CEPHAPIRIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C17H17N3O6S2
Molecular Weight	423.463
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)OCC1=C(N2[C@H](SC1)[C@H](NC(=O)CSC3=CC=NC=C3)C2=O)C(O)=O

InChI

InChIKey=UQLLWWBDSUHNEB-CZUORRHYSA-N

InChI=1S/C17H17N3O6S2/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)/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 234 Target ID: CHEMBL2354204 Sources: https://www.ncbi.nlm.nih.gov/pubmed/808545 \| https://www.ncbi.nlm.nih.gov/pubmed/23336133	Inhibitor 8504

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial infections 235 Sources: https://www.drugs.com/mmx/cefadyl.html	Curative		Approved 8583	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 Health Status: unhealthy Age Group: 31.4 years Sex: M+F 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 Health Status: unhealthy Age Group: 50 years Sex: M 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 Health Status: unhealthy Age Group: 50 years Sex: M 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
Short communication: Rapid antibiotic screening tests detect antibiotic residues in powdered milk products.	2010-09	20723670
Laryngeal Mask Airway for neonatal resuscitation in a developing country: evaluation of an educational intervention. Neonatal LMA: an educational intervention in DRC.	2010-08-31	20807424
Development and validation of a liquid chromatography-tandem mass spectrometry method for the determination of goserelin in rabbit plasma.	2010-08-15	20655813
Bacteriological and cytological findings during the late puerperal period after two different treatments of retained placenta followed by acute puerperal metritis.	2010-06-15	20550666
Evaluation of executive functioning in people with intellectual disabilities.	2010-04	20433573
Specific strains of Escherichia coli are pathogenic for the endometrium of cattle and cause pelvic inflammatory disease in cattle and mice.	2010-02-12	20169203
Item Response Theory Analysis of Two Questionnaire Measures of Arthritis-Related Self-Efficacy Beliefs from Community-Based US Samples.	2010	22046509
Factor analysis of the transcultural self-efficacy tool (TSET).	2010	20806653
Efficacy of a 5-day extended therapy program during lactation with cephapirin sodium in dairy cows chronically infected with Staphylococcus aureus.	2009-12	20190974
Newly identified degradation products of ceftiofur and cephapirin impact the analytical approach for quantitative analysis of kidney.	2009-11-13	19406407
Microbial screening methods for detection of antibiotic residues in slaughter animals.	2009-10	19484227
Comparison of two methods of detecting purulent vaginal discharge in postpartum dairy cows and effect of intrauterine cephapirin on reproductive performance.	2009-09	19703140
Effect of milking frequency and dosing interval on the pharmacokinetics of cephapirin after intramammary infusion in lactating dairy cows.	2009-09	19700687
Effect of milk fraction on concentrations of cephapirin and desacetylcephapirin in bovine milk after intramammary infusion of cephapirin sodium.	2009-08	19614839
Validation study of a receptor-based lateral flow assay for detection of beta-lactam antibiotics in milk.	2009-07-21	19610391
Identification and characterization of inhibitors of human apurinic/apyrimidinic endonuclease APE1.	2009-06-01	19484131
Relationship between in vitro susceptibility test results and treatment outcomes for gram-positive mastitis pathogens following treatment with cephapirin sodium.	2009-06	19447991
Sorption mechanisms of cephapirin, a veterinary antibiotic, onto quartz and feldspar minerals as detected by Raman spectroscopy.	2009-06	19246140
Occurrence of antimicrobial residues in pasteurized milk commercialized in the state of Paraná, Brazil.	2009-04	19435250
Development and validation of an immunochromatographic assay for rapid multi-residues detection of cephems in milk.	2009-02-16	19154821
Factors associated with the risk of antibiotic residues and intramammary pathogen presence in milk from heifers administered prepartum intramammary antibiotic therapy.	2009-02-16	18945559
Kinetic spectrofluorimetric determination of certain cephalosporins in human plasma.	2009-02-15	19084655
