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Details

Stereochemistry ACHIRAL
Molecular Formula C16H16N2O6S2.C2H7NO
Molecular Weight 457.521
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEPHALOTHIN ETHANOLAMINE

SMILES

NCCO.[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CC3=CC=CS3)C(O)=O

InChI

InChIKey=DZGMMKAGEYLTBD-XRZFDKQNSA-N
InChI=1S/C16H16N2O6S2.C2H7NO/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;3-1-2-4/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23);4H,1-3H2/t12-,15-;/m1./s1

HIDE SMILES / InChI

Molecular Formula C2H7NO
Molecular Weight 61.0831
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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

Description
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

Curator's Comment: # Eli Lilly Co

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P15555
Gene ID: NA
Gene Symbol: NA
Target Organism: Streptomyces sp. (strain R61)
Target ID: Q9Y694
Gene ID: 10864.0
Gene Symbol: SLC22A7
Target Organism: Homo sapiens (Human)
1.41 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
KEFLIN

Approved Use

Cephalothin 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 Date

1.56556804E11
Curative
KEFLIN

Approved Use

Cephalothin 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 Date

1.56556804E11
Curative
KEFLIN

Approved Use

Cephalothin 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 Date

1.56556804E11
Curative
KEFLIN

Approved Use

Cephalothin 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 Date

1.56556804E11
Curative
KEFLIN

Approved Use

Cephalothin 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 Date

1.56556804E11
Curative
KEFLIN

Approved Use

Cephalothin 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 Date

1.56556804E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
20.8 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
25.2 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
28 min
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

