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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

Molecular Formula C8H18N2
Molecular Weight 142.2419
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

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
Cephaloridine, cephalothin and the kidney.
1975
Acute interstitial nephritis.
1976 Jan
Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy.
1990 Nov
[Fosfomycin: an underrated antibiotic for urinary tract infections due to Escherichia coli].
2001 Dec
Antimicrobial susceptibility of udder pathogens isolated from dairy herds in the west littoral region of Uruguay.
2002
Effect of matrix metalloprotease inhibitors on the 95 kDa metallopeptidase of Candida albicans.
2002 Jun
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
Mitochondrial cytochrome c oxidase as a target site for cephalosporin antibiotics in renal epithelial cells (LLC-PK(1)) and renal cortex.
2002 Nov 22
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
Studies on calf diarrhoea in Mozambique: prevalence of bacterial pathogens.
2004
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
Molecular characterisation and mechanisms of resistance of multidrug-resistant human Salmonella enterica serovar Typhimurium isolated in Amiens (France).
2005 Sep
Flare up to betalactams.
2005 Sep-Oct
[Community-acquired methicillin-resistant Staphylococcus aureus disseminated disease].
2006
[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
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
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
Predictive analysis of ceftazidime hydrolysis in CTX-M-type beta-lactamase family members with a mutational substitution at position 167.
2007 Mar
[Serratia rubidaea bacteremia].
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
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
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
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

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 Dec 16 14:08:27 GMT 2023
Edited
by admin
on Sat Dec 16 14:08:27 GMT 2023
Record UNII
2QFS1UDW47
Record Status Validated (UNII)
Record Version
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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
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