Irinotecan HCl trihydrate
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MedKoo CAT#: 100480

CAS#: 136572-09-3 (HCl trihydrate)

Description: Irinotecan hydrochloride is the hydrochloride salt of a semisynthetic derivative of camptothecin, a cytotoxic, quinoline-based alkaloid extracted from the Asian tree Camptotheca acuminata. Irinotecan, a prodrug, is converted to a biologically active metabolite 7-ethyl-10-hydroxy-camptothecin (SN-38) by a carboxylesterase-converting enzyme. One thousand-fold more potent than its parent compound irinotecan, SN-38 inhibits topoisomerase I activity by stabilizing the cleavable complex between topoisomerase I and DNA, resulting in DNA breaks that inhibit DNA replication and trigger apoptotic cell death.


Chemical Structure

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Irinotecan HCl trihydrate
CAS# 136572-09-3 (HCl trihydrate)

Theoretical Analysis

MedKoo Cat#: 100480
Name: Irinotecan HCl trihydrate
CAS#: 136572-09-3 (HCl trihydrate)
Chemical Formula: C33H45ClN4O9
Exact Mass: 676.29
Molecular Weight: 677.19
Elemental Analysis: C, 58.53; H, 6.70; Cl, 5.23; N, 8.27; O, 21.26

Price and Availability

Size Price Availability Quantity
50.0mg USD 90.0 Ready to ship
200.0mg USD 150.0 Ready to ship
500.0mg USD 250.0 Ready to ship
1.0g USD 450.0 Ready to ship
2.0g USD 750.0 Ready to ship
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Related CAS #: 100286-90-6 (HCl)   143490-53-3 (Lactone Impurity)   136572-09-3 (HCl trihydrate)   97682-44-5 (Free base)   1329502-92-2 (Carboxylate Sodium Salt)  

Synonym: CPT11; CPT-11; CPT 11; U101440E; HSDB 7607; HSDB-7607; HSDB7607; camptothecin-11; irinotecan; irinotecan HCl; Bbrand name: Camptosa; Campto.

IUPAC/Chemical Name: (S)-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 hydrochloride trihydrate.

InChi Key: KLEAIHJJLUAXIQ-JDRGBKBRSA-N

InChi Code: InChI=1S/C33H38N4O6.ClH.3H2O/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;3*1H2/t33-;;;;/m0..../s1

SMILES Code: O=C(N1CCC(N2CCCCC2)CC1)OC3=CC=C4N=C5C(CN6C(C(COC([C@@]7(CC)O)=O)=C7C=C65)=O)=C(CC)C4=C3.[H]Cl.[H]O[H].[H]O[H].[H]O[H]

Appearance: Yellow solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Topoisomerase I inhibitor.
In vitro activity: The potential of folic acid-tailored solid lipid nanoparticles (SLNs) for encapsulation as well as for in vitro cytotoxicity study of irinotecan hydrochloride trihydrate (IHT) against colorectal cancer (CRC) was evaluated by using HT-29 cells. The uncoupled SLNs (IRSLNs) and folic acid-coupled SLNs (IRSLNFs) formulations revealed not only high % entrapment efficiency but also small particle size. Moreover, in vitro drug release results from IRSLNs and IRSLNFs confirmed that they followed sustained-release effect for up to 144 h. Whereas, in vitro cell viability study against HT-29 cell line suggested significantly (p < 0.05) higher cytotoxicity (IC50 = 15 µg/ml) of IRSLNFs over IRSLNs and IHT solution. Reference: J Microencapsul. 2019 Nov;36(7):659-676. https://pubmed.ncbi.nlm.nih.gov/31495238/
In vivo activity: An 'in vivo complexes of enzyme to DNA' (ICE) bioassay was adapted to assess irinotecan activity in the stomach, duodenum, colon and liver of male Wistar rats after a single treatment with irinotecan (100 mg/kg body weight, intraperitoneally). This was compared to the control group receiving 0.9% sodium chloride intraperitoneally. In addition, the DNA strand breaking properties of irinotecan were measured in mucosal cells from the distal colon by single-cell gel electrophoresis (comet assay) to investigate the association of topoisomerase poisoning and DNA damage in vivo. 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 showed significantly higher amounts of DNA strand breaks in colon mucosa cells compared to the control group. Reference: Biotechnol J. 2010 Mar;5(3):321-7. https://onlinelibrary.wiley.com/doi/abs/10.1002/biot.200900174

