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

Molecular Formula	C17H16N3O6S2
Molecular Weight	422.455
Charge	-1
Count

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

Molecular Formula	Na
Molecular Weight	22.9898
Charge	1
Count

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

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
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
In vitro susceptibilities of Mycobacterium tuberculosis to 10 antimicrobial agents.	1988 Sep	3143305
Drugs as allergens: an immunoassay for detecting IgE antibodies to cephalosporins.	1990	2083978
beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies.	1996 Jul-Aug	9131470
Prevalence of mastitis in dairy heifers and effectiveness of antibiotic therapy.	2001 Apr	11352157
A luminescent Escherichia coli biosensor for the high throughput detection of beta-lactams.	2002 Apr	12006111
Screening and mass spectral confirmation of beta-lactam antibiotic residues in milk using LC-MS/MS.	2002 Jan 16	11782216
In vivo contribution of LCAT to apolipoprotein B lipoprotein cholesteryl esters in LDL receptor and apolipoprotein E knockout mice.	2002 Mar	11893779
Synthesis and screening of a molecularly imprinted polymer library targeted for penicillin G.	2003 Jan-Feb	12523836
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
Development of a novel and automated fluorescent immunoassay for the analysis of beta-lactam antibiotics.	2005 Aug 24	16104778
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
Effect of milk fraction on concentrations of cephapirin and desacetylcephapirin in bovine milk after intramammary infusion of cephapirin sodium.	2009 Aug	19614839
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
Validation study of a receptor-based lateral flow assay for detection of beta-lactam antibiotics in milk.	2009 May-Jun	19610391
Effect of milking frequency and dosing interval on the pharmacokinetics of cephapirin after intramammary infusion in lactating dairy cows.	2009 Sep	19700687
Laryngeal Mask Airway for neonatal resuscitation in a developing country: evaluation of an educational intervention. Neonatal LMA: an educational intervention in DRC.	2010 Aug 31	20807424
Specific strains of Escherichia coli are pathogenic for the endometrium of cattle and cause pelvic inflammatory disease in cattle and mice.	2010 Feb 12	20169203

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 14:59:14 GMT 2023` Edited by `admin` on `Fri Dec 15 14:59:14 GMT 2023`
Record UNII	431LFF7I7J
Record Status	`Validated (UNII)`
Record Version

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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