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Also known as: 16595-80-5, Levamisole hcl, Ergamisol, (s)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole hydrochloride, Ascaridil, Tramisol

Molecular Formula

C₁₁H₁₃ClN₂S

Molecular Weight

240.75 g/mol

InChI Key

LAZPBGZRMVRFKY-HNCPQSOCSA-N

FDA UNII

DL9055K809

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

2D Structure

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;hydrochloride

2.1.2 InChI

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

2.1.3 InChI Key

LAZPBGZRMVRFKY-HNCPQSOCSA-N

2.1.4 Canonical SMILES

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

2.1.5 Isomeric SMILES

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

2.2 Other Identifiers

2.2.1 UNII

DL9055K809

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Decaris

2. Dekaris

3. Hydrochloride, Levamisole

4. L-tetramisole

5. Levamisole

6. Levotetramisole

7. Solaskil

2.3.2 Depositor-Supplied Synonyms

1. 16595-80-5

2. Levamisole Hcl

3. Ergamisol

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

5. Ascaridil

6. Tramisol

7. (-)-tetramisole Hydrochloride

8. Tramisole

9. Decaris

10. Niratic Hydrochloride

11. Stimamizol Hydrochloride

12. (-)-tetramisole

13. Nsc-177023

14. Niratic-puron Hydrochloride

15. Spartakon L

16. L-narpenol

17. Levamisole (hydrochloride)

18. R 12,564

19. Spartakon

20. R 12564

21. R-12,564

22. Chebi:6433

23. Tetramisole Hydrochloride, (s)-

24. (-)-2,3,5,6-tetrahydro-6-phenylimidazo(2,1-b)thiazole Monohydrochloride

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

26. Dl9055k809

27. Dekaris

28. Levacide

29. Levadin

30. Levasole

31. Nemicide

32. Solaskil

33. Meglum

34. Nilverm Forte

35. Worm-chek

36. (6s)-6-phenyl-2h,3h,5h,6h-imidazo[2,1-b][1,3]thiazole Hydrochloride

37. Ripercol-l

38. Citarin L

39. 16595-80-5 (hcl)

40. Dsstox_cid_27518

41. Dsstox_rid_82391

42. Dsstox_gsid_47518

43. R 12654

44. R-12564

45. 74191-78-9

46. Levomysol Hydrochloride

47. (6s)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole;hydrochloride

48. (7s)-7-phenyl-4-thia-1,6-diazabicyclo[3.3.0]oct-5-ene Hydrochloride

49. Kw 2le-t

50. Smr001230807

51. Kw-2-le-t

52. Nsc177023

53. Levamisole Hydrochloride [usan]

54. Levamisol Hydrochloride

55. Sr-01000075969

56. Einecs 240-654-6

57. L-tetramisole Hydrochloride

58. (-)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole Hydrochloride

59. Unii-dl9055k809

60. Lev Hydrochloride

61. Ergamisol (tn)

62. Ncgc00094446-03

63. Prestwick_294

64. Levamisole Hydrochloride [usan:usp]

65. Mfcd00012675

66. Levamisoli Hydrochloridum

67. Levamisole Hcl(ergamisol)

68. L-(-)-2,3,5,6-tetrahydro-6-phenyl-imidazo(2,1-b)thiazole Hydrochloride

69. Ergamisol (tn) (janssen)

70. Cas-16595-80-5

71. Chembl1770

72. Schembl19226

73. Bmk1-h6

74. Levamisole Hydrochloride,(s)

75. Imidazo[2, 2,3,5,6-tetrahydro-6-phenyl-, Monohydrochloride

76. Mls002153440

77. Mls002222198

78. Mls002695941

79. Spectrum1503245

80. Levamisole Hydrochloride (usp)

81. ((-)-tetramisole Hydrochloride

82. Dtxsid7047518

83. Hms1568f05

84. Hms1922m11

85. Bcp13755

86. Levamisole Hydrochloride (ergamisol)

87. Tox21_111282

88. Tox21_500690

89. Ccg-40301

90. Levamisole Hydrochloride [mi]

91. S1939

92. Levamisole Hydrochloride [jan]

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

94. Akos015951350

95. L(-)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole Hydrochloride

96. Tox21_111282_1

97. Kw-2299

98. Lp00690

99. Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, Monohydrochloride, (-)-

100. Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, Monohydrochloride, L-(-)-

101. Levamisole Hydrochloride [mart.]

102. Levamisole Hydrochloride [usp-rs]

103. Levamisole Hydrochloride [who-dd]

104. Levamisole Hydrochloride [who-ip]

105. Ncgc00094046-01

106. Ncgc00261375-01

107. Ncgc00263461-01

108. Ac-23973

109. As-13370

110. Bl166245

111. Hy-13666

112. Eu-0100690

113. L0231

114. Levamisole Hydrochloride [green Book]

115. T1215

116. (-)-tetramisole Hydrochloride, >=99% (gc)

117. Levamisole Hydrochloride [orange Book]

118. C07906

119. D00750

120. D78137

121. L 9756

122. Levamisole Hydrochloride [ep Monograph]

123. Levamisole Hydrochloride [usp Monograph]

124. Levamisoli Hydrochloridum [who-ip Latin]

125. J-010244

126. J-521642

127. Levamisole Hydrochloride 100 Microg/ml In Methanol

128. Sr-01000075969-1

129. Sr-01000075969-6

130. Levamisol Hydrochloride 100 Microg/ml In Acetonitrile

131. Q27107205

132. Z1550648764

133. Levamisol Hydrochloride, Vetranal(tm), Analytical Standard

134. Levamisole Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

135. Imidazo[2, 2,3,5,6-tetrahydro-6-phenyl-, Monohydrochloride, (-)-

136. Imidazo[2, 2,3,5,6-tetrahydro-6-phenyl-, Monohydrochloride, (s)-

137. (-)-2,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole Monohydrochloride

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

139. Imidazo[2, 2,3,5,6-tetrahydro-6-phenyl-, Monohydrochloride, L-(-)-

140. Levamisole Hydrochloride, European Pharmacopoeia (ep) Reference Standard

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

142. Levamisole Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

143. Levamisole Hydrochloride, United States Pharmacopeia (usp) Reference Standard

144. Levamisole Hydrochloride For System Suitability, European Pharmacopoeia (ep) Reference Standard

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₁₁H₁₃ClN₂S
Molecular Weight	240.75 g/mol
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	1
Exact Mass	240.0487973 g/mol
Monoisotopic Mass	240.0487973 g/mol
Topological Polar Surface Area	40.9 Å²
Heavy Atom Count	15
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	2

4 Drug and Medication Information

4.1 Drug Indication

Treatment of glomerulonephritis and nephrotic syndrome

5 Pharmacology and Biochemistry

5.1 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.)

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.)

Antirheumatic Agents

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

CAS-16595-80-5

CAS-16595-80-5

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