Irinotecan HCl
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MedKoo CAT#: 413337

CAS#: 100286-90-6 (HCl)

Description: Irinotecan HCl a polymeric micellar preparation of S-38. Irinotecan Hydrochloride is the hydrochlorideN salt of a semisynthetic derivative of camptothecin, a cytotoxic, quinoline-based alkaloid extracted from the Asian tree Camptotheca acuminata.

Chemical Structure

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Irinotecan HCl
CAS# 100286-90-6 (HCl)
Instruction

Theoretical Analysis

MedKoo Cat#: 413337
Name: Irinotecan HCl
CAS#: 100286-90-6 (HCl)
Chemical Formula: C33H39ClN4O6
Exact Mass: 622.26
Molecular Weight: 623.150
Elemental Analysis: C, 63.61; H, 6.31; Cl, 5.69; N, 8.99; O, 15.40

Price and Availability

Size Price Availability Quantity
50mg USD 250 2 Weeks
100mg USD 450 2 Weeks
250mg USD 850 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 HCl; CPT 11; CPT 11; CPT 11

IUPAC/Chemical Name: (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, monohydrochloride

InChi Key: GURKHSYORGJETM-WAQYZQTGSA-N

InChi Code: InChI=1S/C33H38N4O6.ClH/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/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

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: NCI: irinotecan hydrochloride [irinotecan; irinotecan HCl] 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. Because ongoing DNA synthesis is necessary for irinotecan to exert its cytotoxic effects, it is classified as an S-phase-specific agent. (NCI Thesaurus)

Biological target:
In vitro activity:
In vivo activity:

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Soluble in DMSO 0.0 100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 623.15 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:
In vitro protocol:
In vivo protocol:

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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.

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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.

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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.

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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.

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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.