CEFOSELIS SULFATE

Possibly Marketed Outside US

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H22N8O6S2.H2O4S
Molecular Weight	620.636
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.CO\N=C(/C(=O)N[C@H]1[C@H]2SCC(CN3C=CC(=N)N3CCO)=C(N2C1=O)C(O)=O)C4=CSC(N)=N4

InChI

InChIKey=LZOLCSVRFKCSEM-ZQCAECPKSA-N

InChI=1S/C19H22N8O6S2.H2O4S/c1-33-24-12(10-8-35-19(21)22-10)15(29)23-13-16(30)27-14(18(31)32)9(7-34-17(13)27)6-25-3-2-11(20)26(25)4-5-28;1-5(2,3)4/h2-3,8,13,17,20,28H,4-7H2,1H3,(H2,21,22)(H,23,29)(H,31,32);(H2,1,2,3,4)/b20-11?,24-12-;/t13-,17-;/m1./s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25027339 | https://www.astellas.com/en/corporate/news/fujisawa/980907.html
Curator's Comment: http://psjd.icm.edu.pl/psjd/element/bwmeta1.element.psjd-bcc86349-7720-450f-8027-017dafa5ba9c

Cefoselis sulphate is a new parenteral cephalosporin, which was launched into therapy in Japan on 9 September, 1998, under the brand name Wincef. Cefoselis sulphate, like all the other beta-lactams, exhibits its bactericidal eff ects by binding to penicillinbinding proteins. It has a spectrum of activity that covers aerobic and anaerobic gram-positive and gram-negative bacteria. Cefoselis sulphate has been approved to treat infections caused by Staphylococcus and Pseudomonas especially respiratory and urinary tract infections. The recommended dose of cefoselis is 1 g twice a day as an intravenous infusion. The duration of therapy is from 5 to 14 days. Cefoselis sulfate has a potent antibacterial activity against Gram-positive bacteria involving Staphylococcus, Pneumococcus, and Streptococcus, as well as Gram-negative bacteria involving Pseudomonas, Escherichia coli, Klebsiella, Enterobacter, Serratia, Proteus, Morganella, and Providencia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Staphylococcus aureus 70 Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8460925	Inhibitor 8504
Peptidoglycan biosynthesis 20 Target ID: map00550 Sources: http://www.genome.jp/dbget-bin/www_bget?dr:D07646	Inhibitor 8504
Pseudomonas aeruginosa 12 Target ID: CHEMBL348 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8460925	Inhibitor 8504
GABA-A receptor; alpha-1/beta-2/gamma-2 28 Target ID: CHEMBL2095172 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11815378	Antagonist 2849	185.0 mM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Bacterial Staphylococcus infections 1 Sources: http://www.adwia.com/index.php?option=com_content&view=article&id=26&Itemid=235&lang=en https://www.astellas.com/en/corporate/news/fujisawa/980907.html https://www.ncbi.nlm.nih.gov/pubmed/25027339	Curative		Approved 8583	Wincef Approved Use Wincef is indicated to treat a variety of infections with moderate severity or higher caused by cefoselis-susceptible strains such as Staphylococcus and Pseudomonas, including respiratory tract infections and urinary tract infections. Launch Date 1998
Bacterial Pseudomonas infections 1 Sources: http://www.adwia.com/index.php?option=com_content&view=article&id=26&Itemid=235&lang=en https://www.astellas.com/en/corporate/news/fujisawa/980907.html https://www.ncbi.nlm.nih.gov/pubmed/25027339	Curative		Approved 8583	Wincef Approved Use Wincef is indicated to treat a variety of infections with moderate severity or higher caused by cefoselis-susceptible strains such as Staphylococcus and Pseudomonas, including respiratory tract infections and urinary tract infections. Launch Date 1998

C_max

Value	Dose	Co-administered	Analyte	Population
83.8 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7840572/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		CEFOSELIS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
142.6 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7840572/	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:		CEFOSELIS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
159.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7840572/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		CEFOSELIS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
303.7 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7840572/	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:		CEFOSELIS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7840572/	1 g single, oral dose: 1 g route of administration: Oral experiment type: SINGLE co-administered:		CEFOSELIS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/7840572/	2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered:		CEFOSELIS plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
2 g 2 times / day multiple, intravenous Studied dose Dose: 2 g, 2 times / day Route: intravenous Route: multiple Dose: 2 g, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25027339/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25027339/	Sources: https://pubmed.ncbi.nlm.nih.gov/25027339/

PubMed

Title	Date	PubMed
Stability studies of cefoselis sulfate in the solid state.	2015-10-10	26073113
Multicenter, double-blind, randomized clinical trial of parenterally administered Cefoselis versus Cefepime for the treatment of acute bacterial infections.	2014	25027339

Patents

Sample Use Guides

In Vivo Use Guide

1.0 g of for moderate infection or 2.0 g intravenous infusion for severe infection administered at an interval of 12 hours for 7 to 14 days

Route of Administration: Intravenous

In Vitro Use Guide

Cefoselis sulphate inhibited methicillin-susceptible staphylocci at < or = 4 ug/ml. Of 98 isolates of homogenous methicillin-resistant Staphylococcus aureus, 55 (56.1%) were inhibited by 8 ug of FK-037 per ml

Name

Type

Language

CEFOSELIS SULFATE

Common Name

English

WINSEF

Preferred Name

English

FK 037

Common Name

English

5-AMINO-2-(((6R,7R)-7-(((Z)-2-(2-AMINO-4-THIAZOLYL)-2-(METHOXYIMINO)ACETYL)-AMINO)-2-CARBOXY-8-OXO-5-THIA-1-AZABICYCLO(4.2.0)OCT-2-EN-3-YL)METHYL)-1-(2-HYDROXYETHYL)-1H-PYRAZOLIUM HYDROXIDE SULFATE

Common Name

English

5-THIA-1-AZABICYCLO(4.2.0)OCT-2-ENE-2-CARBOXYLIC ACID, 7-(((2Z)-2-(2-AMINO-4-THIAZOLYL)-2-(METHOXYIMINO)ACETYL)AMINO)-3-((2,3-DIHYDRO-2-(2-HYDROXYETHYL)-3-IMINO-1H-PYRAZOL-1-YL)METHYL)-8-OXO-, (6R,7R)-, SULFATE (1:1)

Common Name

English

FK-037

Common Name

English

Cefoselis sulfate [WHO-DD]

Common Name

English

CEFOSELIS SULFATE [MI]

Common Name

English

CEFOSELIS SULFATE [JAN]

Common Name

English

Code System Code Type Description

CAS

122841-12-7