CEPHALOTHIN SODIUM

US Previously Marketed

First approved in 1964

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C16H15N2O6S2.Na
Molecular Weight	418.42
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Na+].CC(=O)OCC1=C(N2[C@H](SC1)[C@H](NC(=O)CC3=CC=CS3)C2=O)C([O-])=O

InChI

InChIKey=VUFGUVLLDPOSBC-XRZFDKQNSA-M

InChI=1S/C16H16N2O6S2.Na/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);/q;+1/p-1/t12-,15-;/m1./s1

HIDE SMILES / InChI

Molecular Formula	C16H15N2O6S2
Molecular Weight	395.43
Charge	-1
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	Na
Molecular Weight	22.98976928
Charge	1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421	Inhibitor 8504
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 8504
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 8504	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 8583	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 8583	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 8583	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 8583	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 28 Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf	Curative	Approved 8583	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 8583	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 Health Status: unhealthy Age Group: 18 - 91 years Sex: M+F 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 Health Status: healthy Age Group: 23 - 28 years Sex: M+F 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 Health Status: unhealthy Age Group: 18 - 91 years Sex: M+F 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 Health Status: unhealthy Age Group: 18 - 91 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/12495602/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
OAT4 150 OAT1 725 OAT2 153 OAT3 747

Drug as perpetrator

Target	Modality	Activity
OAT2 155	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [IC50 1500 uM]
OAT1 730	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [IC50 570 uM]
OAT3 749	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [IC50 80 uM]
OAT4 150	inhibitor 4027 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
Aaron Chemicals	AR007IEY	http://www.aaronchem.com/153-61-7
abcr GmbH	AB436526	http://www.abcr.com/shop/en/AB436526
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/
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
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
BioSynth	C-2484	https://www.biosynth.com/products/biochemistry/culture-media-additives/products/C-2484.html
BLD Pharm	BD160111	http://www.bldpharm.com/products/153-61-7.html
Chem Scene	CS-W008776	http://www.chemscene.com/153-61-7.html
Chemenu	CM110466	http://www.chemenu.com/products/CM110466
ChemMol	49402722	http://www.chemmol.com/chemmol/49402722.html
ChemReagents	80007602	http://www.chemreagents.com/Product/Product.asp?ProductID=80007602
Chemspace	CSSB00016988946	https://chem-space.com/CSSB00016988946
CSNpharm	CSN23657	https://www.csnpharm.com/products/cephalothin.html
DC Chemicals	DC31586	http://www.dcchemicals.com//product_show-Cefalotin.html
Enamine	Z1741977144	https://www.enaminestore.com/catalog/Z1741977144
eNovation Chemicals	D674200	https://www.enovationchem.com/ProductDetails.asp?ProductID=D674200
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
Oakwood	79464	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=64638&ExtHyperLink=1
OChem	10283	http://www.ocheminc.com/index.php?act=psearch&pid=153C617
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

