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I1406

Sigma-Aldrich

Irinotecan hydrochloride

powder, ≥97% (HPLC)

Synonyme(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

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About This Item

Formule empirique (notation de Hill):
C33H38N4O6 · HCl
Numéro CAS:
100286-90-6
Poids moléculaire :
623.14
Numéro MDL:
MFCD01862255
Code UNSPSC :
12352204
ID de substance PubChem :
329815350
Nomenclature NACRES :
NA.77

product name

Irinotecan hydrochloride, topoisomerase inhibitor

Source biologique

plant (Fructus camptothecae)

Pureté

≥97% (HPLC)

Forme

powder

Solubilité

DMSO: 50 mg/mL

Température de stockage

2-8°C

Chaîne 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

Clé InChI

GURKHSYORGJETM-WAQYZQTGSA-N

Informations sur le gène

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.

Actions biochimiques/physiologiques

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.

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Point d'éclair (°F)

Not applicable

Point d'éclair (°C)

Not applicable

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

Recherchez un Certificats d'analyse (COA) en saisissant le numéro de lot du produit. Les numéros de lot figurent sur l'étiquette du produit après les mots "Lot" ou "Batch".

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Consulter la Bibliothèque de documents

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)
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.
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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