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Also known as: 66-81-9, Actidione, Cicloheximide, Naramycin a, Kaken, Actidion

Molecular Formula

C₁₅H₂₃NO₄

Molecular Weight

281.35 g/mol

InChI Key

YPHMISFOHDHNIV-FSZOTQKASA-N

FDA UNII

98600C0908

Antibiotic substance isolated from streptomycin-producing strains of Streptomyces griseus. It acts by inhibiting elongation during protein synthesis.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[(2R)-2-[(1S,3S,5S)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione

2.1.2 InChI

InChI=1S/C15H23NO4/c1-8-3-9(2)15(20)11(4-8)12(17)5-10-6-13(18)16-14(19)7-10/h8-12,17H,3-7H2,1-2H3,(H,16,18,19)/t8-,9-,11-,12+/m0/s1

2.1.3 InChI Key

YPHMISFOHDHNIV-FSZOTQKASA-N

2.1.4 Canonical SMILES

CC1CC(C(=O)C(C1)C(CC2CC(=O)NC(=O)C2)O)C

2.1.5 Isomeric SMILES

C[C@H]1C[C@@H](C(=O)[C@@H](C1)[C@@H](CC2CC(=O)NC(=O)C2)O)C

2.2 Other Identifiers

2.2.1 UNII

98600C0908

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Actidione

2. Cicloheximide

2.3.2 Depositor-Supplied Synonyms

1. 66-81-9

2. Actidione

3. Cicloheximide

4. Naramycin A

5. Kaken

6. Actidion

7. Actidone

8. Hizarocin

9. Naramycin

10. Neocycloheximide

11. Acti-aid

12. Cycloheximid

13. Actispray

14. Actidione Pm

15. Cicloheximida

16. Cicloheximidum

17. Zykloheximid

18. Nsc-185

19. Cycloheximide [usan]

20. C15h23no4

21. Nsc 185

22. U-4527

23. Acti-dione Br

24. 4-[(2r)-2-[(1s,3s,5s)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]piperidine-2,6-dione

25. 4-{(2r)-2-[(1s,3s,5s)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl}piperidine-2,6-dione

26. Cbc 500046

27. 3-((r)-2-((1s,3s,5s)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide

28. Nsc185

29. Cicloheximide [inn]

30. Acti-dione

31. Actidione Tgf

32. Tcmdc-125838

33. U 4527

34. Aktidion

35. Chembl123292

36. Tza

37. Chebi:27641

38. Gnf-pf-5118

39. Beta-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide

40. 3-(2r)-2-((1s,3s,5s)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethylglutarimide

41. Cicloheximide (inn)

42. (1s-(1alpha(s*),3alpha,5beta))-4-(2-(3,5-dimethyl-2-oxo-cyclohexyl))-2-hydroxyethyl-2,6-piperidinedione

43. Cx

44. Cycloheximide (usan)

45. Actidione Br

46. Dsstox_cid_4882

47. 2,6-piperidinedione, 4-[(2r)-2-[(1s,3s,5s)-3,5-dimethyl-2-oxocyclohexyl]-2-hydroxyethyl]-

48. 4-((r)-2-((1s,3s,5s)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)piperidine-2,6-dione

49. 4-[(2r)-2-[(1s,3s,5s)-3,5-dimethyl-2-oxo-cyclohexyl]-2-hydroxy-ethyl]piperidine-2,6-dione

50. Aktidion [czech]

51. Dsstox_rid_77565

52. Cyclohemimide

53. Cyclohexamide

54. Dsstox_gsid_24882

55. 98600c0908

56. 3-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)glutarimide

57. 3-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide

58. Caswell No. 270a

59. .beta.-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]glutarimide

60. 4-[2-(3,5-dimethyl-2-oxo-cyclohexyl)-2-hydroxyethyl]-2,6-piperidinedione

61. Cicloheximidum [inn-latin]

62. Cicloheximida [inn-spanish]

63. Smr000686067

64. Ccris 937

65. Hsdb 1552

66. Sr-01000597484

67. Sr-05000001596

68. Einecs 200-636-0

69. Cycloheximide [bsi:iso]

70. Epa Pesticide Chemical Code 043401

71. Brn 0088868

72. Nm-mcd 80

73. Ai3-15541

74. Dtxsid6024882

75. Acti-dione Pm

76. Acti-dione Tgf

77. Cas-66-81-9

78. Ncgc00024910-01

79. 2,6-piperidinedione, 4-((2r)-2-((1s,3s,5s)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-

80. 4-((2r)-2-((1s,3s,5s)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)piperidine-2,6-dione

