OZENOXACIN

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H21N3O3
Molecular Weight	363.4097
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CNC1=C(C)C=C(C=N1)C2=C(C)C3=C(C=C2)C(=O)C(=CN3C4CC4)C(O)=O

InChI

InChIKey=XPIJWUTXQAGSLK-UHFFFAOYSA-N

InChI=1S/C21H21N3O3/c1-11-8-13(9-23-20(11)22-3)15-6-7-16-18(12(15)2)24(14-4-5-14)10-17(19(16)25)21(26)27/h6-10,14H,4-5H2,1-3H3,(H,22,23)(H,26,27)

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25340832
Curator's Comment: description was created based on several sources, including https://www.drugs.com/history/ozenoxacin.html | https://clinicaltrials.gov/ct2/show/NCT02090764 | https://www.ncbi.nlm.nih.gov/pubmed/11864945

Ozenoxacin is an experimental quinolone antibiotic being developed for the treatment of impetigo and other dermatological bacterial infections. Ozenoxacin is active against some bacteria that have developed resistance to currently used quinolone and fluoroquinolone antibiotics. In two phase 3 studies, Ozenoxacin cream, 1%, applied topically twice daily for 5 days vs. placebo, demonstrated superiority on both clinical and bacteriological endpoints, according to the release. Superior bacteriological cure of Ozenoxacin compared to placebo was demonstrated as early as day 4. In both adults and a pediatric population aged 2 months and older, Ozenoxacin treatment was reported to be safe and well tolerated.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Topoisomerase IV 62 Target ID: CHEMBL3038508 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11864945	Inhibitor 8297
Bacterial DNA gyrase 66 Target ID: CHEMBL2311224 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11864945	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
impetigo 1 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2017/208945lbl.pdf	Curative		Approved 8429	XEPI Approved Use XEPI™ is indicated for the topical treatment of impetigo due to Staphylococcus aureus or Streptococcus pyogenes in adult and pediatric patients 2 months of age and older Launch Date 2017
Impetigo 1 Sources: https://clinicaltrials.gov/ct2/show/NCT02090764	Curative		Phase III 656	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
10796 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29745239/	100 mg/kg bw 1 times / day multiple, oral dose: 100 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered:		OZENOXACIN plasma	Canis lupus population: HEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
63458 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29745239/	100 mg/kg bw 1 times / day multiple, oral dose: 100 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered:		OZENOXACIN plasma	Canis lupus population: HEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
2.9 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/29745239/	100 mg/kg bw 1 times / day multiple, oral dose: 100 mg/kg bw route of administration: Oral experiment type: MULTIPLE co-administered:		OZENOXACIN plasma	Canis lupus population: HEALTHY age: CHILD sex: FEMALE / MALE food status: FASTED

Doses

Dose	Population	Adverse events
1 % 2 times / day multiple, topical Recommended Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf Page: 208945Orig1s000MedR.pdf - p.49 \| 208945Orig1s000MedR.pdf - p.102	unhealthy, 2 months of age and above n = 206 Health Status: unhealthy Condition: impetigo Age Group: 2 months of age and above Sex: M+F Population Size: 206 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf Page: 208945Orig1s000MedR.pdf - p.49 \| 208945Orig1s000MedR.pdf - p.102	Disc. AE: Rosacea, Seborrheic dermatitis... AEs leading to discontinuation/dose reduction: Rosacea (grade 1, 0.5%) Seborrheic dermatitis (grade 2, 0.5%) Skin tightness (grade 3, 0.5%) Eczema (grade 4, 0.5%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf Page: 208945Orig1s000MedR.pdf - p.49 \| 208945Orig1s000MedR.pdf - p.102
50 mg 1 times / day single, topical Highest studied dose Dose: 50 mg, 1 times / day Route: topical Route: single Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25209519/ https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf	healthy, adult n = 8 Health Status: healthy Age Group: adult Sex: M Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/25209519/ https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf	Other AEs: Application site itching... Other AEs: Application site itching (grade 1, 12.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/25209519/ https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf

