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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 of CEPHAPIRIN

SMILES

[H][C@]12SCC(COC(C)=O)=C(N1C(=O)[C@H]2NC(=O)CSC3=CC=NC=C3)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

Molecular Formula C17H17N3O6S2
Molecular Weight 423.463
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Originator

Curator's Comment: reference retrieved from http://www.drugfuture.com/chemdata/cephapirin-sodium.html

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
92 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
72 μg × h/mL
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
0.36 h
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

Doses

DosePopulationAdverse 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:
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:
1 g 4 times / day multiple, intramuscular
Dose: 1 g, 4 times / day
Route: intramuscular
Route: multiple
Dose: 1 g, 4 times / day
Sources:
unhealthy, 50 years
n = 1
Health Status: unhealthy
Age Group: 50 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Neutropenia...
AEs leading to
discontinuation/dose reduction:
Neutropenia (1 patient)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
unhealthy, 50 years
n = 1
Health Status: unhealthy
Age Group: 50 years
Sex: M
Population Size: 1
Sources:
PubMed

PubMed

TitleDatePubMed
Relative incidence of phlebitis caused by continuous intravenous infusion of cephapirin and cephalothin.
1972 Sep
Comparative incidence of phlebitis due to buffered cephalothin, cephapirin, and cefamandole.
1976 Apr
Phlebitis associated with the intravenous use of cephalothin and cephapirin.
1976 Jul
Recovery without a diuresis after protracted acute tubular necrosis.
1980 Jan
[Comparison of side effects of intravenous cephapirin and cephalothin with special reference to the incidence of phlebitis].
1983 Dec
In vitro susceptibilities of Mycobacterium tuberculosis to 10 antimicrobial agents.
1988 Sep
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 Jul
The in vitro activity of beta-lactamase inhibitors in combination with cephalosporins against M. tuberculosis.
1995 Apr
beta-Lactam drug allergens: fine structural recognition patterns of cephalosporin-reactive IgE antibodies.
1996 Jul-Aug
Effect of intrauterine antibiotic treatment on reproductive performance of dairy cows following periparturient disease.
2001 Aug
Use of charge-transfer complexation in the spectrophotometric analysis of certain cephalosporins.
2001 Jul 6
Screening method for identification of beta-lactams in bovine urine by use of liquid chromatography and a microbial inhibition test.
2001 Mar
Dietary assessment in Whitehall II: comparison of 7 d diet diary and food-frequency questionnaire and validity against biomarkers.
2001 Sep
Antibacterial effect of bovine lactoferrin against udder pathogens.
2003
Residues of beta-lactam antibiotics in bovine milk: confirmatory analysis by liquid chromatography tandem mass spectrometry after microbial assay screening.
2003 Jun
Study on the protein binding of ketoprofen using capillary electrophoresis frontal analysis compared with liquid chromatography frontal analysis.
2003 Mar
Automated microarray system for the simultaneous detection of antibiotics in milk.
2004 Feb 1
Structural determinants of substrate binding to Bacillus cereus metallo-beta-lactamase.
2004 Jun 18
Persistence of a Staphylococcus aureus small-colony variant under antibiotic pressure in vivo.
2004 May 1
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
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 Dec 21
Effects of prepartum intramammary antibiotic therapy on udder health, milk production, and reproductive performance in dairy heifers.
2006 Jun
Molecular engineering of fluorescent penicillins for molecularly imprinted polymer assays.
2006 Mar 15
Trace determination of beta-lactam antibiotics in surface water and urban wastewater using liquid chromatography combined with electrospray tandem mass spectrometry.
2006 May 19
Treatment practices and quantification of antimicrobial drug usage in conventional and organic dairy farms in Wisconsin.
2007 Jan
Carbon partitioning between oil and carbohydrates in developing oat (Avena sativa L.) seeds.
2008
Occurrence of antimicrobial residues in pasteurized milk commercialized in the state of Paraná, Brazil.
2009 Apr
Development and validation of an immunochromatographic assay for rapid multi-residues detection of cephems in milk.
2009 Feb 16
Factors associated with the risk of antibiotic residues and intramammary pathogen presence in milk from heifers administered prepartum intramammary antibiotic therapy.
2009 Feb 16
Relationship between in vitro susceptibility test results and treatment outcomes for gram-positive mastitis pathogens following treatment with cephapirin sodium.
2009 Jun
Identification and characterization of inhibitors of human apurinic/apyrimidinic endonuclease APE1.
2009 Jun 1
Newly identified degradation products of ceftiofur and cephapirin impact the analytical approach for quantitative analysis of kidney.
2009 Nov 13
Comparison of two methods of detecting purulent vaginal discharge in postpartum dairy cows and effect of intrauterine cephapirin on reproductive performance.
2009 Sep
Factor analysis of the transcultural self-efficacy tool (TSET).
2010
Evaluation of executive functioning in people with intellectual disabilities.
2010 Apr
Patents

Sample Use Guides

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
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 Sat Dec 16 18:02:28 GMT 2023
Edited
by admin
on Sat Dec 16 18:02:28 GMT 2023
Record UNII
89B59H32VN
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEPHAPIRIN
MI   VANDF  
Common Name English
CEPHAPIRIN [MI]
Common Name English
cefapirin [INN]
Common Name English
7-(.ALPHA.-(4-PYRIDYLTHIO)ACETAMIDO)CEPHALOSPORANIC ACID
Common Name English
CEFAPIRIN
HSDB   INN   WHO-DD  
INN  
Official 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
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
WHO-VATC QJ01DB08
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
WHO-VATC QG51AA05
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
NCI_THESAURUS C357
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
WHO-VATC QJ51DB08
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
WHO-ATC J01DB08
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
Code System Code Type Description
CHEBI
554446
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
PUBCHEM
30699
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
EVMPD
SUB07375MIG
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
DAILYMED
89B59H32VN
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL1599
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
RXCUI
2238
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB01139
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
FDA UNII
89B59H32VN
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
CAS
21593-23-7
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
INN
2871
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
WIKIPEDIA
CEFAPIRIN
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
SMS_ID
100000081791
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
ECHA (EC/EINECS)
244-466-5
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
HSDB
3215
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
MESH
D002514
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID9022784
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
MERCK INDEX
m3253
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY Merck Index
DRUG CENTRAL
575
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
NCI_THESAURUS
C61670
Created by admin on Sat Dec 16 18:02:28 GMT 2023 , Edited by admin on Sat Dec 16 18:02:28 GMT 2023
PRIMARY
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