FINAFLOXACIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C20H19FN4O4
Molecular Weight	398.3877
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

SMILES

[H][C@]12CN(C[C@]1([H])OCCN2)C3=C(C#N)C4=C(C=C3F)C(=O)C(=CN4C5CC5)C(O)=O

InChI

InChIKey=FYMHQCNFKNMJAV-HOTGVXAUSA-N

InChI=1S/C20H19FN4O4/c21-14-5-11-17(25(10-1-2-10)7-13(19(11)26)20(27)28)12(6-22)18(14)24-8-15-16(9-24)29-4-3-23-15/h5,7,10,15-16,23H,1-4,8-9H2,(H,27,28)/t15-,16-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C20H19FN4O4
Molecular Weight	398.3877
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description

Finafloxacin is a fluoroquinolone antimicrobial agent that exhibits optimum efficacy in slightly acidic environments and is a highly potent eradicator of Helicobacter pylori. Being developed to treat serious bacterial infections associated with an acidic environment, including urinary tract infections and Helicobacter pylori infections finafloxacin is approved for treatment of acute otitis externa (swimmer’s ear) caused by the bacteria Pseudomonas aeruginosa and Staphylococcus aureus. XTORO (finafloxacin otic suspension), 0.3% is supplied as a sterile, preserved, aqueous suspension. Finafloxacin is a drug with a favorable safety profile.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA gyrase subunit A 7	Inhibitor 8,297
DNA topoisomerase IV subunit A 2	Inhibitor 8,297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acute otitis externa 2	Curative		Approved 8,429	XTORO

C_max

Value	Dose	Analyte	Population
0.44 mg/L	50 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
1.9 mg/L	200 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
11.1 mg/L	800 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
1.69 mg/L	150 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
1.5 mg/L	150 mg 1 times / day multiple, oral	FINAFLOXACIN plasma	Homo sapiens
2.96 mg/L	300 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
4.15 mg/L	300 mg 1 times / day multiple, oral	FINAFLOXACIN plasma	Homo sapiens
7.67 mg/L	600 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
6.76 mg/L	600 mg 1 times / day multiple, oral	FINAFLOXACIN plasma	Homo sapiens
8.68 mg/L	800 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
8.95 mg/L	800 mg 1 times / day multiple, oral	FINAFLOXACIN plasma	Homo sapiens
2.56 mg/L	200 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
6 mg/L	400 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
8 mg/L	600 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
13.3 mg/L	800 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
20.2 mg/L	1000 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
8.84 mg/L	600 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
9.15 mg/L	600 mg 1 times / day multiple, intravenous	FINAFLOXACIN plasma	Homo sapiens
11.5 mg/L	800 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
37.8 mg/L	800 mg 1 times / day multiple, intravenous	FINAFLOXACIN plasma	Homo sapiens
17.1 mg/L	1000 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
18.1 mg/L	1000 mg 1 times / day multiple, intravenous	FINAFLOXACIN plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
1.26 mg × h/L	50 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
4.08 mg × h/L	200 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
29.2 mg × h/L	800 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
3.76 mg × h/L	150 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
4.01 mg × h/L	150 mg 1 times / day multiple, oral	FINAFLOXACIN plasma	Homo sapiens
8.75 mg × h/L	300 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
9.09 mg × h/L	300 mg 1 times / day multiple, oral	FINAFLOXACIN plasma	Homo sapiens
18.7 mg × h/L	600 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
19.2 mg × h/L	600 mg 1 times / day multiple, oral	FINAFLOXACIN plasma	Homo sapiens
20.8 mg × h/L	800 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
26.1 mg × h/L	800 mg 1 times / day multiple, oral	FINAFLOXACIN plasma	Homo sapiens
6.85 mg × h/L	200 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
14.7 mg × h/L	400 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
21.8 mg × h/L	600 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
31.7 mg × h/L	800 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
46.9 mg × h/L	1000 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
21.8 mg × h/L	600 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
24.3 mg × h/L	600 mg 1 times / day multiple, intravenous	FINAFLOXACIN plasma	Homo sapiens
32 mg × h/L	800 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
35.4 mg × h/L	800 mg 1 times / day multiple, intravenous	FINAFLOXACIN plasma	Homo sapiens
49.8 mg × h/L	1000 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
64.1 mg × h/L	1000 mg 1 times / day multiple, intravenous	FINAFLOXACIN plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
3.8 h	50 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
4.06 h	200 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
10.5 h	800 mg single, oral	FINAFLOXACIN plasma	Homo sapiens
5.3 h	150 mg 1 times / day multiple, oral	FINAFLOXACIN plasma	Homo sapiens
6.5 h	300 mg 1 times / day multiple, oral	FINAFLOXACIN plasma	Homo sapiens
8.8 h	600 mg 1 times / day multiple, oral	FINAFLOXACIN plasma	Homo sapiens
14 h	800 mg 1 times / day multiple, oral	FINAFLOXACIN plasma	Homo sapiens
10.6 h	200 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
12.1 h	400 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
11.7 h	600 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
15.3 h	800 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
17.1 h	1000 mg single, intravenous	FINAFLOXACIN plasma	Homo sapiens
11.9 h	600 mg 1 times / day multiple, intravenous	FINAFLOXACIN plasma	Homo sapiens
15 h	800 mg 1 times / day multiple, intravenous	FINAFLOXACIN plasma	Homo sapiens
16.9 h	1000 mg 1 times / day multiple, intravenous	FINAFLOXACIN plasma	Homo sapiens

