CEPHALOTHIN

First approved in 1964

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 Search

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
Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf
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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421	Inhibitor 8297
D-alanyl-D-alanine carboxypeptidase 4 Target ID: P15555 Gene ID: NA Gene Symbol: NA Target Organism: Streptomyces sp. (strain R61) Sources: https://www.ncbi.nlm.nih.gov/pubmed/105727 \| https://www.ncbi.nlm.nih.gov/pubmed/7626623	Inhibitor 8297
Solute carrier family 22 member 7 5 Target ID: Q9Y694 Gene ID: 10864.0 Gene Symbol: SLC22A7 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/12650826	Inhibitor 8297	1.41 mM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Respiratory tract infections 85 Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf	Curative	Approved 8429	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
Skin and soft tissue infections 33 Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf	Curative	Approved 8429	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
Urogenital infections 4 Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf	Curative	Approved 8429	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
Septicaemia 15 Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf	Curative	Approved 8429	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
Bone and joint infections 27 Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf	Curative	Approved 8429	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
Endocarditis 16 Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf	Curative	Approved 8429	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

C_max

Value	Dose	Co-administered	Analyte	Population
20.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15830475/	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

Value	Dose	Co-administered	Analyte	Population
25.2 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15830475/	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

T_1/2

Value	Dose	Co-administered	Analyte	Population
28 min EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/15830475/	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

Dose	Population	Adverse 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: https://pubmed.ncbi.nlm.nih.gov/12495602/	unhealthy, 18 - 91 years n = 159 Health Status: unhealthy Condition: infections Age Group: 18 - 91 years Sex: M+F Population Size: 159 Sources: https://pubmed.ncbi.nlm.nih.gov/12495602/	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: https://pubmed.ncbi.nlm.nih.gov/12495602/
1 g single, intramuscular Recommended Dose: 1 g Route: intramuscular Route: single Dose: 1 g Sources: https://pubmed.ncbi.nlm.nih.gov/833342/	healthy, 23 - 28 years n = 7 Health Status: healthy Age Group: 23 - 28 years Sex: M+F Population Size: 7 Sources: https://pubmed.ncbi.nlm.nih.gov/833342/	Sources: https://pubmed.ncbi.nlm.nih.gov/833342/

AEs

AE	Significance	Dose	Population
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: https://pubmed.ncbi.nlm.nih.gov/12495602/	unhealthy, 18 - 91 years n = 159 Health Status: unhealthy Condition: infections Age Group: 18 - 91 years Sex: M+F Population Size: 159 Sources: https://pubmed.ncbi.nlm.nih.gov/12495602/
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: https://pubmed.ncbi.nlm.nih.gov/12495602/	unhealthy, 18 - 91 years n = 159 Health Status: unhealthy Condition: infections Age Group: 18 - 91 years Sex: M+F Population Size: 159 Sources: https://pubmed.ncbi.nlm.nih.gov/12495602/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT4 146 OAT1 599 OAT2 145 OAT3 642

Drug as perpetrator

Target	Modality	Activity
OAT2 147	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [IC50 1500 uM]
OAT1 603	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [IC50 570 uM]
OAT3 644	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [IC50 80 uM]
OAT4 146	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [Ki 200 uM]

