Idarubicin Free Base | CAS# 58957-92-9 (free base) | anthracycline antineoplastic

MedKoo Cat#: 413483 | Name: Idarubicin Free Base

Description:

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

Idarubicin Free Base is an orally administered anthracycline antineoplastic. The compound has shown activity against BREAST NEOPLASMS; LYMPHOMA; and LEUKEMIA.

Chemical Structure

Idarubicin Free Base

CAS#58957-92-9 (free base)

Theoretical Analysis

MedKoo Cat#: 413483

Name: Idarubicin Free Base

CAS#: 58957-92-9 (free base)

Chemical Formula: C26H27NO9

Exact Mass: 497.1686

Molecular Weight: 497.50

Elemental Analysis: C, 62.77; H, 5.47; N, 2.82; O, 28.94

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Related CAS #

58957-92-9 (free base) 57852-57-0(HCl)

Synonym

Idarubicin Free Base; CCRIS5083; CCRIS-5083; CCRIS 5083

IUPAC/Chemical Name

(7S,9S)-9-acetyl-7-(((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione

InChi Key

XDXDZDZNSLXDNA-TZNDIEGXSA-N

InChi Code

InChI=1S/C26H27NO9/c1-10-21(29)15(27)7-17(35-10)36-16-9-26(34,11(2)28)8-14-18(16)25(33)20-19(24(14)32)22(30)12-5-3-4-6-13(12)23(20)31/h3-6,10,15-17,21,29,32-34H,7-9,27H2,1-2H3/t10-,15-,16-,17-,21+,26-/m0/s1

SMILES Code

C[C@@H]1O[C@@H](O[C@H]2C[C@@](Cc3c2c(O)c4c(C(c5c(C4=O)cccc5)=O)c3O)(C(C)=O)O)C[C@@H]([C@@H]1O)N

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

To be determined

Shelf Life

>2 years if stored properly

Drug Formulation

to be determined

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Idarubicin is an orally active and potent anthracycline antileukemic agent. Idarubicin inhibits the topoisomerase II interfering with the replication of DNA and RNA transcription.

In vitro activity:

Idarubicin inhibited the growth of all of the five gram-positive cocci, one of five gram-negative rods and one of three yeast strains studied in the standard bottles but not in the FAN bottles. Reference: Eur J Clin Microbiol Infect Dis. 2009 Mar;28(3):301-3. https://pubmed.ncbi.nlm.nih.gov/18763001/

In vivo activity:

The morphometric data show that on day 14 after angioplasty, an aggressive neointimal plaque develops (see vehicle control, Figure 5A). However, rat arteries treated with idarubicin were found to have an 80% reduction in intimal hyperplasia (Figure 5B and C) compared to vehicle control. Reference: PLoS One. 2014 Feb 24;9(2):e89349. https://pubmed.ncbi.nlm.nih.gov/24586708/

	Solvent	mg/mL	mM
Solubility
	To be determined	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 497.50 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.

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. Kinnunen U, Syrjälä H, Koistinen P, Koskela M. Idarubicin inhibits the growth of bacteria and yeasts in an automated blood culture system. Eur J Clin Microbiol Infect Dis. 2009 Mar;28(3):301-3. doi: 10.1007/s10096-008-0613-4. Epub 2008 Sep 2. PMID: 18763001. 2. Orlandi P, Barbara C, Bocci G, Fioravanti A, Di Paolo A, Del Tacca M, Danesi R. Idarubicin and idarubicinol effects on breast cancer multicellular spheroids. J Chemother. 2005 Dec;17(6):663-7. doi: 10.1179/joc.2005.17.6.663. PMID: 16433198. 3. Goel SA, Guo LW, Wang B, Guo S, Roenneburg D, Ananiev GE, Hoffmann FM, Kent KC. High-throughput screening identifies idarubicin as a preferential inhibitor of smooth muscle versus endothelial cell proliferation. PLoS One. 2014 Feb 24;9(2):e89349. doi: 10.1371/journal.pone.0089349. Erratum in: PLoS One. 2014;9(10):e110098. PMID: 24586708; PMCID: PMC3933427.

