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Prestwick3_000924

Prestwick3_000924

Synopsis, Chemistry

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Also known as: 61413-54-5, (r,s)-rolipram, Zk 62711, Rolipramum [latin], Adeo, (+/-)-rolipram

Molecular Formula

C₁₆H₂₁NO₃

Molecular Weight

275.34 g/mol

InChI Key

HJORMJIFDVBMOB-UHFFFAOYSA-N

FDA UNII

K676NL63N7

A phosphodiesterase 4 inhibitor with antidepressant properties.

1 2D Structure

Prestwick3_000924

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one

2.1.2 InChI

InChI=1S/C16H21NO3/c1-19-14-7-6-11(12-9-16(18)17-10-12)8-15(14)20-13-4-2-3-5-13/h6-8,12-13H,2-5,9-10H2,1H3,(H,17,18)

2.1.3 InChI Key

HJORMJIFDVBMOB-UHFFFAOYSA-N

2.1.4 Canonical SMILES

COC1=C(C=C(C=C1)C2CC(=O)NC2)OC3CCCC3

2.2 Other Identifiers

2.2.1 UNII

K676NL63N7

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Zk 62711

2. Zk-62711

3. Zk62711

2.3.2 Depositor-Supplied Synonyms

1. 61413-54-5

2. (r,s)-rolipram

3. Zk 62711

4. Rolipramum [latin]

5. Adeo

6. (+/-)-rolipram

7. Rolipramum

8. 4-(3-(cyclopentyloxy)-4-methoxyphenyl)pyrrolidin-2-one

9. 4-[3-(cyclopentyloxy)-4-methoxyphenyl]-2-pyrrolidinone

10. 4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidin-2-one

11. Zk-62711

12. 4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidin-2-one

13. 4-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-pyrrolidinone

14. Sb 95952

15. Chembl63

16. Nsc-760125

17. 4-(3-cyclopentyloxy-4-methoxyphenyl)-2-pyrrolidone

18. C16h21no3

19. Mls000069691

20. Zk 62 711

21. 2-pyrrolidinone, 4-[3-(cyclopentyloxy)-4-methoxyphenyl]-

22. Chebi:104872

23. K676nl63n7

24. Sb-95952

25. Smr000058510

26. Zk-62771

27. (4s)-4-[3-(cyclopentyloxy)-4-methoxyphenyl]-pyrrolidin-2-one

28. (r,s)-rolipram;sb 95952;zk 62711

29. Dsstox_cid_24124

30. Dsstox_rid_80104

31. Dsstox_gsid_44124

32. 4-(3-cyclopentyloxy-4-methoxy-phenyl)-pyrrolidin-2-one

33. 2-pyrrolidinone, 4-(3-(cyclopentyloxy)-4-methoxyphenyl)-

34. (4r)-4-[3-(cyclopentyloxy)-4 Methoxyphenyl)pyrrolidin-2-one

35. Rolipram [usan:inn]

36. [3h]rolipram

37. [3h]-rolipram

38. Sr-01000000162

39. Einecs 262-771-1

40. 4-(3-(cyclopentyloxy)-4-methoxyphenyl)-2-pyrrolidinon

41. Brn 1588548

42. Unii-k676nl63n7

43. (plusmn)-rolipram

44. Ncgc00016899-01

45. Cas-61413-54-5

46. Mfcd00270906

47. R-(-)-rolipram

48. Me-3167

49. Rolipram [usan]

50. Rolipram [inn]

51. Rolipram [jan]

52. Rolipram [mi]

53. Opera_id_1749

54. Prestwick0_000924

55. Prestwick1_000924

56. Prestwick2_000924

57. Prestwick3_000924

58. Rolipram [mart.]

59. Rolipram [who-dd]

60. Upcmld-dp110

61. Lopac0_001072

62. Schembl27930

63. Bspbio_000828

64. Bspbio_001356

65. Kbiogr_000076

66. Kbioss_000076

67. Rolipram (jan/usan/inn)

68. Mls000758273

69. Mls000759531

70. Mls001146912

71. Mls001424084

72. Mls006010272

73. Spbio_003007

74. (+)-rolipram; (s)-rolipram

75. Bpbio1_000912

76. Gtpl5260

77. Gtpl5313

78. 4-[3-(cyclopentoxy)-4-methoxy-phenyl]pyrrolidin-2-one

79. Dtxsid3044124

80. Upcmld-dp110:001

81. Upcmld-dp110:002

82. Bdbm14361

83. Kbio2_000076

84. Kbio2_002644

85. Kbio2_005212

86. Kbio3_000151

87. Kbio3_000152