AEs

AE	Significance	Dose	Population
Rosacea	grade 1, 0.5% Disc. AE	1 % 2 times / day multiple, topical Recommended Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf Page: 208945Orig1s000MedR.pdf - p.49 \| 208945Orig1s000MedR.pdf - p.102	unhealthy, 2 months of age and above n = 206 Health Status: unhealthy Condition: impetigo Age Group: 2 months of age and above Sex: M+F Population Size: 206 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf Page: 208945Orig1s000MedR.pdf - p.49 \| 208945Orig1s000MedR.pdf - p.102
Seborrheic dermatitis	grade 2, 0.5% Disc. AE	1 % 2 times / day multiple, topical Recommended Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf Page: 208945Orig1s000MedR.pdf - p.49 \| 208945Orig1s000MedR.pdf - p.102	unhealthy, 2 months of age and above n = 206 Health Status: unhealthy Condition: impetigo Age Group: 2 months of age and above Sex: M+F Population Size: 206 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf Page: 208945Orig1s000MedR.pdf - p.49 \| 208945Orig1s000MedR.pdf - p.102
Skin tightness	grade 3, 0.5% Disc. AE	1 % 2 times / day multiple, topical Recommended Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf Page: 208945Orig1s000MedR.pdf - p.49 \| 208945Orig1s000MedR.pdf - p.102	unhealthy, 2 months of age and above n = 206 Health Status: unhealthy Condition: impetigo Age Group: 2 months of age and above Sex: M+F Population Size: 206 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf Page: 208945Orig1s000MedR.pdf - p.49 \| 208945Orig1s000MedR.pdf - p.102
Eczema	grade 4, 0.5% Disc. AE	1 % 2 times / day multiple, topical Recommended Dose: 1 %, 2 times / day Route: topical Route: multiple Dose: 1 %, 2 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf Page: 208945Orig1s000MedR.pdf - p.49 \| 208945Orig1s000MedR.pdf - p.102	unhealthy, 2 months of age and above n = 206 Health Status: unhealthy Condition: impetigo Age Group: 2 months of age and above Sex: M+F Population Size: 206 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf Page: 208945Orig1s000MedR.pdf - p.49 \| 208945Orig1s000MedR.pdf - p.102
Application site itching	grade 1, 12.5%	50 mg 1 times / day single, topical Highest studied dose Dose: 50 mg, 1 times / day Route: topical Route: single Dose: 50 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25209519/ https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf	healthy, adult n = 8 Health Status: healthy Age Group: adult Sex: M Population Size: 8 Sources: https://pubmed.ncbi.nlm.nih.gov/25209519/ https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/208945Orig1s000MedR.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 1587	inhibitor 1767	inhibitor 1852	inhibitor 1612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2B6 810 CYP2C8 911 CYP2C19 1478 CYP2E1 882

Drug as perpetrator

Target	Modality	Activity
CYP1A2 1692	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209570Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no
CYP2B6 1001	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209570Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no
CYP2C19 1553	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209570Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no
CYP2C8 965	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209570Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no
CYP2D6 1891	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209570Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no
CYP2E1 970	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209570Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	no
CYP2C9 1819	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209570Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	yes [IC50 >=100 uM]
CYP3A4 1925	inhibitor 3277 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209570Orig1s000ClinPharmR.pdf#page=8 Page: 8.0	yes [IC50 >=100 uM]

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inhibitor 1626 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2017/209570Orig1s000ClinPharmR.pdf#page=7 Page: 7.0

