4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
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Grundinformationen
- CAS
130144-34-2- Standard-SMILES
CCc1c2c(nc3ccc(O)cc13)-c1cc3c(c(=O)n1C2)COC(=O)C3(O)CC- InChIKey
FJHBVJOVLFPMQE-UHFFFAOYSA-N- Summenformel
- C22H20N2O5
- Durchschnittliche Molmasse
- 392,411 g/mol
- Monoisotopische Masse
- 392,13722174
Namen und Bezeichner
- Bevorzugter Name
- 4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
- IUPAC
- 4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
- Englischer Name
- 7-Ethyl-10-hydroxycamptothecin
- Summenformel
- C22H20N2O5
- Molmasse
- 392.41
Namen und Synonyme
Camptothecin Impurity 217-Ethyl-10-hydroxycamptothecin(rac)-7-Ethyl-10-Hydroxy camptothecinrac-4,11-Diethyl-9-hydroxycamptothecin7-Ethyl-10-hydroxycamptothecin, racemic7-Ethyl-10-Hydroxycamptothecin7-Ethyl-10-Hydroxycamptothecin1H-Pyrano[3,4:6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy-4,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
Datenbank-Bezeichner
- CAS
130144-34-2- PubChem CID
- 4014291
- DTXSID
DTXSID70861089- ChEMBL
CHEMBL10206- ChEBI
CHEBI:94969- UNII
- A8E798PHC2
- Nikkaji
- J360.578G
Eigenschaften
Physikochemische Eigenschaften
- Siedepunkt
- 810.3 · 810.3±65.0 °C(Predicted)
- Dichte
- 1.51 · 1.51
- pka
- 9.13 · 9.13±0.40(Predicted)
- InChI
- InChI=1S/C22H20N2O5/c1-3-12-13-7-11(25)5-6-17(13)23-19-14(12)9-24-18(19)8-16-15(20(24)26)10-29-21(27)22(16,28)4-2/h5-8,25,28H,3-4,9-10H2,1-2H3
- InChIKey
- FJHBVJOVLFPMQE-UHFFFAOYSA-N
- SMILES
- N1C2C(=CC(O)=CC=2)C(CC)=C2CN3C(C=12)=CC1C(CC)(O)C(=O)OCC=1C3=O
Chemie und Industrie
Anwendungen
Beschreibung7-Ethyl-10-hydroxycamptothecin: a potent topoisomerase I inhibitor7-Ethyl-10-hydroxycamptothecin (SN-38), as a highly active topoisomerase (Topo) I inhibitor, is the active metabolic product of its prodrug irinotecan (CPT-11) commercially available as Camptosar. By combining with the Topo I-DNA covalent conjugate, the camptothecin analogue forms a ternary complex that blocks the repolymerization of the DNA strands during their replication, eventually leading to the cell apoptosis. Although SN-38 is about 100- to 1000-fold more potent than irinotecan, its clinical application is limited by its poor solubility and nonspecific toxicity[1].
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