7-Ethyl-10-hydroxy camptothecin, (rac)-
基本情報
- CAS
130144-34-2- 標準SMILES
CCc1c2c(nc3ccc(O)cc13)-c1cc3c(c(=O)n1C2)COC(=O)C3(O)CC- InChIKey
FJHBVJOVLFPMQE-UHFFFAOYSA-N- 分子式
- C22H20N2O5
- 平均分子量
- 392.4 g/mol
- 単同位体質量
- 392.13722174
概要
LSM-6189 is a pyranoindolizinoquinoline.
名称と識別子
- 優先名称
- 7-Ethyl-10-hydroxy camptothecin, (rac)-
- IUPAC
- 10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione
- 英語名
- 7-Ethyl-10-hydroxycamptothecin
- 分子式
- C22H20N2O5
- 分子量
- 392.41
名称と別名
130144-34-24,11-Diethyl-4,9-dihydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dioneA8E798PHC2DTXSID708610897-Ethyl-10-hydroxy camptothecin, (rac)-4,11-Diethyl-4,9-dihydroxy-1H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H,12H)-dioneRefChem:1074425DTXCID5020962210,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaene-14,18-dione10,19-diethyl-7,19-dihydroxy-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaene-14,18-dione4,11-DIETHYL-4,9-DIHYDROXY-1,12-DIHYDRO-14H-PYRANO[3',4':6,7]INDOLIZINO[1,2-B]QUINOLINE-3,14(4H)-DIONE1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione, 4,11-diethyl-4,9-dihydroxy-
名称をさらに表示
7-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-
113015-38-6Camptothecin Impurity 21CHEMBL10206SCHEMBL733477orb3181515SCHEMBL13420265SCHEMBL29787648CHEBI:94969
データベース識別子
- CAS
130144-34-2- PubChem CID
- 4014291
- DTXSID
DTXSID70861089- ChEMBL
CHEMBL10206- ChEBI
CHEBI:94969- UNII
- A8E798PHC2
- Nikkaji
- J360.578G
物性
構造計算による物性
- XLogP
- 1.4
- 極性表面積
- 100 Ų
- 水素結合供与体数
- 2
- 水素結合受容体数
- 6
- 回転可能結合数
- 2
- 重原子数
- 29
- 形式電荷
- 0
- 複雑度
- 820
物理化学的性質
- 沸点
- 810.3 · 810.3±65.0 °C(Predicted)
- 比重(密度)
- 1.51 · 1.51
- 酸解離定数(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
化学と産業
薬理情報
Metabolism/Metabolites
7-ethyl-10-hydroxycamptothecin has known human metabolites that include (2S,3S,4S,5R)-6-[(10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl)oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid.
応用分野
説明7-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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