(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate trihydrate hydrochloride

• ChemBase编号: 72905
• 分子式: C33H45ClN4O9
• 平均质量: 677.1848
• 单一同位素质量: 676.28750672
• SMILES: C1CCN(CC1)C1CCN(CC1)C(=O)Oc1ccc2c(c1)c(c1c(n2)c2n(C1)c(=O)c1c(c2)[C@](C(=O)OC1)(CC)O)CC.O.O.O.Cl
• Canonical SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)CC)OC(=O)N1CCC(CC1)N1CCCCC1.O.O.O.Cl
• InChI: InChI=1S/C33H38N4O6.ClH.3H2O/c1-3-22-23-16-21(43-32(40)36-14-10-20(11-15-36)35-12-6-5-7-13-35)8-9-27(23)34-29-24(22)18-37-28(29)17-26-25(30(37)38)19-42-31(39)33(26,41)4-2;;;;/h8-9,16-17,20,41H,3-7,10-15,18-19H2,1-2H3;1H;3*1H2/t33-;;;;/m0..../s1
• InChIKey: KLEAIHJJLUAXIQ-JDRGBKBRSA-N

名称和登记号

名称

• IUPAC标准名: (19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate trihydrate hydrochloride; (19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate trihydrate hydrochloride
• IUPAC传统名: (19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate trihydrate hydrochloride; (19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.0^2,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2,4,6,8,10,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate trihydrate hydrochloride
• 别名: CPT 11; Camptosar; Campto; Irinotecan; Irinotecan Hcl Trihydrate; Irinotecan hydrochloride trihydrate

登记号

• CAS号: 136572-09-3
• MDL号: MFCD01765731
• PubChem SID: 162037825
• PubChem CID: 60837

理论计算性质

• Acid pKa: 11.713039
• 质子受体: 6
• 质子供体: 1
• LogD (pH = 5.5): -0.6070732
• LogD (pH = 7.4): 0.7157881
• Log P: 2.776473
• 摩尔折射率: 161.3303 cm^3
• 极化性: 63.005684 Å^3
• 极化表面积: 112.51 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: false

分子性质

安全信息

• 保存条件: -20°C

药理学性质

• 作用靶点: Topoisomerase

产品相关信息

• 纯度: 95+%
• 成盐信息: hydrate

详细说明

Selleck Chemicals - S2217

Biological Activity:
Irinotecan hydrochloride trihydrate is a hydrochloride trihydrate of irinotecan (Camptosar, Campto, CPT-11) which is a topoisomerase I inhibitor with IC50 of 15.8 and 5.17 μM for LoVo cells and HT-29 cells, respectively. As a Topo I inhibitor, Irinotecan (Camptosar, Campto, CPT-11) inhibits the religation step of the enzyme’s normal action, inducing single stranded DNA breaks. These single stranded breaks are then converted to double-stranded breaks within the course of DNA replication which is reported to induce apoptosis or repair mechanisms as a result. Irinotecan is activated by esterases to produce the activated metabolite and has been reported to be associated with cleavage of poly (ADP-ribose) polymerase (PARP) in colon carcinoma cells. Irinotecan’s active metabolite is additionally noted to activate p53 in the Huh7 cell line. [1][2][3]

参考文献

• Hofmann C et al. Anticancer Res. 2005 Mar-Apr;25(2A):795-804.