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Overview of CAS 7689-03-4

Client Email Product
(4S)-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
PharmaCompass
(4S)-4-ethyl-4-hydroxy-1H-pyrano[3
Also known as: Camptothecine, (s)-(+)-camptothecin, 7689-03-4, Campathecin, (+)-camptothecine, D-camptothecin
Molecular Formula
C20H16N2O4
Molecular Weight
348.358  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 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
2.1.2 InChI Key
VSJKWCGYPAHWDS-FQEVSTJZSA-N
2.1.3 Canonical SMILES
CCC1(C2=C(COC1=O)C(=O)N3CC4=CC5=CC=CC=C5N=C4C3=C2)O
2.1.4 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 Depositor-Supplied Synonyms

1. Camptothecine

2. (s)-(+)-camptothecin

3. 7689-03-4

4. Campathecin

5. (+)-camptothecine

6. D-camptothecin

7. 20(s)-camptothecine

8. (+)-camptothecin

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

10. Nsc94600

11. (s)-camptothecin

12. 20(s)-camptothecin

13. Camptothecine (8ci)

14. Camptothecine (s,+)

15. Chembl65

16. Unii-xt3z54z28a

17. Mls000766223

18. Xt3z54z28a

19. Chebi:27656

20. Vsjkwcgypahwds-fqevstjzsa-n

21. Camptothecin, Camptotheca Acuminata

22. Nsc-94600

23. (4s)-4-ethyl-4-hydroxy-1h-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

24. Camptothecin Derivative

25. Ak-39842

26. Q-200785

27. Mfcd00081076

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

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

30. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 4-ethyl-4-hydroxy-, (s)-

31. 4-ethyl-4-hydroxy-1h-pyrano[3′,4′:6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)dione

32. D-camptothecine

33. (s)-camptothecine

34. ( )-camptothecin

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

36. 1h-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4h,12h)-dione, 4-ethyl-4-hydroxy-, (4s)-

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

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

39. 4-ethyl-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione

40. Prestwick_102

41. Camptothecinum

42. (+)-camptothecin;

