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

Details

Stereochemistry ABSOLUTE
Molecular Formula C16H16N2O6S2
Molecular Weight 396.4408
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEPHALOTHIN

SMILES

CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@]([H])([C@@]2([H])SC1)N=C(Cc3cccs3)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 396.4408
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
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
Comparison of phlebitis produced by cephapirin and cephalothin.
1976 Apr
Significant reduction in the incidence of phlebitis with buffered versus unbuffered cephalothin.
1976 Apr
Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity.
1992
[Coagulase negative staphylococci isolated on blood cultures].
2001 Aug
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
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
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
beta-Lactam allergenic determinants: fine structural recognition of a cross-reacting determinant on benzylpenicillin and cephalothin.
2002 Nov
Antibiotic resistance of E. coli in sewage and sludge.
2003 Apr
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
Role of beta-lactam carboxyl group on binding of penicillins and cephalosporins to class C beta-lactamases.
2003 May 15
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
"Streptococcus milleri" endocarditis caused by Streptococcus anginosus.
2004 Feb
Antimicrobial susceptibility of bifidobacteria.
2005 Jan
[Taxonomical study of bacteria from genera Alteromonas and Pseudoalteromonas isolated from Black Sea water and invertebrates].
2005 Jul-Aug
[Community-acquired methicillin-resistant Staphylococcus aureus disseminated disease].
2006
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
Helicobacter equorum sp. nov., a urease-negative Helicobacter species isolated from horse faeces.
2007 Feb
[Short communication: comparison of susceptibilities of Escherichia coli urinary tract isolates against fosfomycin tromethamine and different antibiotics].
2007 Jan
Serratia marcescens infection in a swallow-tailed hummingbird.
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
[Serratia rubidaea bacteremia].
2007 May
A Case of Helicobacter cinaedi Bacteraemia in a Previously Healthy Person with Cellulitis.
2008
A reservoir of drug-resistant pathogenic bacteria in asymptomatic hosts.
2008
[Study on Acinetobacter baumannii plasmid with 3 types of beta-lactamase genes in a burn ward].
2008 Apr
Antimicrobial resistance of Salmonella enterica isolates from apparently healthy and clinically ill finishing pigs in Spain.
2008 May
[Antimicrobial resistance of uropathogens among outpatients, 2000-2004].
2008 May-Jun
[Distribution and drug resistance of the isolated bacteria from children with acute respiratory infection].
2008 Oct
Determination of cephalosporins in solid binary mixtures by polarized IR- and Raman spectroscopy.
2008 Sep 10
Frequency of Escherichia coli O157:H7 in children with diarrhoea in Zahedan, Islamic Republic of Iran.
2008 Sep-Oct
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
Isolation of bacteria from remote high altitude Andean lakes able to grow in the presence of antibiotics.
2009 Jan
[Are antimicrobials useful in closed thoracostomy due to trauma?].
2009 Jan-Feb
Effects of mosapride on motility of the small intestine and caecum in normal horses after jejunocaecostomy.
2009 Jun
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 Sat Jun 26 00:10:39 UTC 2021
Edited
by admin
on Sat Jun 26 00:10:39 UTC 2021
Record UNII
R72LW146E6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEPHALOTHIN
GREEN BOOK   HSDB   MI   VANDF  
Common Name English
CEFALOTIN [WHO-DD]
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 [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 Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
WHO-ATC J01DB03
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
WHO-VATC QJ01DB03
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
Code System Code Type Description
PUBCHEM
6024
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
EVMPD
SUB06170MIG
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
INN
1477
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
MERCK INDEX
M3251
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY Merck Index
EPA CompTox
153-61-7
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
NCI_THESAURUS
C62021
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-815-7
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
WIKIPEDIA
CEFALOTIN
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
DRUG CENTRAL
574
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
ChEMBL
CHEMBL617
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
IUPHAR
8798
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
DRUG BANK
DB00456
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
MESH
D002512
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
RXCUI
2236
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY RxNorm
HSDB
3024
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
FDA UNII
R72LW146E6
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
CAS
153-61-7
Created by admin on Sat Jun 26 00:10:39 UTC 2021 , Edited by admin on Sat Jun 26 00:10:39 UTC 2021
PRIMARY
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