Synonym
IMI30; IMI-30; IMI 30; NSC256439; NSC-256439; NSC 256439; 4-DMDR; IDA; 4-Demethoxydaunomycin; brand name: Idamycin; IDAMYCIN PFS.
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 hydrochloride
InChi Key
JVHPTYWUBOQMBP-RVFAQHLVSA-N
InChi Code
InChI=1S/C26H27NO9.ClH/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;1H/t10-,15-,16-,17-,21+,26-;/m0./s1
SMILES Code
O=C1C2=C(O)C([C@@H](O[C@H]3C[C@H](N)[C@H](O)[C@H](C)O3)C[C@](O)(C(C)=O)C4)=C4C(O)=C2C(C5=C1C=CC=C5)=O.[H]Cl
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, not in water
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
Related CAS#
CAS#57852-57-0( Idarubicin HCl)
CAS#58957-92-9 ( Idarubicin free base).
Biological target:
Idarubicin hydrochloride is an anthracycline antileukemic drug. It inhibits the topoisomerase II interfering with the replication of DNA and RNA transcription. Idarubicin hydrochloride inhibits the growth of bacteria and yeasts.
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 |
| DMF |
10.0 |
18.73 |
| DMSO |
64.4 |
120.69 |
| DMSO:PBS (pH 7.2) (1:1) |
0.5 |
0.94 |
| Water |
7.0 |
13.11 |
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
533.96
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:
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.
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: Vigliotti ML, Dell'Olio M, La Sala A, Romano G, Tartarone A, Mele G, Musto C, Carella AM, Di Renzo N. Primary central nervous system lymphoma (PCNSL) in immunocompetent adults: analysis of a retrospective series of patients treated using idarubicin-containing regimen and radiotherapy. Hematol J. 2004;5(5):453-5. Review. PubMed PMID: 15448676.
2: Crivellari D, Lombardi D, Spazzapan S, Veronesi A, Toffoli G. New oral drugs in older patients: a review of idarubicin in elderly patients. Crit Rev Oncol Hematol. 2004 Feb;49(2):153-63. Review. PubMed PMID: 15012975.
3: Leone G, Sica S, Pagano L. Idarubicin including regimens in acute myelogenous leukemia in elderly patients. Crit Rev Oncol Hematol. 1999 Sep;32(1):59-68. Review. PubMed PMID: 10586356.
4: Zinzani PL. Idarubicin in low-grade non-Hodgkin's lymphomas. Haematologica. 1997 Sep-Oct;82(5 Suppl):23-4. Review. PubMed PMID: 9402750.
5: Buckley MM, Lamb HM. Oral idarubicin. A review of its pharmacological properties and clinical efficacy in the treatment of haematological malignancies and advanced breast cancer. Drugs Aging. 1997 Jul;11(1):61-86. Review. PubMed PMID: 9237041.
6: Borchmann P, Hübel K, Schnell R, Engert A. Idarubicin: a brief overview on pharmacology and clinical use. Int J Clin Pharmacol Ther. 1997 Feb;35(2):80-3. Review. PubMed PMID: 9147715.
7: Tamura K. A phase I study of idarubicin hydrochloride in patients with acute leukemia. The Idarubicin Study Group of Japan. Semin Hematol. 1996 Oct;33(4 Suppl 3):2-11. Review. PubMed PMID: 8916310.
8: Leoni F, Ciolli S, Giuliani G, Pascarella A, Caporale R, Salti F, Cervi L, Rossi Ferrini P. Attenuated-dose idarubicin in acute myeloid leukaemia of the elderly: pharmacokinetic study and clinical results. Br J Haematol. 1995 May;90(1):169-74. Review. PubMed PMID: 7786781.
9: Gabel C, Eifel PJ, Tornos C, Burke TW. Radiation recall reaction to idarubicin resulting in vaginal necrosis. Gynecol Oncol. 1995 May;57(2):266-9. Review. PubMed PMID: 7729748.
10: Chalmers EA, Franklin IM, Kelsey S, Clarke R, Sproul AM, Goldstone AH, Hepplestone A, Watson W, Sharp S, Tansey P. Mobilisation of Ph-negative peripheral blood stem cells in CML with idarubicin and cytarabine. Bone Marrow Transplant. 1994;14 Suppl 3:S38-41. Review. PubMed PMID: 7697006.
