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Haloprogin

Haloprogin

Synopsis, Chemistry

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Also known as: 777-11-7, Halotex, Mycanden, Mycilan, Polik, M-1028 (meiji)

Molecular Formula

C₉H₄Cl₃IO

Molecular Weight

361.4 g/mol

InChI Key

CTETYYAZBPJBHE-UHFFFAOYSA-N

FDA UNII

AIU7053OWL

Haloprogin is an antifungal agent used as a topical cream. It was discontinued in favor of newer antifungals with fewer side effects.

1 2D Structure

Haloprogin

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1,2,4-trichloro-5-(3-iodoprop-2-ynoxy)benzene

2.1.2 InChI

InChI=1S/C9H4Cl3IO/c10-6-4-8(12)9(5-7(6)11)14-3-1-2-13/h4-5H,3H2

2.1.3 InChI Key

CTETYYAZBPJBHE-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=C(C(=CC(=C1Cl)Cl)Cl)OCC#CI

2.2 Other Identifiers

2.2.1 UNII

AIU7053OWL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-iodo-2-propynyl 2,4,5-trichlorophenyl Ether

2. Halotex

3. Mycilan

2.3.2 Depositor-Supplied Synonyms

1. 777-11-7

2. Halotex

3. Mycanden

4. Mycilan

5. Polik

6. M-1028 (meiji)

7. 1,2,4-trichloro-5-(3-iodoprop-2-ynoxy)benzene

8. M 1028

9. 3-iodo-2-propynyl 2,4,5-trichlorophenyl Ether

10. 2,4,5-trichlorophenyl Iodopropargyl Ether

11. Nsc-100071

12. Ether, 3-iodo-2-propynyl 2,4,5-trichlorophenyl

13. Haloprogina

14. Haloprogine

15. Aiu7053owl

16. Chembl1289

17. Benzene, 1,2,4-trichloro-5-((3-iodo-2-propynyl)oxy)-

18. Haloprogin (200 Mg)

19. Haloproginum

20. M-1028

21. Nsc100071

22. Haloprogine [inn-french]

23. Haloproginum [inn-latin]

24. Ncgc00181134-01

25. Haloprogina [inn-spanish]

26. 1,2,4-trichloro-5-((3-iodoprop-2-yn-1-yl)oxy)benzene

27. 1,2,4-trichloro-5-[(3-iodoprop-2-yn-1-yl)oxy]benzene

28. Benzene, 1,2,4-trichloro-5-[(3-iodo-2-propynyl)oxy]-

29. Halotex (tn)

30. Component Of Halotex

31. Einecs 212-286-6

32. 2,4,5-trichlorophenyl Gamma-iodopropargil Ether

33. 2,4,5-trichlorophenyl-gamma-iodopropargyl Ether

34. Unii-aiu7053owl

35. Nsc 100071

36. (3-iod-2-propinyl)-(2,4,5-trichlorphenyl)ether

37. Brn 1976771

38. Haloprogen

39. Haloprogin (jan/usan/inn)

40. Haloprogin [usan:usp:inn:jan]

41. Prestwick_232

42. Halotex (salt/mix)

43. Spectrum_001852

44. Haloprogin [mi]

45. Haloprogin [inn]

46. Haloprogin [jan]

47. Haloprogin [usan]

48. Haloprogin [vandf]

49. Ether,4,5-trichlorophenyl

50. Haloprogin [mart.]

51. Schembl3649

52. Haloprogin(200mg)

53. Dsstox_cid_26865

54. Dsstox_rid_81972

55. Haloprogin [who-dd]

56. Dsstox_gsid_46865

57. Kbioss_002369

58. 2,4,5-trichlorophenyl .gamma.-iodopropargyl Ether

59. Divk1c_000762

60. 1,2,4-trichloro-5-[(3-iodo-2-propynyl) Oxy]benzene

61. Chebi:5614

62. Benzene,1,2,4-trichloro-5-[(3-iodo-2-propynyl)oxy]

63. Dtxsid9046865

64. Haloprogin [orange Book]

65. Hms502g04

66. Kbio1_000762

67. Kbio2_002365

68. Kbio2_004933

69. Kbio2_007501

70. Wln: I1uu2or Bg Dg Eg

71. Ninds_000762

72. Hms3713a06

73. Bcp20218

74. Zinc1530649

75. Tox21_112741

76. Bdbm50194601

77. Ccg-220402

78. Db00793

79. 2,5-trichlorophenyl Iodopropargyl Ether

80. Idi1_000762

81. Ncgc00181134-02

82. Ncgc00181134-04

83. Cas-777-11-7

84. Hy-16246

85. Cs-0006262

86. 3-iodo-2-propynyl 2,5-trichlorophenyl Ether

87. D00339

88. 2,5-trichlorophenyl .gamma.-iodopropargil Ether

89. 2,5-trichlorophenyl .gamma.-iodopropargyl Ether

90. 777h117

91. 1,2,4-trichloro-5-(3-iodoprop-2-ynyloxy)benzene

92. Q5643439

93. 1,2,4-trichloro-5-(3-iodo-prop-2-ynyloxy)-benzene

94. Benzene,2,4-trichloro-5-[(3-iodo-2-propynyl)oxy]-

95. Brd-k13238168-001-01-2

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₉H₄Cl₃IO
Molecular Weight	361.4 g/mol
XLogP3	4.6
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	2
Exact Mass	359.83725 g/mol
Monoisotopic Mass	359.83725 g/mol
Topological Polar Surface Area	9.2 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	247
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

4 Drug and Medication Information

4.1 Drug Indication

Used to treat fungal (Tinea) skin infections such as athlete's foot, jock itch, ringworm, and tinea versicolor.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Used as a topical ointment or cream in the treatment of Tinea infections. Tinea infections are superficial fungal infections caused by three species of fungi collectively known as dermatophytes (Trichophyton, Microsporum and Epidermophyton). Commonly these infections are named for the body part affected, including tinea corporis (general skin), tinea cruris (groin), and tinea pedis (feet).

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 ATC Code

D - Dermatologicals

D01 - Antifungals for dermatological use

D01A - Antifungals for topical use

D01AE - Other antifungals for topical use

D01AE11 - Haloprogin

5.4 Mechanism of Action

Haloprogin is a halogenated phenolic ether administered topically for dermotaphytic infections. The mechanism of action is unknown, but is thought to be via inhibition of oxygen uptake and disruption of yeast membrane structure and function. There is a higher incidence of cutaneous side effects with haloprogin, including irritation, burning, vesiculation (blisters), scaling, and itching. It is generally used when the infection is unresponsive to other antifungals.