Doses

DosePopulationAdverse 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)
Urinary tract yeast infection (1 patient)
Sources:
1 g single, intramuscular
Recommended
Dose: 1 g
Route: intramuscular
Route: single
Dose: 1 g
Sources:
healthy, 23 - 28 years
n = 7
Health Status: healthy
Age Group: 23 - 28 years
Sex: M+F
Population Size: 7
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [IC50 1500 uM]
yes [IC50 570 uM]
yes [IC50 80 uM]
yes [Ki 200 uM]
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Cephaloridine, cephalothin and the kidney.
1975
Penicillin-induced immune hemolytic anemia. Occurrence of massive intravascular hemolysis.
1975 Aug 4
Nephrotoxicity associated with cephalothin administration.
1975 Jun
Acute renal failure associated with cephalosporin therapy.
1975 Jun
Significant reduction in the incidence of phlebitis with buffered versus unbuffered cephalothin.
1976 Apr
Acute interstitial nephritis.
1976 Jan
Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy.
1990 Nov
Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity.
1992
Occurrence and antibiotic resistance of mesophilic Aeromonas in three riverine freshwaters of Marrakech, Morocco.
2001 Dec 1
Antimicrobial sensitivity and adherence study in strains of coagulase-negative Staphylococcus spp.
2001 Jul-Sep
Antimicrobial susceptibility of udder pathogens isolated from dairy herds in the west littoral region of Uruguay.
2002
Patterns and mechanisms of resistance to beta-lactams and beta-lactamase inhibitors in uropathogenic Escherichia coli isolated from dogs in Portugal.
2002 Jan
Effect of matrix metalloprotease inhibitors on the 95 kDa metallopeptidase of Candida albicans.
2002 Jun
Interaction of human organic anion transporters with various cephalosporin antibiotics.
2002 Mar 8
Mitochondrial cytochrome c oxidase as a target site for cephalosporin antibiotics in renal epithelial cells (LLC-PK(1)) and renal cortex.
2002 Nov 22
[Activity of 14 antimicrobials against Eikenella corrodens].
2002 Oct-Dec
A detailed kinetic study of Mox-1, a plasmid-encoded class C beta-lactamase.
2003 Aug 29
Antibiotics induce apoptosis of human peritoneal mesothelial cells.
2003 Jun
Antimicrobial resistance in Gram-negative bacilli isolated from infant formulas.
2003 Nov 21
The vitro efficacy of beta-lactam and beta-lactamase inhibitors against multidrug resistant clinical strains of Mycobacterium tuberculosis.
2004 Apr
[Necrotizing lymphadenitis caused by Nocardia asteroides in a healthy girl].
2004 Apr-Jun
[Profile of antimicrobial resistance of agents causing urinary tract infections in children].
2004 Mar
Molecular evaluation of antibiotic susceptibility of Tropheryma whipplei in axenic medium.
2005 Feb
Antimicrobial resistance in Salmonella enteritidis strains isolated from broiler carcasses, food, human and poultry-related samples.
2005 Jan 1
Identification of antimicrobial resistance and class 1 integrons in Shiga toxin-producing Escherichia coli recovered from humans and food animals.
2005 Jul
In-vitro antibacterial and cytotoxic activity of cobalt (ii), copper (ii), nickel (ii) and zinc (ii) complexes of the antibiotic drug cephalothin (Keflin).
2005 Oct
Characterization of Staphylococcus aureus isolates recovered from bovine mastitis in Rio de Janeiro, Brazil.
2005 Sep
Flare up to betalactams.
2005 Sep-Oct
Occurrence and characterization of Aeromonas spp. in mussels from the Adriatic Sea.
2006 Aug
Conjunctival bacterial flora and antibiotic resistance pattern in patients undergoing cataract surgery.
2006 Jan-Feb
Integron presence in a multiresistant Morganella morganii isolate.
2006 Jun
In vivo selection of OmpK35-deficient mutant after cefuroxime therapy for primary liver abscess caused by Klebsiella pneumoniae.
2006 Oct
Antimicrobial resistance of Yersinia enterocolitica strains from human patients, pigs and retail pork in Switzerland.
2007 Apr 1
Bacteriological findings in patients with ocular infection and antibiotic susceptibility patterns of isolated pathogens.
2007 Aug
Antibiotic and heavy metal resistance in motile aeromonads and pseudomonads from rainbow trout (Oncorhynchus mykiss) farms in Australia.
2007 Aug
[Short communication: comparison of susceptibilities of Escherichia coli urinary tract isolates against fosfomycin tromethamine and different antibiotics].
2007 Jan
Inadequate antimicrobial prophylaxis during surgery: a study of beta-lactam levels during burn debridement.
2007 Jul
Pulsed-field gel electrophoresis in the identification of the origin of bacterial keratitis caused by Pseudomonas aeruginosa.
2007 Jul
Characterization of antimicrobial resistance patterns and class 1 integrons in Escherichia coli O26 isolated from humans and animals.
2007 Mar
Studies on the mechanisms of beta-lactam resistance in Bordetella bronchiseptica.
2007 Mar
Predictive analysis of ceftazidime hydrolysis in CTX-M-type beta-lactamase family members with a mutational substitution at position 167.
2007 Mar
Molecular characterization of the gene encoding a new AmpC beta-lactamase in Acinetobacter baylyi.
2007 May
Campylobacter canadensis sp. nov., from captive whooping cranes in Canada.
2007 Nov
[Review of the actions in prevention of infections in total arthroplasty of hip].
2007 Nov-Dec
[Integrons and their relationship with resistance phenotype in Gram negative bacilli isolated in the Hospital Torres Galdames, Iquique, Chile].
2007 Oct
Antibiotic resistance of commensal Escherichia coli of food-producing animals from three Vojvodinian farms, Serbia.
2008 Apr
Interaction of beta-lactam antibiotics with the mitochondrial carnitine/acylcarnitine transporter.
2008 Jun 17
Determination of cephalosporins in solid binary mixtures by polarized IR- and Raman spectroscopy.
2008 Sep 10
Development and validation of an immunochromatographic assay for rapid multi-residues detection of cephems in milk.
2009 Feb 16
Rapid evolution of virulence and drug resistance in the emerging zoonotic pathogen Streptococcus suis.
2009 Jul 15
Patents

Sample Use Guides

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
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 Wed Jul 05 22:39:58 UTC 2023
Edited
by admin
on Wed Jul 05 22:39:58 UTC 2023
Record UNII
IW6KLJ5ANA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEPHALOTHIN ETHANOLAMINE
Common Name English
5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-((ACETYLOXY)METHYL)-8-OXO-7-((2-THIENYLACETYL)AMINO)-, (6R-TRANS)-, COMPD. WITH 2-AMINOETHANOL (1:1)
Systematic Name English
7-(2-THIENYLACETAMIDO)CEPHALOSPORANIC ACID ETHANOLAMINE SALT
Common Name English
Code System Code Type Description
FDA UNII
IW6KLJ5ANA
Created by admin on Wed Jul 05 22:39:58 UTC 2023 , Edited by admin on Wed Jul 05 22:39:58 UTC 2023
PRIMARY
PUBCHEM
133082149
Created by admin on Wed Jul 05 22:39:58 UTC 2023 , Edited by admin on Wed Jul 05 22:39:58 UTC 2023
PRIMARY
CAS
22199-74-2
Created by admin on Wed Jul 05 22:39:58 UTC 2023 , Edited by admin on Wed Jul 05 22:39:58 UTC 2023
PRIMARY
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ACTIVE MOIETY