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Diloxanide Furoate

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Chemistry

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Also known as: 3736-81-0, Dichlofurazol, Furentomin, Histomibal, Diloxanid furoate, 4-(2,2-dichloro-n-methylacetamido)phenyl furan-2-carboxylate

Molecular Formula

C₁₄H₁₁Cl₂NO₄

Molecular Weight

328.1 g/mol

InChI Key

BDYYDXJSHYEDGB-UHFFFAOYSA-N

FDA UNII

YP4N72IW34

1 2D Structure

Diloxanide Furoate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[4-[(2,2-dichloroacetyl)-methylamino]phenyl] furan-2-carboxylate

2.1.2 InChI

InChI=1S/C14H11Cl2NO4/c1-17(13(18)12(15)16)9-4-6-10(7-5-9)21-14(19)11-3-2-8-20-11/h2-8,12H,1H3

2.1.3 InChI Key

BDYYDXJSHYEDGB-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN(C1=CC=C(C=C1)OC(=O)C2=CC=CO2)C(=O)C(Cl)Cl

2.2 Other Identifiers

2.2.1 UNII

YP4N72IW34

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2,2-dichloro-4'-hydroxy-n-methylacetanilide 2-furoate

2. 2-furamide

3. Diloxanide

4. Entamide Furoate

5. Furamide

2.3.2 Depositor-Supplied Synonyms

1. 3736-81-0

2. Dichlofurazol

3. Furentomin

4. Histomibal

5. Diloxanid Furoate

6. 4-(2,2-dichloro-n-methylacetamido)phenyl Furan-2-carboxylate

7. [4-[(2,2-dichloroacetyl)-methylamino]phenyl] Furan-2-carboxylate

8. Diloxanidefuroate

9. Mls000028653

10. Amebiazol

11. Diloxanide Furoate [usp]

12. Nsc-759146

13. 2-furoic Acid, Ester With 2,2-dichloro-4'-hydroxy-n-methylacetanilide

14. Smr000058857

15. Chebi:4601

16. Yp4n72iw34

17. Diclofurazol

18. Entamide Furoate

19. Ncgc00016637-07

20. Miforon

21. Cas-3736-81-0

22. Diloxanide Furoate (usp)

23. Dsstox_cid_28925

24. Dsstox_rid_83191

25. 2,2-dichloroacetamido-4-n-methylphenyl 2-furoate

26. Dsstox_gsid_48999

27. Entamide 2-furoate

28. 4-(n-methyl-2,2-dichloroacetamido)phenyl 2-furoate

29. Furamide (amebicide)

30. 2,2-dichloro-n-(4-hydroxyphenyl)-n-methylacetamide 2-furoic Acid Ester

31. 2,2-dichloro-n-[4-hydroxyphenyl]-n-methylacetamide 2-furoic Acid Ester

32. Sr-01000003134

33. Einecs 223-108-1

34. 8073 Cb

35. Unii-yp4n72iw34

36. Diloxanidi Furoas

37. Cb 8073

38. Diloxanide Furoate (tn)

39. 2-furancarboxylic Acid, 4-((dichloroacetyl)methylamino)phenyl Ester

40. Opera_id_1633

41. Prestwick0_000903

42. Prestwick1_000903

43. Prestwick2_000903

44. Prestwick3_000903

45. 4-((dichloroacetyl)methylamino)phenyl 2-furoate

46. Schembl23381

47. Bspbio_000746

48. 2,2-dichloroacetamideo-4-n-methylphenyl 2-furoate

49. 4-(2,2-dichlor-n-methylacetamido)phenyl 2-furoat

50. Cid_19529

51. Mls001148648

52. Spbio_002945

53. 4-(n-methyl-2,2-dichloroacetamideo)phenyl 2-furoate

54. Bpbio1_000822

55. Zinc1300

56. Diloxanide Furoate [mi]

57. Chembl1334860

58. Dtxsid8048999

59. Bdbm70295

60. 4-(2,2-dichlor-n-methylacetamido)phenyl 2-furancarboxylat

61. 4-(2,2-dichlor-n-methylacetamido)phenyl 2-furoat [iupac]

