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Levamisole

Synopsis, Chemistry

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Also known as: 14769-73-4, Levamisol, L-tetramisole, Ketrax, Wormicid, Lepuron

Molecular Formula

C₁₁H₁₂N₂S

Molecular Weight

204.29 g/mol

InChI Key

HLFSDGLLUJUHTE-SNVBAGLBSA-N

FDA UNII

2880D3468G

An antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. (From Smith and Reynard, Textbook of Pharmacology, 1991, p435-6)

1 2D Structure

Levamisole

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole

2.1.2 InChI

InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1

2.1.3 InChI Key

HLFSDGLLUJUHTE-SNVBAGLBSA-N

2.1.4 Canonical SMILES

C1CSC2=NC(CN21)C3=CC=CC=C3

2.1.5 Isomeric SMILES

C1CSC2=N[C@H](CN21)C3=CC=CC=C3

2.2 Other Identifiers

2.2.1 UNII

2880D3468G

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Decaris

2. Dekaris

3. Hydrochloride, Levamisole

4. L-tetramisole

5. Levamisole Hydrochloride

6. Levotetramisole

7. Solaskil

2.3.2 Depositor-Supplied Synonyms

1. 14769-73-4

2. Levamisol

3. L-tetramisole

4. Ketrax

5. Wormicid

6. Lepuron

7. Levomysol

8. Levamisolum

9. (s)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole

10. Levamisol [inn-spanish]

11. Levamisolum [inn-latin]

12. (-)-tetramisole

13. (6s)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole

14. (s)-(-)-levamisole

15. Tcmdc-125847

16. Vermisol 150

17. Dl-tetramisole

18. L-tetramisol

19. Levamisole (inn)

20. Tetramisole, (s)-

21. (6s)-6-phenyl-2h,3h,5h,6h-imidazo[2,1-b][1,3]thiazole

22. Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, (s)-

23. Chembl1454

24. Chebi:6432

25. (6s)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole

26. 14769-73-4 (free Base)

