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Details

Stereochemistry RACEMIC
Molecular Formula C19H22FN3O3
Molecular Weight 359.3947
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GREPAFLOXACIN

SMILES

CC1CN(CCN1)C2=C(F)C(C)=C3C(=O)C(=CN(C4CC4)C3=C2)C(O)=O

InChI

InChIKey=AIJTTZAVMXIJGM-UHFFFAOYSA-N
InChI=1S/C19H22FN3O3/c1-10-8-22(6-5-21-10)15-7-14-16(11(2)17(15)20)18(24)13(19(25)26)9-23(14)12-3-4-12/h7,9-10,12,21H,3-6,8H2,1-2H3,(H,25,26)

HIDE SMILES / InChI

Molecular Formula C19H22FN3O3
Molecular Weight 359.3947
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

Grepafloxacin is a monofluorinated quinolone with a cyclopropyl group at position 1, a 3-methyl-1piperazinyl group at position 7 and a methyl substitution at the 5 position, that was synthesized by Otsuka in Japan. It exhibited in vitro activity against a wide variety of both Gram-positive and Gram-negative bacteria including anaerobic species. The compound was reported to have a broad spectrum of activity, particularly against pathogens responsible for community-acquired respiratory infections including those caused by beta-lactam and macrolide-resistant strains of Streptococcus pneumoniae and Haemophilus influenzae. Japanese researchers also reported that unlike other quinolones, grepafloxacin reached high levels in the bile and might also be useful in the treatment of biliary tract infection. Grepafloxacin was administered once daily and did not require dosage adjustment for renal insufficiency, but grepafloxacin tablets were contraindicated in patients with hepatic failure. Otsuka Pharmaceutical signed a licensing agreement for grepafloxacin with GlaxoSmithKline. According to this agreement, GlaxoSmithKline had marketing rights to grepafloxacin in Europe, USA, and certain other markets. Otsuka retained rights for Japan and some Asian countries

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
RAXAR
Curative
RAXAR
Curative
RAXAR

Cmax

ValueDoseCo-administeredAnalytePopulation
1.43 mg/L
400 mg 1 times / day steady-state, oral
GREPAFLOXACIN plasma
Homo sapiens
2.63 mg/L
800 mg 1 times / day steady-state, oral
GREPAFLOXACIN plasma
Homo sapiens
0.93 mg/L
400 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
1.41 mg/L
600 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
2.26 mg/L
800 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
3.17 mg/L
1200 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
0.47 mg/L
200 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
14.6 mg × h/L
400 mg 1 times / day steady-state, oral
GREPAFLOXACIN plasma
Homo sapiens
32.2 mg × h/L
800 mg 1 times / day steady-state, oral
GREPAFLOXACIN plasma
Homo sapiens
11.35 mg × h/L
400 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
19.73 mg × h/L
600 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
27.69 mg × h/L
800 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
45.04 mg × h/L
1200 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
5.08 mg × h/L
200 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
11.68 h
400 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
12.67 h
600 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
12.25 h
800 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
11.68 h
1200 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
10.14 h
200 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
50%
400 mg 1 times / day steady-state, oral
GREPAFLOXACIN plasma
Homo sapiens
50%
800 mg 1 times / day steady-state, oral
GREPAFLOXACIN plasma
Homo sapiens
50%
400 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
50%
600 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
50%
800 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
50%
1200 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens
50%
200 mg single, oral
GREPAFLOXACIN plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
RAXAR (Grepafloxacin) Tablets may be taken with or without meals. The usual dose for RAXAR is 400 mg or 600 mg orally every 24 hours. Sucralfate; antacids containing magnesium, calcium, or aluminum; multivitamins containing iron or zinc; or VIDEX (didanosine) chewable/buffered tablets or the pediatric powder for oral solution should not be taken within 4 hours before or 4 hours after taking grepafloxacin.
Route of Administration: Oral
In Vitro Use Guide
The activity of grepafloxacin was evaluated against five isolates of Chlamydia pneumonia and 21 isolates of Chlamydia trachomatis. MICs were determined using a tissue culture incorporation technique in McCoy cell monolayers treated with Grepafloxacin. After 48–72 h incubation, cover slips were fixed in methanol and stained with an immunofluorescent monoclonal antibody against the major outer membrane protein. Grepafloxacin MIC range was 0.06–0.12 mg/L.
Substance Class Chemical
Record UNII
L1M1U2HC31
Record Status Validated (UNII)
Record Version