Identification
- Summary
Idarubicin is an anthracycline antineoplastic agent used to treat acute myeloid leukemia (AML) in adults.
- Brand Names
- Idamycin
- Generic Name
- Idarubicin
- DrugBank Accession Number
- DB01177
- Background
An orally administered anthracycline antineoplastic. The compound has shown activity against breast cancer, lymphomas and leukemias, together with the potential for reduced cardiac toxicity.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Idarubicin (DB01177)
- Weight
- Average: 497.4939
Monoisotopic: 497.168581467 - Chemical Formula
- C26H27NO9
- Synonyms
- (1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydronaphthacen-1-yl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside
- 4-Demethoxydaunomycin
- 4-Demethoxydaunorubicin
- Idarubicin
- Idarubicina
- Idarubicine
- Idarubicinum
Pharmacology
- Indication
For the treatment of acute myeloid leukemia (AML) in adults. This includes French-American-British (FAB) classifications M1 through M7.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to treat Acute myeloid leukemia ••• ••••• ••••••••• Used in combination to treat Acute myeloid leukemia •••••••••••• ••••• - Contraindications & Blackbox Warnings
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Idarubicin is an antineoplastic in the anthracycline class. General properties of drugs in this class include: interaction with DNA in a variety of different ways including intercalation (squeezing between the base pairs), DNA strand breakage and inhibition with the enzyme topoisomerase II. Most of these compounds have been isolated from natural sources and antibiotics. However, they lack the specificity of the antimicrobial antibiotics and thus produce significant toxicity. The anthracyclines are among the most important antitumor drugs available. Doxorubicin is widely used for the treatment of several solid tumors while daunorubicin and idarubicin are used exclusively for the treatment of leukemia. Idarubicin may also inhibit polymerase activity, affect regulation of gene expression, and produce free radical damage to DNA. Idarubicin possesses an antitumor effect against a wide spectrum of tumors, either grafted or spontaneous. The anthracyclines are cell cycle-nonspecific.
- Mechanism of action
Idarubicin has antimitotic and cytotoxic activity through a number of proposed mechanisms of action: Idarubicin forms complexes with DNA by intercalation between base pairs, and it inhibits topoisomerase II activity by stabilizing the DNA-topoisomerase II complex, preventing the religation portion of the ligation-religation reaction that topoisomerase II catalyzes.
Target Actions Organism ADNA intercalationHumans ADNA topoisomerase 2-alpha inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
97%
- Metabolism
- Not Available
- Route of elimination
The drug is eliminated predominately by biliary and to a lesser extent by renal excretion, mostly in the form of idarubicinol.
- Half-life
22 hours
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbatacept The metabolism of Idarubicin can be increased when combined with Abatacept. Abciximab The risk or severity of bleeding can be increased when Abciximab is combined with Idarubicin. Abiraterone The metabolism of Idarubicin can be decreased when combined with Abiraterone. Abrocitinib The metabolism of Abrocitinib can be decreased when combined with Idarubicin. Acebutolol The metabolism of Idarubicin can be decreased when combined with Acebutolol. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Idarubicin hydrochloride 5VV3MDU5IE 57852-57-0 JVHPTYWUBOQMBP-RVFAQHLVSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Idamycin Injection, powder, lyophilized, for solution 1 mg/1mL Intravenous Pharmacia and Upjohn Company LLC 1990-09-27 2010-06-01 US 
Idamycin - Cap 10mg Capsule 10 mg Oral Pfizer Canada Ulc 1996-12-31 2006-08-02 Canada 
