U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of CEPHALOTHIN

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

HIDE SMILES / InChI

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
Therapeutic efficacy of tobramycin--a clinical and laboratory evaluation.
1975 Dec
Acute renal failure associated with cephalosporin therapy.
1975 Jun
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
[Beta-lactam resistance in aquatic Enterobacter cloacae strains using phenotypic and genotypic criteria].
2002 Jul-Dec
Emergence and rapid spread of tetracycline-resistant Vibrio cholerae strains, Madagascar.
2002 Mar
Interaction of human organic anion transporters with various cephalosporin antibiotics.
2002 Mar 8
[Activity of 14 antimicrobials against Eikenella corrodens].
2002 Oct-Dec
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
Antimicrobial resistance in Gram-negative bacilli isolated from infant formulas.
2003 Nov 21
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
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
[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
Antibiotic resistance of commensal Escherichia coli of food-producing animals from three Vojvodinian farms, Serbia.
2008 Apr
Assay for integrons and pattern of antibiotic resistance in clinical Escherichia coli strains by PCR-RFLP in Southern Iran.
2008 Jan
Interaction of beta-lactam antibiotics with the mitochondrial carnitine/acylcarnitine transporter.
2008 Jun 17
Antimicrobial resistance of Salmonella enterica isolates from apparently healthy and clinically ill finishing pigs in Spain.
2008 May
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
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 22:34:17 UTC 2023
Edited
by admin
on Wed Jul 05 22:34:17 UTC 2023
Record UNII
R72LW146E6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEPHALOTHIN
GREEN BOOK   HSDB   MI   VANDF  
Common Name English
CEPHALOTHIN [HSDB]
Common Name English
CEFALOTIN
INN   WHO-DD  
INN  
Official 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)-
Common Name English
Cefalotin [WHO-DD]
Common Name English
cefalotin [INN]
Common Name English
CEPHALOTHIN [MI]
Common Name English
CEPHALOTHIN [VANDF]
Common Name English
CEPHALOTHIN [GREEN BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
WHO-ATC J01DB03
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
WHO-VATC QJ01DB03
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
Code System Code Type Description
PUBCHEM
6024
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
SMS_ID
100000081576
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
EVMPD
SUB06170MIG
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
INN
1477
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
MERCK INDEX
M3251
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY Merck Index
EPA CompTox
DTXSID4022783
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
NCI_THESAURUS
C62021
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
ECHA (EC/EINECS)
205-815-7
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
WIKIPEDIA
CEFALOTIN
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
DRUG CENTRAL
574
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
ChEMBL
CHEMBL617
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
IUPHAR
8798
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
DRUG BANK
DB00456
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
MESH
D002512
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
RXCUI
2236
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY RxNorm
HSDB
3024
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
CHEBI
124991
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
FDA UNII
R72LW146E6
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
CAS
153-61-7
Created by admin on Wed Jul 05 22:34:17 UTC 2023 , Edited by admin on Wed Jul 05 22:34:17 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
ENZYME->SUBSTRATE
Leads to resistance to the antibiotic.
BINDER->LIGAND
BINDING
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY