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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H16N2O6S2.C8H18N2
Molecular Weight 538.68
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEPHALOTHIN HEMI(TRANS-1,4-BIS(AMINOMETHYL)CYCLOHEXANE)

SMILES

NC[C@H]1CC[C@H](CN)CC1.[H][C@]23SCC(COC(C)=O)=C(N2C(=O)[C@H]3NC(=O)CC4=CC=CS4)C(O)=O

InChI

InChIKey=IJGMMRGFMSDAGX-FBXLDSNPSA-N
InChI=1S/C16H16N2O6S2.C8H18N2/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;9-5-7-1-2-8(6-10)4-3-7/h2-4,12,15H,5-7H2,1H3,(H,17,20)(H,22,23);7-8H,1-6,9-10H2/t12-,15-;7-,8-/m1./s1

HIDE SMILES / InChI

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

1974
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

1974
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

1974
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

1974
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

1974
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

1974
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
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
[Beta-lactam resistance in aquatic Enterobacter cloacae strains using phenotypic and genotypic criteria].
2002 Jul-Dec
Antibiotics induce apoptosis of human peritoneal mesothelial cells.
2003 Jun
Studies on calf diarrhoea in Mozambique: prevalence of bacterial pathogens.
2004
The vitro efficacy of beta-lactam and beta-lactamase inhibitors against multidrug resistant clinical strains of Mycobacterium tuberculosis.
2004 Apr
"Streptococcus milleri" endocarditis caused by Streptococcus anginosus.
2004 Feb
[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 susceptibility of bifidobacteria.
2005 Jan
Identification of antimicrobial resistance and class 1 integrons in Shiga toxin-producing Escherichia coli recovered from humans and food animals.
2005 Jul
[Taxonomical study of bacteria from genera Alteromonas and Pseudoalteromonas isolated from Black Sea water and invertebrates].
2005 Jul-Aug
[Prevalence of Listeria spp. in dairy farm and evaluation of antibiotic-resistance of isolates].
2005 May-Jun
[Phenotypical differences of Helicobacter pylori strains isolated in Georgia].
2005 Nov-Dec
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
Molecular characterisation and mechanisms of resistance of multidrug-resistant human Salmonella enterica serovar Typhimurium isolated in Amiens (France).
2005 Sep
Characterization of Staphylococcus aureus isolates recovered from bovine mastitis in Rio de Janeiro, Brazil.
2005 Sep
Flare up to betalactams.
2005 Sep-Oct
[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
Bacteriological findings in patients with ocular infection and antibiotic susceptibility patterns of isolated pathogens.
2007 Aug
Helicobacter equorum sp. nov., a urease-negative Helicobacter species isolated from horse faeces.
2007 Feb
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
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
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
Antimicrobial resistance of Salmonella enterica isolates from apparently healthy and clinically ill finishing pigs in Spain.
2008 May
[Distribution and drug resistance of the isolated bacteria from children with acute respiratory infection].
2008 Oct
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
[Are antimicrobials useful in closed thoracostomy due to trauma?].
2009 Jan-Feb
[Characterization of Listeria monocytogenes isolates obtained from raw cheese samples acquired from different Costa Rican producer zones].
2009 Mar
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.
Name Type Language
CEPHALOTHIN HEMI(TRANS-1,4-BIS(AMINOMETHYL)CYCLOHEXANE)
Systematic Name English
1,4-CYCLOHEXANEDIMETHANAMINE, TRANS-, BIS((6R-TRANS)-3-((ACETYLOXY)METHYL)-8-OXO-7-((2-THIENYLACETYL)AMINO)-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLATE)
Systematic 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 TRANS-1,4-CYCLOHEXANEDIMETHANAMINE (2:1)
Common Name English
Code System Code Type Description
CAS
23277-68-1
Created by admin on Sat Dec 16 14:08:27 GMT 2023 , Edited by admin on Sat Dec 16 14:08:27 GMT 2023
PRIMARY
FDA UNII
2QFS1UDW47
Created by admin on Sat Dec 16 14:08:27 GMT 2023 , Edited by admin on Sat Dec 16 14:08:27 GMT 2023
PRIMARY