Irinotecan

Modify Date: 2024-01-02 12:03:09

Irinotecan Structure
Irinotecan structure
 Common Name Irinotecan
CAS Number 97682-44-5 Molecular Weight 586.678
Density 1.4±0.1 g/cm3 Boiling Point 873.4±65.0 °C at 760 mmHg
Molecular Formula C33H38N4O6 Melting Point N/A
MSDS N/A Flash Point 482.0±34.3 °C

 Use of Irinotecan


Irinotecan is a water soluble topoisomerase I inhibitor, preventing religation of the DNA strand by binding to topoisomerase I-DNA complex.

 Names

Name Irinotecan
Synonym More Synonyms

 Irinotecan Biological Activity

Description Irinotecan is a water soluble topoisomerase I inhibitor, preventing religation of the DNA strand by binding to topoisomerase I-DNA complex.
Related Catalog
Target

Topoisomerase I
In Vitro Irinotecan is a topoisomerase I inhibitor. Irinotecan inhibits the growth of LoVo and HT-29 cells, with IC50s of 15.8 ± 5.1 and 5.17 ± 1.4 μM, respectively, and induces similar amounts of cleavable complexes in both in LoVo and HT-29 cells[2]. Irinotecan suppresses the proliferation of human umbilical vein endothelial cells (HUVEC), with an IC50 of 1.3 μM[3].
In Vivo Irinotecan (CPT-11, 5 mg/kg) significantly inhibits the growth of tumors by intratumoral injection daily for 5 days, on two consecutive weeks in rats, and such effects also occur via continuous intraperitoneal infusion by osmotic minipump into mice. However, Irinotecan (10 mg/kg) shows no effect on the growth of tumor by i.p[1]. Irinotecan (CPT-11, 100-300 mg/kg, i.p.) apparently suppresses tumor growth of HT-29 xenografts in athymic female mice by day 21. The two groups of Irinotecan (125 mg/kg) plus TSP-1 (10 mg/kg per day) or Irinotecan (150 mg/kg) in combination TSP-1 (20 mg/kg per day) are nearly equally effective and inhibit tumor growth 84% and 89%, respectively, and both are more effective than Irinotecan alone at doses of 250 and 300 mg/kg[3].
Cell Assay Exponentially growing cells are seeded in 20 cm2 dishes with an optimal cell number for each cell line (20,000 for LoVo cells, 100,000 for HT-29 cells). They are treated 2 days later with increasing concentrations of irinotecan or SN-38 for one cell doubling time (24 h for LoVo cells, 40 h for HT-29 cells). After washing with 0.15 M NaCl, the cells are further grown for two doubling times in normal medium, detached from the support with trypsin-EDTA and counted in a hemocytometer. The IC50 values are then estimated as the drug concentrations responsible for 50% growth inhibition as compared with cells incubated without drug[2].
Animal Admin Irinotecan has been administered by intratumoral injection at 0.1 cc volume of the appropriate solution, for a doses of 5 mg/kg daily for 5 days, on two consecutive weeks, followed by a 7-days rest period, referred to as one cycle of therapy. Rats receive three cycles over a period of 8 weeks. Control animals receive 0.1 cc of sterile 0.9% sodium chloride solution by intratumoral injection in the same rule of administration as that of animals of group II[1].
References

[1]. Morales C, et al. Antitumoral effect of irinotecan (CPT-11) on an experimental model of malignant neuroectodermal tumor. J Neurooncol. 2002 Feb;56(3):219-26.

[2]. Pavillard V, et al. Determinants of the cytotoxicity of irinotecan in two human colorectal tumor cell lines. Cancer Chemother Pharmacol. 2002 Apr;49(4):329-35. Epub 2002 Jan 30.

[3]. Allegrini G, et al. Thrombospondin-1 plus irinotecan: a novel antiangiogenic-chemotherapeutic combination that inhibits the growth of advanced human colon tumor xenografts in mice. Cancer Chemother Pharmacol. 2004 Mar;53(3):261-6. Epub 2003 Dec 5.

[4]. Dela Cruz FS, et al. A case study of an integrative genomic and experimental therapeutic approach for rare tumors: identification of vulnerabilities in a pediatric poorly differentiated carcinoma. Genome Med. 2016 Oct 31;8(1):116.

[5]. Huang MY, et al. Chemotherapeutic agent CPT-11 eliminates peritoneal resident macrophages by inducing apoptosis. Apoptosis. 2016 Feb;21(2):130-42.

 Chemical & Physical Properties

Density 1.4±0.1 g/cm3
Boiling Point 873.4±65.0 °C at 760 mmHg
Molecular Formula C33H38N4O6
Molecular Weight 586.678
Flash Point 482.0±34.3 °C
Exact Mass 586.279114
PSA 114.20000
LogP 4.35
Vapour Pressure 0.0±0.3 mmHg at 25°C
Index of Refraction 1.689
Storage condition 2-8°C

 Safety Information

Hazard Codes Xn
Risk Phrases 22
RTECS DW1061000

 Synthetic Route

 Synonyms

Irinotecan
7-ethoxyxanthone-3-carboxylic acid
Campto
(+)-Irinotecan
9H-Xanthene-3-carboxylic acid,7-ethoxy-9-oxo
MFCD01862255
(4S)-4,11-Diethyl-4-hydroxy-3,14-dioxo-3,4,12,14-tetrahydro-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinolin-9-yl 1,4'-bipiperidine-1'-carboxylate
[1,4'-Bipiperidine]-1'-carboxylic acid, (4S)-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
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Related Compounds: More...
irinotecan
130144-33-1
Irinotecan-d10
718613-28-6
Irinotecan Hcl
100286-90-6
8-Ethyl Irinotecan
947687-02-7
12-Hydroxy Irinotecan
185336-12-3
Irinotecan Impurity 8
936348-90-2
Irinotecan Impurity 3
200619-21-2
Irinotecan Impurity 1
116269-53-5
Irinotecan Impurity 7
206182-51-6
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