CEPHAPIRIN SODIUM

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H16N3O6S2.Na
Molecular Weight	445.445
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)CSC3=CC=NC=C3)C([O-])=O

InChI

InChIKey=VGEOUKPOQQEQSX-OALZAMAHSA-M

InChI=1S/C17H17N3O6S2.Na/c1-9(21)26-6-10-7-28-16-13(15(23)20(16)14(10)17(24)25)19-12(22)8-27-11-2-4-18-5-3-11;/h2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25);/q;+1/p-1/t13-,16-;/m1./s1

HIDE SMILES / InChI

Description
Sources: https://www.drugs.com/mmx/cefadyl.html
Curator's Comment: Description was created based on several sources, including http://www.msd-animal-health.co.nz/products/Metricure_/020_Product_Details.aspx | http://pharm-sci.tbzmed.ac.ir/Drug-Information/Integrative%20Medicine%20Professional%20Access/ProfDrugs/Cephapirinpd.html

Cephapirin is a first-generation cephalosporin. Cephapirin has been indicated for the treatment of infections when caused by susceptible strains in respiratory, genitourinary, gastrointestinal, skin and soft tissue, bone and joint infections, septicemia; treatment of susceptible gram-positive bacilli and cocci (never enterococcus); some gram-negative bacilli including E. coli, Proteus, and Klebsiella may be susceptible. Cephapirin is used in veterinary as an intra-uterine antibiotic infusion for the treatment of subacute and chronic endometritis in cows and repeat breeders.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 233 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/808545 \| https://www.ncbi.nlm.nih.gov/pubmed/23336133	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 234 Sources: https://www.drugs.com/mmx/cefadyl.html	Curative		Approved 8429	CEFADYL Approved Use Treatment of infections when caused by susceptible strains in respiratory, genitourinary, gastrointestinal, skin and soft tissue, bone and joint infections, septicemia; treatment of susceptible gram-positive bacilli and cocci (never enterococcus); some gram-negative bacilli including E. coli, Proteus, and Klebsiella may be susceptible Launch Date 1974

C_max

Value	Dose	Co-administered	Analyte	Population
92 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/984783/	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:		CEPHAPIRIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
72 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/984783/	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:		CEPHAPIRIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
0.36 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/984783/	2 g single, intravenous dose: 2 g route of administration: Intravenous experiment type: SINGLE co-administered:		CEPHAPIRIN serum	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
2 g 6 times / day multiple, intramuscular Highest studied dose Dose: 2 g, 6 times / day Route: intramuscular Route: multiple Dose: 2 g, 6 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6703681	unhealthy, 31.4 years n = 16 Health Status: unhealthy Condition: Staphylococcus aureus Endocarditis Age Group: 31.4 years Sex: M+F Population Size: 16 Sources: https://pubmed.ncbi.nlm.nih.gov/6703681	Sources: https://pubmed.ncbi.nlm.nih.gov/6703681
1 g 4 times / day multiple, intramuscular Dose: 1 g, 4 times / day Route: intramuscular Route: multiple Dose: 1 g, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4680807	unhealthy, 50 years n = 1 Health Status: unhealthy Age Group: 50 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4680807	Disc. AE: Neutropenia... AEs leading to discontinuation/dose reduction: Neutropenia (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/4680807

AEs

AE	Significance	Dose	Population
Neutropenia	1 patient Disc. AE	1 g 4 times / day multiple, intramuscular Dose: 1 g, 4 times / day Route: intramuscular Route: multiple Dose: 1 g, 4 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/4680807	unhealthy, 50 years n = 1 Health Status: unhealthy Age Group: 50 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/4680807

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:554446	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:554446
MolPort	MolPort-006-123-516	https://www.molport.com/shop/molecule-link/MolPort-006-123-516
ZINC	ZINC000003830511	http://zinc15.docking.org/substances/ZINC000003830511

