CEFQUINOME

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C23H24N6O5S2
Molecular Weight	528.604
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CO\N=C(/C(=O)N[C@H]1[C@H]2SCC(C[N+]3=CC=CC4=C3CCCC4)=C(N2C1=O)C([O-])=O)C5=CSC(N)=N5

InChI

InChIKey=YWKJNRNSJKEFMK-PQFQYKRASA-N

InChI=1S/C23H24N6O5S2/c1-34-27-16(14-11-36-23(24)25-14)19(30)26-17-20(31)29-18(22(32)33)13(10-35-21(17)29)9-28-8-4-6-12-5-2-3-7-15(12)28/h4,6,8,11,17,21H,2-3,5,7,9-10H2,1H3,(H3-,24,25,26,30,32,33)/b27-16-/t17-,21-/m1/s1

HIDE SMILES / InChI

Description
Sources: http://www.msd-animal-health.co.in/products/cobactan_2.5/020_product_details.aspx

Cefquinome is a 4th generation cephalosporin which is active against a broad spectrum of Gram positive and Gram negative bacteria. As many cephalosporin it acts by binding to bacterial PBP and thus inhibiting the cell wall synthesis. Cefquinome is approved for veterinary use in cattles with respiratory tract infections, skin infections, bacterial mastitis and septicaemia.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial penicillin-binding protein 234 Target ID: CHEMBL2354204 Sources: http://www.ema.europa.eu/docs/en_GB/document_library/Scientific_guideline/2009/10/WC500004307.pdf	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Sub-clinical mastitis 5 Sources: http://www.msd-animal-health.co.in/products/cobactan_2.5/020_product_details.aspx	Curative	Approved 8583	COBACTAN Approved Use Treatment of infections caused by bacteria sensitive to cefquinome, such as: (1) Respiratory tract infections caused by Pasteurella multocida and Mannheimia haemolytica. (2) Digital dermatitis, infectious bulbar necrosis and interdigital necrobacillosis (foul in foot). (3) Acute E.coli mastitis with signs of systemic involvement. (4) Calf-E.coli septicaemia. Launch Date 2006
Respiratory tract infections 85 Sources: http://www.msd-animal-health.co.in/products/cobactan_2.5/020_product_details.aspx	Curative	Approved 8583	COBACTAN Approved Use Treatment of infections caused by bacteria sensitive to cefquinome, such as: (1) Respiratory tract infections caused by Pasteurella multocida and Mannheimia haemolytica. (2) Digital dermatitis, infectious bulbar necrosis and interdigital necrobacillosis (foul in foot). (3) Acute E.coli mastitis with signs of systemic involvement. (4) Calf-E.coli septicaemia. Launch Date 2006
Septicaemia 15 Sources: http://www.msd-animal-health.co.in/products/cobactan_2.5/020_product_details.aspx	Curative	Approved 8583	COBACTAN Approved Use Treatment of infections caused by bacteria sensitive to cefquinome, such as: (1) Respiratory tract infections caused by Pasteurella multocida and Mannheimia haemolytica. (2) Digital dermatitis, infectious bulbar necrosis and interdigital necrobacillosis (foul in foot). (3) Acute E.coli mastitis with signs of systemic involvement. (4) Calf-E.coli septicaemia. Launch Date 2006
Digital dermatitis 2 Sources: http://www.msd-animal-health.co.in/products/cobactan_2.5/020_product_details.aspx	Curative	Approved 8583	COBACTAN Approved Use Treatment of infections caused by bacteria sensitive to cefquinome, such as: (1) Respiratory tract infections caused by Pasteurella multocida and Mannheimia haemolytica. (2) Digital dermatitis, infectious bulbar necrosis and interdigital necrobacillosis (foul in foot). (3) Acute E.coli mastitis with signs of systemic involvement. (4) Calf-E.coli septicaemia. Launch Date 2006
Infectious bulbar necrosis 2 Sources: http://www.msd-animal-health.co.in/products/cobactan_2.5/020_product_details.aspx	Curative	Approved 8583	COBACTAN Approved Use Treatment of infections caused by bacteria sensitive to cefquinome, such as: (1) Respiratory tract infections caused by Pasteurella multocida and Mannheimia haemolytica. (2) Digital dermatitis, infectious bulbar necrosis and interdigital necrobacillosis (foul in foot). (3) Acute E.coli mastitis with signs of systemic involvement. (4) Calf-E.coli septicaemia. Launch Date 2006
Interdigital necrobacillosis 2 Sources: http://www.msd-animal-health.co.in/products/cobactan_2.5/020_product_details.aspx	Curative	Approved 8583	COBACTAN Approved Use Treatment of infections caused by bacteria sensitive to cefquinome, such as: (1) Respiratory tract infections caused by Pasteurella multocida and Mannheimia haemolytica. (2) Digital dermatitis, infectious bulbar necrosis and interdigital necrobacillosis (foul in foot). (3) Acute E.coli mastitis with signs of systemic involvement. (4) Calf-E.coli septicaemia. Launch Date 2006

