(19S)-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(11),3,5,7,9,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate hydrochloride

• ChemBase编号: 155676
• 分子式: C33H39ClN4O6
• 平均质量: 623.13896
• 单一同位素质量: 622.25581267
• SMILES: CCc1c2cc(ccc2nc2c1Cn1c2cc2c(c1=O)COC(=O)[C@@]2(CC)O)OC(=O)N1CCC(CC1)N1CCCCC1.Cl
• Canonical SMILES: CC[C@@]1(O)C(=O)OCc2c1cc1c3nc4ccc(cc4c(c3Cn1c2=O)CC)OC(=O)N1CCC(CC1)N1CCCCC1.Cl
• InChI: InChI=1S/C33H38N4O6.ClH/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/t33-;/m0./s1
• InChIKey: GURKHSYORGJETM-WAQYZQTGSA-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,^1^1.0^4,^9.0^1^5,^2^0]henicosa-1(21),2(11),3,5,7,9,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate 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 hydrochloride
• IUPAC传统名: irinotecan 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 hydrochloride
• 别名: Irinotecan 盐酸盐; (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(11),3,5,7,9,15(20)-heptaen-7-yl 4-(piperidin-1-yl)piperidine-1-carboxylate hyd rochloride; (S)-4,11-diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3′,4′:6,7]indolizino[1,2-b]quinolin-9-yl ester; CPT-11; [1,4′-Bipiperidine]-1′-carboxylic acid; Irinotecan hydrochloride; [1,4’-Bipiperidine]-1’-carboxylic Acid (4S)-4,11-Diethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-1H-pyrano[3’,4’:6,7]indolizino[1,2-b]quinolin-9-yl Ester Hydrochloride Trihydrate; Campto; Camptosar; CPT11,; Irinotecan Hydrochloride Trihydrate

登记号

• CAS号: 136572-09-3; 100286-90-6
• MDL号: MFCD01862255
• PubChem SID: 162249814
• PubChem CID: 74990

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

理化性质

• 溶解度: Methanol; Water
• 外观: Light Yellow Solid
• 熔点: >245°C (dec.)
• 疏水性(logP): 2.728

安全信息

• 保存条件: -20°C Freezer
• RTECS编号: DW1061000
• 欧盟危险性物质标志: 有害性(Harmful) (Xn)
• 德国WGK号: 3
• 危险公开号: 22
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H302
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... TOP1(7150)

产品相关信息

• 纯度: 95%
• Empirical Formula (Hill Notation): C33H38N4O6 · HCl

详细说明

Sigma Aldrich - I1406

Biochem/physiol Actions
The anticancer agent, irinotecan, is a prodrug that is converted by tissue carboxylesterase to 7-ethyl-10-hydroxycamptothecin (SN-38), a potent inhibitor of DNA topoisomerase I. Its action is terminated by glucuronidation by UDP glucuronosyl transferase 1A1 (UGT1A1). It proves useful in radiation treatment of tumors by sensitizing tissue to radiation damage.1
The anticancer agent, irinotecan, is a prodrug that is converted by tissue carboxylesterase to 7-ethyl-10-hydroxycamptothecin (SN-38), a potent inhibitor of DNA topoisomerase I. Its action is terminated by glucuronidation by UDP glucuronosyl transferase.

Toronto Research Chemicals - I767500

A DNA topoisomerase inhibitor.

参考文献

• Kunimoto, T., et al.: Cancer Res., 47, 5944 (1987)
• Shimada, Y., et al.: J. Clin. Oncol., 11, 909 (1993)