Irinotecan Chemical Properties

Melting point:

222-223°

Boiling point:

873.4±65.0 °C(Predicted)

Density 

1.40±0.1 g/cm3(Predicted)

storage temp. 

Sealed in dry,2-8°C

solubility 

Acetonitrile (Slightly, Heated, Sonicated), DMSO (Slightly), Methanol (Slightly)

pka

11.20±0.20(Predicted)

form 

Solid

color 

White to Brown

CAS DataBase Reference

97682-44-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xn

Risk Statements 

22

RTECS 

DW1061000

Hazardous Substances Data

97682-44-5(Hazardous Substances Data)

Irinotecan Usage And Synthesis

Uses

(+)-Irinotecan is a Topo I inhibitor.

Uses

Irinotecan is a topoisomerase I inhibitor for LoVo cells and HT-29 cells with IC50 of 15.8 μM and 5.17 μM, respectively

Definition

ChEBI: A member of the class of pyranoindolizinoquinolines that is the carbamate ester obtained by formal condensation of the carboxy group of [1,4'-bipiperidine]-1'-carboxylic acid with the phenolic hydroxy group of (4S)-4,11-diethyl-4,9-dihydro y-1H-pyrano[3',4':6,7]indolizino[1,2- hydrochloride]quinoline-3,14-dione. Used (in the form of its hydrochloride salt trihydrate) in combination with fluorouracil and leucovorin, for the treatment of patients with metastatic adenocarcino a of the pancreas after disease progression following gemcitabine-based therapy. It is converted via hydrolysis of the carbamate linkage to its active metabolite, SN-38, which is ~1000 times more active.

brand name

Camptosar (Pharmacia &Upjohn) .

Biological Activity

irinotecan (cpt-11), a prodrug for treating metastatic colorectal cancer, is a topoisomerase i inhibitor for lovo cells and ht-29 cells with ic50 of 15.8 μm and 5.17 μm, respectively [1].in vivo, irinotecan is converted to sn-38, its most active metabolite, by carboxylesterase converting enzyme (cce) [2].

in vitro

irinotecan induced similar amounts of cleavable complexes in lovocells and ht-29 cell lines with the ic50 of 15.8 μm and 5.17 μm, respectively [1].after addition of 157 mm irinotecan to plasma, sn-38 concentration showed linear increase during the first 60-min period, followed by a plateau.in the first 60 min, mean and standard deviation of the conversion rate were 515.9 ± 50.1 pmol/ml/h (n = 69), with a coefficient of variation of 0.097 [2]. irinotecan (cpt-11) was significantly more active in sclc than in nsclccelllines (p = 0.0036). ce activity appeared to be associated with higher sensitivity to cpt-11 in human lung cancercelllines and may partly explain the difference in the in vitro sensitivity to cpt-11 between sclc and nsclccells [3].in vitro, the sensitivity to cpt-11 and sn-38 was highest in ls174t and colo 320cells, intermediate in sw1398cellsand lowest in colo 205 and widr cells. the activity of sn-38 was 130 to 570 times than cpt-11[4].

in vivo

in colo 320 xenografts, irinotecan induced a maximum growth inhibition of 92% [4].a single dose of irinotecan significantly increased amounts of topoisomerase i covalently bound to dna in stomach, duodenum, colon and liver. concomitantly, the irinotecan-treated group exihibited significantly higher amounts of dna strand breaks in colon mucosa cells compared to the control group [5].

References

[1]. tobin p, clarke s, seale j p, et al. the in vitro metabolism of irinotecan (cpt‐11) by carboxylesterase and β‐glucuronidase in human colorectal tumours[j]. british journal of clinical pharmacology, 2006, 62(1): 122-129.
[2]. shingyoji m, takiguchi y, watanabe‐uruma r, et al. in vitro conversion of irinotecan to sn‐38 in human plasma[j]. cancer science, 2004, 95(6): 537-540.
[3]. van ark-otte j, kedde m a, van der vijgh w j, et al. determinants of cpt-11 and sn-38 activities in human lung cancer cells[j]. british journal of cancer, 1998, 77(12): 2171.
[4]. jansen w j m, zwart b, hulscher s t m, et al. cpt-11 in human colon-cancer cell lines and xenografts: characterization of cellular sensitivity determinants[j]. international journal of cancer, 1997, 70(3): 335-340.
[5]. na y s, jung k a, kim s m, et al. the histone deacetylase inhibitor pxd101 increases the efficacy of irinotecan in in vitro and in vivo colon cancer models[j]. cancer chemotherapy and pharmacology, 2011, 68(2): 389-398.

Irinotecan(97682-44-5)Related Product Information

• Paclitaxel
• Docetaxel
• (+)-Camptothecin
• Diethyl malonate
• Diethyl carbonate
• IRINOTECAN HCL,IRINOTECAN HYDROCHLORIDE
• Mefenpyr-diethyl
• Diethyl phthalate
• sodium:(2S)-2-[12-ethyl-8-(hydroxymethyl)-9-oxo-2-(4-piperidin-1-ylpiperidine-1-carbonyl)oxy-11H-indolizino[1,2-b]quinolin-7-yl]-2-hydroxybutanoate
• 7,11-Diethyl-10-hydroxycaMptothecin
• Irinotecan Impurity 6
• Irinotecan EP Impurity H
• 12-Hydroxy Irinotecan
• SN-38 GLUCURONIDE
• 10-Hydroxycamptothecin
• 7-Ethylcamptothecin
• 7-Ethyl-10-hydroxycamptothecin
• Irinotecan IMpurity G