43. Pubchem10183

44. Spectrum_000299

45. Tocris-1100

46. Specplus_000712

47. Ac1l2ndr

48. Prestwick0_000200

49. Prestwick1_000200

50. Prestwick2_000200

51. Prestwick3_000200

52. Spectrum2_000903

53. Spectrum3_001203

54. Spectrum4_000738

55. Spectrum5_001126

56. Lopac-c-9911

57. D09ydm

58. Ac1q2c5x

59. Schembl6038

60. Lopac0_000341

61. Bspbio_000159

62. Bspbio_002586

63. Kbiogr_001036

64. Kbioss_000779

65. Kbioss_002283

66. Cid_24360

67. Bio-0611

68. Divk1c_000826

69. Divk1c_006808

70. Spectrum1502232

71. Spbio_000746

72. Spbio_002080

73. Ac1q2c60

74. Bpbio1_000175

75. Jsp000050

76. Dtxsid0030956

77. Hms502j08

78. Kbio1_000826

79. Kbio1_001752

80. Kbio2_000779

81. Kbio2_003347

82. Kbio2_005915

83. Kbio3_002086

84. Bic8442

85. 4-ethyl-4-hydroxy-1h-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

86. Molport-001-738-745

87. Ninds_000826

88. Zx-afc000426

89. Bio1_000400

90. Bio1_000889

91. Bio1_001378

92. Hms1568h21

93. Hms1921n08

94. Hms2089f08

95. Hms2095h21

96. Hms3261e03

97. Hms3654d13

98. Zinc105309

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

100. Act02668

101. Zx-at019935

102. Tox21_500341

103. Ac-202

104. Bbl033963

105. Bdbm50008923

106. Bg0120

107. Ccg-40255

108. Gr-301

109. S1288

110. Stk801886

111. Akos004119861

112. Api0001826

113. Cs-1049

114. Db04690

115. Ks-5235

116. Lp00341

117. Mcule-1654983682

118. Sdccgmls-0066688.p001

119. Cas-2114454

120. Idi1_000826

121. Ncgc00015290-01

122. Ncgc00016994-01

123. Ncgc00016994-02

124. Ncgc00016994-03

125. Ncgc00016994-04

126. Ncgc00016994-05

127. Ncgc00016994-06

128. Ncgc00016994-07

129. Ncgc00016994-08

130. Ncgc00016994-09

131. Ncgc00016994-10

132. Ncgc00016994-11

133. Ncgc00016994-12

134. Ncgc00016994-16

135. Ncgc00024997-01

136. Ncgc00024997-02

137. Ncgc00024997-03

138. Ncgc00024997-04

139. Ncgc00024997-05

140. Ncgc00024997-06

141. Ncgc00178592-01

142. Ncgc00178592-02

143. Ncgc00261026-01

144. Aj-11194

145. An-16065

146. Bc203226

147. Br-39842

148. Dr001749

149. Hy-16560

150. K332

151. Kb-38584

152. Nci60_042105

153. Smr000445686

154. Sy010324

155. Ax8038860

156. St2412720

157. Eu-0100341

158. Ft-0623436

159. N1868

160. C 9911

161. C01897

162. J10012

163. M01564

164. S-2515

165. 32320-ep2270008a1

166. 32320-ep2272827a1

167. 32320-ep2275420a1

168. 32320-ep2277507a1

169. 32320-ep2277865a1

170. 32320-ep2280013a1

171. 32320-ep2281815a1

172. 32320-ep2286795a1

173. 32320-ep2286812a1

174. 32320-ep2289892a1

175. 32320-ep2292615a1

176. 32320-ep2292617a1

177. 32320-ep2295055a2

178. 32320-ep2295416a2

179. 32320-ep2298748a2

180. 32320-ep2298764a1

181. 32320-ep2298765a1

182. 32320-ep2298778a1

183. 32320-ep2301933a1

184. 32320-ep2305640a2

185. 32320-ep2305642a2

186. 32320-ep2305671a1

187. 32320-ep2308855a1

188. 32320-ep2311453a1

189. 32320-ep2311827a1

190. 32320-ep2311840a1

191. Ab00052452-08

192. Ab00052452-09

193. Ab00052452_10

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

195. 157594-ep2277507a1

196. 157594-ep2286795a1

197. 179002-ep2280013a1

198. 689c034

199. Brd-k37890730-001-09-4

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

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

202. 4-ethyl-4-hydroxy-1h-pyrano-[3[,4[:6,7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione

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

204. (19s)-19-ethyl-19-hydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0(2),(1)(1).0?,?.0(1)?,(2)?]henicosa-1(21),2,4,6,8,10,15(20)-heptaene-14,18-dione

205. 1h-pyrano[3',7]indolizino[1,2-b]quinoline-3,14(4h,12h)-dione, 4-ethyl-4-hydroxy-, (s)-

206. 4(s)-ethyl-4-hydroxy-1h-pyrano-[3',4':6,7]indolizino[1,2-b]quinoline-3,14 (4h,12h)-dione

207. 4-ethyl-4-hydroxy-(4s)-3,4,12,14-tetrahydro-1h-pyrano[3'',4'':6,7]indolizino[1,2-b]quinoline-3,14-dione

208. 4-ethyl-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione (camptothecin Or Cpt)

209. 4-ethyl-4-hydroxy-1,12-dihydro-4h-2-oxa-6,12a-diaza-dibenzo[b,h]fluorene-3,13-dione (camptothecin)

210. 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 Weight 348.358 g/mol
Molecular Formula C20H16N2O4
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count5
Rotatable Bond Count1
Exact Mass348.111 g/mol
Monoisotopic Mass348.111 g/mol
Topological Polar Surface Area79.7 A^2
Heavy Atom Count26
Formal Charge0
Complexity742
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

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.


Camptothecin is an alkaloid isolated from the Chinese tree Camptotheca acuminata, with antineoplastic activity. During the S phase of the cell cycle, camptothecin selectively stabilizes topoisomerase I-DNA covalent complexes, thereby inhibiting religation of topoisomerase I-mediated single-strand DNA breaks and producing potentially lethal double-strand DNA breaks when encountered by the DNA replication machinery. (NCI)


5.2 MeSH Pharmacological Classification

Topoisomerase I Inhibitors

Compounds that inhibit the activity of DNA TOPOISOMERASE I.


Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity.


5.3 Mechanism of Action

Camptothecin binds to the topoisomerase I and DNA complex (the covalent complex) resulting in a ternary complex, and thereby stabilizing it. This prevents DNA relegation and therefore causes DNA damage which results in apoptosis.


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