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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 Ų
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.


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PharmaCompass offers a list of Levamisole API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Levamisole manufacturer or Levamisole supplier for your needs.

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PharmaCompass also assists you with knowing the Levamisole API Price utilized in the formulation of products. Levamisole API Price is not always fixed or binding as the Levamisole Price is obtained through a variety of data sources. The Levamisole Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Levamisole

Synonyms

14769-73-4, Levamisol, L-tetramisole, Ketrax, Wormicid, Lepuron

Cas Number

14769-73-4

Unique Ingredient Identifier (UNII)

2880D3468G

About 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)

Vermisol 150 Manufacturers

A Vermisol 150 manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Vermisol 150, including repackagers and relabelers. The FDA regulates Vermisol 150 manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Vermisol 150 API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Vermisol 150 manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Vermisol 150 Suppliers

A Vermisol 150 supplier is an individual or a company that provides Vermisol 150 active pharmaceutical ingredient (API) or Vermisol 150 finished formulations upon request. The Vermisol 150 suppliers may include Vermisol 150 API manufacturers, exporters, distributors and traders.

click here to find a list of Vermisol 150 suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Vermisol 150 USDMF

A Vermisol 150 DMF (Drug Master File) is a document detailing the whole manufacturing process of Vermisol 150 active pharmaceutical ingredient (API) in detail. Different forms of Vermisol 150 DMFs exist exist since differing nations have different regulations, such as Vermisol 150 USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Vermisol 150 DMF submitted to regulatory agencies in the US is known as a USDMF. Vermisol 150 USDMF includes data on Vermisol 150's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Vermisol 150 USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Vermisol 150 suppliers with USDMF on PharmaCompass.

Vermisol 150 CEP

A Vermisol 150 CEP of the European Pharmacopoeia monograph is often referred to as a Vermisol 150 Certificate of Suitability (COS). The purpose of a Vermisol 150 CEP is to show that the European Pharmacopoeia monograph adequately controls the purity of Vermisol 150 EP produced by a given manufacturer. Suppliers of raw materials can prove the suitability of Vermisol 150 to their clients by showing that a Vermisol 150 CEP has been issued for it. The manufacturer submits a Vermisol 150 CEP (COS) as part of the market authorization procedure, and it takes on the role of a Vermisol 150 CEP holder for the record. Additionally, the data presented in the Vermisol 150 CEP (COS) is managed confidentially and offers a centralized system acknowledged by numerous nations, exactly like the Vermisol 150 DMF.

A Vermisol 150 CEP (COS) is recognised by all 36 nations that make up the European Pharmacopoeia Convention. Vermisol 150 CEPs may be accepted in nations that are not members of the Ph. Eur. at the discretion of the authorities there.

click here to find a list of Vermisol 150 suppliers with CEP (COS) on PharmaCompass.

Vermisol 150 NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Vermisol 150 as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Vermisol 150 API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Vermisol 150 as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Vermisol 150 and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Vermisol 150 NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Vermisol 150 suppliers with NDC on PharmaCompass.

Vermisol 150 GMP

Vermisol 150 Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Vermisol 150 GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Vermisol 150 GMP manufacturer or Vermisol 150 GMP API supplier for your needs.

Vermisol 150 CoA

A Vermisol 150 CoA (Certificate of Analysis) is a formal document that attests to Vermisol 150's compliance with Vermisol 150 specifications and serves as a tool for batch-level quality control.

Vermisol 150 CoA mostly includes findings from lab analyses of a specific batch. For each Vermisol 150 CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Vermisol 150 may be tested according to a variety of international standards, such as European Pharmacopoeia (Vermisol 150 EP), Vermisol 150 JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Vermisol 150 USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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