In vitro protocol:

In vivo protocol:

1. Goel SA, Guo LW, Wang B, Guo S, Roenneburg D, Ananiev GE, Hoffmann FM, Kent KC. High-throughput screening identifies idarubicin as a preferential inhibitor of smooth muscle versus endothelial cell proliferation. PLoS One. 2014 Feb 24;9(2):e89349. doi: 10.1371/journal.pone.0089349. Erratum in: PLoS One. 2014;9(10):e110098. PMID: 24586708; PMCID: PMC3933427.

1: Padia SA. Is Idarubicin the Future of TACE? Radiology. 2019 Jun;291(3):809-810. doi: 10.1148/radiol.2019190789. Epub 2019 Apr 30. PMID: 31039076. 2: Fields SM, Koeller JM. Idarubicin: a second-generation anthracycline. DICP. 1991 May;25(5):505-17. doi: 10.1177/106002809102500511. PMID: 2068836. 3: Betcher DL, Burnham N. Idarubicin. J Pediatr Oncol Nurs. 1990 Jul;7(3):117-20. doi: 10.1177/104345429000700307. PMID: 2206474. 4: Adige S, Lapidus RG, Carter-Cooper BA, Duffy A, Patzke C, Law JY, Baer MR, Ambulos NP, Zou Y, Bentzen SM, Emadi A. Equipotent doses of daunorubicin and idarubicin for AML: a meta-analysis of clinical trials versus in vitro estimation. Cancer Chemother Pharmacol. 2019 Jun;83(6):1105-1112. doi: 10.1007/s00280-019-03825-2. Epub 2019 Apr 9. PMID: 30968179; PMCID: PMC7334867. 5: Guiu B, Chevallier P, Assenat E, Barbier E, Merle P, Bouvier A, Dumortier J, Nguyen-Khac E, Gugenheim J, Rode A, Oberti F, Valette PJ, Yzet T, Chevallier O, Barbare JC, Latournerie M, Boulin M. Idarubicin-loaded Beads for Chemoembolization of Hepatocellular Carcinoma: The IDASPHERE II Single-Arm Phase II Trial. Radiology. 2019 Jun;291(3):801-808. doi: 10.1148/radiol.2019182399. Epub 2019 Apr 30. PMID: 31038408. 6: Ohtake S, Miyawaki S, Fujita H, Kiyoi H, Shinagawa K, Usui N, Okumura H, Miyamura K, Nakaseko C, Miyazaki Y, Fujieda A, Nagai T, Yamane T, Taniwaki M, Takahashi M, Yagasaki F, Kimura Y, Asou N, Sakamaki H, Handa H, Honda S, Ohnishi K, Naoe T, Ohno R. Randomized study of induction therapy comparing standard-dose idarubicin with high-dose daunorubicin in adult patients with previously untreated acute myeloid leukemia: the JALSG AML201 Study. Blood. 2011 Feb 24;117(8):2358-65. doi: 10.1182/blood-2010-03-273243. Epub 2010 Aug 6. PMID: 20693429. 7: Guiu B, Jouve JL, Schmitt A, Minello A, Bonnetain F, Cassinotto C, Piron L, Cercueil JP, Loffroy R, Latournerie M, Wendremaire M, Lepage C, Boulin M. Intra- arterial idarubicin_lipiodol without embolisation in hepatocellular carcinoma: The LIDA-B phase I trial. J Hepatol. 2018 Jun;68(6):1163-1171. doi: 10.1016/j.jhep.2018.01.022. Epub 2018 Feb 8. PMID: 29427728. 8: Guiu B, Hincapie G, Thompson L, Wu Y, Boulin M, Cassinotto C, Cruise GM. An In Vitro Evaluation of Four Types of Drug-Eluting Embolics Loaded with Idarubicin. J Vasc Interv Radiol. 2019 Aug;30(8):1303-1309. doi: 10.1016/j.jvir.2018.12.022. Epub 2019 May 31. PMID: 31155500. 9: Robert J. Clinical pharmacokinetics of idarubicin. Clin Pharmacokinet. 1993 Apr;24(4):275-88. doi: 10.2165/00003088-199324040-00002. Erratum in: Clin Pharmacokinet 1993 Oct;25(4):350. PMID: 8491056. 10: Hollingshead LM, Faulds D. Idarubicin. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic potential in the chemotherapy of cancer. Drugs. 1991 Oct;42(4):690-719. doi: 10.2165/00003495-199142040-00010. PMID: 1723369.