62. Hms1570f08

63. Hms2093n21

64. Hms2097f08

65. Hms2234p06

66. Hms3371i07

67. Hms3714f08

68. Pharmakon1600-01505532

69. Diloxanide Furoate [mart.]

70. Diloxanide Furoate [usp-rs]

71. Diloxanide Furoate [who-dd]

72. Diloxanide Furoate [who-ip]

73. Hy-b1147

74. Tox21_113492

75. 4-(2,2-dichlor-n-methylacetamido)phenyl 2-furancarboxylat [iupac]

76. Nsc759146

77. Akos016014036

78. Tox21_113492_1

79. Ccg-213477

80. Cs-4751

81. Db14638

82. Nsc 759146

83. Diloxanidi Furoas [who-ip Latin]

84. Ncgc00016637-01

85. Ncgc00016637-02

86. Ncgc00016637-03

87. Ncgc00016637-04

88. Ncgc00016637-05

89. Ncgc00016637-06

90. Ncgc00016637-10

91. Ncgc00023178-03

92. Ncgc00023178-04

93. Ncgc00023178-05

94. Diloxanide Furoate [usp Monograph]

95. Sbi-0206798.p001

96. Ab00383052

97. Ft-0752403

98. C07637

99. D02480

100. Ab00383052_13

101. Diloxanide Furoate 100 Microg/ml In Acetonitrile

102. Q799564

103. Q-200989

104. Sr-01000003134-2

105. Sr-01000003134-4

106. Brd-k10974103-001-03-9

107. Brd-k10974103-001-14-6

108. [4-[(2,2-dichloroacetyl)-methyl-amino]phenyl] Furan-2-carboxylate

109. [4-[2,2-bis(chloranyl)ethanoyl-methyl-amino]phenyl] Furan-2-carboxylate

110. 2-furancarboxylic Acid, 4-[(2,2-dichloroacetyl)methylamino]phenyl Ester

111. Diloxanide Furoate, United States Pharmacopeia (usp) Reference Standard

112. 2-furancarboxylic Acid [4-[(2,2-dichloro-1-oxoethyl)-methylamino]phenyl] Ester

113. Furan-2-carboxylic Acid [4-[(2,2-dichloroacetyl)-methyl-amino]phenyl] Ester

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₄H₁₁Cl₂NO₄
Molecular Weight	328.1 g/mol
XLogP3	3.4
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	5
Exact Mass	327.0065132 g/mol
Monoisotopic Mass	327.0065132 g/mol
Topological Polar Surface Area	59.8 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	383
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

Diloxanide is used alone as a primary agent in the treatment of asymptomatic (cyst passers) intestinal amebiasis caused by Entamoeba histolytica. Diloxanide may also be used concurrently, or sequentially, with other agents such as the nitroimidazoles (eg. metronidazole) in the treatment of invasive or extraintestinal forms of amebiasis.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Diloxanide is a luminal amebicide, however the mechanism of action of diloxanide is unknown. Diloxanide destroys the trophozoites of E. histolytica that eventually form into cysts. The cysts are then excreted by persons infected with asymptomatic amebiasis. Diloxanide furoate is a prodrug, and is hydrolyzed in the gastrointestinal tract to produce diloxanide, the active ingredient.

5.2 MeSH Pharmacological Classification

Amebicides

Agents which are destructive to amebae, especially the parasitic species causing AMEBIASIS in man and animal. (See all compounds classified as Amebicides.)

5.3 Absorption, Distribution and Excretion

Absorption

Bioavailability is 90% (in diloxanide parental form), however diloxanide furoate is slowly absorbed from the gastrointestinal tract.

Route of Elimination

Renal (90%, rapidly excreted as glucuronide metabolite). 10% is excreted in the feces as diloxanide.

5.4 Metabolism/Metabolites

Hydrolyzed to furoic acid and diloxanide, which undergoes extensive glucuronidation (99% of diloxanide occurs as glucuronide and 1% as free diloxanide in the systemic circulation).

5.5 Biological Half-Life

3 hours

5.6 Mechanism of Action

Unknown. Diloxanide may inhibit protein synthesis.

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API Reference Price

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