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Details

Stereochemistry ACHIRAL
Molecular Formula C21H23F2N3O4.ClH
Molecular Weight 455.883
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of ACORAFLOXACIN HYDROCHLORIDE

SMILES

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

InChI

InChIKey=RDXCNSOGHLLWDV-YFMOEUEHSA-N
InChI=1S/C21H23F2N3O4.ClH/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);1H/b16-11+;

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 01:26:05 GMT 2023
Edited
by admin
on Sat Dec 16 01:26:05 GMT 2023
Record UNII
1NWW5SKQ0N
Record Status Validated (UNII)
Record Version
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Name Type Language
ACORAFLOXACIN HYDROCHLORIDE
USAN  
USAN  
Official Name English
ACORAFLOXACIN HYDROCHLORIDE [USAN]
Common 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 HYDROCHLORIDE
Systematic Name English
JNJ-32729463-AAC
Code English
AVAROFLOXACIN HYDROCHLORIDE
Common Name English
JNJ-32729463
Common Name English
JNJ-Q2 HYDROCHLORIDE
Common Name English
JNJ-32729463AAC
Code English
Classification Tree Code System Code
NCI_THESAURUS C126712
Created by admin on Sat Dec 16 01:26:05 GMT 2023 , Edited by admin on Sat Dec 16 01:26:05 GMT 2023
Code System Code Type Description
SMS_ID
300000041310
Created by admin on Sat Dec 16 01:26:05 GMT 2023 , Edited by admin on Sat Dec 16 01:26:05 GMT 2023
PRIMARY
USAN
ZZ-146
Created by admin on Sat Dec 16 01:26:05 GMT 2023 , Edited by admin on Sat Dec 16 01:26:05 GMT 2023
PRIMARY
FDA UNII
1NWW5SKQ0N
Created by admin on Sat Dec 16 01:26:05 GMT 2023 , Edited by admin on Sat Dec 16 01:26:05 GMT 2023
PRIMARY
PUBCHEM
67311433
Created by admin on Sat Dec 16 01:26:05 GMT 2023 , Edited by admin on Sat Dec 16 01:26:05 GMT 2023
PRIMARY
ChEMBL
CHEMBL1257096
Created by admin on Sat Dec 16 01:26:05 GMT 2023 , Edited by admin on Sat Dec 16 01:26:05 GMT 2023
PRIMARY
NCI_THESAURUS
C142898
Created by admin on Sat Dec 16 01:26:05 GMT 2023 , Edited by admin on Sat Dec 16 01:26:05 GMT 2023
PRIMARY
CAS
1001162-01-1
Created by admin on Sat Dec 16 01:26:05 GMT 2023 , Edited by admin on Sat Dec 16 01:26:05 GMT 2023
PRIMARY
EPA CompTox
DTXSID70142966
Created by admin on Sat Dec 16 01:26:05 GMT 2023 , Edited by admin on Sat Dec 16 01:26:05 GMT 2023
PRIMARY
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