Idamycin - Cap 25mg Capsule 25 mg Oral Pfizer Canada Ulc 1996-12-30 2006-08-02 Canada Idamycin - Cap 5mg Capsule 5 mg Oral Pfizer Canada Ulc 1996-12-31 2006-08-02 Canada Idamycin PFS Solution 1 mg/1mL Intravenous Pfizer Laboratories Div Pfizer Inc 1997-02-17 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Aj-idarubicin Solution 1 mg / mL Intravenous Agila Jamp Canada Inc Not applicable Not applicable Canada Idarubicin Hydrochloride Injection, solution 1 mg/1mL Intravenous Bedford Pharmaceuticals 2007-05-15 2011-09-30 US Idarubicin Hydrochloride Injection, solution 1 mg/1mL Intravenous Fresenius Kabi USA, LLC 2009-08-11 2019-08-31 US Idarubicin Hydrochloride Injection, solution 1 mg/1mL Intravenous Hikma Pharmaceuticals USA Inc. 2018-01-12 Not applicable US Idarubicin Hydrochloride Injection, solution 1 mg/1mL Intravenous Hikma Pharmaceuticals USA Inc. 2017-01-30 Not applicable US
Categories
- ATC Codes
- L01DB06 — Idarubicin
- Drug Categories
- Anthracycline Topoisomerase Inhibitor
- Anthracyclines
- Anthracyclines and Related Substances
- Antibiotics, Antineoplastic
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Carbohydrates
- Cardiotoxic antineoplastic agents
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP2C9 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 CYP2D6 Substrates
- Cytochrome P-450 CYP2D6 Substrates with a Narrow Therapeutic Index
- Cytochrome P-450 Substrates
- Cytotoxic Antibiotics and Related Substances
- Enzyme Inhibitors
- Glycosides
- Immunosuppressive Agents
- Myelosuppressive Agents
- Naphthacenes
- Narrow Therapeutic Index Drugs
- Topoisomerase II Inhibitors
- Topoisomerase Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as anthracyclines. These are polyketides containing a tetracenequinone ring structure with a sugar attached by glycosidic linkage.
- Kingdom
- Organic compounds
- Super Class
- Phenylpropanoids and polyketides
- Class
- Anthracyclines
- Sub Class
- Not Available
- Direct Parent
- Anthracyclines
- Alternative Parents
- Tetracenequinones / Aminoglycosides / Anthraquinones / Hexoses / O-glycosyl compounds / Tetralins / Aryl ketones / Oxanes / Vinylogous acids / Tertiary alcohols show 10 more
- Substituents
- 1,2-aminoalcohol / 1,4-anthraquinone / 9,10-anthraquinone / Acetal / Alcohol / Alpha-hydroxy ketone / Amine / Amino saccharide / Aminoglycoside core / Anthracene show 29 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- monosaccharide derivative, anthracycline antibiotic, deoxy hexoside (CHEBI:42068)
- Affected organisms
- Humans and other mammals
- Bacteria
Chemical Identifiers
- UNII
- ZRP63D75JW
- CAS number
- 58957-92-9
- InChI Key
- XDXDZDZNSLXDNA-TZNDIEGXSA-N
- InChI
- 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
- IUPAC Name
- (7S,9S)-9-acetyl-7-{[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy}-6,9,11-trihydroxy-5,7,8,9,10,12-hexahydrotetracene-5,12-dione
- SMILES
- C[C@@H]1O[C@H](C[C@H](N)[C@@H]1O)O[C@H]1C[C@@](O)(CC2=C1C(O)=C1C(=O)C3=CC=CC=C3C(=O)C1=C2O)C(C)=O
References
- Synthesis Reference
Marco Villa, Roberto Arosio, Roberta Fretta, Nicola Diulgheroff, "Synthesis of idarubicin aglycone." U.S. Patent US20060047108, issued March 02, 2006.
US20060047108- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015308
- PubChem Compound
- 42890
- PubChem Substance
- 46506973
- ChemSpider
- 39117
- BindingDB
- 58490
- 5650
- ChEBI
- 42068
- ChEMBL
- CHEMBL1117
- ZINC
- ZINC000003920266
- Therapeutic Targets Database
- DAP000050
- PharmGKB
- PA449961
- PDBe Ligand
- DM5
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Idarubicin
- PDB Entries
- 198d / 1d38 / 1d67 / 3arq / 4lb2
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Treatment Acute Myeloid Leukemia 1 4 Completed Treatment Acute Myeloid Leukemia / Myelodysplastic Syndrome 1 4 Completed Treatment Acute Promyelocytic Leukemia 1 4 Completed Treatment Leukemia, Lymphocytic, Acute, Adult 4 4 Recruiting Treatment Acute Lymphoblastic Leukaemias (ALL) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Bedford Labs
- Ben Venue Laboratories Inc.
