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MedKoo Cat#: 540224 | Name: Irinotecan Free base
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Irinotecan Free base is a camptothecin analog and topoisomerase I inhibitor. It may inhibit AChE. It is uesed to treat colon cancer, but it also moderates inhibition of dendritic cell differentiation and decreases the number of tumor vessels in glioma models.

Chemical Structure

Irinotecan Free base
Irinotecan Free base
CAS#97682-44-5 (Free base)

Theoretical Analysis

MedKoo Cat#: 540224

Name: Irinotecan Free base

CAS#: 97682-44-5 (Free base)

Chemical Formula: C33H38N4O6

Exact Mass: 586.2791

Molecular Weight: 586.68

Elemental Analysis: C, 67.56; H, 6.53; N, 9.55; O, 16.36

Price and Availability

Size Price Availability Quantity
200mg USD 90.00 Ready to ship
500mg USD 150.00 Ready to ship
1g USD 250.00 Ready to ship
2g USD 450.00 Ready to ship
5g USD 950.00 Ready to ship
10g USD 1,650.00 2 Weeks
20g USD 2,950.00 2 Weeks
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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
(+)-Irinotecan; Camptosar; Irinophore C; Irinotecan; Irinotecan lactone; Irinotecanum
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
InChi Key
UWKQSNNFCGGAFS-XIFFEERXSA-N
InChi Code
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
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
Appearance
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
More Info
Solvent mg/mL mM
Solubility
Soluble in DMSO 0.0 100.00
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 586.68 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
1: Fujita K, Kubota Y, Ishida H, Sasaki Y. Irinotecan, a key chemotherapeutic drug for metastatic colorectal cancer. World J Gastroenterol. 2015 Nov 21;21(43):12234-48. doi: 10.3748/wjg.v21.i43.12234. Review. PubMed PMID: 26604633; PubMed Central PMCID: PMC4649109. 2: Matsuoka A, Ando Y. [UGT1A1 Genotyping for Proper Use of Irinotecan]. Rinsho Byori. 2015 Jul;63(7):876-82. Review. Japanese. PubMed PMID: 26591441. 3: Tanabe K, Fujii M, Nishikawa K, Kunisaki C, Tsuji A, Matsuhashi N, Takagane A, Ohno T, Kawase T, Kochi M, Yoshida K, Kakeji Y, Ichikawa W, Chin K, Terashima M, Takeuchi M, Nakajima T; JACCRO GC-05 study group. Phase II/III study of second-line chemotherapy comparing irinotecan-alone with S-1 plus irinotecan in advanced gastric cancer refractory to first-line treatment with S-1 (JACCRO GC-05). Ann Oncol. 2015 Sep;26(9):1916-22. doi: 10.1093/annonc/mdv265. Epub 2015 Jun 24. PubMed PMID: 26109630. 4: Ma J, Zhang Y, Shen H, Kapesa L, Liu W, Zeng M, Zeng S. Association between mismatch repair gene and irinotecan-based chemotherapy in metastatic colon cancer. Tumour Biol. 2015 Dec;36(12):9599-609. doi: 10.1007/s13277-015-3723-5. Epub 2015 Jul 5. PubMed PMID: 26142736. 5: Filipski E, Berland E, Ozturk N, Guettier C, van der Horst GT, Lévi F, Okyar A. Optimization of irinotecan chronotherapy with P-glycoprotein inhibition. Toxicol Appl Pharmacol. 2014 Feb 1;274(3):471-9. doi: 10.1016/j.taap.2013.12.018. Epub 2013 Dec 29. PubMed PMID: 24380837. 6: Hironaka S, Ueda S, Yasui H, Nishina T, Tsuda M, Tsumura T, Sugimoto N, Shimodaira H, Tokunaga S, Moriwaki T, Esaki T, Nagase M, Fujitani K, Yamaguchi K, Ura T, Hamamoto Y, Morita S, Okamoto I, Boku N, Hyodo I. Randomized, open-label, phase III study comparing irinotecan with paclitaxel in patients with advanced gastric cancer without severe peritoneal metastasis after failure of prior combination chemotherapy using fluoropyrimidine plus platinum: WJOG 4007 trial. J Clin Oncol. 2013 Dec 10;31(35):4438-44. doi: 10.1200/JCO.2012.48.5805. Epub 2013 Nov 4. PubMed PMID: 24190112. 7: Choi SH, Hong HK, Cho YB, Lee WY, Yoo HY. Identification of Sestrin3 Involved in the In vitro Resistance of Colorectal Cancer Cells to Irinotecan. PLoS One. 2015 May 14;10(5):e0126830. doi: 10.1371/journal.pone.0126830. eCollection 2015. PubMed PMID: 25973791; PubMed Central PMCID: PMC4431826. 8: Higuchi K, Tanabe S, Shimada K, Hosaka H, Sasaki E, Nakayama N, Takeda Y, Moriwaki T, Amagai K, Sekikawa T, Sakuyama T, Kanda T, Sasaki T, Azuma M, Takahashi F, Takeuchi M, Koizumi W; Tokyo Cooperative Oncology Group, Tokyo, Japan. Biweekly irinotecan plus cisplatin versus irinotecan alone as second-line treatment for advanced gastric cancer: a randomised phase III trial (TCOG GI-0801/BIRIP trial). Eur J Cancer. 