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I1406

Sigma-Aldrich

Irinotecan hydrochloride

topoisomerase inhibitor

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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:
Molecular Weight:
623.14
MDL number:
PubChem Substance ID:
NACRES:
NA.77

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)

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This Item
1347609C99111347642
Irinotecan hydrochloride topoisomerase inhibitor

I1406

Irinotecan hydrochloride

USP

1347609

Irinotecan hydrochloride

(S)-(+)-Camptothecin ≥90% (HPLC), powder

C9911

(S)-(+)-Camptothecin

USP

1347642

Irinotecan Related Compound C

biological source

plant (Fructus camptothecae)

biological source

-

biological source

-

biological source

-

Gene Information

human ... TOP1(7150)

Gene Information

-

Gene Information

human ... TOP1(7150)
mouse ... Prkca(18750)
rat ... Sstr2(54305)

Gene Information

-

form

powder

form

-

form

powder

form

-

solubility

DMSO: 50 mg/mL

solubility

-

solubility

chloroform/methanol (4:1): 5 mg/mL

solubility

-

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

storage temp.

2-8°C

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.

pictograms

Exclamation mark

signalword

Warning

hcodes

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves


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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)
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
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)
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.

Articles

Quinolones are a key group of antibiotics that interfere with DNA synthesis by inhibiting topoisomerase, most frequently topoisomerase II (DNA gyrase), an enzyme involved in DNA replication.

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