27. Levamisole [inn]

28. Imidazo[2,1-b]thiazole, 2,3,5,6-tetrahydro-6-phenyl-, (6s)-

29. 2880d3468g

30. Levamisole [inn:ban]

31. Levovermax

32. Totalon

33. 49548-36-9

34. L-2,3,5,6-tetrahyro-6-phenylimidazo(2,1-b)thiazole

35. Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, (6s)-

36. (-)-tetramisole Hydrochloride

37. L(-)-levamisole

38. Ketrax (tn)

39. Nsc177023

40. Einecs 238-836-5

41. Mfcd00792481

42. Unii-2880d3468g

43. Levamisol 100 Microg/ml In Acetonitrile

44. (-)-levamisole

45. Spectrum_001609

46. Levamisole [mi]

47. (s)-(-)-tetramisole

48. Prestwick0_000182

49. Prestwick1_000182

50. Prestwick2_000182

51. Spectrum2_000865

52. Spectrum3_000962

53. Spectrum4_001078

54. Spectrum5_001645

55. Levamisole [vandf]

56. P00039

57. Levamisole [mart.]

58. (-)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole

59. (s)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole

60. Levamisole [who-dd]

61. Lopac0_000690

62. Schembl19227

63. Bspbio_002563

64. Kbiogr_001436

65. Kbioss_002089

66. Cid_68628

67. Bidd:gt0372

68. Divk1c_000667

69. Spbio_000909

70. Spbio_002024

71. Gtpl7210

72. Levamisole [green Book]

73. Dtxsid4023206

74. Kbio1_000667

75. Kbio2_002089

76. Kbio2_004657

77. Kbio2_007225

78. Kbio3_001783

79. Ninds_000667

80. Hms2090o04

81. Zinc119839

82. Hy-a0106

83. Bdbm50241179

84. Dl-429

85. Levamisol 100 Microg/ml In Methanol

86. Akos001637203

87. Ccg-204775

88. Cs-w009271

89. Db00848

90. Ds-4066

91. Sdccgsbi-0050668.p004

92. Idi1_000667

93. Ncgc00162225-02

94. Ncgc00162225-03

95. Ncgc00162225-04

96. Ncgc00162225-05

97. Ncgc00162225-08

98. Ncgc00162225-14

99. Ac-18929

100. Nci60_001476

101. Sbi-0050668.p003

102. C07070

103. C72809

104. D08114

105. Ab00053661-07

106. Ab00053661-08

107. Ab00053661_09

108. Ab00053661_10

109. A808675

110. Q417097

111. Brd-k73107279-003-03-4

112. 2,3,5,6-tetrahydro-6-phenyl-imidazo[2,1-b]thiazole, (s)-

113. (-)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole

114. 6-phenyl-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazole (levamisole)

115. 6-phenyl-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazole(levamisole)

116. 6-phenyl-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazole(tetramisole)

117. Levamisole;6-phenyl-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazole

118. Tetramisole;6-phenyl-2,3,5,6-tetrahydro-imidazo[2,1-b]thiazole

119. (-)-levamisole Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₂N₂S
Molecular Weight	204.29 g/mol
XLogP3	1.8
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Exact Mass	204.07211956 g/mol
Monoisotopic Mass	204.07211956 g/mol
Topological Polar Surface Area	40.9 Å²
Heavy Atom Count	14
Formal Charge	0
Complexity	246
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
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

For adjuvant treatment in combination with fluorouracil after surgical resection in patients with Dukes' stage C colon cancer. Also used to treat malignant melanoma and head/neck cancer.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Levamisole is a synthetic imidazothiazole derivative that has been widely used in treatment of worm infestations in both humans and animals. As an anthelmintic, it probably works by targeting the nematode nicotinergic acetylcholine receptor. As an immunomodulator, it appears that Levamisole is an immunostimulant which has been shown to increase NK cells and activated T-cells in patients receiving this adjuvantly along with 5FU for Stage III colon cancer.

5.2 MeSH Pharmacological Classification

Adjuvants, Immunologic

Substances that augment, stimulate, activate, potentiate, or modulate the immune response at either the cellular or humoral level. The classical agents (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contain bacterial antigens. Some are endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Their mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy of many biological response modifiers is related to their antigen-specific immunoadjuvanticity. (See all compounds classified as Adjuvants, Immunologic.)

Antirheumatic Agents

Drugs that are used to treat RHEUMATOID ARTHRITIS. (See all compounds classified as Antirheumatic Agents.)

Antinematodal Agents

Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. (See all compounds classified as Antinematodal Agents.)

5.3 ATC Code

P - Antiparasitic products, insecticides and repellents

P02 - Anthelmintics

P02C - Antinematodal agents

P02CE - Imidazothiazole derivatives

P02CE01 - Levamisole

5.4 Absorption, Distribution and Excretion

Absorption

Levamisole is rapidly absorbed (2 hours) from the gastrointestinal tract.

5.5 Metabolism/Metabolites

Primarily hepatic (extensive) with both active and inactive metabolites.

5.6 Biological Half-Life

4.4-5.6 hours (biphasic)

5.7 Mechanism of Action

The mechanism of action of levamisole as an antiparasitic agent appears to be tied to its agnositic activity towards the L-subtype nicotinic acetylcholine receptors in nematode muscles. This agonistic action reduces the capacity of the males to control their reproductive muscles and limits their ability to copulate. The mechanism of action of Levamisole as an anticancer drug in combination with fluorouracil is unknown. The effects of levamisole on the immune system are complex. The drug appears to restore depressed immune function rather than to stimulate response to above-normal levels. Levamisole can stimulate formation of antibodies to various antigens, enhance T-cell responses by stimulating T-cell activation and proliferation, potentiate monocyte and macrophage functions including phagocytosis and chemotaxis, and increase neutrophil mobility, adherence, and chemotaxis.