- Greenstone LLC
- Pfizer Inc.
- Pharmacia Inc.
- Teva Pharmaceutical Industries Ltd.
- Dosage Forms
Form Route Strength Injection, solution 1 mg/1ml Injection, powder, lyophilized, for solution Intravenous 1 mg/1mL Solution Intravenous 1 mg/1mL Powder, for solution Intravenous 10 mg / vial Powder, for solution Intravenous 5 mg / vial Injection, powder, lyophilized, for solution Parenteral 10 mg Injection, powder, lyophilized, for solution Intravenous 10 mg Injection, powder, lyophilized, for solution Intravenous 20 mg Solution Intravenous 1 mg / mL Injection, solution Parenteral 10 mg/10ml Injection, solution Parenteral 20 mg/20ml Injection, solution Parenteral 5 mg/5ml Injection, solution, concentrate Intravenous 1 mg/ml Injection Intravenous 1 mg/1mL Injection Intravenous 10 mg/10mL Injection Intravenous 20 mg/20mL Injection Intravenous 5 mg/5mL Injection, solution Intravenous 1 mg/1mL Injection, solution Intravenous 10 MG/10ml Injection, solution Intravenous 20 MG/20ml Injection, solution Intravenous 5 MG/5ml Solution, concentrate Intravenous 10 mg Injection, solution Injection, solution, concentrate Intravenous; Parenteral 1 MG/ML Solution Intravenous 5.000 mg Solution Parenteral 5.000 mg Injection, powder, for solution Intravenous; Parenteral 10 MG Injection, powder, for solution Intravenous; Parenteral 5 MG/5ML Injection, powder, for solution Parenteral 10 mg Injection, powder, lyophilized, for solution Intravenous 5 mg Capsule Oral 10 mg Capsule Oral 25 mg Capsule Oral 5 mg Injection, solution Intravenous Injection, powder, for solution Intravenous 10 mg Injection, powder, for solution Intravenous 5 mg Solution Intravenous 1 mg - Prices
Unit description Cost Unit Idamycin pfs 1 mg/ml vial 60.0USD ml DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 0.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.772 mg/mL ALOGPS logP 1.69 ALOGPS logP 1.52 Chemaxon logS -2.8 ALOGPS pKa (Strongest Acidic) 8.04 Chemaxon pKa (Strongest Basic) 10.04 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 176.61 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 126.43 m3·mol-1 Chemaxon Polarizability 50.84 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.5153 Blood Brain Barrier - 0.975 Caco-2 permeable - 0.7492 P-glycoprotein substrate Substrate 0.7862 P-glycoprotein inhibitor I Non-inhibitor 0.7328 P-glycoprotein inhibitor II Non-inhibitor 0.956 Renal organic cation transporter Non-inhibitor 0.9214 CYP450 2C9 substrate Non-substrate 0.8004 CYP450 2D6 substrate Non-substrate 0.8937 CYP450 3A4 substrate Substrate 0.5419 CYP450 1A2 substrate Inhibitor 0.9106 CYP450 2C9 inhibitor Non-inhibitor 0.9439 CYP450 2D6 inhibitor Non-inhibitor 0.9382 CYP450 2C19 inhibitor Non-inhibitor 0.9316 CYP450 3A4 inhibitor Non-inhibitor 0.9514 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9516 Ames test AMES toxic 0.9107 Carcinogenicity Non-carcinogens 0.9456 Biodegradation Not ready biodegradable 0.9762 Rat acute toxicity 4.3474 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9896 hERG inhibition (predictor II) Non-inhibitor 0.882
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 220.902591 predictedDarkChem Lite v0.1.0 [M-H]- 216.498891 predictedDarkChem Lite v0.1.0 [M-H]- 208.91301 predictedDeepCCS 1.0 (2019) [M+H]+ 221.521091 predictedDarkChem Lite v0.1.0 [M+H]+ 218.086891 predictedDarkChem Lite v0.1.0 [M+H]+ 210.73793 predictedDeepCCS 1.0 (2019) [M+Na]+ 221.931591 predictedDarkChem Lite v0.1.0 [M+Na]+ 220.054891 predictedDarkChem Lite v0.1.0 [M+Na]+ 216.34373 predictedDeepCCS 1.0 (2019)
Targets
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Yes
Intercalation
References
- Zahraei Z, Rabbani-Chadegani A: A comparison of the effect of anticancer drugs, idarubicin and adriamycin, on soluble chromatin. Eur J Pharmacol. 2007 Dec 1;575(1-3):28-33. Epub 2007 Jul 31. [Article]
- 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. [Article]
- Bigioni M, Zunino F, Capranico G: Base mutation analysis of topoisomerase II-idarubicin-DNA ternary complex formation. Evidence for enzyme subunit cooperativity in DNA cleavage. Nucleic Acids Res. 1994 Jun 25;22(12):2274-81. [Article]
- Fukushima T, Ueda T, Uchida M, Nakamura T: Action mechanism of idarubicin (4-demethoxydaunorubicin) as compared with daunorubicin in leukemic cells. Int J Hematol. 1993 Apr;57(2):121-30. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Ubiquitin binding
- Specific Function
- Control of topological states of DNA by transient breakage and subsequent rejoining of DNA strands. Topoisomerase II makes double-strand breaks. Essential during mitosis and meiosis for proper segr...
