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

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 of CEFTIOFUR

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

Molecular Formula C19H17N5O7S3
Molecular Weight 523.563
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED

Description
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.

Originator

Curator's Comment: First described in 1987

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
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
Curative
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

PubMed

TitleDatePubMed
PHARMACOKINETICS OF CEFTIOFUR CRYSTALLINE FREE ACID, A LONG-ACTING CEPHALOSPORIN, IN AMERICAN FLAMINGOS (PHOENICOPTERUS RUBER).
2016 Jun
Randomized noninferiority trial comparing 2 commercial intramammary antibiotics for the treatment of nonsevere clinical mastitis in dairy cows.
2016 Oct
Randomized, controlled clinical trial on the efficacy of nonsteroidal antiinflammatory drugs for the treatment of acute puerperal metritis in dairy cows.
2016 Oct
Plasma, subcutaneous tissue and bone concentrations of ceftiofur sodium after regional limb perfusion in horses.
2017 May
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: Can also be administered subcutaneously
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 16:19:43 GMT 2023
Edited
by admin
on Sat Dec 16 16:19:43 GMT 2023
Record UNII
83JL932I1C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFTIOFUR
HSDB   INN   MART.   MI   WHO-DD  
INN  
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
GREEN BOOK  
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
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
CFR 21 CFR 522.313
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS NAXCEL [AUTHORIZED]
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
CFR 21 CFR 556.113
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
CFR 21 CFR 526.313
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
EMA VETERINARY ASSESSMENT REPORTS NAXCEL [AUTHORIZED]
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
CFR 21 CFR 522.313A
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
WHO-VATC QJ01DD99
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
NCI_THESAURUS C357
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
WHO-VATC QJ51DD90
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
Code System Code Type Description
SMS_ID
100000081834
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY
ChEMBL
CHEMBL222913
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY
HSDB
7445
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY
FDA UNII
83JL932I1C
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY
PUBCHEM
6328657
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY
DRUG BANK
DB11485
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY
NCI_THESAURUS
C81036
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY
EPA CompTox
DTXSID7046702
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY
CAS
80370-57-6
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY
INN
5703
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY
MERCK INDEX
m3221
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
CEFTIOFUR
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY
EVMPD
SUB07426MIG
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY
RXCUI
1311521
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY RxNorm
DAILYMED
83JL932I1C
Created by admin on Sat Dec 16 16:19:43 GMT 2023 , Edited by admin on Sat Dec 16 16:19:43 GMT 2023
PRIMARY
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