Terizidone

Synopsis, Chemistry

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Also known as: 25683-71-0, Terizidonum, Terizidone [inn], 1199lex5n8, Terizidone (inn), 4,4'-(((1e,1'e)-1,4-phenylenebis(methanylylidene))bis(azanylylidene))bis(isoxazolidin-3-one)

Molecular Formula

C₁₄H₁₄N₄O₄

Molecular Weight

302.29 g/mol

InChI Key

ODKYYBOHSVLGNU-UHFFFAOYSA-N

FDA UNII

1199LEX5N8

Terizidone is a broad spectrum antibiotic used as a second-line antitubercular drug, effective against pulmonary and extrapulmonary tuberculosis. Terizidone has activity against Mycobacterium strains that are resistant to first-line drugs.

1 2D Structure

Terizidone

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[[4-[(3-oxo-1,2-oxazolidin-4-yl)iminomethyl]phenyl]methylideneamino]-1,2-oxazolidin-3-one

2.1.2 InChI

InChI=1S/C14H14N4O4/c19-13-11(7-21-17-13)15-5-9-1-2-10(4-3-9)6-16-12-8-22-18-14(12)20/h1-6,11-12H,7-8H2,(H,17,19)(H,18,20)

2.1.3 InChI Key

ODKYYBOHSVLGNU-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1C(C(=O)NO1)N=CC2=CC=C(C=C2)C=NC3CONC3=O

2.2 Other Identifiers

2.2.1 UNII

1199LEX5N8

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 4,4'-(p-phenylenebis(methyleneimino))bis-3-isoxazolidone

2. Terazolidone

3. Terivalidin

4. Terivalidine

5. Terizidon

6. Terizidone, Calcium Salt, (r-(r*,r*))-isomer

2.3.2 Depositor-Supplied Synonyms

1. 25683-71-0

2. Terizidonum

3. Terizidone [inn]

4. 1199lex5n8

5. Terizidone (inn)

6. 4,4'-(((1e,1'e)-1,4-phenylenebis(methanylylidene))bis(azanylylidene))bis(isoxazolidin-3-one)

7. 4-[[4-[(3-oxo-1,2-oxazolidin-4-yl)iminomethyl]phenyl]methylideneamino]-1,2-oxazolidin-3-one

8. Terizidona

9. 4,4'-(p-phenylenebis(methyleneamino))di-(isoxazolidin-3-one)

10. Terizidonum [inn-latin]

11. Terizidona [inn-spanish]

12. Unii-1199lex5n8

13. Terivalidin (tn)

14. Einecs 247-186-1

15. D-terizidone

16. Terizidone [mart.]

17. Terizidone [who-dd]

18. Schembl193690

19. Fmoc-d-3-(2-furyl)-alanine

20. Chembl2107553

21. Dtxsid30865245

22. Dtxsid70905098

23. Chebi:135278

24. 4,4'-[1,4-phenylenebis(methylidynenitrilo)]bis-3-isoxazolidinone

25. Bcp15839

26. Mfcd00866818

27. Akos025311219

28. Db12954

29. As-16056

30. Hy-112324

31. Cs-0045228

32. Ft-0674867

33. C13574

34. D07247

35. A911347

36. Q1318344

37. 4,4'-[1,4-phenylenebis(methanylylideneazanylylidene)]di(1,2-oxazolidin-3-one)

38. 4,4'-((1e,1'e)-(1,4-phenylenebis(methanylylidene))bis(azanylylidene))bis(isoxazolidin-3-one)

39. 4,4'-(1e,1'e)-(1,4-phenylenebis(methan-1-yl-1-ylidene))bis(azan-1-yl-1-ylidene)diisoxazolidin-3-one

40. 6819-23-4

2.4 Create Date

2005-08-01

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₁₄N₄O₄
Molecular Weight	302.29 g/mol
XLogP3	-0.2
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	4
Exact Mass	302.10150494 g/mol
Monoisotopic Mass	302.10150494 g/mol
Topological Polar Surface Area	101 Å²
Heavy Atom Count	22
Formal Charge	0
Complexity	441
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	2
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1