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Zoliflodacin

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Chemistry

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Also known as: 1620458-09-4, Azd0914, Azd-0914, Zoliflodacin [usan], Etx0914, Etx-0914

Molecular Formula

C₂₂H₂₂FN₅O₇

Molecular Weight

487.4 g/mol

InChI Key

ZSWMIFNWDQEXDT-ZESJGQACSA-N

FDA UNII

FWL2263R77

Zoliflodacin has been used in trials studying the basic science and treatment of Gonorrhoea.

1 2D Structure

Zoliflodacin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(4'R,6'S,7'S)-17'-fluoro-4',6'-dimethyl-13'-[(4S)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]spiro[1,3-diazinane-5,8'-5,15-dioxa-2,14-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(17),10,12(16),13-tetraene]-2,4,6-trione

2.1.2 InChI

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

2.1.3 InChI Key

ZSWMIFNWDQEXDT-ZESJGQACSA-N

2.1.4 Canonical SMILES

CC1CN2C(C(O1)C)C3(CC4=CC5=C(C(=C42)F)ON=C5N6C(COC6=O)C)C(=O)NC(=O)NC3=O

2.1.5 Isomeric SMILES

C[C@@H]1CN2[C@H]([C@@H](O1)C)C3(CC4=CC5=C(C(=C42)F)ON=C5N6[C@H](COC6=O)C)C(=O)NC(=O)NC3=O

2.2 Other Identifiers

2.2.1 UNII

FWL2263R77

2.3 Synonyms

2.3.1 MeSH Synonyms

1. (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

2. Azd-0914

3. Azd0914

4. Etx-0914

5. Etx0914

2.3.2 Depositor-Supplied Synonyms

1. 1620458-09-4

2. Azd0914

3. Azd-0914

4. Zoliflodacin [usan]

5. Etx0914

6. Etx-0914

7. Fwl2263r77

8. (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

9. Unii-fwl2263r77

10. Zoliflodacin(azd0914)

11. Zoliflodacin (usan/inn)

12. Zoliflodacin [inn]

13. Zoliflodacin [who-dd]

14. Azd 0914 - Bio-x

15. Chembl3544978

16. Schembl15879500

17. Gtpl10875

18. Azd0914etx0914

19. Ext0914

20. Bdbm139376

21. Dtxsid101028418

22. Azd 0914

23. Ex-a2620

24. Ext-0914

25. Etx0914; Azd0914; Zoliflodacin

26. Db12817

27. Ac-35757

28. Ba164192

29. Hy-17647

30. Cs-0016917

31. D11726

32. Us8889671, 5

33. Q27278240

34. (2r,4s,4as)-11-fluoro-2,4-dimethyl-8-((s)-4-methyl-2-oxooxazolidin-3-yl)-1,2,4,4a-tetrahydro-2'h,6h-spiro[isoxazolo[4,5-g][1,4]oxazino[4,3-a]quinoline-5,5'-pyrimidine]-2',4',6'(1'h,3'h)-trione

35. (2r,4s,4as)-11-fluoro-2,4-dimethyl-8-((s)-4-methyl-2-oxooxazolidin-3-yl)-2,4,4a,6-tetrahydro-1h,1'h-spiro[isoxazolo[4,5-g][1,4]oxazino[4,3-a]quinoline-5,5'-pyrimidine]-2',4',6'(3'h)-trione

36. (4'r,6's,7's)-17'-fluoro-4',6'-dimethyl-13'-[(4s)-4-methyl-2-oxo-1,3-oxazolidin-3-yl]spiro[1,3-diazinane-5,8'-5,15-dioxa-2,14-diazatetracyclo[8.7.0.02,7.012,16]heptadeca-1(17),10,12(16),13-tetraene]-2,4,6-trione

37. (7s,11r,13s)-3-((4s)-2-oxo-4-methyltetrahydrooxazole-3-yl)-9-fluoro-11,13-dimethyl-8,7-(ethanoxymethano)-7,8,1',2',3',4'-hexahydrospiro[isoxazolo[4,5-g]quinoline-6(5h),5'(6'h)-pyrimidine]-2',4',6'-trione

38. 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)-

2.4 Create Date

2014-08-04

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₂FN₅O₇
Molecular Weight	487.4 g/mol
XLogP3	1.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	10
Rotatable Bond Count	1
Exact Mass	487.15032622 g/mol
Monoisotopic Mass	487.15032622 g/mol
Topological Polar Surface Area	143 Å²
Heavy Atom Count	35
Formal Charge	0
Complexity	962
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Treatment of gonococcal infection

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Topoisomerase II Inhibitors

Compounds that inhibit the activity of DNA TOPOISOMERASE II. Included in this category are a variety of ANTINEOPLASTIC AGENTS which target the eukaryotic form of topoisomerase II and ANTIBACTERIAL AGENTS which target the prokaryotic form of topoisomerase II. (See all compounds classified as Topoisomerase II Inhibitors.)

Drugs in Development