VIQUIDACIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C25H29FN2O4S2
Molecular Weight	504.637
Optical Activity	UNSPECIFIED
Defined Stereocenters	3 / 3
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C2N=CC(F)=C([C@@H](O)CC[C@@H]3CCN(CCSC4=CC=CS4)C[C@@H]3C(O)=O)C2=C1

InChI

InChIKey=USGHRRVFKSLEJT-WVBUVRCRSA-N

InChI=1S/C25H29FN2O4S2/c1-32-17-5-6-21-18(13-17)24(20(26)14-27-21)22(29)7-4-16-8-9-28(15-19(16)25(30)31)10-12-34-23-3-2-11-33-23/h2-3,5-6,11,13-14,16,19,22,29H,4,7-10,12,15H2,1H3,(H,30,31)/t16-,19+,22+/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18625781 | Marinelli Flavia, Genilloud Olga, Antimicrobials: New and Old Molecules in the Fight Against Multi-resistant, p. 318, retrieved from: https://books.google.ru/books?id=FTwnAQAAQBAJ&pg=PA317&lpg=PA317&dq=VIQUIDACIN+Novexel&source=bl&ots=pJ2UF9PClE&sig=ACfU3U1QDA_qTrGcKqnNM9F4n7IoT0b35g&hl=ru&sa=X&ved=2ahUKEwiVhJTC_a7jAhUJFpoKHeaPCr4Q6AEwCHoECAkQAQ#v=onepage&q=VIQUIDACIN%20Novexel&f=false

Viquidacin (also known as NXL-101), a quinoline antibacterial agent, was studied as a bacterial DNA gyrase and topoisomerase IV inhibitor. Viquidacin showed potent activity against gram-positive bacteria, including methicillin- and fluoroquinolone-resistant strains. The drug participated in phase I clinical trial. Viquidacin achieved homogeneous and potent bactericidal concentrations in human volunteer plasma. However, further, development was discontinued after QT interval prolongation, which was observed in a healthy volunteer.

Originator

Approval Year

PubMed

Title	Date	PubMed
Mechanism of action of the antibiotic NXL101, a novel nonfluoroquinolone inhibitor of bacterial type II topoisomerases.	2008 Sep	18625781

Patents

Name

Type

Language

VIQUIDACIN

Official Name

English

viquidacin [INN]

Common Name

English

NXL-101

Code

English

3-PIPERIDINECARBOXYLIC ACID, 4-((3S)-3-(3-FLUORO-6-METHOXY-4-QUINOLINYL)-3-HYDROXYPROPYL)-1-(2-(2-THIENYLTHIO)ETHYL)-, (3R,4R)-

Common Name

English

(3R,4R)-4-((3S)-3-(3-FLUORO-6-METHOXYQUINOLIN-4-YL)-3-HYDROXYPROPYL)-1-(2-((THIOPHEN-2-YL)SULFANYL)ETHYL)PIPERIDINE-3-CARBOXYLIC ACID

Systematic Name

English

NXL 101

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C258