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA007HN6	http://www.aablocks.com/goods/Goods/detail?id=AA007HN6
AEchem Scientific Corp., USA	AE1-019588	http://www.aechemsc.com/info_products/AE1-019588.php
AK Scientific, Inc. (AKSCI)	69130	http://www.aksci.com/item_detail.php?cat=69130
Aaron Chemicals	AR007IEY	http://www.aaronchem.com/153-61-7
Achemo Scientific Limited	AC-77101	http://www.achemo.com/search/?Keyword= 153-61-7
Achemtek	0104-019721	http://www.achemtek.com/153-61-7
Acorn PharmaTech	ACN-045431	http://www.acornpharmatech.com/
Alichem	169005178	http://www.alichem.com/en/products/153-61-7.html
Allbio Pharm Co., Ltd	AD09734	http://www.allbiopharm.com/product/n/AD09734
Alsachim	4890	http://www.alsachim.com/product-C6273-glo.bal-view.html
AstaTech, Inc.	35994	http://www.astatechinc.com/CPSResult.php?CRNO=36343
Aurum Pharmatech LLC	S-1796	http://www.Aurumpharmatech.com/Product/ProductDetails/S_1796
Avantor Inc	TCC2769-25G	https://us.vwr.com/store/product/16810959/cephalothin-98-0-by-hplc-titration-analysis
Avantor Inc	TCC2769-5G	https://us.vwr.com/store/product/16810959/cephalothin-98-0-by-hplc-titration-analysis
BLD Pharm	BD160111	http://www.bldpharm.com/products/153-61-7.html
BioSynth	C-2484	https://www.biosynth.com/products/biochemistry/culture-media-additives/products/C-2484.html
CSNpharm	CSN23657	https://www.csnpharm.com/products/cephalothin.html
Chem Scene	CS-W008776	http://www.chemscene.com/153-61-7.html
ChemMol	49402722	http://www.chemmol.com/chemmol/49402722.html
ChemReagents	80007602	http://www.chemreagents.com/Product/Product.asp?ProductID=80007602
Chemenu	CM110466	http://www.chemenu.com/products/CM110466
Chemspace	CSSB00016988946	https://chem-space.com/CSSB00016988946
DC Chemicals	DC31586	http://www.dcchemicals.com//product_show-Cefalotin.html
Enamine	Z1741977144	https://www.enaminestore.com/catalog/Z1741977144
Glentham Life Sciences	GA3485	http://www.glentham.com/products/product/GA3485/
Hairui	HR132475	http://www.hairuichem.com/en/product/153-61-7.html
Lab Network	LN00176152	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00176152
Matrix Scientific	76118	https://www.matrixscientific.com/076118.html
MedChem Express	HY-B1275A	https://www.medchemexpress.com/cephalothin.html
OChem	10283	http://www.ocheminc.com/index.php?act=psearch&pid=153C617
Oakwood	79464	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=64638&ExtHyperLink=1
Smolecule	S523065	http://www.smolecule.com/products/s523065
TCI (Tokyo Chemical Industry)	C2769	http://www.tcichemicals.com/eshop/en/us/commodity/C2769/index.html
THE BioTek	bt-263296	https://www.thebiotek.com/product/inhibitors/bt-263296
Yuhao Chemical	LQ0630	http://www.chemyuhao.com/153-61-7.html
abcr GmbH	AB436526	http://www.abcr.com/shop/en/AB436526
eNovation Chemicals	D674200	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674200