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 56.67 83.68
Water 1.26 1.86
Ethanol 12.0 17.72
DMF 20.0 29.53
DMSO:PBS (pH 7.2) (1:1) 0.5 0.74

Preparing Stock Solutions

The following data is based on the product molecular weight 677.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Rajpoot K, Jain SK. Irinotecan hydrochloride trihydrate loaded folic acid-tailored solid lipid nanoparticles for targeting colorectal cancer: development, characterization, and in vitro cytotoxicity study using HT-29 cells. J Microencapsul. 2019 Nov;36(7):659-676. doi: 10.1080/02652048.2019.1665723. Epub 2019 Sep 18. Erratum in: J Microencapsul. 2019 Nov;36(7):I. PMID: 31495238. 2. Barth SW, Briviba K, Watzl B, Jäger N, Marko D, Esselen M. In vivo bioassay to detect irinotecan-stabilized DNA/topoisomerase I complexes in rats. Biotechnol J. 2010 Mar;5(3):321-7. doi: 10.1002/biot.200900174. PMID: 20213647.
In vitro protocol: 1. Rajpoot K, Jain SK. Irinotecan hydrochloride trihydrate loaded folic acid-tailored solid lipid nanoparticles for targeting colorectal cancer: development, characterization, and in vitro cytotoxicity study using HT-29 cells. J Microencapsul. 2019 Nov;36(7):659-676. doi: 10.1080/02652048.2019.1665723. Epub 2019 Sep 18. Erratum in: J Microencapsul. 2019 Nov;36(7):I. PMID: 31495238.
In vivo protocol: 1. Barth SW, Briviba K, Watzl B, Jäger N, Marko D, Esselen M. In vivo bioassay to detect irinotecan-stabilized DNA/topoisomerase I complexes in rats. Biotechnol J. 2010 Mar;5(3):321-7. doi: 10.1002/biot.200900174. PMID: 20213647.

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1: Schwartzman AD, Sethi R, Smith R. Multiorgan failure in a patient treated with the 5-fluorouracil, leucovorin, oxaliplatin, and irinotecan regimen. Clin Colorectal Cancer. 2013 Jun;12(2):136-9. doi: 10.1016/j.clcc.2012.09.005. Epub 2012 Oct 24. Review. PubMed PMID: 23098664.

2: Petitprez A, Larsen AK. Irinotecan resistance is accompanied by upregulation of EGFR and Src signaling in human cancer models. Curr Pharm Des. 2013;19(5):958-64. Review. PubMed PMID: 22973964.

3: Qi WX, Shen Z, Lin F, Sun YJ, Min DL, Tang LN, He AN, Yao Y. Overall survival benefits for irinotecan-containing regimens as first-line treatment for advanced gastric cancer: an updated meta-analysis of ten randomized controlled trials. Int J Cancer. 2013 Jan 15;132(2):E66-73. doi: 10.1002/ijc.27775. Epub 2012 Sep 1. Review. PubMed PMID: 22890856.

4: Carrillo JA, Munoz CA. Alternative chemotherapeutic agents: nitrosoureas, cisplatin, irinotecan. Neurosurg Clin N Am. 2012 Apr;23(2):297-306, ix. doi: 10.1016/j.nec.2012.01.005. Epub 2012 Feb 18. Review. PubMed PMID: 22440873.

5: Mollica A, Stefanucci A, Feliciani F, Cacciatore I, Cornacchia C, Pinnen F. Delivery methods of camptothecin and its hydrosoluble analogue irinotecan for treatment of colorectal cancer. Curr Drug Deliv. 2012 Mar;9(2):122-31. Review. PubMed PMID: 22283650.

6: Paulík A, Grim J, Filip S. Predictors of irinotecan toxicity and efficacy in treatment of metastatic colorectal cancer. Acta Medica (Hradec Kralove). 2012;55(4):153-9. Review. PubMed PMID: 23631285.

7: Di Paolo A, Bocci G, Polillo M, Del Re M, Di Desidero T, Lastella M, Danesi R. Pharmacokinetic and pharmacogenetic predictive markers of irinotecan activity and toxicity. Curr Drug Metab. 2011 Dec;12(10):932-43. Review. PubMed PMID: 21787264.

