I1406

Irinotecan hydrochloride

powder, ≥97% (HPLC)

• Synonym(s): (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
• Empirical Formula (Hill Notation): C₃₃H₃₈N₄O₆ · HCl
• CAS Number: 100286-90-6
• Molecular Weight: 623.14
• MDL number: MFCD01862255
• UNSPSC Code: 12352204
• PubChem Substance ID: 329815350
• NACRES: NA.77

Properties

• product name: Irinotecan hydrochloride, topoisomerase inhibitor
• biological source: plant (Fructus camptothecae)
• Assay: ≥97% (HPLC)
• form: powder
• solubility: DMSO: 50 mg/mL
• storage temp.: 2-8°C
• SMILES string: Cl.CCc1c2CN3C(=O)C4=C(C=C3c2nc5ccc(OC(=O)N6CCC(CC6)N7CCCCC7)cc15)[C@@](O)(CC)C(=O)OC4
• 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
• InChI key: GURKHSYORGJETM-WAQYZQTGSA-N
• Gene Information: human ... TOP1(7150)

Description

Application

Irinotecan hydrochloride has been used:

• in combination with 5-fluorouracil for screening growth inhibitory functionality in MDA-MB-231 breast cancer cells.
• in chemosensitivity screening of high-grade appendiceal (HGA) and low-grade appendiceal (LGA) organoids.
• as a chemotherapeutic agent in the cytotoxicity studies in combination with heat shock proteins inhibitors (HPSC1) in HT29 colon cancer cells.

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.

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.

Safety Information

• Pictograms: GHS07
• Signal Word: Warning
• Hazard Statements: H302
• Hazard Classifications: Acute Tox. 4 Oral
• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves