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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

CC(=O)OCC1=C(N2[C@H](SC1)[C@H](NC(=O)CC3=CC=CS3)C2=O)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
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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.

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy.
1990 Nov
Antimicrobial sensitivity and adherence study in strains of coagulase-negative Staphylococcus spp.
2001 Jul-Sep
[Phenotypical differences of Helicobacter pylori strains isolated in Georgia].
2005 Nov-Dec
[Community-acquired methicillin-resistant Staphylococcus aureus disseminated disease].
2006
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
[Nonpuerperal breast abscess caused by Finegoldia magna].
2007 Apr-Jun
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
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
Genotypic and phenotypic profiles of enterotoxigenic Escherichia coli associated with acute diarrhea in Tunis, Tunisia.
2007 Jul
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
[Serratia rubidaea bacteremia].
2007 May
Characterization of Klebsiella pneumoniae isolates from New Zealand sea lion (Phocarctos hookeri) pups during and after the epidemics on Enderby Island, Auckland Islands.
2007 May 16
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
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
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
[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
The photosynthetic apparatus and its regulation in the aerobic gammaproteobacterium Congregibacter litoralis gen. nov., sp. nov.
2009
Effect of iron-chelator deferiprone on the in vitro growth of staphylococci.
2009 Apr
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
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

In Vivo Use Guide
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: Intravenous; Intramuscular
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 Mon Oct 21 19:50:05 UTC 2019
Edited
by admin
on Mon Oct 21 19:50:05 UTC 2019
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 Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
WHO-ATC J01DB03
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
WHO-VATC QJ01DB03
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
Code System Code Type Description
PUBCHEM
6024
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY
EVMPD
SUB06170MIG
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY
INN
1477
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY
MERCK INDEX
M3251
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY Merck Index
EPA CompTox
153-61-7
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY
NCI_THESAURUS
C62021
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY
ECHA (EC/EINECS)
205-815-7
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY
WIKIPEDIA
CEFALOTIN
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY
ChEMBL
CHEMBL617
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY
IUPHAR
8798
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY
DRUG BANK
DB00456
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY
MESH
D002512
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY
RXCUI
2236
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY RxNorm
HSDB
153-61-7
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY
CAS
153-61-7
Created by admin on Mon Oct 21 19:50:05 UTC 2019 , Edited by admin on Mon Oct 21 19:50:05 UTC 2019
PRIMARY
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