PRULIFLOXACIN

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C21H20FN3O6S
Molecular Weight	461.463
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

CC1SC2=C(C(O)=O)C(=O)C3=CC(F)=C(C=C3N12)N4CCN(CC5=C(C)OC(=O)O5)CC4

InChI

InChIKey=PWNMXPDKBYZCOO-UHFFFAOYSA-N

InChI=1S/C21H20FN3O6S/c1-10-16(31-21(29)30-10)9-23-3-5-24(6-4-23)15-8-14-12(7-13(15)22)18(26)17(20(27)28)19-25(14)11(2)32-19/h7-8,11H,3-6,9H2,1-2H3,(H,27,28)

HIDE SMILES / InChI

Molecular Formula	C21H20FN3O6S
Molecular Weight	461.463
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description

Prulifloxacin is a prodrug of ulifloxacin which has been approved in Italy, Japan, China, India and Greece, for treatment of infections caused by susceptible bacteria, in the following conditions: acute uncomplicated lower urinary tract infections (simple cystitis); complicated lower urinary tract infections; acute exacerbation of chronic bronchitis; gastroenteritis, including infectious diarrheas. Like other fluoroquinolones, prulifloxacin prevents bacterial DNA replication, transcription, repair and recombination through inhibition of bacterial DNA gyrase.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Bacterial DNA gyrase 66	Inhibitor 8,297
Topoisomerase IV 62	Inhibitor 8,297

Conditions

Condition	Modality	Highest Phase	Product
Lower urinary tract infections 4	Curative	Approved 8,429	Unidrox
Chronic bronchitis 51	Curative	Approved 8,429	Unidrox
Gastroenteritis 10	Curative	Approved 8,429	Quisnon

C_max

Value	Dose	Analyte	Population
1.03 μg/mL	300 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
1.4 μg/mL	450 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
1.6 μg/mL	600 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
0.68 μg/mL	100 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
1.88 μg/mL	400 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
1.09 μg/mL	200 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
0.81 μg/mL	200 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
1.41 μg/mL	300 mg 2 times / day steady-state, oral	ULIFLOXACIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
5 μg × h/mL	300 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
6.6 μg × h/mL	450 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
7.3 μg × h/mL	600 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
3.99 μg × h/mL	100 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
9.72 μg × h/mL	400 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
6.41 μg × h/mL	200 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
6.13 μg × h/mL	200 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
9.67 μg × h/mL	300 mg 2 times / day steady-state, oral	ULIFLOXACIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
12.1 h	300 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
10.6 h	450 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
10.7 h	600 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
7.72 h	100 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
7.94 h	400 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
8.92 h	200 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
7.44 h	200 mg single, oral	ULIFLOXACIN plasma	Homo sapiens
8.3 h	300 mg 2 times / day steady-state, oral	ULIFLOXACIN plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
54.8%	300 mg 2 times / day steady-state, oral		ULIFLOXACIN plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
600 mg 1 times / day steady-state, oral Highest studied dose	unhealthy, ADULT
600 mg 1 times / day steady-state, oral Studied dose	unhealthy, ADULT	Other AEs: Gastric pain, Diarrhoea...

Showing 1 to 2 of 2 entries

Previous1Next

AEs

Show entries

AE	Significance	Dose	Population
Diarrhoea	1 pt	600 mg 1 times / day steady-state, oral Studied dose	unhealthy, ADULT
Dyspepsia	1 pt	600 mg 1 times / day steady-state, oral Studied dose	unhealthy, ADULT
Headache	1 pt	600 mg 1 times / day steady-state, oral Studied dose	unhealthy, ADULT
Vomiting	2 patients	600 mg 1 times / day steady-state, oral Studied dose	unhealthy, ADULT
Gastric pain	9 patients	600 mg 1 times / day steady-state, oral Studied dose	unhealthy, ADULT

Showing 1 to 5 of 5 entries

Previous1Next

PubMed

Show entries

Title	Date	PubMed
Therapeutic effect of the quinolone prodrug prulifloxacin against experimental urinary tract infections in mice.	1996 Dec	9006794
Involvement of multiple transport systems in the disposition of an active metabolite of a prodrug-type new quinolone antibiotic, prulifloxacin.	2003	15618759
Prulifloxacin.	2004	15456336
Molecular characterization of clinical Streptococcus pneumoniae isolates with reduced susceptibility to fluoroquinolones emerging in Italy.	2004 Fall	15383164
Interpretive criteria for disk diffusion susceptibility testing of ulifloxacin, the active metabolite of prulifloxacin.	2005 Apr	15920898

Showing 1 to 5 of 15 entries

Previous1 2 3Next

Patents

Sample Use Guides

In Vivo Use Guide

One 600 mg tablet is sufficient. For patients with complicated lower urinary tract infections or acute exacerbation of bronchitis - one 600 mg tablet once daily for up to a maximum of 10 days of treatment

Route of Administration: Oral

In Vitro Use Guide

Ulifloxacin was highly active against many Enterobacteriaceae, including Italian community or nosocomial isolates including Streptococcus spp., Staphylococcus aureus, and Spanish clinical isolates of E. coli (with activity against some nalidixic acid-resistant isolates) and Klebsiella spp. (MIC90 ≤0.015–4.0 mg/L). Ulifloxacin showed good activity against Spanish clinical isolates of ciprofloxacin-susceptible P. aeruginosa (MIC90 1.0 mg/L) and gentamicin resistant P. aeruginosa (MIC90 0.2 mg/L).

Substance Class	Chemical
Record UNII	J42298IESW
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

PRULIFLOXACIN

Official Name

English

Prulifloxacin [WHO-DD]

Common Name

English

NM-441

Code

English

PRULIFLOXACIN [JAN]

Common Name

English

PRUVEL

Brand Name

English

Showing 1 to 5 of 11 entries

Previous1 2 3Next

Show entries

Classification Tree

Code System

Code

Fluoroquinolones

WHO-ATC

J01MA17

Fluoroquinolones

WHO-VATC

QJ01MA17

Antibiotic

NCI_THESAURUS

C795

Showing 1 to 3 of 3 entries

Previous1Next

Show entries

Code System

Code

Type

Description

SMS_ID

100000080843

PRIMARY

CAS

123447-62-1

PRIMARY

NSC

759833

PRIMARY

MERCK INDEX

m9286

PRIMARY

Merck Index

PUBCHEM

65947

PRIMARY

Showing 1 to 5 of 15 entries

Previous1 2 3Next

Show entries

Related Record

Type

Details


					C38638H76Y

ULIFLOXACIN

METABOLITE ACTIVE -> PRODRUG

Amount:

Showing 1 to 1 of 1 entries

Previous1Next

Show entries

Related Record

Type

Details


					C38638H76Y

ULIFLOXACIN

ACTIVE MOIETY

Amount:

Showing 1 to 1 of 1 entries

Previous1Next

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound