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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H17N5O7S3.ClH
Molecular Weight 560.0275
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of CEFTIOFUR HYDROCHLORIDE

SMILES

CO/N=C(/c1csc(=N)[nH]1)\C(=N[C@]2([H])C(=O)N3C(=C(CS[C@]23[H])CSC(=O)c4ccco4)C(=O)O)O.Cl

InChI

InChIKey=KEQFDTJEEQKVLM-JUODUXDSSA-N
InChI=1S/C19H17N5O7S3.ClH/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);1H/b23-11-;/t12-,16-;/m1./s1

HIDE SMILES / InChI
Molecular Formula ClH
Molecular Weight 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C19H17N5O7S3
Molecular Weight 523.5666
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.

CNS Activity

Originator

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

Approval Year

1988
109
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
7728
Target ID: Mannheimia haemolytica growth
Inhibitor
7728
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
Approved
8043
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

1.14912002E12
Curative
Approved
8043
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

1.11075839E12
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 Jun 25 22:08:22 UTC 2021
Edited
by admin
on Fri Jun 25 22:08:22 UTC 2021
Record UNII
6822A07436
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CEFTIOFUR HYDROCHLORIDE
GREEN BOOK   MART.   USAN  
USAN  
Official Name English
U-64279A
Code English
CEFTIOFUR HYDROCHLORIDE [MART.]
Common Name English
CEFTIOFUR MONOHYDROCHLORIDE [MI]
Common Name English
CEFTIOFUR HYDROCHLORIDE [USAN]
Common Name English
CEFTIOFUR HYDROCHLORIDE [GREEN BOOK]
Common Name English
CEFTIOFUR MONOHYDROCHLORIDE
MI  
Common Name English
CEFTIOFUR HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
NSC-759845
Code 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-, MONOHYDROCHLORIDE, (6R-(6.ALPHA.,7.BETA.(Z)))-
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), MONOHYDROCHLORIDE
Common Name English
CEFTIOFUR HCL
Common Name English
CEFTIOFUR HYDROCHLORIDE [USP-RS]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C357
Created by admin on Fri Jun 25 22:08:22 UTC 2021 , Edited by admin on Fri Jun 25 22:08:22 UTC 2021
CFR 21 CFR 522.313B
Created by admin on Fri Jun 25 22:08:22 UTC 2021 , Edited by admin on Fri Jun 25 22:08:22 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL222913
Created by admin on Fri Jun 25 22:08:22 UTC 2021 , Edited by admin on Fri Jun 25 22:08:22 UTC 2021
PRIMARY
DRUG BANK
DBSALT001643
Created by admin on Fri Jun 25 22:08:22 UTC 2021 , Edited by admin on Fri Jun 25 22:08:22 UTC 2021
PRIMARY
PUBCHEM
9937686
Created by admin on Fri Jun 25 22:08:22 UTC 2021 , Edited by admin on Fri Jun 25 22:08:22 UTC 2021
PRIMARY
EVMPD
SUB180294
Created by admin on Fri Jun 25 22:08:22 UTC 2021 , Edited by admin on Fri Jun 25 22:08:22 UTC 2021
PRIMARY
RXCUI
1311520
Created by admin on Fri Jun 25 22:08:22 UTC 2021 , Edited by admin on Fri Jun 25 22:08:22 UTC 2021
PRIMARY RxNorm
MERCK INDEX
M3221
Created by admin on Fri Jun 25 22:08:22 UTC 2021 , Edited by admin on Fri Jun 25 22:08:22 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C76174
Created by admin on Fri Jun 25 22:08:22 UTC 2021 , Edited by admin on Fri Jun 25 22:08:22 UTC 2021
PRIMARY
FDA UNII
6822A07436
Created by admin on Fri Jun 25 22:08:22 UTC 2021 , Edited by admin on Fri Jun 25 22:08:22 UTC 2021
PRIMARY
USP_CATALOG
1098071
Created by admin on Fri Jun 25 22:08:22 UTC 2021 , Edited by admin on Fri Jun 25 22:08:22 UTC 2021
PRIMARY USP-RS
MESH
C053503
Created by admin on Fri Jun 25 22:08:22 UTC 2021 , Edited by admin on Fri Jun 25 22:08:22 UTC 2021
PRIMARY
CAS
103980-44-5
Created by admin on Fri Jun 25 22:08:22 UTC 2021 , Edited by admin on Fri Jun 25 22:08:22 UTC 2021
PRIMARY
Related Record Type Details
Structure of CEFTIOFUR
PARENT -> SALT/SOLVATE
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Structure of 2-FUROIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of S-(4-HYDROXY-5-OXO-2,5-DIHYDROTHIOPHEN-3-YL)METHYL FURAN-2- CARBOTHIOATE
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of N-DEACYL CEFTIOFUR
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of N-TRITYL CEFTIOFUR OXIME
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of 7-AMINOCEPHALOSPORANIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of CEFOTAXIME
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of (6R,7R)-7-((E)-2-(2-AMINOTHIAZOL-4-YL)-2-(METHOXYIMINO)ACETAMIDO)-3-((FURAN-2-CARBONYLTHIO)METHYL)-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of CEFTIOFUR OXIME ETHYL ESTER
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Structure of CEFTIOFUR AMIDE DIMER
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
Structure of CEFTIOFUR
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