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Merck

I1406

Irinotecan hydrochloride

powder, ≥97% (HPLC)

Sinónimos:

(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

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Acerca de este artículo

Fórmula empírica (notación de Hill):
C33H38N4O6 · HCl
Número CAS:
Peso molecular:
623.14
UNSPSC Code:
12352204
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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Nombre del producto

Irinotecan hydrochloride, topoisomerase inhibitor

SMILES string

Cl.CCc1c2CN3C(=O)C4=C(C=C3c2nc5ccc(OC(=O)N6CCC(CC6)N7CCCCC7)cc15)[C@@](O)(CC)C(=O)OC4

InChI key

GURKHSYORGJETM-WAQYZQTGSA-N

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

biological source

plant (Fructus camptothecae)

assay

≥97% (HPLC)

form

powder

solubility

DMSO: 50 mg/mL

storage temp.

2-8°C

Gene Information

human ... TOP1(7150)

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).
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.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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Visite la Librería de documentos

Francesco Crea et al.
Molecular cancer therapeutics, 8(7), 1964-1973 (2009-06-18)
Irinotecan is a topoisomerase-I (Top-I) inhibitor used for the treatment of colorectal cancer. DNA demethylating agents, including 5-azacytidine (5-aza), display synergistic antitumor activity with several chemotherapy drugs. 5-Aza may enhance irinotecan cytotoxicity by at least one of the following mechanisms:
Re-examining HSPC1 inhibitors
Lee S, et al.
Cell Stress & Chaperones, 22(2), 293-306 (2017)
Appendiceal Cancer Patient-Specific Tumor Organoid Model for Predicting Chemotherapy Efficacy Prior to Initiation of Treatment: A Feasibility Study
Votanopoulos K, et al.
Annals of Surgical Oncology, 26(1), 139-147 (2019)
Olivia Jones et al.
Scientific reports, 11(1), 8967-8967 (2021-04-28)
Cholangiocarcinoma (CCA) is a rare biliary tract cancer with a low five-year survival rate and high recurrence rate after surgical resection. Currently treatment approaches include systemic chemotherapeutics such as FOLFIRINOX, a chemotherapy regimen is a possible treatment for severe CCA
Hiroshi Kimura et al.
Journal of laboratory automation, 20(3), 265-273 (2014-11-12)
Testing of drug effects and cytotoxicity by using cultured cells has been widely performed as an alternative to animal testing. However, the estimation of pharmacokinetics by conventional cell-based assay methods is difficult because of the inability to evaluate multiorgan effects.

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