Please Wait
Applying Filters...
Menu
$ API Ref.Price (USD/KG) : 435Xls
2D Structure
Also known as: 187164-19-8, Lulicon, Nnd-502, Luzu, Pr-2699, (2e)-2-[(4r)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile
Molecular Formula
C14H9Cl2N3S2
Molecular Weight
354.3  g/mol
InChI Key
YTAOBBFIOAEMLL-REQDGWNSSA-N
FDA UNII
RE91AN4S8G

Luliconazole is a topical antifungal agent that acts by unknown mechanisms but is postulated to involve altering the synthesis of fungi cell membranes. It was approved by the FDA (USA) in November 2013 and is marketed under the brand name Luzu. Luliconazole is also approved in Japan.
Luliconazole is an Azole Antifungal. The mechanism of action of luliconazole is as a Cytochrome P450 2C19 Inhibitor.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2E)-2-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile
2.1.2 InChI
InChI=1S/C14H9Cl2N3S2/c15-9-1-2-10(11(16)5-9)13-7-20-14(21-13)12(6-17)19-4-3-18-8-19/h1-5,8,13H,7H2/b14-12+/t13-/m0/s1
2.1.3 InChI Key
YTAOBBFIOAEMLL-REQDGWNSSA-N
2.1.4 Canonical SMILES
C1C(SC(=C(C#N)N2C=CN=C2)S1)C3=C(C=C(C=C3)Cl)Cl
2.1.5 Isomeric SMILES
C1[C@H](S/C(=C(\C#N)/N2C=CN=C2)/S1)C3=C(C=C(C=C3)Cl)Cl
2.2 Other Identifiers
2.2.1 UNII
RE91AN4S8G
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (2e)-((4r)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene)(1h-imidazol-1-yl)acetonitrile

2. 4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile

3. Lulicon

4. Nnd 502

5. Nnd-502

6. Nnd502

2.3.2 Depositor-Supplied Synonyms

1. 187164-19-8

2. Lulicon

3. Nnd-502

4. Luzu

5. Pr-2699

6. (2e)-2-[(4r)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile

7. Nnd 502

8. Re91an4s8g

9. Ncgc00182704-01

10. Ncgc00182704-02

11. Chebi:34825

12. (2e)-2-[(4r)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-yl-acetonitrile

13. (r,e)-2-(4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene)-2-(1h-imidazol-1-yl)acetonitrile

14. Ncgc00182704-03

15. 2-[(2e,4r)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1h-imidazol-1-yl)acetonitrile

16. Dsstox_cid_28533

17. Dsstox_rid_82805

18. Dsstox_gsid_48607

19. (-)-(e)-((4r)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene)(1h-imidazol-1-yl)acetonitrile

20. Luliconazole [inn]

21. Nnd502

22. Cas-187164-19-8

23. Luliconazole [usan:inn]

24. Unii-re91an4s8g

25. 4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene-1-imidazolylacetonitrile

26. Lulicon (tn)

27. Imidazole Antimycotic

28. Luzu (tn)

29. Luliconazole [mi]

30. Luliconazole [jan]

31. Luliconazole [usan]

32. Luliconazole [vandf]

33. Luliconazole [mart.]

34. Luliconazole [who-dd]

35. Schembl342362

36. Gtpl7366

37. Luliconazole (jan/usan/inn)

38. Chembl2105689

39. Dtxsid3048607

40. Luliconazole, >=98% (hplc)

41. Luliconazole [orange Book]

42. Zinc3929486

43. Tox21_112942

44. Tox21_112974

45. Mfcd00953915

46. S4258

47. Akos015897320

48. Tox21_112974_1

49. Am84645

50. Bcp9000863

51. Ccg-268075

52. Cs-0587

53. Db08933

54. Ds-3278

55. (2e)-((4r)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene)(1h-imidazol-1-yl)acetonitrile

56. Ncgc00182704-08

57. Hy-14283

58. L0306

59. Sw219226-1

60. D01980

61. 164l198

62. A813122

63. Sr-01000945039

64. Sr-01000945039-1

65. Q15624030

66. 1h-imidazole-1-acetonitrile, Alpha-((4r)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene)-, (alphae)-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 354.3 g/mol
Molecular Formula C14H9Cl2N3S2
XLogP34
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass352.9614950 g/mol
Monoisotopic Mass352.9614950 g/mol
Topological Polar Surface Area92.2 Ų
Heavy Atom Count21
Formal Charge0
Complexity476
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameLuzu
PubMed HealthLuliconazole (On the skin)
Drug ClassesAntifungal
Drug LabelLUZU (luliconazole) Cream, 1% contains 1% luliconazole, an azole antifungal agent, in a white cream for topical application.Luliconazole is (2E)-2-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile. Its structural formu...
Active IngredientLuliconazole
Dosage FormCream
RouteTopical
Strength1%
Market StatusPrescription
CompanyMedicis

2 of 2  
Drug NameLuzu
PubMed HealthLuliconazole (On the skin)
Drug ClassesAntifungal
Drug LabelLUZU (luliconazole) Cream, 1% contains 1% luliconazole, an azole antifungal agent, in a white cream for topical application.Luliconazole is (2E)-2-[(4R)-4-(2,4-dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-imidazol-1-ylacetonitrile. Its structural formu...
Active IngredientLuliconazole
Dosage FormCream
RouteTopical
Strength1%
Market StatusPrescription
CompanyMedicis

4.2 Drug Indication

Luliconazole is indicated in adults aged 18 years and older for the topical treatment of fungal infections caused by Trichophyton rubrum and Epidermophyton floccosum, specifically tinea pedis, cruris, and corporis.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Luliconazole kills the organisms Trichophyton rubrum and Epidermophyton floccosum, most likely by altering their fungal cell membranes.


5.2 MeSH Pharmacological Classification

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
LULICONAZOLE
5.3.2 FDA UNII
RE91AN4S8G
5.3.3 Pharmacological Classes
Azoles [CS]; Cytochrome P450 2C19 Inhibitors [MoA]; Azole Antifungal [EPC]
5.4 ATC Code

D - Dermatologicals

D01 - Antifungals for dermatological use

D01A - Antifungals for topical use

D01AC - Imidazole and triazole derivatives

D01AC18 - Luliconazole


5.5 Absorption, Distribution and Excretion

Absorption

Although luliconazole is administered topically, clinical studies have shown that after the first dose in patients with tina pedis, a maximum plasma concentration of 0.40 0.76 ng/mL (mean SD) occurred in 16.9 9.39 hours (mean SD).


Route of Elimination

The route of elimination of luliconazole has yet to be determined.


Volume of Distribution

The volume of distribution was not quantified.


Clearance

The clearance of luliconazole has yet to be determined.


5.6 Metabolism/Metabolites

The metabolism of luliconazole has yet to be determined.


5.7 Biological Half-Life

The half life of luliconazole has yet to be determined.


5.8 Mechanism of Action

The exact mechanism of action for luliconazole's anti-fungal activity is still not known, but luliconazole is thought to inhibit the enzyme lanosterol demethylase. Lanosterol demethylase is needed for the synthesis of ergosterol, which is a major component of the fungus cell membranes.