- Gene Name
- TOP2A
- Uniprot ID
- P11388
- Uniprot Name
- DNA topoisomerase 2-alpha
- Molecular Weight
- 174383.88 Da
References
- Willmore E, Errington F, Tilby MJ, Austin CA: Formation and longevity of idarubicin-induced DNA topoisomerase II cleavable complexes in K562 human leukaemia cells. Biochem Pharmacol. 2002 May 15;63(10):1807-15. [Article]
- Zhou R, Wang Y, Gruber A, Larsson R, Castanos-Velez E, Liliemark E: Topoisomerase II-mediated alterations of K562 drug resistant sublines. Med Oncol. 1999 Sep;16(3):191-8. [Article]
- De Renzo A, Santoro LF, Notaro R, Pane F, Buonaiuto MR, Luciano L, Rotoli B: Acute promyelocytic leukemia after treatment for non-Hodgkin's lymphoma with drugs targeting topoisomerase II. Am J Hematol. 1999 Apr;60(4):300-4. [Article]
- Gonzalez-Cid M, Fundia AF, Cuello MT, Larripa I: Correlation between chromosome damage and apoptosis induced by fludarabine and idarubicin in normal human lymphocytes. Toxicology. 2002 Feb 28;171(2-3):215-22. [Article]
- Bigioni M, Zunino F, Capranico G: Base mutation analysis of topoisomerase II-idarubicin-DNA ternary complex formation. Evidence for enzyme subunit cooperativity in DNA cleavage. Nucleic Acids Res. 1994 Jun 25;22(12):2274-81. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Colburn DE, Giles FJ, Oladovich D, Smith JA: In vitro evaluation of cytochrome P450-mediated drug interactions between cytarabine, idarubicin, itraconazole and caspofungin. Hematology. 2004 Jun;9(3):217-21. doi: 10.1080/10245330410001701585. [Article]
- Cizkova K, Konieczna A, Erdosova B, Ehrmann J: Time-dependent expression of cytochrome p450 epoxygenases during human prenatal development. Organogenesis. 2014 Jan 1;10(1):53-61. doi: 10.4161/org.27911. Epub 2014 Feb 3. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Colburn DE, Giles FJ, Oladovich D, Smith JA: In vitro evaluation of cytochrome P450-mediated drug interactions between cytarabine, idarubicin, itraconazole and caspofungin. Hematology. 2004 Jun;9(3):217-21. doi: 10.1080/10245330410001701585. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Transporter activity
- Specific Function
- Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
- Gene Name
- ABCC1
- Uniprot ID
- P33527
- Uniprot Name
- Multidrug resistance-associated protein 1
- Molecular Weight
- 171589.5 Da
References
- Heijn M, Hooijberg JH, Scheffer GL, Szabo G, Westerhoff HV, Lankelma J: Anthracyclines modulate multidrug resistance protein (MRP) mediated organic anion transport. Biochim Biophys Acta. 1997 May 22;1326(1):12-22. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54