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Details

Stereochemistry ACHIRAL
Molecular Formula C21H23F2N3O4
Molecular Weight 419.4218
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ACORAFLOXACIN

SMILES

COC1=C(N2CCC\C(C2)=C(/F)CN)C(F)=CC3=C1N(C=C(C(O)=O)C3=O)C4CC4

InChI

InChIKey=VMKVDAAFMQKZJS-LFIBNONCSA-N
InChI=1S/C21H23F2N3O4/c1-30-20-17-13(19(27)14(21(28)29)10-26(17)12-4-5-12)7-15(22)18(20)25-6-2-3-11(9-25)16(23)8-24/h7,10,12H,2-6,8-9,24H2,1H3,(H,28,29)/b16-11+

HIDE SMILES / InChI

Molecular Formula C21H23F2N3O4
Molecular Weight 419.4218
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Acorafloxacin (JNJ-Q2) is a fluoroquinolone that was developed by Furiex Pharmaceuticals (a subsidiary of Forest Laboratories) for the treatment of complicated skin and and soft tissue infections. Acorafloxacin was originally developed by Janssen, then licensed to Furiex Pharmaceuticals (now a part of Actavis). JNJ-Q2 has excellent in vitro and in vivo activity against a variety of Gram-positive and Gram-negative organisms. In vitro studies indicate that JNJ-Q2 has potent activity against pathogens responsible for acute bacterial skin and skin structure infections (ABSSSI) and community-acquired bacterial pneumonia (CABP), such as Staphylococcus aureus and Streptococcus pneumoniae. JNJ-Q2 also has been shown to have a higher barrier to resistance compared to other agents in the class and it remains highly active against drug-resistant organisms, including methicillin-resistant S. aureus, ciprofloxacin-resistant methicillin-resistant S. aureus, and drug-resistant S. pneumoniae. In two Phase II studies, the efficacy of JNJ-Q2 was comparable to linezolid for ABSSSI and moxifloxacin for CABP. Furthermore, JNJ-Q2 was well tolerated, with adverse event rates similar to or less than other fluoroquinolones. Acorafloxacin inhibits MuRF enzyme, required for cell wall synthesis. Acorafloxacin directly inhibits bacterial DNA synthesis by halting the activity of DNA gyrase (responsible for negative helical supercoiling) and DNA topoisomerase IV (responsible for separating the nucleotide strands). Fast track designation and qualified infectious disease product designation (QIDP) was granted by FDA for the treatment of bacterial infections in 2013.

Approval Year

PubMed

PubMed

TitleDatePubMed
In vitro antibacterial activities of JNJ-Q2, a new broad-spectrum fluoroquinolone.
2010 May
Activity of JNJ-Q2, a novel fluoroquinolone, tested against Neisseria gonorrhoeae, including ciprofloxacin-resistant strains.
2012 Oct
Focus on JNJ-Q2, a novel fluoroquinolone, for the management of community-acquired bacterial pneumonia and acute bacterial skin and skin structure infections.
2016
Patents

Patents

Sample Use Guides

A double-blind, multicenter, phase II noninferiority study treated 161 patients for 7 to 14 days, testing the efficacy of JNJ-Q2 (250 mg, twice a day [BID]) versus linezolid (600 mg, BID) in patients with acute bacterial skin and skin structure infections (ABSSSI).
Route of Administration: Oral
Against a set of 118 recent clinical isolates of Streptococcus pneumoniae, including fluoroquinolone-resistant variants bearing multiple DNA topoisomerase target mutations, an MIC(90) value for JNJ-Q2 of 0.12 ug/ml was determined, indicating that it was 32-fold more potent than moxifloxacin. Against a collection of 345 recently collected methicillin-resistant Staphylococcus aureus (MRSA) isolates, including 256 ciprofloxacin-resistant strains, the JNJ-Q2 MIC(90) value was 0.25 ug/ml, similarly indicating that it was 32-fold more potent than moxifloxacin.
Substance Class Chemical
Created
by admin
on Sat Dec 16 02:16:48 UTC 2023
Edited
by admin
on Sat Dec 16 02:16:48 UTC 2023
Record UNII
070SV15RJA
Record Status Validated (UNII)
Record Version
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Name Type Language
ACORAFLOXACIN
INN   USAN  
INN   USAN  
Official Name English
7-((3E)-3-(2-AMINO-1-FLUOROETHYLIDENE)-1-PIPERIDINYL)-1-CYCLOPROPYL-6-FLUORO-1,4-DIHYDRO-8-METHOXY-4-OXO-3-QUINOLINECARBOXYLIC ACID
Systematic Name English
ACORAFLOXACIN [USAN]
Common Name English
acorafloxacin [INN]
Common Name English
JNJ-32729463-AAA
Code English
JNJ-Q2
Code English
Avarofloxacin [WHO-DD]
Common Name English
AVAROFLOXACIN
WHO-DD  
Common Name English
Code System Code Type Description
ChEMBL
CHEMBL1257096
Created by admin on Sat Dec 16 02:16:49 UTC 2023 , Edited by admin on Sat Dec 16 02:16:49 UTC 2023
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FDA UNII
070SV15RJA
Created by admin on Sat Dec 16 02:16:49 UTC 2023 , Edited by admin on Sat Dec 16 02:16:49 UTC 2023
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WIKIPEDIA
JNJ-Q2
Created by admin on Sat Dec 16 02:16:49 UTC 2023 , Edited by admin on Sat Dec 16 02:16:49 UTC 2023
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NCI_THESAURUS
C171788
Created by admin on Sat Dec 16 02:16:49 UTC 2023 , Edited by admin on Sat Dec 16 02:16:49 UTC 2023
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SMS_ID
300000034050
Created by admin on Sat Dec 16 02:16:49 UTC 2023 , Edited by admin on Sat Dec 16 02:16:49 UTC 2023
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USAN
ZZ-145
Created by admin on Sat Dec 16 02:16:49 UTC 2023 , Edited by admin on Sat Dec 16 02:16:49 UTC 2023
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EPA CompTox
DTXSID20236667
Created by admin on Sat Dec 16 02:16:49 UTC 2023 , Edited by admin on Sat Dec 16 02:16:49 UTC 2023
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PUBCHEM
11546234
Created by admin on Sat Dec 16 02:16:49 UTC 2023 , Edited by admin on Sat Dec 16 02:16:49 UTC 2023
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INN
9761
Created by admin on Sat Dec 16 02:16:49 UTC 2023 , Edited by admin on Sat Dec 16 02:16:49 UTC 2023
PRIMARY
CAS
878592-87-1
Created by admin on Sat Dec 16 02:16:49 UTC 2023 , Edited by admin on Sat Dec 16 02:16:49 UTC 2023
PRIMARY
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