PubMed

Title	Date	PubMed
Protective effect of topical antibiotics in breast augmentation.	2009-08	19644284
Rapid evolution of virulence and drug resistance in the emerging zoonotic pathogen Streptococcus suis.	2009-07-15	19603075
Effects of mosapride on motility of the small intestine and caecum in normal horses after jejunocaecostomy.	2009-06	19461212
Antibacterial effects of Iranian fennel essential oil on isolates of Acinetobacter baumannii.	2009-05-01	19634482
CTX-M beta-lactamases in Escherichia coli from community-acquired urinary tract infections, Cambodia.	2009-05	19402960
[Are antimicrobials useful in closed thoracostomy due to trauma?].	2009-04-07	19344560
Effect of iron-chelator deferiprone on the in vitro growth of staphylococci.	2009-04	19399272
[Characterization of Listeria monocytogenes isolates obtained from raw cheese samples acquired from different Costa Rican producer zones].	2009-03	19480346
Development and validation of an immunochromatographic assay for rapid multi-residues detection of cephems in milk.	2009-02-16	19154821
Frequency of Escherichia coli O157:H7 in children with diarrhoea in Zahedan, Islamic Republic of Iran.	2009-01-24	19161073
Isolation of bacteria from remote high altitude Andean lakes able to grow in the presence of antibiotics.	2009-01	19149698
The photosynthetic apparatus and its regulation in the aerobic gammaproteobacterium Congregibacter litoralis gen. nov., sp. nov.	2009	19287491
[Distribution and drug resistance of the isolated bacteria from children with acute respiratory infection].	2008-10	18947473
Determination of cephalosporins in solid binary mixtures by polarized IR- and Raman spectroscopy.	2008-09-10	18602240
Interaction of beta-lactam antibiotics with the mitochondrial carnitine/acylcarnitine transporter.	2008-06-17	18452908
Antimicrobial resistance of Salmonella enterica isolates from apparently healthy and clinically ill finishing pigs in Spain.	2008-05	18387141
[Review of the actions in prevention of infections in total arthroplasty of hip].	2008-04-05	18386531
[Study on Acinetobacter baumannii plasmid with 3 types of beta-lactamase genes in a burn ward].	2008-04	18785406
Structure-function studies of arginine at position 276 in CTX-M beta-lactamases.	2008-04	18281307
Antibiotic resistance of commensal Escherichia coli of food-producing animals from three Vojvodinian farms, Serbia.	2008-04	18162377
[Antimicrobial resistance of uropathogens among outpatients, 2000-2004].	2008-01-28	18719808
Assay for integrons and pattern of antibiotic resistance in clinical Escherichia coli strains by PCR-RFLP in Southern Iran.	2008-01	18219144
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
Campylobacter canadensis sp. nov., from captive whooping cranes in Canada.	2007-11	17978232
[Integrons and their relationship with resistance phenotype in Gram negative bacilli isolated in the Hospital Torres Galdames, Iquique, Chile].	2007-10	17989843
[Nonpuerperal breast abscess caused by Finegoldia magna].	2007-08-19	17702255
Bacteriological findings in patients with ocular infection and antibiotic susceptibility patterns of isolated pathogens.	2007-08	17657382
Antibiotic and heavy metal resistance in motile aeromonads and pseudomonads from rainbow trout (Oncorhynchus mykiss) farms in Australia.	2007-08	17524624
Genotypic and phenotypic profiles of enterotoxigenic Escherichia coli associated with acute diarrhea in Tunis, Tunisia.	2007-07	17554469
Inadequate antimicrobial prophylaxis during surgery: a study of beta-lactam levels during burn debridement.	2007-07	17504805
Pulsed-field gel electrophoresis in the identification of the origin of bacterial keratitis caused by Pseudomonas aeruginosa.	2007-07	17186257
Characterization of Klebsiella pneumoniae isolates from New Zealand sea lion (Phocarctos hookeri) pups during and after the epidemics on Enderby Island, Auckland Islands.	2007-05-16	17250977
Molecular characterization of the gene encoding a new AmpC beta-lactamase in Acinetobacter baylyi.	2007-05	17403709
[Serratia rubidaea bacteremia].	2007-05	17321092
Antimicrobial resistance of Yersinia enterocolitica strains from human patients, pigs and retail pork in Switzerland.	2007-04-01	17196695
Characterization of antimicrobial resistance patterns and class 1 integrons in Escherichia coli O26 isolated from humans and animals.	2007-03	17390416
Studies on the mechanisms of beta-lactam resistance in Bordetella bronchiseptica.	2007-03	17261565
Predictive analysis of ceftazidime hydrolysis in CTX-M-type beta-lactamase family members with a mutational substitution at position 167.	2007-03	17258896
Helicobacter equorum sp. nov., a urease-negative Helicobacter species isolated from horse faeces.	2007-02	17267952
[Short communication: comparison of susceptibilities of Escherichia coli urinary tract isolates against fosfomycin tromethamine and different antibiotics].	2007-01	17427560
Serratia marcescens infection in a swallow-tailed hummingbird.	2007-01	17347399
Antimicrobial sensitivity and adherence study in strains of coagulase-negative Staphylococcus spp.	2006-10-26	17061495
In vivo selection of OmpK35-deficient mutant after cefuroxime therapy for primary liver abscess caused by Klebsiella pneumoniae.	2006-10	16880175
Occurrence and characterization of Aeromonas spp. in mussels from the Adriatic Sea.	2006-08	16943032
Integron presence in a multiresistant Morganella morganii isolate.	2006-06	16690260
Conjunctival bacterial flora and antibiotic resistance pattern in patients undergoing cataract surgery.	2006-02-24	16491231
[Phenotypical differences of Helicobacter pylori strains isolated in Georgia].	2006-01-28	16438382
[Community-acquired methicillin-resistant Staphylococcus aureus disseminated disease].	2006	17137175
Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy.	1990-11	1701026

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 `Mon Mar 31 17:53:04 GMT 2025` Edited by `admin` on `Mon Mar 31 17:53:04 GMT 2025`
Record UNII	C22G6EYP8B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEFALOTIN SODIUM

Preferred Name

English

CEPHALOTHIN SODIUM

Official Name

English

CEFALOTIN SODIUM [JAN]

Common Name

English

Monosodium (6R,7R)-3-(hydroxymethyl)-8-oxo-7-[2-(2-thienyl)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate acetate (ester)

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-((ACETYLOXY)METHYL)-8-OXO-7-((2-THIENYLACETYL)AMINO)-, MONOSODIUM SALT, (6R-TRANS)-

Common Name

English

38253

Code

English

CEPHALOTHIN SODIUM [ORANGE BOOK]

Common Name

English

SEFFIN

Brand Name

English

NSC-756667

Code

English

KEFLIN

Brand Name

English

CEPHALOTHIN SODIUM [USP MONOGRAPH]

Common Name

English

CEFALOTIN SODIUM [MART.]

Common Name

English

CEPHALOTHIN SODIUM [USAN]

Common Name

English

CEFALOTIN SODIUM [EP IMPURITY]

Common Name

English

Cefalotin sodium [WHO-DD]

Common Name

English

CEPHALOTHIN SODIUM [USP IMPURITY]

Common Name

English

CEPHALOTHIN SODIUM SALT [MI]

Common Name

English

CEPHALOTHIN SODIUM [VANDF]

Common Name

English

SODIUM CEPHALOTHIN

Common Name

English

CEFALOTIN SODIUM [EP MONOGRAPH]

Common Name

English

SODIUM (6R,7R)-3-(ACETOXYMETHYL)-8-OXO-7-((2-THIENYLACETYL)AMINO)-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357