ZOLIFLODACIN

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

[H][C@]12[C@H](C)O[C@H](C)CN1C3=C(CC24C(=O)NC(=O)NC4=O)C=C5C(=NOC5=C3F)N6[C@@H](C)COC6=O

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	3 / 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
In vitro activity of AZD0914, a novel DNA gyrase inhibitor, against Chlamydia trachomatis and Chlamydia pneumoniae.	2014 Dec	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 Sep	24982070
Single-Dose Zoliflodacin (ETX0914) for Treatment of Urogenital Gonorrhea.	2018 Nov 8	30403954
Single-Dose Pharmacokinetics, Excretion, and Metabolism of Zoliflodacin, a Novel Spiropyrimidinetrione Antibiotic, in Healthy Volunteers.	2019 Jan	30373802

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 `Sat Dec 16 09:42:50 UTC 2023` Edited by `admin` on `Sat Dec 16 09:42:50 UTC 2023`
Record UNII	FWL2263R77
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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 [INN]

Common 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