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Prestwick3_000127

Prestwick3_000127

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Also known as: 27523-40-6, Travogen, 1-[2-(2,4-dichlorophenyl)-2-[(2,6-dichlorophenyl)methoxy]ethyl]imidazole, Gri7wfr424, Isoconazol, Chebi:83667

Molecular Formula

C₁₈H₁₄Cl₄N₂O

Molecular Weight

416.1 g/mol

InChI Key

MPIPASJGOJYODL-UHFFFAOYSA-N

FDA UNII

GRI7WFR424

Isoconazole is an azole antifungal drug that has similar effectiveness to clotrimazole in the treatment of foot and vaginal infections.

1 2D Structure

Prestwick3_000127

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[2-(2,4-dichlorophenyl)-2-[(2,6-dichlorophenyl)methoxy]ethyl]imidazole

2.1.2 InChI

InChI=1S/C18H14Cl4N2O/c19-12-4-5-13(17(22)8-12)18(9-24-7-6-23-11-24)25-10-14-15(20)2-1-3-16(14)21/h1-8,11,18H,9-10H2

2.1.3 InChI Key

MPIPASJGOJYODL-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=C(C(=C1)Cl)COC(CN2C=CN=C2)C3=C(C=C(C=C3)Cl)Cl)Cl

2.2 Other Identifiers

2.2.1 UNII

GRI7WFR424

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(2,4-dichloro Beta-(2,6-dichlorobenzyloxy)phenethyl) Imidazole

2. Fazol

3. Gyno Icaden

4. Gyno-travogen

5. Icaden

6. Isoconazole Nitrate

7. R15454

8. Travogyn

2.3.2 Depositor-Supplied Synonyms

1. 27523-40-6

2. Travogen

3. 1-[2-(2,4-dichlorophenyl)-2-[(2,6-dichlorophenyl)methoxy]ethyl]imidazole

4. Gri7wfr424

5. Isoconazol

6. Chebi:83667

7. R-15,454 [as Nitrate Salt]

8. Isoconazolum

9. 1h-imidazole, 1-(2-(2,4-dichlorophenyl)-2-((2,6-dichlorophenyl)methoxy)ethyl)-

10. Dsstox_cid_25447

11. Dsstox_rid_80886

12. Dsstox_gsid_45447

13. Isoconazol [inn-spanish]

14. Isoconazolum [inn-latin]

15. 1h-imidazole, 1-[2-(2,4-dichlorophenyl)-2-[(2,6-dichlorophenyl)methoxy]ethyl]-

16. Einecs 248-508-3

17. Unii-gri7wfr424

18. Isoconazole [usan:inn:ban]

19. R-15,454

20. 1-{2-[(2,6-dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl}-1h-imidazole

21. 1-(2-((2,6-dichlorobenzyl)oxy)-2-(2,4-dichlorophenyl)ethyl)-1h-imidazole

22. Ncgc00016800-01

23. Prestwick_532

24. Cas-27523-40-6

25. Miconazole Impurity D

26. Isoconazole [mi]

27. 1-(2,4-dichloro-beta-((2,6-dichlorobenzyl)oxy)phenethyl)imidazole

28. Prestwick0_000127

29. Prestwick1_000127

30. Prestwick2_000127

31. Prestwick3_000127

32. Isoconazole (usan/inn)

33. Isoconazole [usan]

34. 1-(2-(2,4-dichlorophenyl)-2-((2,6-dichlorophenyl)methoxy)ethyl)1h-imidazole

35. Cid_3760

36. Isoconazole [mart.]

37. Bspbio_000174

38. Isoconazole [who-dd]

39. Mls002154207

40. Schembl148288

41. R15454 Free Base

42. Spbio_002113

43. Miconazole 2,6-isomer

44. Bpbio1_000192

45. Chembl1571863

46. Dtxsid7045447

47. R-15454 Free Base

48. Bdbm31771

49. Isoconazole [ep Impurity]

50. Hms1568i16

51. Hms2095i16

52. Hms2231p05

53. Hms3374m05

54. Hms3712i16

55. Isoconazole [ep Monograph]

56. Amy32539

57. Tox21_110616

58. Imidazole, 1-(2,4-dichloro-beta-((2,6-dichlorobenzyl)oxy)phenethyl)-

59. Akos015896434

60. Tox21_110616_1

61. Ccg-220127

62. Db08943

63. 1-(2-(2,4-dichlorophenyl)-2-((2,6-dichlorophenyl)methoxy)ethyl)-1h-imidazole

64. Ncgc00179642-01

65. Ncgc00179642-02

66. Ncgc00179642-03

67. Ncgc00179642-04

68. Ncgc00179642-05

69. Smr001233493

70. Miconazole Impurity D [ep Impurity]

71. Ft-0657773

72. D04624

73. A819101

74. Q262210

75. Sr-01000838847

76. Miconazole Nitrate Impurity D [ep Impurity]

77. Sr-01000838847-2

78. Brd-a93353767-001-03-5

79. 1-(2-(2,6-dichlorobenzyloxy)-2-(2,4-dichlorophenyl)ethyl)-1h-imidazole

80. 1-[2,4-dichloro-.beta.-[2,6-dichlorobenzyl)oxy]phenylethyl]imidazole

81. 1-{2-[(2,6-dichlorobenzyl)oxy]-2-(2,4-dichlorophenyl)ethyl}imidazole

82. 1-(2,4-dichloro-.beta.-((2,6-dichlorobenzyl)oxy)phenethyl)imidazole

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₄Cl₄N₂O
Molecular Weight	416.1 g/mol
XLogP3	5.3
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	6
Exact Mass	415.983074 g/mol
Monoisotopic Mass	413.986024 g/mol
Topological Polar Surface Area	27 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	407
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 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.)

4.2 ATC Code

D01AC05

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

D - Dermatologicals

D01 - Antifungals for dermatological use

D01A - Antifungals for topical use

D01AC - Imidazole and triazole derivatives

D01AC05 - Isoconazole

G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AF - Imidazole derivatives

G01AF07 - Isoconazole