PubMed

Title	Date	PubMed
Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy.	1990 Nov	1701026
Antimicrobial sensitivity and adherence study in strains of coagulase-negative Staphylococcus spp.	2001 Jul-Sep	17061495
Nosocomial outbreak by Proteus mirabilis producing extended-spectrum beta-lactamase VEB-1 in a Korean university hospital.	2004 Dec	15546971
Molecular evaluation of antibiotic susceptibility of Tropheryma whipplei in axenic medium.	2005 Feb	15650004
Antimicrobial susceptibility of bifidobacteria.	2005 Jan	15574479
Antimicrobial resistance in Salmonella enteritidis strains isolated from broiler carcasses, food, human and poultry-related samples.	2005 Jan 1	15582740
Identification of antimicrobial resistance and class 1 integrons in Shiga toxin-producing Escherichia coli recovered from humans and food animals.	2005 Jul	15911552
[Taxonomical study of bacteria from genera Alteromonas and Pseudoalteromonas isolated from Black Sea water and invertebrates].	2005 Jul-Aug	16250230
[Prevalence of Listeria spp. in dairy farm and evaluation of antibiotic-resistance of isolates].	2005 May-Jun	16041920
[Phenotypical differences of Helicobacter pylori strains isolated in Georgia].	2005 Nov-Dec	16438382
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	16335054
Molecular characterisation and mechanisms of resistance of multidrug-resistant human Salmonella enterica serovar Typhimurium isolated in Amiens (France).	2005 Sep	16122913
Characterization of Staphylococcus aureus isolates recovered from bovine mastitis in Rio de Janeiro, Brazil.	2005 Sep	16107411
Flare up to betalactams.	2005 Sep-Oct	16287548
Occurrence and characterization of Aeromonas spp. in mussels from the Adriatic Sea.	2006 Aug	16943032
Conjunctival bacterial flora and antibiotic resistance pattern in patients undergoing cataract surgery.	2006 Jan-Feb	16491231
Integron presence in a multiresistant Morganella morganii isolate.	2006 Jun	16690260
In vivo selection of OmpK35-deficient mutant after cefuroxime therapy for primary liver abscess caused by Klebsiella pneumoniae.	2006 Oct	16880175
Antimicrobial resistance of Yersinia enterocolitica strains from human patients, pigs and retail pork in Switzerland.	2007 Apr 1	17196695
[Nonpuerperal breast abscess caused by Finegoldia magna].	2007 Apr-Jun	17702255
Antibiotic and heavy metal resistance in motile aeromonads and pseudomonads from rainbow trout (Oncorhynchus mykiss) farms in Australia.	2007 Aug	17524624
Helicobacter equorum sp. nov., a urease-negative Helicobacter species isolated from horse faeces.	2007 Feb	17267952
[Short communication: comparison of susceptibilities of Escherichia coli urinary tract isolates against fosfomycin tromethamine and different antibiotics].	2007 Jan	17427560
Genotypic and phenotypic profiles of enterotoxigenic Escherichia coli associated with acute diarrhea in Tunis, Tunisia.	2007 Jul	17554469
Inadequate antimicrobial prophylaxis during surgery: a study of beta-lactam levels during burn debridement.	2007 Jul	17504805
Characterization of antimicrobial resistance patterns and class 1 integrons in Escherichia coli O26 isolated from humans and animals.	2007 Mar	17390416
Studies on the mechanisms of beta-lactam resistance in Bordetella bronchiseptica.	2007 Mar	17261565
Predictive analysis of ceftazidime hydrolysis in CTX-M-type beta-lactamase family members with a mutational substitution at position 167.	2007 Mar	17258896
Molecular characterization of the gene encoding a new AmpC beta-lactamase in Acinetobacter baylyi.	2007 May	17403709
[Serratia rubidaea bacteremia].	2007 May	17321092
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	17250977
A Case of Helicobacter cinaedi Bacteraemia in a Previously Healthy Person with Cellulitis.	2008	19088908
A reservoir of drug-resistant pathogenic bacteria in asymptomatic hosts.	2008	19015729
[Study on Acinetobacter baumannii plasmid with 3 types of beta-lactamase genes in a burn ward].	2008 Apr	18785406
Assay for integrons and pattern of antibiotic resistance in clinical Escherichia coli strains by PCR-RFLP in Southern Iran.	2008 Jan	18219144
Antimicrobial resistance of Salmonella enterica isolates from apparently healthy and clinically ill finishing pigs in Spain.	2008 May	18387141
[Antimicrobial resistance of uropathogens among outpatients, 2000-2004].	2008 May-Jun	18719808
[Distribution and drug resistance of the isolated bacteria from children with acute respiratory infection].	2008 Oct	18947473
Determination of cephalosporins in solid binary mixtures by polarized IR- and Raman spectroscopy.	2008 Sep 10	18602240
Frequency of Escherichia coli O157:H7 in children with diarrhoea in Zahedan, Islamic Republic of Iran.	2008 Sep-Oct	19161073
The photosynthetic apparatus and its regulation in the aerobic gammaproteobacterium Congregibacter litoralis gen. nov., sp. nov.	2009	19287491
Effect of iron-chelator deferiprone on the in vitro growth of staphylococci.	2009 Apr	19399272
Protective effect of topical antibiotics in breast augmentation.	2009 Aug	19644284
Development and validation of an immunochromatographic assay for rapid multi-residues detection of cephems in milk.	2009 Feb 16	19154821
[Are antimicrobials useful in closed thoracostomy due to trauma?].	2009 Jan-Feb	19344560
Rapid evolution of virulence and drug resistance in the emerging zoonotic pathogen Streptococcus suis.	2009 Jul 15	19603075
Effects of mosapride on motility of the small intestine and caecum in normal horses after jejunocaecostomy.	2009 Jun	19461212
[Characterization of Listeria monocytogenes isolates obtained from raw cheese samples acquired from different Costa Rican producer zones].	2009 Mar	19480346
CTX-M beta-lactamases in Escherichia coli from community-acquired urinary tract infections, Cambodia.	2009 May	19402960
Antibacterial effects of Iranian fennel essential oil on isolates of Acinetobacter baumannii.	2009 May 1	19634482

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: 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 `Fri Dec 15 15:02:14 GMT 2023` Edited by `admin` on `Fri Dec 15 15:02:14 GMT 2023`
Record UNII	R72LW146E6
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEPHALOTHIN

Common Name

English

CEPHALOTHIN [HSDB]

Common Name

English

CEFALOTIN

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