(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 ID: 155676
• Molecular Formular: C33H39ClN4O6
• Molecular Mass: 623.13896
• Monoisotopic Mass: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (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 Traditional name: 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
• Synonyms: (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; Irinotecan 盐酸盐

Database IDs

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

CALCULATED PROPERTIES

• Acid pKa: 11.713039
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -0.6070732
• LogD (pH = 7.4): 0.7157881
• Log P: 2.776473
• Molar Refractivity: 161.3303 cm^3
• Polarizability: 63.005684 Å^3
• Polar Surface Area: 112.51 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Light Yellow Solid
• Melting Point: >245°C (dec.)
• Hydrophobicity(logP): 2.728

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: DW1061000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... TOP1(7150)

Product Information

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

DETAILS

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.

REFERENCES

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