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+].[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CC3=CC=CS3)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	Na
Molecular Weight	22.9898
Charge	1
Count

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

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

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 232 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7447421	Inhibitor 8228
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 8228
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 8228	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 8360	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 1.56556804E11
Skin and soft tissue infections 33 Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf	Curative	Approved 8360	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 1.56556804E11
Urogenital infections 4 Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf	Curative	Approved 8360	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 1.56556804E11
Septicaemia 15 Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf	Curative	Approved 8360	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 1.56556804E11
Bone and joint infections 27 Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf	Curative	Approved 8360	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 1.56556804E11
Endocarditis 16 Sources: https://gp2u.com.au/static/pdf/K/KEFLIN-PI.pdf	Curative	Approved 8360	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 1.56556804E11

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 145 OAT1 595 OAT2 144 OAT3 636

Drug as perpetrator

Target	Modality	Activity
OAT2 146	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [IC50 1500 uM]
OAT1 599	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [IC50 570 uM]
OAT3 638	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/12650826/	yes [IC50 80 uM]
OAT4 145	inhibitor 3240 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
Double-blind comparison of phlebitis produced by cefazolin versus cephalothin.	1975 Apr	1147583
Reversible nephrotoxicity associated with cephalothin therapy.	1975 Apr	1138675
Penicillin-induced immune hemolytic anemia. Occurrence of massive intravascular hemolysis.	1975 Aug 4	1173853
Therapeutic efficacy of tobramycin--a clinical and laboratory evaluation.	1975 Dec	1107297
Nephrotoxicity associated with cephalothin administration.	1975 Jun	1130924
Acute renal failure associated with cephalosporin therapy.	1975 Jun	1130272
Acute interstitial nephritis.	1976 Jan	1246100
Identification of penicillin allergenic determinants that bind IgE antibodies in the sera of subjects with penicillin allergy.	1990 Nov	1701026
Epitope analysis of aztreonam by antiaztreonam monoclonal antibodies and possible consequences in beta-lactams hypersensitivity.	1992	1384868
Comparison of methods for the determination of antimicrobial resistance in Staphylococcus aureus from bovine mastitis.	2001 Feb	11254096
Urinary tract infections in Norway: bacterial etiology and susceptibility. A retrospective study of clinical isolates.	2001 Oct	11683794
[Decreasing susceptibility to vancomycin in isogenic Staphylococcus aureus strains isolated from a single patient].	2001 Oct 13	11602171
Antimicrobial susceptibility of udder pathogens isolated from dairy herds in the west littoral region of Uruguay.	2002	12071114
[Beta-lactam resistance in aquatic Enterobacter cloacae strains using phenotypic and genotypic criteria].	2002 Jul-Dec	15085610
Emergence and rapid spread of tetracycline-resistant Vibrio cholerae strains, Madagascar.	2002 Mar	11927038
Interaction of human organic anion transporters with various cephalosporin antibiotics.	2002 Mar 8	11909604
Microbiological aspects of an urban river used for unrestricted irrigation in the semi-arid region of north-east Brazil.	2003	12639005
Antibiotics induce apoptosis of human peritoneal mesothelial cells.	2003 Jun	15012731
Antimicrobial resistance in Gram-negative bacilli isolated from infant formulas.	2003 Nov 21	14638421
Studies on calf diarrhoea in Mozambique: prevalence of bacterial pathogens.	2004	15535084
The vitro efficacy of beta-lactam and beta-lactamase inhibitors against multidrug resistant clinical strains of Mycobacterium tuberculosis.	2004 Apr	15081094
[Necrotizing lymphadenitis caused by Nocardia asteroides in a healthy girl].	2004 Apr-Jun	15470865
Nosocomial outbreak by Proteus mirabilis producing extended-spectrum beta-lactamase VEB-1 in a Korean university hospital.	2004 Dec	15546971
"Streptococcus milleri" endocarditis caused by Streptococcus anginosus.	2004 Feb	14972375
[Profile of antimicrobial resistance of agents causing urinary tract infections in children].	2004 Mar	15382465
Antimicrobial susceptibility of bifidobacteria.	2005 Jan	15574479
Identification of antimicrobial resistance and class 1 integrons in Shiga toxin-producing Escherichia coli recovered from humans and food animals.	2005 Jul	15911552
[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
Flare up to betalactams.	2005 Sep-Oct	16287548
[Community-acquired methicillin-resistant Staphylococcus aureus disseminated disease].	2006	17137175
Conjunctival bacterial flora and antibiotic resistance pattern in patients undergoing cataract surgery.	2006 Jan-Feb	16491231
Serratia marcescens infection in a swallow-tailed hummingbird.	2007 Jan	17347399
[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
Campylobacter canadensis sp. nov., from captive whooping cranes in Canada.	2007 Nov	17978232
[Integrons and their relationship with resistance phenotype in Gram negative bacilli isolated in the Hospital Torres Galdames, Iquique, Chile].	2007 Oct	17989843
A Case of Helicobacter cinaedi Bacteraemia in a Previously Healthy Person with Cellulitis.	2008	19088908
[Study on Acinetobacter baumannii plasmid with 3 types of beta-lactamase genes in a burn ward].	2008 Apr	18785406
[Antimicrobial resistance of uropathogens among outpatients, 2000-2004].	2008 May-Jun	18719808
Protective effect of topical antibiotics in breast augmentation.	2009 Aug	19644284
Isolation of bacteria from remote high altitude Andean lakes able to grow in the presence of antibiotics.	2009 Jan	19149698
[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
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 `Wed Jul 05 22:48:41 UTC 2023` Edited by `admin` on `Wed Jul 05 22:48:41 UTC 2023`
Record UNII	C22G6EYP8B
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

CEFALOTIN SODIUM

Common 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