Kinetic spectrophotometric determination of certain cephalosporins in pharmaceutical formulations.	2009	20140078
Anticoagulant-induced changes on antibiotic concentrations in the serum and bones.	2008-11-15	19007043
Effect of intrauterine treatment with cephapirin on the reproductive performance of seasonally calving dairy cows at risk of endometritis following periparturient disease.	2008-07	18616474
Validation of the SL3 beta-Lactam Test for screening milk in compliance with U.S. pasteurized milk ordinance: performance tested method 040701.	2008-06-24	18567316
[Simple and rapid microbiological method for determination of residual antibacterials in meat].	2008-06	18633201
Carbon partitioning between oil and carbohydrates in developing oat (Avena sativa L.) seeds.	2008	19036843
A study of 54 cases of left displacement of the abomasum: February to July 2005.	2007-10-01	21851688
Stability of frozen stock solutions of beta-lactam antibiotics, cephalosporins, tetracyclines and quinolones used in antibiotic residue screening and antibiotic susceptibility testing.	2007-03-14	17386725
Treatment practices and quantification of antimicrobial drug usage in conventional and organic dairy farms in Wisconsin.	2007-01	17183093
Effects of a single administration of prostaglandin F2alpha, or a combination of prostaglandin F2alpha and prostaglandin E2, or placebo on fertility variables in dairy cows 3-5 weeks post partum, a randomized, double-blind clinical trial.	2006-12-21	17184541
Impact of experimental trauma and niflumic acid administration on antimicrobials' concentration in serum and mandible of rats.	2006-12-05	17142944
Real-Time Paresthesia Steering Using ContinuousElectric Field Adjustment. Part I: IntraoperativePerformance.	2004-07	22151265
Use of charge-transfer complexation in the spectrophotometric analysis of certain cephalosporins.	2001-07-06	18968341
beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies.	1996-07-01	9131470
The in vitro activity of beta-lactamase inhibitors in combination with cephalosporins against M. tuberculosis.	1995-04	7624446
Comparison of in vitro antimicrobial susceptibilities of Mycobacterium avium-M. intracellulare strains from patients with acquired immunodeficiency syndrome (AIDS), patients without AIDS, and animal sources.	1990-07	2386370
Drugs as allergens: an immunoassay for detecting IgE antibodies to cephalosporins.	1990	2083978
In vitro susceptibilities of Mycobacterium tuberculosis to 10 antimicrobial agents.	1988-09	3143305
In vitro susceptibility of Mycobacterium avium complex to antibacterial agents.	1987-11	3440370
Determination of MICs of conventional and experimental drugs in liquid medium by the radiometric method against Mycobacterium avium complex.	1987	3428133
Determination of in vitro susceptibility of Mycobacterium tuberculosis to cephalosporins by radiometric and conventional methods.	1985-01	3920957
[Comparison of side effects of intravenous cephapirin and cephalothin with special reference to the incidence of phlebitis].	1983-12	6674550
Recovery without a diuresis after protracted acute tubular necrosis.	1980-01	7352791
Comparison of thrombophlebitis associated with three cephalosporin antibiotics.	1976-09	791101
Phlebitis associated with the intravenous use of cephalothin and cephapirin.	1976-07	941915
Comparative incidence of phlebitis due to buffered cephalothin, cephapirin, and cefamandole.	1976-04	5053
Double-blind controlled comparison of phlebitis produced by cephapirin and cephalothin.	1973-02	4597719
Relative incidence of phlebitis caused by continuous intravenous infusion of cephapirin and cephalothin.	1972-09	4790563

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

Common Name

English

CEFAPIRIN

Preferred Name

English

CEPHAPIRIN [MI]

Common Name

English

cefapirin [INN]

Common Name

English

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

Common Name

English

CEFAPIRIN [HSDB]

Common Name

English

CEPHAPIRIN [VANDF]

Common Name

English

(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

Cefapirin [WHO-DD]

Common Name

English

Classification Tree Code System Code

CFR

21 CFR 556.115