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Lonidamine

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Chemistry

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Also known as: 50264-69-2, 1-(2,4-dichlorobenzyl)-1h-indazole-3-carboxylic acid, Diclondazolic acid, Doridamina, Lonidamina, Lonidaminum

Molecular Formula

C₁₅H₁₀Cl₂N₂O₂

Molecular Weight

321.2 g/mol

InChI Key

WDRYRZXSPDWGEB-UHFFFAOYSA-N

FDA UNII

U78804BIDR

Lonidamine is an indazole carboxylic acid derivative that exhibits radiosensitizing and antiparasitic effects and interferes with the multidrug resistance mechanism.

1 2D Structure

Lonidamine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(2,4-dichlorophenyl)methyl]indazole-3-carboxylic acid

2.1.2 InChI

InChI=1S/C15H10Cl2N2O2/c16-10-6-5-9(12(17)7-10)8-19-13-4-2-1-3-11(13)14(18-19)15(20)21/h1-7H,8H2,(H,20,21)

2.1.3 InChI Key

WDRYRZXSPDWGEB-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C2C(=C1)C(=NN2CC3=C(C=C(C=C3)Cl)Cl)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

U78804BIDR

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 1-(2,4-dichlorobenzyl)indazole-3-carboxylic Acid

2. Af 1890

3. Diclondazolic Acid

2.3.2 Depositor-Supplied Synonyms

1. 50264-69-2

2. 1-(2,4-dichlorobenzyl)-1h-indazole-3-carboxylic Acid

3. Diclondazolic Acid

4. Doridamina

5. Lonidamina

6. Lonidaminum

7. Lonidamin

8. 1-[(2,4-dichlorophenyl)methyl]-1h-indazole-3-carboxylic Acid

9. Af 1890

10. 1-(2,4-dichlorbenzyl)-indazole-3-carboxylic Acid

11. Lonidamine (inn)

12. 1-[(2,4-dichlorophenyl)methyl]indazole-3-carboxylic Acid

13. 1-(2,4-dichlorobenzyl)indazole-3-carboxylic Acid

14. Nsc-741419

15. Nsc-758419

16. Af-1890

17. Mls000028822

18. U78804bidr

19. Chebi:50138

20. 1h-indazole-3-carboxylic Acid, 1-((2,4-dichlorophenyl)methyl)-

21. 1h-indazole-3-carboxylic Acid, 1-[(2,4-dichlorophenyl)methyl]-

22. Af-1890;diclondazolic Acid;dica

23. Ncgc00015609-03

24. Smr000058467

25. Lonidamine [inn]

26. Dsstox_cid_782

27. Dsstox_rid_75787

28. Dsstox_gsid_20782

29. Lonidaminum [inn-latin]

30. Lonidamina [inn-spanish]

31. Doridamina (tn)

32. Dichlondazolic Acid

33. Cas-50264-69-2

34. Ccris 3516

35. Lonidamine [inn:ban]

36. Sr-01000075961

37. Einecs 256-510-0

38. Brn 0894483

39. Unii-u78804bidr

40. Kn-228

41. Mfcd00866285

42. Th-070

43. Tocris-1646

44. Lonidamine [mi]

45. Lopac-l-4900

46. L 4900

47. Lonidamine [mart.]

48. Schembl7134

49. Lonidamine [who-dd]

50. Lopac0_000718

51. Cid_39562

52. Zinc1632

53. Chembl1257030

54. Dtxsid5020782

55. Bdbm59775

56. 1h-indazole-3-carboxylic Acid, 1-(2,4-dichlorobenzyl)-

57. Hms2234h24

58. Hms3262o17

59. Hms3268k09

60. Hms3369i01

61. Hms3412p05

62. Hms3651f09

63. Hms3676p05

64. Hms3874d03

65. Pharmakon1600-01503225

66. 1h-indazole-3-carboxylicacid, 1-[(2,4-dichlorophenyl)methyl]-

67. Act02617

68. Bcp06555

69. Hy-b0486

70. Tox21_110181

71. Tox21_202306

72. Tox21_500718

73. Af1890

74. Nsc741419

75. Nsc758419

76. S2610

77. Akos012842739

78. Tox21_110181_1

79. Ac-5626

80. Ccg-204803

81. Db06266

82. Lp00718

83. Nsc 741419

84. Nsc 758419

85. Sdccgsbi-0050696.p003

86. Ncgc00015609-01

87. Ncgc00015609-02

88. Ncgc00015609-04

89. Ncgc00015609-05

90. Ncgc00015609-06

91. Ncgc00015609-07

92. Ncgc00015609-08

93. Ncgc00015609-09

94. Ncgc00015609-16

95. Ncgc00025244-01

96. Ncgc00025244-02

97. Ncgc00025244-03

98. Ncgc00259855-01

99. Ncgc00261403-01

100. As-11653

101. Sbi-0050696.p002

102. Am20060642

103. Eu-0100718

104. Ft-0650359

105. L0283

106. Sw219810-1

107. Lonidamine, Mitochondrial Hexokinase Inhibitor

108. D07257

109. Ab00597141_08

110. Ab00597141_10

111. 264l692

112. A929099

113. Q-201318

114. Q3836670

115. Sr-01000075961-1

116. Sr-01000075961-3

117. Sr-01000075961-6

118. Brd-k78513633-001-03-3

119. Brd-k78513633-001-06-6

120. Z1741977188

121. 1-[(2,4-dichlorophenyl)methyl]-3-indazolecarboxylic Acid

122. 1-[(2,4-dichlorophenyl)methyl]-1h-indazole-3-carboxylicacid

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₀Cl₂N₂O₂
Molecular Weight	321.2 g/mol
XLogP3	4.3
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	3
Exact Mass	320.0119330 g/mol
Monoisotopic Mass	320.0119330 g/mol
Topological Polar Surface Area	55.1 Å²
Heavy Atom Count	21
Formal Charge	0
Complexity	396
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

Investigated for use/treatment in benign prostatic hyperplasia, prostate disorders, and cancer/tumors (unspecified).

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)

Radiation-Sensitizing Agents

Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells. (See all compounds classified as Radiation-Sensitizing Agents.)

Antispermatogenic Agents

Agents, either mechanical or chemical, which destroy spermatozoa in the male genitalia and block spermatogenesis. (See all compounds classified as Antispermatogenic Agents.)

Trypanocidal Agents

Agents destructive to the protozoal organisms belonging to the suborder TRYPANOSOMATINA. (See all compounds classified as Trypanocidal Agents.)

5.2 ATC Code

L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01X - Other antineoplastic agents

L01XX - Other antineoplastic agents

L01XX07 - Lonidamine

5.3 Metabolism/Metabolites

Lonidamine has known human metabolites that include (2S,3S,4S,5R)-6-[1-[(2,4-Dichlorophenyl)methyl]indazole-3-carbonyl]oxy-3,4,5-trihydroxyoxane-2-carboxylic acid.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

5.4 Mechanism of Action

Lonidamine is an orally administered small molecule that inhibits glycolysis by the inactivation of hexokinase. Hexokinase is an enzyme that catalyzes glucose, the first step in glycolysis. The inhibition of hexokinase by lonidamine is well established. In addition, there is evidence that lonidamine may increase programmed cell death. This stems from the observation that mitochondria and mitochondria-bound hexokinase are crucial for induction of apoptosis; agents that directly effect mitochondria may, therefore, trigger apoptosis. Indeed, in vitro models with lonidamine exhibit the hallmarks of apoptosis, including mitochondrial membrane depolarization, release of cytochrome C, phosphatidylserine externalization, and DNA fragmentation. [PMID: 16986057]

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