2014 May;50(8):1437-45. doi: 10.1016/j.ejca.2014.01.020. Epub 2014 Feb 20. PubMed PMID: 24560487. 9: Wood JP, Smith AJ, Bowman KJ, Thomas AL, Jones GD. Comet assay measures of DNA damage as biomarkers of irinotecan response in colorectal cancer in vitro and in vivo. Cancer Med. 2015 Sep;4(9):1309-21. doi: 10.1002/cam4.477. Epub 2015 Jun 23. PubMed PMID: 26108357; PubMed Central PMCID: PMC4567016. 10: Namur J, Pascale F, Maeda N, Sterba M, Ghegediban SH, Verret V, Paci A, Seck A, Osuga K, Wassef M, Reb P, Laurent A. Safety and efficacy compared between irinotecan-loaded microspheres HepaSphere and DC bead in a model of VX2 liver metastases in the rabbit. J Vasc Interv Radiol. 2015 Jul;26(7):1067-1075.e3. doi: 10.1016/j.jvir.2015.03.014. Epub 2015 May 4. PubMed PMID: 25952641. 11: Zhang MQ, Lin X, Li Y, Lu S. Irinotecan as a second-line chemotherapy for small cell lung cancer: a systemic analysis. Asian Pac J Cancer Prev. 2015;16(5):1993-5. PubMed PMID: 25773800. 12: Gnutzmann DM, Mechel J, Schmitz A, Köhler K, Krone D, Bellemann N, Gockner TL, Mokry T, Kortes N, Sommer CM, Kauczor HU, Radeleff BA, Stampfl U. Evaluation of the plasmatic and parenchymal elution kinetics of two different irinotecan-loaded drug-eluting embolics in a pig model. J Vasc Interv Radiol. 2015 May;26(5):746-54. doi: 10.1016/j.jvir.2014.12.016. Epub 2015 Feb 18. PubMed PMID: 25704223. 13: Innocenti F, Schilsky RL, Ramírez J, Janisch L, Undevia S, House LK, Das S, Wu K, Turcich M, Marsh R, Karrison T, Maitland ML, Salgia R, Ratain MJ. Dose-finding and pharmacokinetic study to optimize the dosing of irinotecan according to the UGT1A1 genotype of patients with cancer. J Clin Oncol. 2014 Aug 1;32(22):2328-34. doi: 10.1200/JCO.2014.55.2307. Epub 2014 Jun 23. PubMed PMID: 24958824; PubMed Central PMCID: PMC4105486. 14: Seymour MT, Brown SR, Middleton G, Maughan T, Richman S, Gwyther S, Lowe C, Seligmann JF, Wadsley J, Maisey N, Chau I, Hill M, Dawson L, Falk S, O'Callaghan A, Benstead K, Chambers P, Oliver A, Marshall H, Napp V, Quirke P. Panitumumab and irinotecan versus irinotecan alone for patients with KRAS wild-type, fluorouracil-resistant advanced colorectal cancer (PICCOLO): a prospectively stratified randomised trial. Lancet Oncol. 2013 Jul;14(8):749-59. doi: 10.1016/S1470-2045(13)70163-3. Epub 2013 May 29. PubMed PMID: 23725851; PubMed Central PMCID: PMC3699713. 15: Noble CO, Krauze MT, Drummond DC, Forsayeth J, Hayes ME, Beyer J, Hadaczek P, Berger MS, Kirpotin DB, Bankiewicz KS, Park JW. Pharmacokinetics, tumor accumulation and antitumor activity of nanoliposomal irinotecan following systemic treatment of intracranial tumors. Nanomedicine (Lond). 2014 Jul;9(14):2099-108. doi: 10.2217/nnm.13.201. Epub 2014 Feb 4. PubMed PMID: 24494810. 16: Mego M, Chovanec J, Vochyanova-Andrezalova I, Konkolovsky P, Mikulova M, Reckova M, Miskovska V, Bystricky B, Beniak J, Medvecova L, Lagin A, Svetlovska D, Spanik S, Zajac V, Mardiak J, Drgona L. Prevention of irinotecan induced diarrhea by probiotics: A randomized double blind, placebo controlled pilot study. Complement Ther Med. 2015 Jun;23(3):356-62. doi: 10.1016/j.ctim.2015.03.008. Epub 2015 Apr 4. PubMed PMID: 26051570. 17: Kaku Y, Tsuchiya A, Kanno T, Nishizaki T. Irinotecan induces cell cycle arrest, but not apoptosis or necrosis, in Caco-2 and CW2 colorectal cancer cell lines. Pharmacology. 2015;95(3-4):154-9. doi: 10.1159/000381029. Epub 2015 Apr 1. PubMed PMID: 25833236. 18: Chu C, Abbara C, Tandia M, Polrot M, Gonin P, Farinotti R, Bonhomme-Faivre L. Cetuximab increases concentrations of irinotecan and of its active metabolite SN-38 in plasma and tumour of human colorectal carcinoma-bearing mice. Fundam Clin Pharmacol. 2014 Dec;28(6):652-60. doi: 10.1111/fcp.12071. Epub 2014 Apr 16. PubMed PMID: 24588516. 19: Tanaka K, Maeda N, Osuga K, Higashi Y, Hayashi A, Hori Y, Kishimoto K, Morii E, Ohashi F, Tomiyama N. In vivo evaluation of irinotecan-loaded QuadraSphere microspheres for use in chemoembolization of VX2 liver tumors. J Vasc Interv Radiol. 2014 Nov;25(11):1727-35.e1. doi: 10.1016/j.jvir.2014.07.012. Epub 2014 Sep 18. PubMed PMID: 25239839. 20: Huisman SA, Bijman-Lagcher W, IJzermans JN, Smits R, de Bruin RW. Fasting protects against the side effects of irinotecan but preserves its anti-tumor effect in Apc15lox mutant mice. Cell Cycle. 2015;14(14):2333-9. doi: 10.1080/15384101.2015.1044170. Epub 2015 May 8. PubMed PMID: 25955194; PubMed Central PMCID: PMC4613178.