PubMed

Title	Date	PubMed
Stability-indicating HPLC method for the determination of cefquinome sulfate.	2014-10-03	25272644
Comparative Pharmacokinetics of Cefquinome (Cobactan 2.5%) following Repeated Intramuscular Administrations in Sheep and Goats.	2014	26464946
Development of stability-indicating methods for cefquinome sulphate.	2013-09	24170991
Development and validation of a high-performance liquid chromatography method for determination of cefquinome concentrations in sheep plasma and its application to pharmacokinetic studies.	2011-02	21098247
Factors affecting cure when treating bovine clinical mastitis with cephalosporin-based intramammary preparations.	2009-05	19389951
Selection and persistence of CTX-M-producing Escherichia coli in the intestinal flora of pigs treated with amoxicillin, ceftiofur, or cefquinome.	2008-10	18644956
In vitro activities of cephalosporins and quinolones against Escherichia coli strains isolated from diarrheic dairy calves.	1999-03	10049259
Antibacterial activities in vitro and in vivo and pharmacokinetics of cefquinome (HR 111V), a new broad-spectrum cephalosporin.	1991-01	2014969

Patents

Sample Use Guides

In Vivo Use Guide

1 mg cefquinome/kg (2ml/50 kg body wt.) or 2 mg cefquinome/kg (4ml/50 kg body wt.) given by intramuscular injection (2,5% Cobactan solution).

Route of Administration: Intramuscular

In Vitro Use Guide

The MICs of cefquinome against single laboratory strains of gram-positive and gram-negative anaerobic bacteria were determined. The values were (MIC50): 0.781 ug/ml for Staphylococcus aureus (Methicillin susceptible); 12.5 ug/ml for Staphylococcus aureus (Methicillin resistant); <0.006 ug/ml for Streptococcus spp.; 4.0 ug/ml for Enterococci; 0.049 ug/ml for E.Coli and Klebsiella spp.; 0.098 ug/ml for Salmonella spp., Enterobacter spp. and Proteus mirabilis; 0.195 ug/ml for Serratia marcescens and Proteus spp.; 0.002 ug/ml for Streptococcus pyogenes; 0.008 ug/ml for Streptococcus pneumoniae and Klebsiella pneumoniae; 0.078 ug/ml for Pasteurella multocida, Proteus mirabilis ATCC 14273; 0.03 ug/ml for Escherichia coli 078 and 0.06 ug/ml for Salmonella typhimurium MZ II.

Name

Type

Language

COBACTAN

Preferred Name

English

CEFQUINOME

Official Name

English

1-(((6R,7R)-7-(2-(2-AMINO-4-THIAZOLYL)GLYOXYLAMIDO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-5,6,7,8-TETRAHYDROQUINOLINIUM HYDROXIDE, INNER SALT, 72-(Z)-(O-METHYLOXIME)

Common Name

English

cefquinome [INN]

Common Name

English

QUINOLINIUM, 1-((7-(((2-AMINO-4-THIAZOLYL)(METHOXYIMINO)ACETYL)AMINO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-5,6,7,8-TETRAHYDRO-, HYDROXIDE, INNER SALT, (6R-(6.ALPHA.,7.BETA.(Z)))-

Common Name

English

HR111V

Code

English

CEFQUINOME [MI]

Common Name

English

Classification Tree Code System Code

WHO-VATC

QJ51DE90