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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 88678-31-3, Piritetrate, Liranaftate [inn], Zefnart, M-732, Piritetrate;m-732

Molecular Formula

C₁₈H₂₀N₂O₂S

Molecular Weight

328.4 g/mol

InChI Key

VPHPQNGOVQYUMG-UHFFFAOYSA-N

FDA UNII

5253IGO5X3

Liranaftate is a thiocarbamate and squalene epoxidase inhibitor with antifungal activity. Liranaftate inhibits fungal squalene epoxidase, an enzyme that plays a key role in the synthesis of sterol which is essential for cell membrane integrity. By preventing ergosterol synthesis and causing accumulation of squalene, this agent increases cell membrane permeability, cell leakage and eventually cell lysis.

1 2D Structure

Liranaftate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

O-(5,6,7,8-tetrahydronaphthalen-2-yl) N-(6-methoxypyridin-2-yl)-N-methylcarbamothioate

2.1.2 InChI

InChI=1S/C18H20N2O2S/c1-20(16-8-5-9-17(19-16)21-2)18(23)22-15-11-10-13-6-3-4-7-14(13)12-15/h5,8-12H,3-4,6-7H2,1-2H3

2.1.3 InChI Key

VPHPQNGOVQYUMG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C1=NC(=CC=C1)OC)C(=S)OC2=CC3=C(CCCC3)C=C2

2.2 Other Identifiers

2.2.1 UNII

5253IGO5X3

2.3 Synonyms

2.3.1 MeSH Synonyms

1. O-(5,6,7,8-tetrahydro-2-naphthyl)-6-methoxy-n-methylthio-2-pyridinecarbamate

2.3.2 Depositor-Supplied Synonyms

1. 88678-31-3

2. Piritetrate

3. Liranaftate [inn]

4. Zefnart

5. M-732

6. Piritetrate;m-732

7. O-(5,6,7,8-tetrahydronaphthalen-2-yl) N-(6-methoxypyridin-2-yl)-n-methylcarbamothioate

8. 5253igo5x3

9. O-(5,6,7,8,-tetrahydro-2-naphthyl) 6-methoxy-n-methylthio-2-pyridinecarbamate

10. O-(5,6,7,8-tetrahydronaphthalen-2-yl) (6-methoxypyridin-2-yl)(methyl)carbamothioate

11. Ncgc00164601-01

12. Liranaftato

13. Liranaftatum

14. Dsstox_cid_26470

15. Dsstox_rid_81642

16. Dsstox_gsid_46470

17. Liranaftatum [inn-latin]

18. Liranaftato [inn-spanish]

19. O-(5,6,7,8-tetrahydro-2-naphthyl) N-(6-methoxy-2-pyridyl)-n-methylthiocarbamate

20. Cas-88678-31-3

21. Piritetate

22. Unii-5253igo5x3

23. Zefnart (tn)

24. M-732; Piritetrate

25. Liranaftate (jan/inn)

26. Liranaftate [mi]

27. Liranaftate [jan]

28. Liranaftate [mart.]

29. Liranaftate [who-dd]

30. Mls006011138

31. Schembl180466

32. Chembl1591365

33. Dtxsid6046470

34. Chebi:31775

35. Zinc13936

36. Glxc-25562

37. Hms3714a16

38. Act06298

39. Bcp11494

40. Hy-b0348

41. O-tetralin-6-yl N-(6-methoxy-2-pyridyl)-n-methyl-carbamothioate

42. Tox21 112223

43. Tox21_112223

44. Mfcd00865576

45. S1997

46. Akos015852015

47. Tox21_112223_1

48. Ab07498

49. Ac-3400

50. Ccg-220727

51. Ncgc00164601-02

52. Ncgc00164601-03

53. As-56279

54. Carbamothioic Acid, (6-methoxy-2-pyridinyl)methyl-, O-(5,6,7,8-tetrahydro-2-naphthalenyl) Ester

55. Smr002204143

56. Ft-0630959

57. L0301

58. D01550

59. Ab01566849_01

60. 678l313

61. Sr-01000872646

62. Sr-01000872646-1

63. Q27167100

64. (6-methoxy-2-pyridinyl)-methylcarbamothioic Acid

65. O-(5,6,7,8-tetrahydronaphthalen-2-yl) (6-methoxypyridin-2-yl)methylthiocarbamate

66. O-5,6,7,8-tetrahydronaphthalen-2-yl 6-methoxypyridin-2-yl(methyl)carbamothioate

67. (6-methoxypyridin-2-yl)(methyl)carbamothioic Acid O-(5,6,7,8-tetrahydronaphthalen-2-yl) Ester

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₂₀N₂O₂S
Molecular Weight	328.4 g/mol
XLogP3	4.9
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Exact Mass	328.12454906 g/mol
Monoisotopic Mass	328.12454906 g/mol
Topological Polar Surface Area	66.7 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	407
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1