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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H22FN3O3
Molecular Weight 359.3947
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GREPAFLOXACIN, (R)-

SMILES

C[C@@H]1CN(CCN1)C2=C(F)C(C)=C3C(=O)C(=CN(C4CC4)C3=C2)C(O)=O

InChI

InChIKey=AIJTTZAVMXIJGM-SNVBAGLBSA-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)/t10-/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H22FN3O3
Molecular Weight 359.3947
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/nda/98/20-695S003_Raxar_Prntlbl.pdf | https://www.ncbi.nlm.nih.gov/pubmed/9454812

Grepafloxacin, (S)- is an asymmetric fluoroquinolone derivative which possesses high tissue penetrability as well as strong, broad-spectrum antimicrobial activities. Grepafloxacin has a chiral center and therefore has two optical enantiomeric isomers, R(+)- and S(-)-grepafloxacin. In neutrophil respiratory burst induced by N-formyl-methionyl leucyl-phenylalanine grepafloxacin induces a priming effect. The R(+) enantiomer of grepafloxacin induced a more potent priming effect than did S(-)-grepafloxacin. R(+)-Grepafloxacin also produced a more potent translocation of both p47- and p67-phox proteins to membrane fractions of neutrophils. Grepafloxacin-induced primed superoxide generation was significantly inhibited by pretreatment with PD169316 and SB203580, p38 mitogen-activated protein kinase (MAPK) inhibitors, but not with PD98059, a specific inhibitor of the upstream kinase that activates p44/42 MAPK, or SP600125, an inhibitor of stress-activated protein kinase/c-Jun N-terminal kinase (JNK).

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
RAXAR

Approved Use

RAXAR Tablets are Indicated for treatment of adults with mild to moderate infections caused by susceptible strains of the designated microorganisms in the infections listed below: Acute Bacterial Exacerbations of Chronic Bronchitis caused by Haemophilus influenzae, Streptococcus pneumoniae, or Moraxella catarrhalis. Community-acquired Pneumonia caused by Haemophilus influenzae, Streptococcus pneumoniae, Moraxella catarrhalis, or Mycoplasma pneumonia. Uncomplicated Gonorrhea (urethral In males and endocervical and rectal in females) caused by Neissen'a gononrhoeae. Nongonococcal Urethritis and Cervicitis caused by Chlamydia trachomatis

Launch Date

8.7868801E11
Curative
RAXAR

Approved Use

RAXAR Tablets are Indicated for treatment of adults with mild to moderate infections caused by susceptible strains of the designated microorganisms in the infections listed below: Acute Bacterial Exacerbations of Chronic Bronchitis caused by Haemophilus influenzae, Streptococcus pneumoniae, or Moraxella catarrhalis. Community-acquired Pneumonia caused by Haemophilus influenzae, Streptococcus pneumoniae, Moraxella catarrhalis, or Mycoplasma pneumonia. Uncomplicated Gonorrhea (urethral In males and endocervical and rectal in females) caused by Neissen'a gononrhoeae. Nongonococcal Urethritis and Cervicitis caused by Chlamydia trachomatis

Launch Date

8.7868801E11
Curative
RAXAR

Approved Use

RAXAR Tablets are Indicated for treatment of adults with mild to moderate infections caused by susceptible strains of the designated microorganisms in the infections listed below: Acute Bacterial Exacerbations of Chronic Bronchitis caused by Haemophilus influenzae, Streptococcus pneumoniae, or Moraxella catarrhalis. Community-acquired Pneumonia caused by Haemophilus influenzae, Streptococcus pneumoniae, Moraxella catarrhalis, or Mycoplasma pneumonia. Uncomplicated Gonorrhea (urethral In males and endocervical and rectal in females) caused by Neissen'a gononrhoeae. Nongonococcal Urethritis and Cervicitis caused by Chlamydia trachomatis

Launch Date

8.7868801E11
PubMed

PubMed

TitleDatePubMed
p38 MAPK associated with stereoselective priming by grepafloxacin on O2- production in neutrophils.
2004 May 15
Patents

Sample Use Guides

RAXAR (R/S-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 R/S-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
Created
by admin
on Thu Jul 06 16:41:38 UTC 2023
Edited
by admin
on Thu Jul 06 16:41:38 UTC 2023
Record UNII
B60Q83J4KP
Record Status Validated (UNII)
Record Version
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Name Type Language
GREPAFLOXACIN, (R)-
Common Name English
GREPAFLOXACIN, (+)-
Common Name English
3-QUINOLINECARBOXYLIC ACID, 1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-5-METHYL-7-((3R)-3-METHYL-1-PIPERAZINYL)-4-OXO-
Systematic Name English
D-GREPAFLOXACIN
Common Name English
3-QUINOLINECARBOXYLIC ACID, 1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-5-METHYL-7-(3-METHYL-1-PIPERAZINYL)-4-OXO-, (R)-
Systematic Name English
Code System Code Type Description
FDA UNII
B60Q83J4KP
Created by admin on Thu Jul 06 16:41:38 UTC 2023 , Edited by admin on Thu Jul 06 16:41:38 UTC 2023
PRIMARY
CAS
146761-68-4
Created by admin on Thu Jul 06 16:41:38 UTC 2023 , Edited by admin on Thu Jul 06 16:41:38 UTC 2023
PRIMARY
PUBCHEM
11681977
Created by admin on Thu Jul 06 16:41:38 UTC 2023 , Edited by admin on Thu Jul 06 16:41:38 UTC 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER