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(4S)-4-ETHYL-4-HYDROXY-1H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H,12H)-DIONE

(4S)-4-ETHYL-4-HYDROXY-1H-PYRANO(3',4':6,7)INDOLIZINO(1,2-B)QUINOLINE-3,14(4H,12H)-DIONE

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Also known as: Camptothecine, 7689-03-4, (s)-(+)-camptothecin, Campathecin, (+)-camptothecine, D-camptothecin

Molecular Formula

C₂₀H₁₆N₂O₄

Molecular Weight

348.4 g/mol

InChI Key

VSJKWCGYPAHWDS-FQEVSTJZSA-N

FDA UNII

XT3Z54Z28A

An alkaloid isolated from the stem wood of the Chinese tree, Camptotheca acuminata. This compound selectively inhibits the nuclear enzyme DNA TOPOISOMERASES, TYPE I. Several semisynthetic analogs of camptothecin have demonstrated antitumor activity.

1 2D Structure

(4S)-4-ETHYL-4-HYDROXY-1H-PYRANO(3

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

(19S)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

2.1.2 InChI

InChI=1S/C20H16N2O4/c1-2-20(25)14-8-16-17-12(7-11-5-3-4-6-15(11)21-17)9-22(16)18(23)13(14)10-26-19(20)24/h3-8,25H,2,9-10H2,1H3/t20-/m0/s1

2.1.3 InChI Key

VSJKWCGYPAHWDS-FQEVSTJZSA-N

2.1.4 Canonical SMILES

CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O

2.1.5 Isomeric SMILES

CC[C@@]1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O

2.2 Other Identifiers

2.2.1 UNII

XT3Z54Z28A

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Camptothecine

2.3.2 Depositor-Supplied Synonyms

1. Camptothecine

2. 7689-03-4

3. (s)-(+)-camptothecin

4. Campathecin

5. (+)-camptothecine

6. D-camptothecin

7. (+)-camptothecin

8. 20(s)-camptothecine

9. 21,22-secocamptothecin-21-oic Acid Lactone

10. Nsc94600

11. Camptothecine (s,+)

12. Chembl65

13. (4s)-4-ethyl-4-hydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

14. Nsc-94600

15. Topotecan Related Compound C

16. (s)-4-ethyl-4-hydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

17. Mls000766223

18. Xt3z54z28a

19. Chebi:27656

20. Mfcd00081076

21. (19s)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

22. Nsc 100880

23. 251316-95-7

24. (s)-camptothecin

25. (19s)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione

26. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 4-ethyl-4-hydroxy-, (4s)-

27. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 4-ethyl-4-hydroxy-, (s)-

28. 1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione, 4-ethyl-4-hydroxy-, (4s)-

29. 20(s)-camptothecin

30. 4-ethyl-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

31. Sr-01000075798

32. Sr-01000597379

33. D-camptothecine

34. (s)-camptothecine

35. Camptothecin,(s)

36. ( )-camptothecin

37. (4s)-4-ethyl-4-hydroxy-1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione

38. (s)-4-ethyl-4-hydroxy-1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione

39. (s)-4-ethyl-4-hydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14-(4h,12h)-dione

40. 1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione, 4-ethyl-4-hydroxy-, (s)-

41. Prestwick_102

42. (+)-camptothecin;

43. Camptothecine (8ci)

44. Spectrum_000299

45. Tocris-1100

46. Specplus_000712

47. Prestwick0_000200

48. Prestwick1_000200

49. Prestwick2_000200

50. Prestwick3_000200

51. Spectrum2_000903

52. Spectrum3_001203

53. Spectrum4_000738

54. Spectrum5_001126

55. Camptothecin [mi]

56. Lopac-c-9911

57. Schembl6038

58. Unii-xt3z54z28a

59. Lopac0_000341

60. Bspbio_000159

61. Bspbio_002586

62. Kbiogr_001036

63. Kbioss_000779

64. Kbioss_002283

65. Cid_24360

66. Camptothecin [who-dd]

67. Divk1c_000826

68. Divk1c_006808

69. Spectrum1502232

70. Spbio_000746

71. Spbio_002080

72. Bpbio1_000175

73. Ccris 8162

74. Dtxsid0030956

75. Hms502j08

76. Kbio1_000826

77. Kbio1_001752

78. Kbio2_000779

79. Kbio2_003347

80. Kbio2_005915

81. Kbio3_002086

82. 4-ethyl-4-hydroxy-1h-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

83. Ninds_000826

84. Bio1_000400

85. Bio1_000889

86. Bio1_001378

87. Hms1568h21

88. Hms1921n08

89. Hms2089f08

90. Hms2095h21

91. Hms3261e03

92. Hms3414j17

93. Hms3654d13

94. Hms3678j15

95. Hms3712h21

96. Zinc105309

97. Act02668

98. Bcp02857

99. Tox21_500341

100. Ac-202

101. Bbl033963

102. Bdbm50008923

103. Ccg-40255

104. Gr-301

105. Nsc 94600

106. S1288

107. Stk801886

108. Akos004119861

109. Cs-1049

110. Db04690

111. Ks-5235

112. Lp00341

113. Sdccgmls-0066688.p001

114. Sdccgsbi-0050329.p003

115. Brn 0631069

116. Cas-2114454

117. Idi1_000826

118. Ncgc00015290-01

119. Ncgc00016994-01

120. Ncgc00016994-02

121. Ncgc00016994-03

122. Ncgc00016994-04

123. Ncgc00016994-05

124. Ncgc00016994-06

125. Ncgc00016994-07

126. Ncgc00016994-08

127. Ncgc00016994-09

128. Ncgc00016994-10

129. Ncgc00016994-11

130. Ncgc00016994-12

131. Ncgc00016994-16

132. Ncgc00016994-29

133. Ncgc00024997-01

134. Ncgc00024997-02

135. Ncgc00024997-03

136. Ncgc00024997-04

137. Ncgc00024997-05

138. Ncgc00024997-06

139. Ncgc00178592-01

140. Ncgc00178592-02

141. Ncgc00261026-01

142. Hy-16560

143. Nci60_042105

144. Smr000445686

145. Sy010324

146. Ai3-62475

147. Eu-0100341

148. N1868

149. Sw196414-3

150. Topotecan Related Compound C [usp-rs]

151. C 9911

152. C01897

153. M01564

154. Ab00052452-08

155. Ab00052452-09

156. Ab00052452_10

157. (s)-(+)-camptothecin, >=90% (hplc), Powder

158. 689c034

159. A838882

160. Q419964

161. Q-200785

162. Sr-01000075798-1

163. Sr-01000075798-4

164. Sr-01000597379-1

165. Sr-01000597379-3

166. Brd-k37890730-001-09-4

167. Brd-k37890730-001-10-2

168. (s)-4-ethyl-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo[b,h]florene-3,13-dione

169. (s)-4-ethyl-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

170. 4-ethyl-4-hydroxy-1h-pyrano-[3[,4[:6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

171. Topotecan Related Compound C, United States Pharmacopeia (usp) Reference Standard

172. (s)-4-ethyl-4-hydroxy-1h-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

173. (s)-4-ethyl-4-hydroxy-1h-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione;(s)-(+)-camptothecin

174. (s)-4-ethyl-4-hydroxy-1h-pyrano[3 Inverted Exclamation Mark ,4 Inverted Exclamation Mark :6,7]indolizino[1,2-b]quinoline-3,14-(4h,12h)-dione

175. 1h-pyrano[3',7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione, 4-ethyl-4-hydroxy-, (s)-

176. 4(s)-ethyl-4-hydroxy-1h-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14 (4h,12h)-dione

177. 4-ethyl-4-hydroxy-(4s)-3,4,12,14-tetrahydro-1h-pyrano[3'',4'':6,7]indolizino[1,2-b]quinoline-3,14-dione

178. 4-ethyl-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione (camptothecin Or Cpt)

179. 4-ethyl-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione (camptothecin)

180. 4-ethyl-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione (cpt, Camptothecin)

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₆N₂O₄
Molecular Weight	348.4 g/mol
XLogP3	1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	1
Exact Mass	348.11100700 g/mol
Monoisotopic Mass	348.11100700 g/mol
Topological Polar Surface Area	79.7 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	742
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	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for the treatment of cancer.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Camptothecin demonstrated strong anticancer activity in preliminary clinical trials but also low solubility and adverse drug reaction. Camptothecin is believed to be a potent topoisomerase inhibitor that interferes with the essential function of topoisomerase in DNA replication.

5.2 MeSH Pharmacological Classification

Topoisomerase I Inhibitors

Compounds that inhibit the activity of DNA TOPOISOMERASE I. (See all compounds classified as Topoisomerase I Inhibitors.)

Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

5.3 Mechanism of Action

Camptothecin binds to the topoisomerase I and DNA complex resulting in a ternary complex, stabilizing it and preventing DNA re-ligation and therefore causes DNA damage which results in apoptosis.