Irinotecan

Irinotecan

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Irinotecan
Category Antineoplastic
Catalog number BBF-05861
CAS 97682-44-5
Molecular Weight 586.68
Molecular Formula C33H38N4O6
Purity ≥98%

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Description

Irinotecan is a topoisomerase I inhibitor for LoVo cells and HT-29 cells with IC50 of 15.8 μM and 5.17 μM, respectively. It is used for the treatment of colon and rectum cancers. It binds to topoisomerase I-DNA complex, preventing religation of the DNA strand and leading to double-strand DNA breakage and cell death.

Specification

Related CAS 100286-90-6 (hydrochloride) 136572-09-3 (Hydrochloride Trihydrate)
Synonyms Irinophore C; Irinotecan lactone; Irinotecan mylan; Onivyde; 1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline, [1,4'-Bipiperidine]-1'-carboxylic Acid deriv.; (S)-[1,4'-Bipiperidine]-1'-carboxylic Acid 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; Camptosar; Irinotecanum; CPT-11; CPT 11; CPT11; (+)-Irinotecan
Storage Store at 2-8°C
IUPAC Name [(19S)-10,19-diethyl-19-hydroxy-14,18-dioxo-17-oxa-3,13-diazapentacyclo[11.8.0.02,11.04,9.015,20]henicosa-1(21),2,4(9),5,7,10,15(20)-heptaen-7-yl] 4-piperidin-1-ylpiperidine-1-carboxylate
Canonical SMILES CCC1=C2CN3C(=CC4=C(C3=O)COC(=O)C4(CC)O)C2=NC5=C1C=C(C=C5)OC(=O)N6CCC(CC6)N7CCCCC7
InChI InChI=1S/C33H38N4O6/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/t33-/m0/s1
InChI Key UWKQSNNFCGGAFS-XIFFEERXSA-N

Properties

Appearance White to Brown Solid
Application Topoisomerase I Inhibitors
Antibiotic Activity Spectrum Neoplastics (Tumor)
Boiling Point 873.4±65.0°C (Predicted)
Melting Point >160°C (dec.)
Density 1.40±0.1 g/cm3 (Predicted)
Solubility Soluble in Acetonitrile (Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Slightly)

Reference Reading

1.Pharmacogenetics of irinotecan, doxorubicin and docetaxel transporters in Asian and Caucasian cancer patients: a comparative review.
Chen S;Sutiman N;Zhang CZ;Yu Y;Lam S;Khor CC;Chowbay B Drug Metab Rev. 2016 Nov;48(4):502-540.
Drug efflux and influx transporters play critical roles in regulating the cellular drug disposition and modulating the pharmacokinetics and pharmacodynamics of anti-cancer agents, which may potentially alter treatment outcomes. The efficiency of drug transport is often dependent on the expression and activity of these membrane-bound proteins, factors which have been shown to be regulated by genes that are known to be highly polymorphic in different ethnic populations. The role of drug transporters becomes even more critical for anti-cancer agents due to the narrow therapeutic windows that separate treatment response and toxicities for these agents. Moreover, high inter-individual variability in the disposition of anti-cancer agents often results in variable treatment outcomes among patients receiving standard doses of the same drug. Such variability has been attributed at least in part to polymorphisms in genes encoding drug-metabolizing enzymes and transporter. To date, numerous pharmacogenetic studies have investigated the associations between variants in the ABC and SLC transporters genes with drug disposition, treatment outcomes and drug-induced toxicities. However, the strengths of these associations and their clinical relevance in different ethnic populations have not been critically examined.
2.Evaluation of [
Rapic S;Vangestel C;Verhaeghe J;Thomae D;Pauwels P;Van den Wyngaert T;Staelens S;Stroobants S Mol Imaging Biol. 2017 Feb;19(1):109-119. doi: 10.1007/s11307-016-0974-5.
PURPOSE: ;In oncology, positron emission tomography imaging using dedicated tracers as biomarkers may assist in early evaluation of therapy efficacy. Using 3'-deoxy-3'-[;18;F]fluorothymidine ([;18;F]FLT), we investigated the early effects of chemotherapeutic treatment on cancer cell proliferation in a BRAF-mutated colorectal cancer xenograft model.;PROCEDURES: ;Colo205 subcutaneously inoculated animals underwent 90-min dynamic imaging before and 24 h after treatment with vehicle (control), cetuximab (resistant) or irinotecan (sensitive). Total distribution volume was quantified from dynamic data, and standardized uptake values as well as tumor-to-blood ratios were calculated from static images averaged over the last 20 min. In vivo imaging data was correlated with ex vivo proliferation and thymidine metabolism proteins.;RESULTS: ;All imaging parameters showed a significant post-treatment decrease from [;18;F]FLT baseline uptake for the irinotecan group (p ≤ 0.001) as compared with the cetuximab and vehicle group and correlated strongly with each other (p ≤ 0.0001). In vivo data were in agreement with Ki67 staining, showing a significantly lower percentage of Ki67-positive cells in the irinotecan group as compared with other groups (p ≤ 0.
3.Surface contamination with ten antineoplastic drugs in 83 Canadian centers.
Chauchat L;Tanguay C;Caron NJ;Gagné S;Labrèche F;Bussières JF J Oncol Pharm Pract. 2018 Jan 1:1078155218773862. doi: 10.1177/1078155218773862. [Epub ahead of print]
Purpose The aim of this study was to monitor environmental contamination by 10 antineoplastic drugs in Canadian oncology pharmacy and patient care areas. The secondary objective was to explore the impact of factors that may explain contamination. Methods Twelve standardized sites were sampled in each center (six in the pharmacy and six in patient care areas). Each sample was prepared to allow quantification of seven antineoplastic drugs (cyclophosphamide, ifosfamide, methotrexate, cytarabine, gemcitabine, 5-fluorouracil, irinotecan) by UPLC-MS-MS. Docetaxel, paclitaxel and vinorelbine were also detected, but not quantified due to sensibility limitations. The impact of some factors was evaluated compared with a Kolmogorov-Smirnov test for independent samples. Results Eighty-three Canadian centers were recruited in 2017. A total of 953 surfaces were sampled, 495 in pharmacy and 458 in patient care areas. Cyclophosphamide was most often found on surfaces (36% of samples positive, 75th percentile 0.0040 ng/cm;2;). The arm rest (81.7% of samples positive for at least one antineoplastic drug), the front grille inside the hood (78.3%) and the floor in front of the hood (61.4%) were more frequently contaminated.

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