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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
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 Weight 328.4 g/mol
Molecular Formula C18H20N2O2S
XLogP34.9
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count4
Exact Mass328.12454906 g/mol
Monoisotopic Mass328.12454906 g/mol
Topological Polar Surface Area66.7 Ų
Heavy Atom Count23
Formal Charge0
Complexity407
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

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