8: Jakobsen JN, Hasselbalch B, Stockhausen MT, Lassen U, Poulsen HS. Irinotecan and bevacizumab in recurrent glioblastoma multiforme. Expert Opin Pharmacother. 2011 Apr;12(5):825-33. doi: 10.1517/14656566.2011.566558. Epub 2011 Mar 9. Review. PubMed PMID: 21385110.

9: Illum H. Irinotecan and radiosensitization in rectal cancer. Anticancer Drugs. 2011 Apr;22(4):324-9. doi: 10.1097/CAD.0b013e3283425c14. Review. PubMed PMID: 21160419.

10: Heinemann V, Hoff PM. Bevacizumab plus irinotecan-based regimens in the treatment of metastatic colorectal cancer. Oncology. 2010;79(1-2):118-28. doi: 10.1159/000314993. Epub 2010 Nov 22. Review. PubMed PMID: 21088438.

11: Montagnani F, Chiriatti A, Licitra S, Aliberti C, Fiorentini G. Differences in efficacy and safety between capecitabine and infusional 5-fluorouracil when combined with irinotecan for the treatment of metastatic colorectal cancer. Clin Colorectal Cancer. 2010 Oct;9(4):243-7. doi: 10.3816/CCC.2010.n.036. Review. PubMed PMID: 20920997.

12: Nagaiah G, Almubarak M, Khan M, Altaha R. Cerebrospinal fluid leak during treatment with bevacizumab and irinotecan after carmustine-impregnated wafers placement in patients with grade 2 oligodendroglioma and glioblastoma multiforme: report of two cases and review of literature. Cancer Invest. 2010 Dec;28(10):1048-53. doi: 10.3109/07357907.2010.483499. Epub 2010 Sep 27. Review. PubMed PMID: 20873990.

13: Oostendorp LJ, Stalmeier PF, Pasker-de Jong PC, Van der Graaf WT, Ottevanger PB. Systematic review of benefits and risks of second-line irinotecan monotherapy for advanced colorectal cancer. Anticancer Drugs. 2010 Sep;21(8):749-58. doi: 10.1097/CAD.0b013e32833c57cf. Review. PubMed PMID: 20616701.

14: Marsh S, Hoskins JM. Irinotecan pharmacogenomics. Pharmacogenomics. 2010 Jul;11(7):1003-10. doi: 10.2217/pgs.10.95. Review. PubMed PMID: 20602618; PubMed Central PMCID: PMC2927346.

15: Xu T, Chen J, Lu Y, Wolff JE. Effects of bevacizumab plus irinotecan on response and survival in patients with recurrent malignant glioma: a systematic review and survival-gain analysis. BMC Cancer. 2010 Jun 2;10:252. doi: 10.1186/1471-2407-10-252. Review. PubMed PMID: 20525214; PubMed Central PMCID: PMC2891637.

16: Fujita K, Sparreboom A. Pharmacogenetics of irinotecan disposition and toxicity: a review. Curr Clin Pharmacol. 2010 Aug;5(3):209-17. Review. PubMed PMID: 20406168.

17: Farhat FS, Kattan J, Ghosn MG. Role of capecitabine and irinotecan combination therapy in advanced or metastatic gastric cancer. Expert Rev Anticancer Ther. 2010 Apr;10(4):541-8. doi: 10.1586/era.09.179. Review. PubMed PMID: 20397919.

18: Cartwright T, McCollum D, Boehm KA. Dosing considerations for capecitabine-irinotecan regimens in the treatment of metastatic and/or locally advanced colorectal cancer. Am J Clin Oncol. 2010 Jun;33(3):307-13. doi: 10.1097/COC.0b013e3181d27361. Review. PubMed PMID: 20375835.

19: Hu ZY, Yu Q, Zhao YS. Dose-dependent association between UGT1A1*28 polymorphism and irinotecan-induced diarrhoea: a meta-analysis. Eur J Cancer. 2010 Jul;46(10):1856-65. doi: 10.1016/j.ejca.2010.02.049. Epub 2010 Mar 23. Review. PubMed PMID: 20335017.

20: Fujiwara Y, Minami H. An overview of the recent progress in irinotecan pharmacogenetics. Pharmacogenomics. 2010 Mar;11(3):391-406. doi: 10.2217/pgs.10.19. Review. PubMed PMID: 20235794.



Additional Information

Related CAS#
136572-09-3 (Irinotecan hydrocholide trihydrate);
100286-90-6 (Irinotecan hydrocholide);
97682-44-5 (Irinotecan Free base)