Basic information
- CAS
57852-57-0- Standard SMILES
CC(=O)C1(O)Cc2c(O)c3c(c(O)c2C(OC2CC(N)C(O)C(C)O2)C1)C(=O)c1ccccc1C3=O- InChIKey
XDXDZDZNSLXDNA-UHFFFAOYSA-N- Molecular formula
- C26H27NO9
- Average molar mass
- 497.5 g/mol
- Monoisotopic mass
- 497.16858144
Names & identifiers
- Preferred name
- 9-acetyl-7-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione
- IUPAC
- 9-acetyl-7-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione
- English name
- Idarubicin hydrochloride
- Molecular formula
- C26H28ClNO9
- Molecular weight
- 533.95
Names & synonyms
4-DMD HClIdamyin (TN) (Pharmacia)Neuro_0001209-acetyl-7-(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dioneCHEMBL1974170SCHEMBL13488561SCHEMBL31570023NCGC00015551-02NCGC00181106-01KB-333775(9S)-9-Acetyl-7-[(2R,4S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione5, 9-acetyl-7-[(3-amino-2,3,6-trideoxy- .alpha.-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro- 6,9,11-trihydroxy-, hydrochloride, (7S-cis)-
Show more names
IDARUBICIN HCLZavedosCS-1673(7S,9S)-4-DMDR) HClIdarubicin HCIIda Bixing ketoneIdarubicin HCl APIIdarubicin hcl USP/EP
Properties
Computed structural properties
- XLogP
- 1.9
- Topological polar surface area
- 177 Ų
- Hydrogen bond donors
- 5
- Hydrogen bond acceptors
- 10
- Rotatable bonds
- 3
- Heavy atoms
- 36
- Formal charge
- 0
- Complexity
- 912
Experimental & physicochemical properties
DrugsPharmaceuticals
LogP0.68
Physicochemical properties
- Melting point
- 183 · 183-185 C
- alpha
- 20 · D20 +205° (c = 0.1 in methanol) (Arcamone); D20 +188° (c = 0.10 in methanol) (Kimura)
- storage temp.
- 2 · Inert atmosphere,2-8°C
- solubility
- 26.7 mg/mL · ≥26.7 mg/mL in DMSO; insoluble in EtOH; ≥2.39 mg/mL in H2O with ultrasonic
- form
- solid
- color
- Orange to red
- Stability
- Hygroscopic, Light Sensitive
- InChIKey
- JVHPTYWUBOQMBP-RVFAQHLVSA-N
- SMILES
- C12=C(O)C3=C(C(=O)C4C=CC=CC=4C3=O)C(O)=C1C[C@@](O)(C(=O)C)C[C@]2([H])O[C@@H]1O[C@H]([C@@H](O)[C@@H](N)C1)C.Cl |&1:19,25,28,30,31,33,r|
- CAS DataBase Reference
- 57852 · 57852-57-0
- EWG's Food Scores
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Faceshields, Gloves, type P3 (EN 143) respirator cartridges
- wgk
- 3
- rtecs
- HB7877000
- ridadr
- UN 2811
- hs_code
- 2941906000
- risk_code
- 60-61-28-40
- Signal word
- Danger
- Symbol(GHS)
- GHS06,GHS08
- hazard_code
- T+,Xn
- safety_code
- 53-45-36-22
- Storage Class
- 6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
- Hazard statements
- H300-H351-H360
- Hazard Classifications
- Acute Tox. 2 OralCarc. 2Repr. 1B
- Precautionary statements
- P201-P280-P301+P330+P331+P310-P308+P313
Chemistry & industry
Applications
DescriptionIdarubicin hydrochloride is a derivative of daunorubicin indicated for acute nonlymphocytic leukemia, acute lymphocytic leukemia, and acute myeloid leukemia. Compared with daunorubicin, idarubicin hydrochloride is less cardiotoxic, has milder side effects, is orally active and more potent in experimental leukemias. Idarubicin hydrochloride is also reportedly active in daunorubicin-resistant patients, breast cancer,Hodgkin's and non-Hodgkin's lymphoma.
UsesIdarubicin HCl is a hydrochloride salt form of Idarubicin which is an anthracycline antibiotic and a DNA topoisomerase II (topo II) inhibitor for MCF-7 cells with IC50 of 3.3 ng/mL. It is used to traet acute myeloid leukemia in adults.
General DescriptionIdarubicin is available in 5-, 10-, and 20-mL vials for IV administrationin the treatment of acute myeloid leukemia andacute nonlymphocytic leukemia. The drug has a fast distributive phase anda high volume of distribution reflecting binding to tissue.Concentrations in blood and bone marrow cells are 100 timeshigher than those found in plasma, reflecting its use in treatingleukemias. Metabolism of the agent primarily occurs byconversion to idarubicinol via reduction of the side chain ketoneto the alcohol, which retains activity as an antineoplastic.Elimination occurs primarily in the bile. Adverse effectsare similar to those found for doxorubicin; however, there isa lower incidence of cardiotoxicity.
Upstream & downstream products
Upstream raw materials
Suppliers100 total
Related reactions
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Compound notes
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