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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

Levamisole
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 Weight 204.29 g/mol
Molecular Formula C11H12N2S
XLogP31.8
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count2
Rotatable Bond Count1
Exact Mass204.07211956 g/mol
Monoisotopic Mass204.07211956 g/mol
Topological Polar Surface Area40.9 ā„«Ā²
Heavy Atom Count14
Formal Charge0
Complexity246
Isotope Atom Count0
Defined Atom Stereocenter Count1
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
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.


API SUPPLIERS

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Inabata France S.A.S

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Laboratorium Ofichem B.V

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Nanjing Pharmaceutical

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Levamisole

About the Company : Established in 1990, Inabata France, a part of the Inabata Group, used to export chemical and pharmaceutical products to Japan. In 2006, it acquired PharmasynthĆØse. Today, Inabata...

Established in 1990, Inabata France, a part of the Inabata Group, used to export chemical and pharmaceutical products to Japan. In 2006, it acquired PharmasynthĆØse. Today, Inabata-PharmasynthĆØse offers a wide range of services, including sourcing, manufacturing, and the development of raw materials for the pharmaceutical and cosmetic industries. It supplies these ingredients to Europe, Japan, and other countries. With expertise in fine chemical production, Inabata-PharmasynthĆØse conducts manufacturing operations, ranging from pilot to commercial quantities, at its GMP-certified facility at St. Pierre-Les-Elbeuf in France.
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Suanfarma

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Levamisole

About the Company : Suanfarma founded in 1993, is a B2B life science partner committed to health & innovation by developing, manufacturing, & distributing high-quality APIs for the pharmaceutical indu...

Suanfarma founded in 1993, is a B2B life science partner committed to health & innovation by developing, manufacturing, & distributing high-quality APIs for the pharmaceutical industry innovatively & sustainably. Backed by a robust global network of 12 strategically located local offices, we cater to the needs of over 400 active customers in 70+ countries. At Suanfarma we offer our CDMO capacity for fermentation & chemical synthesis projects, offering a One Stop Shop service with a solid track record, & which allows us to achieve success in the development, scaling, manufacturing, & commercialization of an API, either innovative or generic.
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Levamisole

About the Company : Laboratorium Ofichem is a GMP-certified and FDA-approved API manufacturer with state-of-the-art development and production facilities in the Netherlands. We develop and manufacture...

Laboratorium Ofichem is a GMP-certified and FDA-approved API manufacturer with state-of-the-art development and production facilities in the Netherlands. We develop and manufacture small molecule APIs in a cost-effective, robust, and compliant way. We have our own portfolio of generic APIs, but we also operate as a CDMO for a wide range of customers. We are a stable family-owned business and with nearly 50 years of experience we have a long history of regulatory compliance and a strong reputation for reliability and quality.
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Levamisole

About the Company : Alivira Animal Health Limited has emerged as India's largest and 1st Global integrated animal health company specialising in manufacturing of Active Pharmaceutical Ingredients (API...

Alivira Animal Health Limited has emerged as India's largest and 1st Global integrated animal health company specialising in manufacturing of Active Pharmaceutical Ingredients (API) and Finished Dosage Formulations (FDF).Our logotype is inspired by nature and its different forms and shapes. From a microscopic view to the skin texture, footprint of a chosen animal. The circular shape evokes the idea of protection and control. Itā€™s a closed and perfect shape that is naturally balanced, reminiscing the brand idea ā€œAnimals source of health.
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Levamisole Hydrochloride

About the Company : Hebei Veyong Pharmaceutical Co., Ltd, was established in 2002 and located in Economic and Technological Development Zone in Shijiazhuang. It is a large veterinary enterprise with G...

Hebei Veyong Pharmaceutical Co., Ltd, was established in 2002 and located in Economic and Technological Development Zone in Shijiazhuang. It is a large veterinary enterprise with GMP certificate in China with research and development, production and sales of veterinary API and preparations. It is national high-tech enterprise, Hebei famous trademark enterprise, the vice-chairman company of Hebei Association of Animal Science and Veterinary Medicine, the vice-chairman company of Hebei Animal Health Products Association.
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Levamisole

About the Company : Hubei Aoks Bio-tech is located in Hubei province of China.We specialized in the research, development, production and trade of organic intermediates, pharmaceutical intermediates ,...

Hubei Aoks Bio-tech is located in Hubei province of China.We specialized in the research, development, production and trade of organic intermediates, pharmaceutical intermediates ,chemical solvents and agrochemicals. We have equiped strong professional research and development team, talented personnel and completely equipped laboratory for the quality controlling.Ever since the establishment in 2010, our products are exported to more than hundred countries overseas.
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Levamisole Hydrochloride

About the Company : Xi'an Tian Guangyuan Biotech is a professional company engaged in natural plant extracts, bio-chemical raw materials research and development, production and sale of high-tech tech...

Xi'an Tian Guangyuan Biotech is a professional company engaged in natural plant extracts, bio-chemical raw materials research and development, production and sale of high-tech technology enterprises. Since the planning and design since 2009, the company established its own independent R & D team, and with the local colleges and universities and research institutions have close relations of cooperation in strict accordance with the GMP standard requirements of production safety, the company is committed to maintaining the natural nature of raw materials, raw materials to reduce heavy metals and Pesticide residues and other issues.
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04-Jan-2021
28-Aug-2024
KGS
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