PubMed

Title	Date	PubMed
Relative incidence of phlebitis caused by continuous intravenous infusion of cephapirin and cephalothin.	1972 Sep	4790563
Double-blind controlled comparison of phlebitis produced by cephapirin and cephalothin.	1973 Feb	4597719
Phlebitis associated with the intravenous use of cephalothin and cephapirin.	1976 Jul	941915
Comparison of thrombophlebitis associated with three cephalosporin antibiotics.	1976 Sep	791101
Recovery without a diuresis after protracted acute tubular necrosis.	1980 Jan	7352791
The in vitro activity of beta-lactamase inhibitors in combination with cephalosporins against M. tuberculosis.	1995 Apr	7624446
beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies.	1996 Jul-Aug	9131470
Effect of intrauterine antibiotic treatment on reproductive performance of dairy cows following periparturient disease.	2001 Aug	16032183
Use of charge-transfer complexation in the spectrophotometric analysis of certain cephalosporins.	2001 Jul 6	18968341
In vivo contribution of LCAT to apolipoprotein B lipoprotein cholesteryl esters in LDL receptor and apolipoprotein E knockout mice.	2002 Mar	11893779
Parallux beta-lactam: a capillary-based fluorescent immunoassay for the determination of penicillin-G, ampicillin, amoxicillin, cloxacillin, cephapirin, and ceftiofur in bovine milk.	2002 Mar-Apr	11990019
The effect of treatment of clinical endometritis on reproductive performance in dairy cows.	2002 Sep	12362456
Antibacterial effect of bovine lactoferrin against udder pathogens.	2003	14650542
In vitro activity of 10 antimicrobial agents against bacteria isolated from cows with clinical mastitis.	2003 Apr 12	12723630
Study on the protein binding of ketoprofen using capillary electrophoresis frontal analysis compared with liquid chromatography frontal analysis.	2003 Mar	12725696
Mouse mastitis model of infection for antimicrobial compound efficacy studies against intracellular and extracellular forms of Staphylococcus aureus.	2004 Aug 6	15261998
Automated microarray system for the simultaneous detection of antibiotics in milk.	2004 Feb 1	14750859
Structural determinants of substrate binding to Bacillus cereus metallo-beta-lactamase.	2004 Jun 18	15140877
Persistence of a Staphylococcus aureus small-colony variant under antibiotic pressure in vivo.	2004 May 1	15094165
Minimum inhibitory concentrations of some antimicrobial drugs against bacteria causing uterine infections in cattle.	2004 Sep 25	15499809
Inflammatory cell infiltration as an indicator of Staphylococcus aureus infection and therapeutic efficacy in experimental mouse mastitis.	2005 Apr 8	15734537
Development of a novel and automated fluorescent immunoassay for the analysis of beta-lactam antibiotics.	2005 Aug 24	16104778
Voltammetric analysis of Cu (II), Cd (II) and Zn (II) complexes and their cyclic voltammetry with several cephalosporin antibiotics.	2005 Feb	15713559
The effect of a single administration of cephapirin or cloprostenol on the reproductive performance of dairy cows with subclinical endometritis.	2005 Feb	15629800
Confirmatory and quantitative analysis of beta-lactam antibiotics in bovine kidney tissue by dispersive solid-phase extraction and liquid chromatography-tandem mass spectrometry.	2005 Mar 1	15732933
Short communication: Efficacy of parenteral ceftiofur for treatment of systemically mild clinical mastitis in dairy cattle.	2005 Oct	16162523
A case of Chromobacterium infection after car accident in Korea.	2005 Oct 31	16259070
Evaluation of liquid chromatographic behavior of cephalosporin antibiotics using restricted access medium columns for on-line sample cleanup of bovine milk.	2006 Feb 22	16478234
Impact of experimental trauma and niflumic acid administration on antimicrobials' concentration in serum and mandible of rats.	2006 Jul-Sep	17142944
Effects of prepartum intramammary antibiotic therapy on udder health, milk production, and reproductive performance in dairy heifers.	2006 Jun	16702275
Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays.	2006 Mar 15	16536441
Trace determination of beta-lactam antibiotics in surface water and urban wastewater using liquid chromatography combined with electrospray tandem mass spectrometry.	2006 May 19	16595135
Microemulsion electrokinetic chromatography separation by using hexane-in-water microemulsions without cosurfactant: comparison with MEKC.	2006 Nov	17054085
Treatment practices and quantification of antimicrobial drug usage in conventional and organic dairy farms in Wisconsin.	2007 Jan	17183093
Carbon partitioning between oil and carbohydrates in developing oat (Avena sativa L.) seeds.	2008	19036843
Effect of intrauterine treatment with cephapirin on the reproductive performance of seasonally calving dairy cows at risk of endometritis following periparturient disease.	2008 Jul	18616474
Anticoagulant-induced changes on antibiotic concentrations in the serum and bones.	2008 Jul-Sep	19007043
[Simple and rapid microbiological method for determination of residual antibacterials in meat].	2008 Jun	18633201
Validation of the SL3 beta-Lactam Test for screening milk in compliance with U.S. pasteurized milk ordinance: performance tested method 040701.	2008 May-Jun	18567316
Kinetic spectrophotometric determination of certain cephalosporins in pharmaceutical formulations.	2009	20140078
Efficacy of a 5-day extended therapy program during lactation with cephapirin sodium in dairy cows chronically infected with Staphylococcus aureus.	2009 Dec	20190974
Kinetic spectrofluorimetric determination of certain cephalosporins in human plasma.	2009 Feb 15	19084655
Development and validation of an immunochromatographic assay for rapid multi-residues detection of cephems in milk.	2009 Feb 16	19154821
Factors associated with the risk of antibiotic residues and intramammary pathogen presence in milk from heifers administered prepartum intramammary antibiotic therapy.	2009 Feb 16	18945559
Relationship between in vitro susceptibility test results and treatment outcomes for gram-positive mastitis pathogens following treatment with cephapirin sodium.	2009 Jun	19447991
Sorption mechanisms of cephapirin, a veterinary antibiotic, onto quartz and feldspar minerals as detected by Raman spectroscopy.	2009 Jun	19246140
Newly identified degradation products of ceftiofur and cephapirin impact the analytical approach for quantitative analysis of kidney.	2009 Nov 13	19406407
Factor analysis of the transcultural self-efficacy tool (TSET).	2010	20806653
Development and validation of a liquid chromatography-tandem mass spectrometry method for the determination of goserelin in rabbit plasma.	2010 Aug 15	20655813
Bacteriological and cytological findings during the late puerperal period after two different treatments of retained placenta followed by acute puerperal metritis.	2010 Jun 15	20550666

