaemia, including endocarditis, bone and joint infections. Launch Date1.56556804E11 |
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Curative | KEFLIN Approved UseCephalothin is indicated in the treatment of serious infections caused by susceptible strains of the designated microorganisms in the respiratory tract infections, skin and soft-tissue infections, genito-urinary tract infections, septicaemia, including endocarditis, bone and joint infections. Launch Date1.56556804E11 |
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Curative | KEFLIN Approved UseCephalothin is indicated in the treatment of serious infections caused by susceptible strains of the designated microorganisms in the respiratory tract infections, skin and soft-tissue infections, genito-urinary tract infections, septicaemia, including endocarditis, bone and joint infections. Launch Date1.56556804E11 |
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Curative | KEFLIN Approved UseCephalothin is indicated in the treatment of serious infections caused by susceptible strains of the designated microorganisms in the respiratory tract infections, skin and soft-tissue infections, genito-urinary tract infections, septicaemia, including endocarditis, bone and joint infections. Launch Date1.56556804E11 |
|||
Curative | KEFLIN Approved UseCephalothin is indicated in the treatment of serious infections caused by susceptible strains of the designated microorganisms in the respiratory tract infections, skin and soft-tissue infections, genito-urinary tract infections, septicaemia, including endocarditis, bone and joint infections. Launch Date1.56556804E11 |
|||
Curative | KEFLIN Approved UseCephalothin is indicated in the treatment of serious infections caused by susceptible strains of the designated microorganisms in the respiratory tract infections, skin and soft-tissue infections, genito-urinary tract infections, septicaemia, including endocarditis, bone and joint infections. Launch Date1.56556804E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
20.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15830475/ |
3 g single, intravenous dose: 3 g route of administration: Intravenous experiment type: SINGLE co-administered: |
CEPHALOTHIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
25.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15830475/ |
3 g single, intravenous dose: 3 g route of administration: Intravenous experiment type: SINGLE co-administered: |
CEPHALOTHIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
28 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15830475/ |
3 g single, intravenous dose: 3 g route of administration: Intravenous experiment type: SINGLE co-administered: |
CEPHALOTHIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
2 g 3 times / day steady, oral Recommended Dose: 2 g, 3 times / day Route: oral Route: steady Dose: 2 g, 3 times / day Sources: |
unhealthy, 18 - 91 years n = 159 Health Status: unhealthy Condition: infections Age Group: 18 - 91 years Sex: M+F Population Size: 159 Sources: |
Disc. AE: Death, Urinary tract yeast infection... AEs leading to discontinuation/dose reduction: Death (grade 5, 13 patients) Sources: Urinary tract yeast infection (1 patient) |
1 g single, intramuscular Recommended |
healthy, 23 - 28 years n = 7 Health Status: healthy Age Group: 23 - 28 years Sex: M+F Population Size: 7 Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Urinary tract yeast infection | 1 patient Disc. AE |
2 g 3 times / day steady, oral Recommended Dose: 2 g, 3 times / day Route: oral Route: steady Dose: 2 g, 3 times / day Sources: |
unhealthy, 18 - 91 years n = 159 Health Status: unhealthy Condition: infections Age Group: 18 - 91 years Sex: M+F Population Size: 159 Sources: |
Death | grade 5, 13 patients Disc. AE |
2 g 3 times / day steady, oral Recommended Dose: 2 g, 3 times / day Route: oral Route: steady Dose: 2 g, 3 times / day Sources: |
unhealthy, 18 - 91 years n = 159 Health Status: unhealthy Condition: infections Age Group: 18 - 91 years Sex: M+F Population Size: 159 Sources: |
PubMed
Title | Date | PubMed |
---|---|---|
Cephaloridine, cephalothin and the kidney. | 1975 |
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Penicillin-induced immune hemolytic anemia. Occurrence of massive intravascular hemolysis. | 1975 Aug 4 |
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Therapeutic efficacy of tobramycin--a clinical and laboratory evaluation. | 1975 Dec |
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Acute renal failure associated with cephalosporin therapy. | 1975 Jun |
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Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity. | 1992 |
|
[Fosfomycin: an underrated antibiotic for urinary tract infections due to Escherichia coli]. | 2001 Dec |
|
Seroprevalence and antibiotic sensitivity of serotypes of Salmonella enterica in Greek pig herds. | 2001 Mar 31 |
|
Urinary tract infections in Norway: bacterial etiology and susceptibility. A retrospective study of clinical isolates. | 2001 Oct |
|
[Decreasing susceptibility to vancomycin in isogenic Staphylococcus aureus strains isolated from a single patient]. | 2001 Oct 13 |
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[Beta-lactam resistance in aquatic Enterobacter cloacae strains using phenotypic and genotypic criteria]. | 2002 Jul-Dec |
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Emergence and rapid spread of tetracycline-resistant Vibrio cholerae strains, Madagascar. | 2002 Mar |
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Interaction of human organic anion transporters with various cephalosporin antibiotics. | 2002 Mar 8 |
