U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H17N3O6S2
Molecular Weight 423.4662
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CEPHAPIRIN

SMILES

CC(=O)OCC1=C(C(=O)O)N2C(=O)[C@]([H])([C@@]2([H])SC1)N=C(CSc3ccncc3)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
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

1.32278403E11
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
Double-blind controlled comparison of phlebitis produced by cephapirin and cephalothin.
1973 Feb
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
Comparison of thrombophlebitis associated with three cephalosporin antibiotics.
1976 Sep
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
Determination of in vitro susceptibility of Mycobacterium tuberculosis to cephalosporins by radiometric and conventional methods.
1985 Jan
Determination of MICs of conventional and experimental drugs in liquid medium by the radiometric method against Mycobacterium avium complex.
1987
In vitro susceptibility of Mycobacterium avium complex to antibacterial agents.
1987 Nov
In vitro susceptibilities of Mycobacterium tuberculosis to 10 antimicrobial agents.
1988 Sep
Drugs as allergens: an immunoassay for detecting IgE antibodies to cephalosporins.
1990
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
Prevalence of mastitis in dairy heifers and effectiveness of antibiotic therapy.
2001 Apr
Use of charge-transfer complexation in the spectrophotometric analysis of certain cephalosporins.
2001 Jul 6
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
Synthesis and screening of a molecularly imprinted polymer library targeted for penicillin G.
2003 Jan-Feb
Study on the protein binding of ketoprofen using capillary electrophoresis frontal analysis compared with liquid chromatography frontal analysis.
2003 Mar
Real-Time Paresthesia Steering Using ContinuousElectric Field Adjustment. Part I: IntraoperativePerformance.
2004 Jul
A case of Chromobacterium infection after car accident in Korea.
2005 Oct 31
Evaluation of liquid chromatographic behavior of cephalosporin antibiotics using restricted access medium columns for on-line sample cleanup of bovine milk.
2006 Feb 22
Trace determination of beta-lactam antibiotics in surface water and urban wastewater using liquid chromatography combined with electrospray tandem mass spectrometry.
2006 May 19
Stability of frozen stock solutions of beta-lactam antibiotics, cephalosporins, tetracyclines and quinolones used in antibiotic residue screening and antibiotic susceptibility testing.
2007 Mar 14
A study of 54 cases of left displacement of the abomasum: February to July 2005.
2007 Oct 1
Kinetic spectrophotometric determination of certain cephalosporins in pharmaceutical formulations.
2009
Effect of milk fraction on concentrations of cephapirin and desacetylcephapirin in bovine milk after intramammary infusion of cephapirin sodium.
2009 Aug
Efficacy of a 5-day extended therapy program during lactation with cephapirin sodium in dairy cows chronically infected with Staphylococcus aureus.
2009 Dec
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
Effect of milking frequency and dosing interval on the pharmacokinetics of cephapirin after intramammary infusion in lactating dairy cows.
2009 Sep
Item Response Theory Analysis of Two Questionnaire Measures of Arthritis-Related Self-Efficacy Beliefs from Community-Based US Samples.
2010
Factor analysis of the transcultural self-efficacy tool (TSET).
2010
Evaluation of executive functioning in people with intellectual disabilities.
2010 Apr
Development and validation of a liquid chromatography-tandem mass spectrometry method for the determination of goserelin in rabbit plasma.
2010 Aug 15
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
Specific strains of Escherichia coli are pathogenic for the endometrium of cattle and cause pelvic inflammatory disease in cattle and mice.
2010 Feb 12
Bacteriological and cytological findings during the late puerperal period after two different treatments of retained placenta followed by acute puerperal metritis.
2010 Jun 15
Short communication: Rapid antibiotic screening tests detect antibiotic residues in powdered milk products.
2010 Sep
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.
Name Type Language
CEPHAPIRIN
MI   VANDF  
Common Name English
CEFAPIRIN [WHO-DD]
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
Classification Tree Code System Code
CFR 21 CFR 556.115
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
WHO-VATC QJ01DB08
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
WHO-VATC QG51AA05
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
NCI_THESAURUS C357
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
WHO-VATC QJ51DB08
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
WHO-ATC J01DB08
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
Code System Code Type Description
PUBCHEM
30699
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY
EVMPD
SUB07375MIG
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY
ChEMBL
CHEMBL1599
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY
RXCUI
2238
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY RxNorm
DRUG BANK
DB01139
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY
FDA UNII
89B59H32VN
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY
CAS
21593-23-7
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY
INN
2871
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY
WIKIPEDIA
CEFAPIRIN
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY
ECHA (EC/EINECS)
244-466-5
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY
HSDB
3215
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY
MESH
D002514
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY
EPA CompTox
21593-23-7
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY
MERCK INDEX
M3253
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY Merck Index
DRUG CENTRAL
575
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY
NCI_THESAURUS
C61670
Created by admin on Sat Jun 26 02:14:20 UTC 2021 , Edited by admin on Sat Jun 26 02:14:20 UTC 2021
PRIMARY