Patents

Sample Use Guides

In Vivo Use Guide

Adults: 500 mg to 1 g every 6 hours up to 12 g/day Perioperative prophylaxis: 1-2 g 30 minutes to 1 hour prior to surgery and every 6 hours as needed for 24 hours following

Route of Administration: Other

In Vitro Use Guide

All S aureus isolates were susceptible to cephapirin and ceftiofur. Most coagulase-negative staphylococci were susceptible to cephapirin and ceftiofur. For E coli, 50 (51.0%; cephapirin) and 93 (94.95%; ceftiofur) isolates were susceptible to the parent compounds, but 88 (89.8%) were not inhibited at the maximum concentration of desacetylcephapirin. All S dysgalactiae isolates were susceptible to ceftiofur and cephapirin, and consistent MICs were obtained for all compounds. Most S uberis isolates were susceptible to cephapirin and ceftiofur. Of 98 S aureus isolates classified as susceptible to ceftiofur, 51 (52.0%) and 5 (5.1%) were categorized as intermediate or resistant to desfuroylceftiofur, respectively. For 99 coagulase-negative staphylococci classified as susceptible to ceftiofur, 45 (45.5%) and 17 (17.2%) isolates were categorized as intermediate or resistant to desfuroylceftiofur, respectively. For all staphylococci and streptococci, 100% agreement in cross-classified susceptibility outcomes was detected between cephapirin and desacetylcephapirin. No E coli isolates were classified as susceptible to desacetylcephapirin.

Name

Type

Language

CEPHAPIRIN SODIUM

Official Name

English

CEFAPIRIN SODIUM [JAN]

Common Name

English

CEPHAPIRIN SODIUM [USP MONOGRAPH]

Common Name

English

Monosodium (6R,7R)-3-(hydroxymethyl)-8-oxo-7-[2-(4-pyridylthio)acetamido]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate acetate (ester)

Common Name

English

CEPHAPIRIN SODIUM [ORANGE BOOK]

Common Name

English

Cefapirin sodium [WHO-DD]

Common Name

English

BL-P-1322

Code

English

CEFAPIRIN SODIUM

Common Name

English

CEPHAPIRIN SODIUM [USAN]

Common Name

English

SODIUM CEFAPIRIN

Common Name

English

CEFAPIRIN SODIUM [EP MONOGRAPH]

Common Name

English

CEPHAPIRIN SODIUM [USP-RS]

Common Name

English

CEPHAPIRIN SODIUM [GREEN BOOK]

Common Name

English

BL-P 1322

Code

English

CEPHAPIRIN SODIUM SALT

Common Name

English

CEFAPIRIN SODIUM [MART.]

Common Name

English

CEPHAPIRIN SODIUM [USP IMPURITY]

Common Name

English

CEPHAPIRIN SODIUM SALT [MI]

Common Name

English

CEFADYL

Brand Name

English

NSC-179171

Code

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-((ACETYLOXY)METHYL)-8-OXO-7-(((4-PYRIDYLTHIO)ACETYL)AMINO)-, MONOSODIUM SALT, (6R-TRANS)-

Common Name

English

7-(.ALPHA.-(4-PYRIDYLTHIO)ACETAMIDO)CEPHALOSPORANIC ACID SODIUM SALT

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357