(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

• ChemBase ID: 1048
• Molecular Formular: C26H27NO9
• Molecular Mass: 497.49388
• Monoisotopic Mass: 497.16858145
• SMILES: O([C@H]1C[C@@](O)(Cc2c1c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2)C(=O)C)[C@@H]1O[C@H]([C@@H](O)[C@@H](N)C1)C
• Canonical SMILES: O[C@H]1[C@@H](N)C[C@@H](O[C@H]1C)O[C@H]1C[C@@](O)(Cc2c1c(O)c1c(c2O)C(=O)c2c(C1=O)cccc2)C(=O)C
• 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
• InChIKey: XDXDZDZNSLXDNA-TZNDIEGXSA-N

NAMES AND DATABASE IDS

Names

• 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
• IUPAC Traditional name: idarubicin
• Brand Name: Idamycin; Idamycin PFS; Idarubicin Aglycone; Idarubicin HCl PFS
• Synonyms: Idarubicin Hcl; Idarubicin Hydrochloride; Idarubicina [INN-Spanish]; Idarubicine [INN-French]; Idarubicinum [INN-Latin]; Idarubicin; (7S-cis)-9-Acetyl-7-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione; DMDR; IMI-30; Idamycin; Idarubicin hydrochloride

Database IDs

• CAS Number: 58957-92-9; 57852-57-0
• EC Number: 260-990-7
• MDL Number: MFCD00866457
• PubChem SID: 46506973; 160964511; 24278488
• PubChem CID: 42890

CALCULATED PROPERTIES

JChem

• Acid pKa: 9.54545
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -0.46867308
• LogD (pH = 7.4): 0.69595975
• Log P: 1.8979983
• Molar Refractivity: 126.4283 cm^3
• Polarizability: 49.47403 Å^3
• Polar Surface Area: 176.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.69
• LOG S: -2.81
• Solubility (Water): 7.72e-01 g/l

PROPERTIES

Physical Property

• Apperance: solid
• Hydrophobicity(logP): 0.2

Safety Information

• RTECS: HB7877000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 60-61-28-40
• Safety Statements: 53-45
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H351-H360
• GHS Precautionary statements: P201-P264-P281-P301 + P310-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: 2-8°C

Product Information

• Shipped in: wet ice
• Empirical Formula (Hill Notation): C26H27NO9 · HCl

DETAILS

DrugBank - DB01177

• Drug Groups: approved
• Description: An orally administered anthracycline antineoplastic. The compound has shown activity against breast cancer, lymphomas and leukemias, together with the potential for reduced cardiac toxicity. [PubChem]
• Indication: For the treatment of acute myeloid leukemia (AML) in adults. This includes French-American-British (FAB) classifications M1 through M7.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals; Bacteria
• Half Life: 22 hours
• Protein Binding: 97%
• Elimination: The drug is eliminated predominately by biliary and to a lesser extent by renal excretion, mostly in the form of idarubicinol.
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - I1656

Frequently Asked Questions
Live Chat and Frequently Asked Questions are available for this Product.
Application
Idarubicin is an anthracycline antibiotic that is an anti-leukemia agent with higher DNA binding capacity and greater cytotoxicity than daunorubicin.
Biochem/physiol Actions
Topoisomerase II inhibitor