88. Bio2_000076

89. Bio2_000556

90. Hms1361d18

91. Hms1570j10

92. Hms1791d18

93. Hms1989d18

94. Hms2051n15

95. Hms2090j16

96. Hms2097j10

97. Hms2232f06

98. Hms3263g06

99. Hms3267a05

100. Hms3369j08

101. Hms3393n15

102. Hms3402d18

103. Hms3411f08

104. Hms3654p06

105. Hms3655j21

106. Hms3675f08

107. Hms3714j10

108. Pharmakon1600-01505683

109. Bcp21910

110. Bcp23388

111. Tox21_110672

112. Tox21_501072

113. Nsc760125

114. Rolipram, Solid, >=98% (hplc)

115. S1430

116. Rolipram - Cas 61413-54-5

117. Akos015959793

118. Tox21_110672_1

119. Ccg-100965

120. Ccg-205149

121. Cs-1754

122. Db01954

123. Ks-1400

124. Lp01072

125. Nc00215

126. Nsc 760125

127. Sb12922

128. Sdccgsbi-0051042.p003

129. Idi1_033826

130. Ncgc00015898-03

131. Ncgc00015898-04

132. Ncgc00015898-05

133. Ncgc00015898-06

134. Ncgc00015898-07

135. Ncgc00015898-08

136. Ncgc00015898-09

137. Ncgc00015898-11

138. Ncgc00015898-12

139. Ncgc00015898-15

140. Ncgc00015898-31

141. Ncgc00089796-02

142. Ncgc00089796-04

143. Ncgc00089796-05

144. Ncgc00089796-06

145. Ncgc00089796-07

146. Ncgc00089796-08

147. Ncgc00261757-01

148. Ac-32927

149. Hy-16900

150. Sbi-0051042.p002

151. Db-080675

152. Ab00513966

153. Eu-0101072

154. Ft-0738515

155. R0110

156. Sw196583-4

157. D01783

158. R 6520

159. Ab00384360-17

160. Ab00384360_19

161. A847969

162. Q410285

163. 4-[3-(cyclopentyloxy)-4-methoxyphenyl]pyrrolidinone

164. Sr-01000000162-3

165. Sr-01000000162-4

166. Sr-01000000162-5

167. Sr-01000000162-9

168. 4-[3-cyclopentyloxy-4-methoxyphenyl]-2-pyrrolidinone

169. Brd-a34255068-001-04-8

170. Brd-a34255068-001-26-1

171. Sr-01000000162-12

172. 4-(3-cyclopentyloxy-4-methoxy-phenyl)pyrrolidin-2-one

173. 4-(3-cyclopentyloxy-4-methoxyphenyl)-pyrrolidin-2-one

174. 4-(3-cyclopentyloxy-4-methoxyphenyl)pyrrolidone

175. 4-[4-methoxy-3-(cyclopentyloxy)phenyl]-2-pyrrolidinone

176. 2-pyrrolidinone, 4-[3-(cyclopentyloxy)-4-methoxyphenyl]- (9ci)

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₆H₂₁NO₃
Molecular Weight	275.34 g/mol
XLogP3	2.2
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	4
Exact Mass	275.15214353 g/mol
Monoisotopic Mass	275.15214353 g/mol
Topological Polar Surface Area	47.6 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	341
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	1
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Phosphodiesterase 4 Inhibitors

Compounds that specifically inhibit PHOSPHODIESTERASE 4. (See all compounds classified as Phosphodiesterase 4 Inhibitors.)

Antidepressive Agents

Mood-stimulating drugs used primarily in the treatment of affective disorders and related conditions. Several MONOAMINE OXIDASE INHIBITORS are useful as antidepressants apparently as a long-term consequence of their modulation of catecholamine levels. The tricyclic compounds useful as antidepressive agents (ANTIDEPRESSIVE AGENTS, TRICYCLIC) also appear to act through brain catecholamine systems. A third group (ANTIDEPRESSIVE AGENTS, SECOND-GENERATION) is a diverse group of drugs including some that act specifically on serotonergic systems. (See all compounds classified as Antidepressive Agents.)