81. Prestwick_976

82. Mfcd00082346

83. Unii-98600c0908

84. 2,6-piperidinedione, 4-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-, (1s-(1alpha(s*),3alpha,5beta))-

85. Spectrum_001344

86. Ft 3422-2

87. Prestwick0_000790

88. Prestwick1_000790

89. Prestwick2_000790

90. Prestwick3_000790

91. Spectrum2_000900

92. Spectrum3_001510

93. Spectrum4_000914

94. Spectrum5_001635

95. Cycloheximide [mi]

96. Cycloheximide [iso]

97. Cid_6197

98. 4-((2r)-2-((1s,3s,5s)-(3,5-dimethyl-2-oxocyclohexyl))-2-hydroxyethyl)piperidine-2,6-dione

99. Cycloheximide [hsdb]

100. Schembl26617

101. Bspbio_000900

102. Bspbio_003159

103. Kbiogr_001408

104. Kbioss_001824

105. 5-21-13-00434 (beilstein Handbook Reference)

106. Ksc-8-190

107. Mls001055333

108. Mls002154001

109. Cicloheximide [mart.]

110. Divk1c_000050

111. Spectrum1502112

112. Spbio_000720

113. Spbio_002839

114. 4-[2-(3,6-piperidinedione

115. Bpbio1_000990

116. Gtpl5433

117. Hms500c12

118. Kbio1_000050

119. Kbio2_001824

120. Kbio2_004392

121. Kbio2_006960

122. Kbio3_002659

123. Ninds_000050

124. Hms1570m22

125. Hms1921l04

126. Hms2092d10

127. Hms2097m22

128. Hms3714m22

129. Kuc105858n

130. Pharmakon1600-01502112

131. Cycloheximide, Streptomyces Griseus

132. 2,6-piperidinedione, 4-(2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-, (1s-(1.alpha.(s*),3.alpha.,5.beta.))-

133. Zinc3872170

134. Tox21_113580

135. Tox21_201158

136. Tox21_303652

137. Bdbm50080528

138. Ccg-39902

139. Cycloheximide, >=93.0% (hplc)

140. Nsc758187

141. Akos024282670

142. Tox21_113580_1

143. Cs-4985

144. Nsc-758187

145. Idi1_000050

146. Ncgc00017363-05

147. Ncgc00017363-06

148. Ncgc00017363-07

149. Ncgc00017363-08

150. Ncgc00017363-10

151. Ncgc00017363-18

152. Ncgc00024910-02

153. Ncgc00024910-03

154. Ncgc00024910-04

155. Ncgc00024910-05

156. Ncgc00024910-06

157. Ncgc00169964-05

158. Ncgc00257430-01

159. Ncgc00258710-01

160. 4-[(2r)-2-((1s,3s,5s)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]azaperhydro Ine-2,6-dione

161. Ac-35130

162. As-14624

163. Bp-12396

164. Hy-12320

165. Nci60_001540

166. Sbi-0051732.p002

167. Wln: T6vmvtj E1yq- Bl6vtj D1 F1

168. Cycloheximide 100 Microg/ml In Acetonitrile

169. Cycloheximide, From Microbial, >=94% (tlc)

170. C-9217

171. C06685

172. Cycloheximide Solution, 0.1%, For Microbiology

173. D03625

174. M01527

175. Ab00052279_08

176. Cycloheximide, Pestanal(r), Analytical Standard

177. 082c346

178. Cycloheximide, Biotechnology Performance Certified

179. Q412895

180. Cycloheximide, Antibiotic For Culture Media Use Only

181. Sr-01000597484-1

182. Sr-01000597484-4

183. Sr-05000001596-1

184. Sr-05000001596-3

185. Sr-05000001596-4

186. Brd-k36055864-001-05-1

187. Brd-k36055864-001-07-7

188. Brd-k36055864-001-09-3

189. Brd-k36055864-001-16-8

190. [1s-[1.alpha.(s*),3.alpha.,5.beta.]]-4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]-2,6-piperidinedione

191. 1154-57-0

192. 2, 4-[2-(3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl]-, [1s-[1.alpha.(s*),3.alpha.,5.beta.]]-

193. 4-((2r)-2-((1s,3s,5s)-3,5-dimethyl-2-oxocyclohexyl)-2-hydroxyethyl)-2,6-piperidinedione

194. 4-[(2r)-2-[(1s,3s,5r)-3,5-dimethyl-2-oxo-cyclohexyl]-2-hydroxy-ethyl]piperidine-2,6-dione

