CEPHAPIRIN BENZATHINE

US Previously Marketed

Details

Stereochemistry	ABSOLUTE
Molecular Formula	2C17H17N3O6S2.C16H20N2
Molecular Weight	1087.27
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C(CNCC1=CC=CC=C1)NCC2=CC=CC=C2.[H][C@@]4(NC(=O)CSC3=CC=NC=C3)C(=O)N5C(C(O)=O)=C(COC(C)=O)CS[C@]45[H].[H][C@@]7(NC(=O)CSC6=CC=NC=C6)C(=O)N8C(C(O)=O)=C(COC(C)=O)CS[C@]78[H]

InChI

InChIKey=JAHKOXGROZNHHG-RACYMRPCSA-N

InChI=1S/2C17H17N3O6S2.C16H20N2/c2*1-9(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;1-3-7-15(8-4-1)13-17-11-12-18-14-16-9-5-2-6-10-16/h2*2-5,13,16H,6-8H2,1H3,(H,19,22)(H,24,25);1-10,17-18H,11-14H2/t2*13-,16-;/m11./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

Molecular Formula	C16H20N2
Molecular Weight	240.3434
Charge	0
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
Double-blind controlled comparison of phlebitis produced by cephapirin and cephalothin.	1973 Feb	4597719
Comparison of thrombophlebitis associated with three cephalosporin antibiotics.	1976 Sep	791101
Recovery without a diuresis after protracted acute tubular necrosis.	1980 Jan	7352791
Determination of in vitro susceptibility of Mycobacterium tuberculosis to cephalosporins by radiometric and conventional methods.	1985 Jan	3920957
Determination of MICs of conventional and experimental drugs in liquid medium by the radiometric method against Mycobacterium avium complex.	1987	3428133
Charm Safe-Level beta-Lactam Test for amoxicillin, ampicillin, ceftiofur, cephapirin, and penicillin G in raw commingled milk.	2001 Jan-Feb	11234843
Screening method for identification of beta-lactams in bovine urine by use of liquid chromatography and a microbial inhibition test.	2001 Mar	11277195
A luminescent Escherichia coli biosensor for the high throughput detection of beta-lactams.	2002 Apr	12006111
In vitro activity of 10 antimicrobial agents against bacteria isolated from cows with clinical mastitis.	2003 Apr 12	12723630
Simultaneous determination of different antibiotic residues in bovine and in porcine kidneys by solid-phase fluorescence immunoassay.	2003 Mar-Apr	12723911
Structural determinants of substrate binding to Bacillus cereus metallo-beta-lactamase.	2004 Jun 18	15140877
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
Item Response Theory Analysis of Two Questionnaire Measures of Arthritis-Related Self-Efficacy Beliefs from Community-Based US Samples.	2010	22046509

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 15:30:50 GMT 2023` Edited by `admin` on `Fri Dec 15 15:30:50 GMT 2023`
Record UNII	90G868409O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CEPHAPIRIN BENZATHINE

Common Name

English

CEPHAPIRIN COMPD WITH N,N'-DIBENZYLETHYLENEDIAMINE [MI]

Common Name

English

CEFAPIRIN BENZATHINE

Common Name

English

CEPHAPIRIN BENZATHINE [USP-RS]

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 3-((ACETYLOXY)METHYL)-8-OXO-7-(((4-PYRIDINYLTHIO)ACETYL)AMINO)-, (6R-TRANS)-, COMPD. WITH N,N'-BIS(PHENYLMETHYL)-1,2-ETHANEDIAMINE (2:1)

Common Name

English

METRICURE

Brand Name

English

CEPHAPIRIN BENZATHINE [GREEN BOOK]

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-CARBOXYLIC ACID COMPOUND WITH N,N'-DIBENZYLETHYLENEDIAMINE (2:1)

Common Name

English

CEPHAPIRIN BENZATHINE [USP IMPURITY]

Common Name

English

CEPHAPIRIN BENZATHINE [USP MONOGRAPH]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C357