Sourcing

Vendor/Aggregator	ID	URL
AA Blocks	AA00BI6F	https://www.aablocks.com/goods/Goods/detail?id=AA00BI6F
Aaron Chemicals	AR00BIY7	http://www.aaronchem.com/245765-41-7
Achemtek	0102-013521	http://www.achemtek.com/245765-41-7
Acorn PharmaTech	ACN-053795	http://www.acornpharmatech.com/
Adooq BioScience	A12996	https://www.adooq.com/ozenoxacin.html
Alsachim	1329	http://www.alsachim.com/product-C1703-glo.bal-view.html
Ambeed	A724760	https://www.ambeed.com/products/245765-41-7.html
Ark Pharma Scientific Limited	A-0748	http://www.arkpharmtech.com/product/32699.html
BLD Pharm	BD00864253	http://www.bldpharm.com/products/245765-41-7.html
BOC Sciences	245765-41-7	https://www.bocsci.com/ozenoxacin-cas-245765-41-7-item-91100.html
BioChemPartner	BCP16621	http://www.biochempartner.com/245765-41-7-BCP16621
CSNpharm	CSN23836	https://www.csnpharm.com/products/ozenoxacin.html
Chem Scene	CS-0003657	http://www.chemscene.com/245765-41-7.html
Chemspace	CSSB00102518758	https://chem-space.com/CSSB00102518758
Clearsynth	CS-EK-02014	https://www.clearsynth.com/en/CSEK02014.html
DC Chemicals	DC32078	http://www.dcchemicals.com//product_show-GF-001001-00.html
Debye Scientific	DA-31712	http://www.debyesci.com/cas_245765-41-7.html
Excenen	EX-A2693	https://www.excenen.com/searchresultlist.php?id=245765-41-7
Finetech	FT-0701296	http://www.finetechnology-ind.com/online_service.shtml
LGC Standards	DRE-A15825000AL-100	https://www.lgcstandards.com/US/en/p/DRE-A15825000AL-100
LGC Standards	DRE-C15825000	https://www.lgcstandards.com/US/en/p/DRE-C15825000
MedChem Express	HY-14957	https://www.medchemexpress.com/Ozenoxacin.html
Smolecule	S515623	http://www.smolecule.com/products/s515623
Synblock Inc	SB16801	http://www.synblock.com/product/245765-41-7.html
THE BioTek	bt-256473	https://www.thebiotek.com/product/inhibitors/bt-256473
eNovation Chemicals	D549289	https://www.enovationchem.com/ProductDetails.asp?ProductID=D549289
eNovation Chemicals	D676039	https://www.enovationchem.com/ProductDetails.asp?ProductID=D676039
eNovation Chemicals	D764380	https://www.enovationchem.com/ProductDetails.asp?ProductID=D764380
eNovation Chemicals	Y0974452	https://www.enovationchem.com/ProductDetails.asp?ProductID=Y0974452

PubMed

Title	Date	PubMed
Ozenoxacin 1% cream in the treatment of impetigo: a multicenter, randomized, placebo- and retapamulin-controlled clinical trial.	2014	25340832

Patents

Sample Use Guides

In Vivo Use Guide

1% cream was applied topically on affected area of 1–100 cm^2 twice dally for 5 days

Route of Administration: Topical

In Vitro Use Guide

In vitro development of resistance was carried out using a broth microdilution method by exposing bacteria to stepwise increasing concentrations of T-3912 (Ozenoxacin). Selection of drug-resistant derivatives was carried out by exposure of 5. aureus SA113 and P. ctcnes JCM6425 to stepwise increasing concentrations of T-3912. A series of microtitre wells containing two-fold serial dilutions of T-3912 was inoculated with a final concentration of 10^5 cfu/mL and then incubated for 24 h for S. aureus SA113 and for 48 h for P. acnes JCM6425. In the next step, the well with the highest T-3912 concentration still showing turbidity was used to inoculate a new series of microtitre tray. The procedure was repeated, and the MICs were determined for up to 28 passages.

Name

Type

Language

OZENOXACIN

Official Name

English

OZENOXACIN [JAN]

Common Name

English

XEPI

Brand Name

English

OZENOXACIN [ORANGE BOOK]

Common Name

English

1-CYCLOPROPYL-8-METHYL-7-(5-METHYL-6-(METHYLAMINO)PYRIDIN-3-YL)-4-OXO-1,4-DIHYDROQUINOLINE-3-CARBOXYLIC ACID

Systematic Name

English

OZENOXACIN [MI]

Common Name

English

Ozenoxacin [WHO-DD]

Common Name

English

3-QUINOLINECARBOXYLIC ACID, 1-CYCLOPROPYL-1,4-DIHYDRO-8-METHYL-7-(5-METHYL-6-(METHYLAMINO)-3-PYRIDINYL)-4-OXO-

Systematic Name

English

OZENOXACIN [USAN]

Common Name

English

GF-001001-00

Code

English

T-3912

Code

English

ozenoxacin [INN]

Common Name

English

Classification Tree Code System Code

WHO-ATC

D06AX14