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I1406

Sigma-Aldrich

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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About This Item

Fórmula empírica (notación de Hill):
C33H38N4O6 · HCl
Número de CAS:
100286-90-6
Peso molecular:
623.14
Número MDL:
MFCD01862255
Código UNSPSC:
12352204
ID de la sustancia en PubChem:
329815350
NACRES:
NA.77

Nombre del producto

Irinotecan hydrochloride, topoisomerase inhibitor

origen biológico

plant (Fructus camptothecae)

Ensayo

≥97% (HPLC)

Formulario

powder

solubilidad

DMSO: 50 mg/mL

temp. de almacenamiento

2-8°C

cadena SMILES

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

Clave InChI

GURKHSYORGJETM-WAQYZQTGSA-N

Información sobre el gen

human ... TOP1(7150)

Aplicación

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.

Acciones bioquímicas o fisiológicas

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.

Pictogramas

Exclamation mark
GHS07

Palabra de señalización

Warning

Frases de peligro

H302

Clasificaciones de peligro

Acute Tox. 4 Oral

Código de clase de almacenamiento

11 - Combustible Solids

Clase de riesgo para el agua (WGK)

WGK 3

Punto de inflamabilidad (°F)

Not applicable

Punto de inflamabilidad (°C)

Not applicable

Equipo de protección personal

dust mask type N95 (US), Eyeshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
WXBF5520V
WXBF1756V
WXBD4657V
WXBD5905V
WXBD0667V

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Visite la Librería de documentos

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)
Re-examining HSPC1 inhibitors
Lee S, et al.
Cell Stress & Chaperones, 22(2), 293-306 (2017)
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:
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.
T C Chang et al.
Cancer chemotherapy and pharmacology, 75(3), 579-586 (2015-01-13)
To define the dose-limiting toxicity (DLT), maximum tolerated dose (MTD) and pharmacokinetics (PK) of PEP02, a novel liposome-encapsulated irinotecan, in patients with advanced refractory solid tumors. Patients were enrolled in cohorts of one to three to receive escalating dose of
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