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[Activity of 14 antimicrobials against Eikenella corrodens]. | 2002 Oct-Dec |
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Microbiological aspects of an urban river used for unrestricted irrigation in the semi-arid region of north-east Brazil. | 2003 |
|
A detailed kinetic study of Mox-1, a plasmid-encoded class C beta-lactamase. | 2003 Aug 29 |
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Antimicrobial resistance in Gram-negative bacilli isolated from infant formulas. | 2003 Nov 21 |
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Nosocomial outbreak by Proteus mirabilis producing extended-spectrum beta-lactamase VEB-1 in a Korean university hospital. | 2004 Dec |
|
Molecular evaluation of antibiotic susceptibility of Tropheryma whipplei in axenic medium. | 2005 Feb |
|
[Taxonomical study of bacteria from genera Alteromonas and Pseudoalteromonas isolated from Black Sea water and invertebrates]. | 2005 Jul-Aug |
|
[Phenotypical differences of Helicobacter pylori strains isolated in Georgia]. | 2005 Nov-Dec |
|
Characterization of Staphylococcus aureus isolates recovered from bovine mastitis in Rio de Janeiro, Brazil. | 2005 Sep |
|
Occurrence and characterization of Aeromonas spp. in mussels from the Adriatic Sea. | 2006 Aug |
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In vivo selection of OmpK35-deficient mutant after cefuroxime therapy for primary liver abscess caused by Klebsiella pneumoniae. | 2006 Oct |
|
Antibiotic and heavy metal resistance in motile aeromonads and pseudomonads from rainbow trout (Oncorhynchus mykiss) farms in Australia. | 2007 Aug |
|
Pulsed-field gel electrophoresis in the identification of the origin of bacterial keratitis caused by Pseudomonas aeruginosa. | 2007 Jul |
|
Predictive analysis of ceftazidime hydrolysis in CTX-M-type beta-lactamase family members with a mutational substitution at position 167. | 2007 Mar |
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[Review of the actions in prevention of infections in total arthroplasty of hip]. | 2007 Nov-Dec |
|
Structure-function studies of arginine at position 276 in CTX-M beta-lactamases. | 2008 Apr |
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Antibiotic resistance of commensal Escherichia coli of food-producing animals from three Vojvodinian farms, Serbia. | 2008 Apr |
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Assay for integrons and pattern of antibiotic resistance in clinical Escherichia coli strains by PCR-RFLP in Southern Iran. | 2008 Jan |
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Interaction of beta-lactam antibiotics with the mitochondrial carnitine/acylcarnitine transporter. | 2008 Jun 17 |
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Antimicrobial resistance of Salmonella enterica isolates from apparently healthy and clinically ill finishing pigs in Spain. | 2008 May |
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Determination of cephalosporins in solid binary mixtures by polarized IR- and Raman spectroscopy. | 2008 Sep 10 |
|
Protective effect of topical antibiotics in breast augmentation. | 2009 Aug |
|
Development and validation of an immunochromatographic assay for rapid multi-residues detection of cephems in milk. | 2009 Feb 16 |
|
[Are antimicrobials useful in closed thoracostomy due to trauma?]. | 2009 Jan-Feb |
|
Rapid evolution of virulence and drug resistance in the emerging zoonotic pathogen Streptococcus suis. | 2009 Jul 15 |
|
Effects of mosapride on motility of the small intestine and caecum in normal horses after jejunocaecostomy. | 2009 Jun |
|
[Characterization of Listeria monocytogenes isolates obtained from raw cheese samples acquired from different Costa Rican producer zones]. | 2009 Mar |
|
CTX-M beta-lactamases in Escherichia coli from community-acquired urinary tract infections, Cambodia. | 2009 May |
|
Antibacterial effects of Iranian fennel essential oil on isolates of Acinetobacter baumannii. | 2009 May 1 |
Sample Use Guides
In Vivo Use Guide
Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf
The usual dosage range is 500 mg to 1 g of cefalotin every four to six hours. In severe infections, this may be increased by giving the injections every four hours or, when the desired response is not obtained, by raising the dose to 1 g. In lifethreatening infections, in patients with normal renal function, doses up to 2 g every four hours may be required.
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7571387
Cephalothin was very effective in vitro against staphylococcal
isolates, with an MIC90 of 0.12 ug/mL. The cephalothin MIC90 for E.coli was 64 ug/mL.
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 22:34:17 UTC 2023
by
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on
Wed Jul 05 22:34:17 UTC 2023
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Record UNII |
R72LW146E6
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Record Status |
Validated (UNII)
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Record Version |
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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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SALT/SOLVATE -> PARENT | |||
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
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ENZYME->SUBSTRATE |
Leads to resistance to the antibiotic.
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BINDER->LIGAND |
BINDING
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
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ACTIVE MOIETY |