Doses

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Dose	Population	Adverse events
0.3 % 2 times / day multiple, topical Recommended	unhealthy, 11 months - 84 years	Other AEs: Ear pruritus, Nausea...
1000 mg 1 times / day multiple, intravenous Highest studied dose	healthy, 53 (5.9)
800 mg 1 times / day multiple, oral Highest studied dose	healthy
0.3 % 2 times / day multiple, topical Recommended	unhealthy	Other AEs: Overgrowth of nonsusceptible organisms, Allergic reaction...

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AEs

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AE	Significance	Dose	Population
Nausea	1.1%	0.3 % 2 times / day multiple, topical Recommended	unhealthy, 11 months - 84 years
Ear pruritus	1.3%	0.3 % 2 times / day multiple, topical Recommended	unhealthy, 11 months - 84 years
Allergic reaction		0.3 % 2 times / day multiple, topical Recommended	unhealthy
Overgrowth of nonsusceptible organisms		0.3 % 2 times / day multiple, topical Recommended	unhealthy

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Sourcing

Sourcing

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Vendor/Aggregator	ID	URL
ChEBI	CHEBI:85176	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:85176
ChemicalBook	CB42605885	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB42605885
MolPort	MolPort-046-418-103	https://www.molport.com/shop/molecule-link/MolPort-046-418-103
MolPort	MolPort-047-151-608	https://www.molport.com/shop/molecule-link/MolPort-047-151-608
ZINC	ZINC000003985346	http://zinc15.docking.org/substances/ZINC000003985346

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PubMed

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Title	Date	PubMed
Activity of the investigational fluoroquinolone finafloxacin and seven other antimicrobial agents against 114 obligately anaerobic bacteria.	2014 Nov	25264128
Finafloxacin: first global approval.	2015 Apr	25808831

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Patents

Sample Use Guides

In Vivo Use Guide

Instill four drops into the affected ear(s) twice daily for seven days. For patients requiring use of an otowick, the initial dose can be doubled (to 8 drops), followed by 4 drops instilled into the affected ear twice daily for seven days.

Route of Administration: Otic (auricular)

In Vitro Use Guide

At low pH=5,8 and in range of concentrations: 0,006 - 0,25 mg/L finafloxacin showed the highest activity among all tested fluoroquinolones against S. aureus, including the methicillin-resistant S. aureus (MRSA) pairs and coagulase-negative staphylococcal (CoNS) tested

Substance Class	Chemical
Record UNII	D26OSN9Q4R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FINAFLOXACIN

Official Name

English

FINAFLOXACIN [MI]

Common Name

English

(-)-8-CYANO-1-CYCLOPROPYL-6-FLUORO-7-((4AS,7AS)-HEXAHYDROPYRROLO(3,4-B)-1,4-OXAZIN-6(2H)-YL)-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID

Common Name

English

finafloxacin [INN]

Common Name

English

AL-60371

Code

English

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Classification Tree

Code System

Code

Established Pharmacologic Class

NDF-RT

N0000175937

Antibiotic

NCI_THESAURUS

C795

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Code System

Code

Type

Description

PUBCHEM

11567473

PRIMARY

SMS_ID

300000034190

PRIMARY

CAS

209342-40-5

PRIMARY

MESH

C560572

PRIMARY

WIKIPEDIA

Finafloxacin

PRIMARY

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SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2