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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H16N5O7S3.Na
Molecular Weight 545.544
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFTIOFUR SODIUM

SMILES

[Na+].[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=RFLHUYUQCKHUKS-JUODUXDSSA-M
InChI=1S/C19H17N5O7S3.Na/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);/q;+1/p-1/b23-11-;/t12-,16-;/m1./s1

HIDE SMILES / InChI
Molecular Formula C19H16N5O7S3
Molecular Weight 522.555
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 1
Optical Activity UNSPECIFIED
Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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.

CNS Activity

Originator

Yancey, R.J. et al.
3
Curator's Comment: First described in 1987

Approval Year

1988
111
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Mannheimia haemolytica growth
3
Target ID: Mannheimia haemolytica growth
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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
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

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

Patents

EP2367572A2
3
US20060149054
3
US5721359
3

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 Fri Dec 15 17:40:23 GMT 2023
Edited
by admin
on Fri Dec 15 17:40:23 GMT 2023
Record UNII
NHI34IS56E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFTIOFUR SODIUM
GREEN BOOK   JAN   MART.   USAN   USP-RS  
USAN  
Official Name English
CEFTIOFUR SODIUM [USAN]
Common Name English
CEFTIOFUR MONOSODIUM SALT
MI  
Common Name English
CEFTIOFUR SODIUM [GREEN BOOK]
Common Name English
CEFTIOFUR SODIUM [USP MONOGRAPH]
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-, MONOSODIUM SALT, (6R-(6.ALPHA.,7.BETA.(Z)))-
Common Name English
CM-31-916
Code English
SODIUM CEFTIOFUR
Common Name English
U-64279E
Code English
Sodium (6R,7R)-7-[2-(2-amino-4-thiazolyl)glyoxylamido]-3-(mercaptomethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate, 72-(Z)-(O-methyloxime), 2-furoate (ester)
Common Name English
CEFTIOFUR SODIUM [MART.]
Common Name English
CEFTIOFUR NATRIUM
WHO-DD  
Common Name English
CM 31-916
Code English
Ceftiofur natrium [WHO-DD]
Common Name English
CEFTIOFUR MONOSODIUM SALT [MI]
Common Name English
CEFTIOFUR SODIUM [JAN]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 522.313C
Created by admin on Fri Dec 15 17:40:23 GMT 2023 , Edited by admin on Fri Dec 15 17:40:23 GMT 2023
NCI_THESAURUS C357
Created by admin on Fri Dec 15 17:40:23 GMT 2023 , Edited by admin on Fri Dec 15 17:40:23 GMT 2023
Code System Code Type Description
DRUG BANK
DBSALT001644
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PRIMARY
RXCUI
1370372
Created by admin on Fri Dec 15 17:40:23 GMT 2023 , Edited by admin on Fri Dec 15 17:40:23 GMT 2023
PRIMARY RxNorm
USAN
Y-84
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PRIMARY
NCI_THESAURUS
C77190
Created by admin on Fri Dec 15 17:40:23 GMT 2023 , Edited by admin on Fri Dec 15 17:40:23 GMT 2023
PRIMARY
EVMPD
SUB33576
Created by admin on Fri Dec 15 17:40:23 GMT 2023 , Edited by admin on Fri Dec 15 17:40:23 GMT 2023
PRIMARY
MERCK INDEX
m3221
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PRIMARY Merck Index
CAS
104010-37-9
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PRIMARY
EPA CompTox
DTXSID30891706
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PRIMARY
PUBCHEM
23671563
Created by admin on Fri Dec 15 17:40:23 GMT 2023 , Edited by admin on Fri Dec 15 17:40:23 GMT 2023
PRIMARY
ChEMBL
CHEMBL222913
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PRIMARY
FDA UNII
NHI34IS56E
Created by admin on Fri Dec 15 17:40:23 GMT 2023 , Edited by admin on Fri Dec 15 17:40:23 GMT 2023
PRIMARY
SMS_ID
100000127526
Created by admin on Fri Dec 15 17:40:23 GMT 2023 , Edited by admin on Fri Dec 15 17:40:23 GMT 2023
PRIMARY
DAILYMED
NHI34IS56E
Created by admin on Fri Dec 15 17:40:23 GMT 2023 , Edited by admin on Fri Dec 15 17:40:23 GMT 2023
PRIMARY
Related Record Type Details
Structure of CEFTIOFUR
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of CEFTIOFUR DIOXIME
IMPURITY -> PARENT
Related Record Type Details
Structure of CEFTIOFUR
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