CEFTIOFUR

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H17N5O7S3
Molecular Weight	523.563
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@]12SCC(CSC(=O)C3=CC=CO3)=C(N1C(=O)[C@H]2NC(=O)C(=N/OC)\C4=CSC(N)=N4)C(O)=O

InChI

InChIKey=ZBHXIWJRIFEVQY-IHMPYVIRSA-N

InChI=1S/C19H17N5O7S3/c1-30-23-11(9-7-34-19(20)21-9)14(25)22-12-15(26)24-13(17(27)28)8(5-32-16(12)24)6-33-18(29)10-3-2-4-31-10/h2-4,7,12,16H,5-6H2,1H3,(H2,20,21)(H,22,25)(H,27,28)/b23-11-/t12-,16-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.drugs.com/vet/naxcel.html
Curator's Comment: Description was created based on several sources, including https://www.zoetisus.com/dairy/avoidresidues/PDF/EXCEDE_PRESCRIBING_INFO.pdf and http://www.ncbi.nlm.nih.gov/pubmed/12052187

Ceftiofur is an antibiotic of the cephalosporin type (third generation), licensed for use in veterinary medicine only. It was first described in 1987. It is marketed by pharmaceutical company Zoetis as Excenel, Naxcel, and Excede and is also the active ingredient in that company's Spectramast LC (lactating cow formulation) and Spectramast DC (dry cow formulation) product. Ceftiofur has worldwide approvals for respiratory disease in swine, ruminants (cattle, sheep and goats) and horses and has also been approved for foot rot and metritis infections in cattle. Ceftiofur has also been approved in various countries for early mortality infections in day-old chicks and turkey poults. Ceftiofur (NAXCEL) is indicated for treatment of bovine respiratory disease (shipping fever, pneumonia) associated with Mannheimia haemolytica, Pasteurella multocida, and Histophilus somni. NAXCEL is also indicated for treatment of acute bovine interdigital necrobacillosis (foot rot, pododermatitis) associated with Fusobacterium necrophorum and Bacteroides melaninogenicus.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Staphylococcus aureus growth 27 Target ID: Staphylococcus aureus growth Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm118053.pdf	Inhibitor 8297
Mannheimia haemolytica growth 3 Target ID: Mannheimia haemolytica growth Sources: http://www.ncbi.nlm.nih.gov/pubmed/22914822	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bovine respiratory disease 8 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm049847.pdf	Curative		Approved 8429	NAXCEL Sterile Powder Approved Use Indicated for treatment of bovine respiratory disease (shipping fever, pneumonia) associated with Mannheimia haemolytica, Pasteurella multocida, and Histophilus somni. NAXCEL Sterile Powder is also indicated for treatment of acute bovine interdigital necrobacillosis (foot rot, pododermatitis) associated with Fusobacterium necrophorum and Bacteroides melaninogenicus Launch Date 2006
Subclinical mastitis in dairy cattle 3 Sources: http://www.fda.gov/downloads/AnimalVeterinary/Products/ApprovedAnimalDrugProducts/FOIADrugSummaries/ucm118053.pdf	Curative		Approved 8429	SPECTRAMAST DC Sterile Suspension Approved Use SPECTRAMAST DC Ceftiofur Hydrochloride Sterile Suspension is indicated for the treatment of subclinical mastitis in dairy cattle at the time of dry off associated with Staphylococcus aureus, Streptococcus dysgalactiae, and Streptococcus uberis. Launch Date 2005

PubMed

Title	Date	PubMed
PHARMACOKINETICS OF CEFTIOFUR CRYSTALLINE FREE ACID, A LONG-ACTING CEPHALOSPORIN, IN AMERICAN FLAMINGOS (PHOENICOPTERUS RUBER).	2016 Jun	27468016
Randomized noninferiority trial comparing 2 commercial intramammary antibiotics for the treatment of nonsevere clinical mastitis in dairy cows.	2016 Oct	27522408
Plasma, subcutaneous tissue and bone concentrations of ceftiofur sodium after regional limb perfusion in horses.	2017 May	27458113

Patents

Sample Use Guides

In Vivo Use Guide

Administer to cattle by intramuscular or subcutaneous injection at the dosage of 0.5 to 1.0 mg ceftiofur per pound (1.1 to 2.2 mg/kg) of body weight (1-2 mL reconstituted sterile solution per 100 lbs body weight). Treatment should be repeated at 24-hour intervals for a total of three consecutive days. Additional treatments may be given on days four and five for animals which do not show a satisfactory response (not recovered) after the initial three treatments. Selection of dosage (0.5 to 1.0 mg/lb) should be based on the practitioner’s judgement of severity of disease.

Route of Administration: Intramuscular

In Vitro Use Guide

Ceftiofur had the highest in vitro activity with an MIC(50) of 2.2 ug/ml against isolates of A. pleuropneumoniae collected from pigs with hemorrhagic pneumonia

Name

Type

Language

CEFTIOFUR

Official Name

English

CEFTIOFUR [EMA EPAR VETERINARY]

Common Name

English

ceftiofur [INN]

Common Name

English

CEFTIOFUR [HSDB]

Common Name

English

Ceftiofur [WHO-DD]

Common Name

English

CEFTIOFUR CRYSTALLINE FREE ACID [GREEN BOOK]

Common Name

English

CEFTIOFUR [MI]

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2-AMINO-4-THIAZOLYL)(METHOXYIMINO)ACETYL)AMINO)-3-(((2-FURANYLCARBONYL)THIO)METHYL)-8-OXO-, (6R-(6.ALPHA.,7.BETA.(Z)))-

Common Name

English

CEFTIOFUR CRYSTALLINE FREE ACID

Common Name

English

CEFTIOFUR [MART.]

Common Name

English

(6R,7R)-7-(2-(2-AMINO-4-THIAZOLYL)GLYOXYLAMIDO)-3-(MERCAPTOMETHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7(SUP 2)-(Z)-(O-METHYLOXIME), 2-FUROATE (ESTER)

Common Name

English

NAXCEL

Brand Name

English

Classification Tree Code System Code

WHO-VATC

QJ01DD90