ZOLIFLODACIN

Investigational

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H22FN5O7
Molecular Weight	487.4378
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@H]1COC(=O)N1C2=NOC3=C(F)C4=C(CC6([C@H]5[C@H](C)O[C@H](C)CN45)C(=O)NC(=O)NC6=O)C=C23

InChI

InChIKey=ZSWMIFNWDQEXDT-ZESJGQACSA-N

InChI=1S/C22H22FN5O7/c1-8-7-33-21(32)28(8)17-12-4-11-5-22(18(29)24-20(31)25-19(22)30)16-10(3)34-9(2)6-27(16)14(11)13(23)15(12)35-26-17/h4,8-10,16H,5-7H2,1-3H3,(H2,24,25,29,30,31)/t8-,9+,10-,16+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H22FN5O7
Molecular Weight	487.4378
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://clinicaltrials.gov/ct2/show/NCT02257918 | https://www.ncbi.nlm.nih.gov/pubmed/30373802 | https://www.entasistx.com/pipeline

Zoliflodacin (also known as AZD0914 or ETX0914) is a spiropyrimidinetrione with activity against bacterial type II topoisomerases that inhibits DNA biosynthesis and results in accumulation of double-strand cleavages in bacteria. This drug is being a DNA gyrase inhibitor, targeting Neisseria gonorrhoeae and is currently in phase II clinical trial in adults to treat uncomplicated urogenital gonorrhea.

Originator

Approval Year

PubMed

Title	Date	PubMed
Single-Dose Pharmacokinetics, Excretion, and Metabolism of Zoliflodacin, a Novel Spiropyrimidinetrione Antibiotic, in Healthy Volunteers.	2019-01	30373802
Single-Dose Zoliflodacin (ETX0914) for Treatment of Urogenital Gonorrhea.	2018-11-08	30403954
In vitro activity of AZD0914, a novel DNA gyrase inhibitor, against Chlamydia trachomatis and Chlamydia pneumoniae.	2014-12	25288086
High in vitro activity of the novel spiropyrimidinetrione AZD0914, a DNA gyrase inhibitor, against multidrug-resistant Neisseria gonorrhoeae isolates suggests a new effective option for oral treatment of gonorrhea.	2014-09	24982070

Sample Use Guides

In Vivo Use Guide

AZD0914 (ZOLIFLODACIN) is an antimicrobial amorphous nonsterile powder. Group 1 receive 2000 mg; Group 2 receive 3000 mg.

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:48:56 GMT 2025` Edited by `admin` on `Mon Mar 31 22:48:56 GMT 2025`
Record UNII	FWL2263R77
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

zoliflodacin [INN]

Preferred Name

English

ZOLIFLODACIN

Official Name

English

AZD0914

Code

English

ETX-0914

Code

English

AZD-0914

Code

English

(2R,4S,4AS)-11-FLUORO-2,4-DIMETHYL-8-((4S)-4-METHYL-2-OXO-1,3-OXAZOLIDIN-3-YL)-1,2,4,4A-TETRAHYDRO-2'H,6H-SPIRO((1,2)-OXAZOLO(4,5-G)(1,4)OXAZINO(4,3-A)QUINOLINE-5,5'-PYRIMIDINE)-2',4',6'(1'H,3'H)-TRIONE

Systematic Name

English

ZOLIFLODACIN [USAN]

Common Name

English

SPIRO(ISOXAZOLO(4,5-G)(1,4)OXAZINO(4,3-A)QUINOLINE-5(6H),5'(2'H)-PYRIMIDINE)-2',4',6'(1'H,3'H)-TRIONE, 11-FLUORO-1,2,4,4A-TETRAHYDRO-2,4-DIMETHYL-8-((4S)-4-METHYL-2-OXO-3-OXAZOLIDINYL)-, (2R,4S,4AS)-

Systematic Name

English

ETX0914

Code

English

Zoliflodacin [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C258