195. Cycloheximide Solution, Ready-made Solution, Microbial, 100 Mg/ml In Dmso, 0.2 Mum Filtered

2.4 Create Date

2005-06-08

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₂₃NO₄
Molecular Weight	281.35 g/mol
XLogP3	0.5
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	3
Exact Mass	281.16270821 g/mol
Monoisotopic Mass	281.16270821 g/mol
Topological Polar Surface Area	83.5 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	404
Isotope Atom Count	0
Defined Atom Stereocenter Count	4
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 Therapeutic Uses

Antibiotics, Antifungal; Protein Synthesis Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

MEDICATION (VET): ANTIBIOTIC, ANTIFUNGAL, TRICHOMONACIDAL ... ESPECIALLY EFFECTIVE AGAINST MALIGNANT LYMPHOMAS IN DOGS.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 148

Cycloheximide ... was used in the treatment of cryptococcal infections (Cryptococcus neoformans) before the development of amphotericin B.

Kirk-Othmer Encyclopedia of Chemical Technology. 3rd ed., Volumes 1-26. New York, NY: John Wiley and Sons, 1978-1984., p. 5(79) 489-513

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Protein Synthesis Inhibitors

Compounds which inhibit the synthesis of proteins. They are usually ANTI-BACTERIAL AGENTS or toxins. Mechanism of the action of inhibition includes the interruption of peptide-chain elongation, the blocking the A site of ribosomes, the misreading of the genetic code or the prevention of the attachment of oligosaccharide side chains to glycoproteins. (See all compounds classified as Protein Synthesis Inhibitors.)

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

5.2 Mechanism of Action

STIMULATED TRANSPORT OF NUCLEAR RIBONUCLEOPROTEIN COMPLEXES TO CYTOPLASM AFTER ADMIN CYCLOHEXIMIDE TO RATS WAS STUDIED. ADMIN OF 2 MG/KG CYCLOHEXIMIDE CAUSED A DECR IN CONTENT OF TOTAL LIVER NUCLEAR RIBONUCLEOPROTEIN COMPLEX WITHIN 2 HR. THE OVERALL DECR WAS DUE TO AN INCREASED TRANSPORT INTO THE CYTOPLASM, NOT DECREASED SYNTHESIS. OTHER RESULTS SUGGEST THAT DURING INHIBITORY PHASE OF PROTEIN SYNTHESIS, GENE TRANSCRIPTION CONTINUES & GENE PRODUCT IS TRANSPORTED TO CYTOPLASM FOR TRANSLATION.

PMID:454372 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1186565 CHIH JJ ET AL; BIOCHEM J 178 (3): 643-9 (1979)

CYCLOHEXIMIDE (2-5 MG/KG BODY WT) CAUSED COMPLETE INHIBITION OF PROTEIN SYNTHESIS IN RAT LIVER WITHIN 30 MIN, & THE LABELING OF NUCLEAR PROTEINS WAS STRONGLY INHIBITED. UNDER THESE CONDITIONS, THE AMT OF NUCLEOLAR 45 S PRE-rRNA & ITS OROTATE-(14)C LABELING REMAINED UNAFFECTED FOR AT LEAST 4 HR, INDICATING THAT INITIALLY THE RATES OF SYNTHESIS & PROCESSING OF 45 S PRE-rRNA WERE NOT APPRECIABLY ALTERED. DRASTIC ALTERATIONS IN THE 45 S PRE-rRNA PROCESSING PATHWAYS OCCURRED AT THE EARLY STAGES OF CYCLOHEXIMIDE ACTION. THE CHANNELING OF NUCLEAR PRE-rRNA ALONG ALTERNATIVE PROCESSING PATHWAYS IS UNDER STRINGENT CONTROL BY THE CONTINUOUS SUPPLY OF CRITICAL PROTEINS.

PMID:456380 STOYANOVA BB, HADJIOLOV AA; EUR J BIOCHEM 96 (2): 349-56 (1979)

CYCLOHEXIMIDE IS A POTENT INHIBITOR OF PROTEIN SYNTHESIS IN FUNGI & ANIMALS. IT CAUSES AN INCREASE IN ADRENAL RNA, INCREASED PRODUCTION OF GLUCOCORTICOIDS ... & DECREASE IN PYRUVATE UTILIZATION IN ISOLATED ADIPOSE TISSUE.

Gosselin, R.E., R.P. Smith, H.C. Hodge. Clinical Toxicology of Commercial Products. 5th ed. Baltimore: Williams and Wilkins, 1984., p. II-265

Cycloheximide

Cycloheximide

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