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Idarubicin hydrochloride

CAS No.
57852-57-0
Chemical Name:
Idarubicin hydrochloride
Synonyms
IDARUBICIN HCL;Zavedos;CS-1673;(7S,9S)-;4-DMD HCl;4-DMDR) HCl;Idarubicin HCI;Ida Bixing ketone;Idarubicin HCl API;Idarubicin hcl USP/EP
CBNumber:
CB3727751
Molecular Formula:
C26H28ClNO9
Molecular Weight:
533.95
MDL Number:
MFCD00897212
MOL File:
57852-57-0.mol
MSDS File:
SDS
Last updated:2023-12-07 17:54:45

Idarubicin hydrochloride Properties

Melting point 183-185 C
alpha D20 +205° (c = 0.1 in methanol) (Arcamone); D20 +188° (c = 0.10 in methanol) (Kimura)
storage temp. Inert atmosphere,2-8°C
solubility ≥26.7 mg/mL in DMSO; insoluble in EtOH; ≥2.39 mg/mL in H2O with ultrasonic
form solid
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 57852-57-0
EWG's Food Scores 2
FDA UNII 5VV3MDU5IE
NCI Dictionary of Cancer Terms idarubicin hydrochloride
NCI Drug Dictionary idarubicin hydrochloride
Proposition 65 List Idarubicin Hydrochloride

Pharmacokinetic data

Protein binding 97%
Excreted unchanged in urine 1-2 (4.6% as idarubicinol)
Volume of distribution 64(L/kg)
Biological half-life 10-35 (oral), 15 (IV) / -

SAFETY

Risk and Safety Statements

Symbol(GHS)  GHS hazard pictogramsGHS hazard pictograms
GHS06,GHS08
Signal word  Danger
Hazard statements  H300-H351-H360
Precautionary statements  P201-P280-P301+P330+P331+P310-P308+P313
Hazard Codes  T+,Xn
Risk Statements  60-61-28-40
Safety Statements  53-45-36-22
RIDADR  UN 2811
WGK Germany  3
RTECS  HB7877000
HS Code  2941906000
NFPA 704
0
4 0

Idarubicin hydrochloride price More Price(29)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich PHR2704 Idarubicin hydrochloride pharmaceutical secondary standard, certified reference material 57852-57-0 75MG $575 2024-03-01 Buy
Sigma-Aldrich I1656 Idarubicin hydrochloride solid 57852-57-0 10mg $261 2024-03-01 Buy
Sigma-Aldrich 1335701 Idarubicin 57852-57-0 50mg $1340 2024-03-01 Buy
Cayman Chemical 14176 Idarubicin (hydrochloride) ≥98% 57852-57-0 1mg $36 2024-03-01 Buy
Cayman Chemical 14176 Idarubicin (hydrochloride) ≥98% 57852-57-0 5mg $85 2024-03-01 Buy
Product number Packaging Price Buy
PHR2704 75MG $575 Buy
I1656 10mg $261 Buy
1335701 50mg $1340 Buy
14176 1mg $36 Buy
14176 5mg $85 Buy

Idarubicin hydrochloride Chemical Properties,Uses,Production

Description

Idarubicin 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.

Chemical Properties

Orange Solid

Originator

Erbamont (Italy)

Uses

Idarubicin 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

Uses

Orally active anthracycline; analog of Daunorubicin. Antineoplastic

Uses

Idarubicin hydrochloride (Idamycin) is used to traet acute myeloid leukemia in adults.

Definition

ChEBI: Idarubicin hydrochloride is an anthracycline.

brand name

Zavedos

General Description

Idarubicin is available in 5-, 10-, and 20-mL vials for IV administrationin the treatment of acute myeloid leukemia andacute nonlymphocytic leukemia. The compound lacks the4-methoxy group and terminal side-chain alcohol of doxorubicinmaking it the most lipophilic of the four major anthracyclines(doxorubicin, daunorubicin, epirubicin, idarubicin),and it is considered less cardiotoxic than doxorubicin. Theremoval of the 4-methoxy group also increases inhibition oftopoisomerase II. 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.

Mechanism of action

Increased rates of remission have been noted with the use of idarubicin compared to other anthracyclines antineoplastic agents. Unlike its congeners, idarubicin shows significant oral bioavailability and is lipophilic enough to penetrate the blood-brain barrier. Currently, however, it is given only by the IV route and is not used in the treatment of brain cancer.

Clinical Use

Its primary indication is in acute myeloid leukemia, and it is administered in combination with other antileukemic drug.

Side effects

Common adverse reactions to Idarubicin hydrochloride may include nausea and vomiting, mucositis, and some patients may experience serious adverse reactions including transient elevation of hepatic aminotransferases and total bilirubin, alopecia, transient rash, urticaria at the site of injection, and skin toxicity[1].

Safety Profile

A poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. When heated to decomposition it emits toxic vapors of NOx, HCl, and Cl-.

Drug interactions

Potentially hazardous interactions with other drugs
Other myelosuppressant medication and radiotherapy: increased risk of myelosuppression.
Antipsychotics: avoid concomitant use with clozapine, increased risk of agranulocytosis.
Ciclosporin: concentration increased by ciclosporin.
Cytotoxics: possible increased cardiotoxicity with trastuzumab.
Live vaccines: risk of generalised infections - avoid.

Metabolism

Idarubicin is reduced by aldoketoreductases to idarubicinol, which is as active as the parent drug. Because there is no aromatic methoxy group, there is no O-dealkylation to the C4-phenol. The major metabolite is free, unconjugated idarubicinol. The half-lives of both idarubicin and idarubicinol are 22 and 45 hours, respectively. Idarubicin is administered IV at a dose of 10 to 12 mg/m2 /day for 3 to 4 days, and the idarubicinol metabolite can still be found in therapeutic concentrations in the blood 8 days after administration. Like other anthracyclines, excretion primarily is fecal, with a lesser dependence on renal elimination.

References

[1] S M FIELDS  J M K. Idarubicin: a second-generation anthracycline.[J]. DICP?: the annals of pharmacotherapy, 1991, 25 5: 505-517. DOI:10.1177/106002809102500511.

References

[1] h. dorota halicka, m. fevzi ozkaynak, oya levendoglu-tugal, claudio sandoval , karen seiter, malgorzata kajstura, frank traganos, somasunadaram jayabose, and zbigniew darzynkiewicz. dna damage response as a biomarker in treatment of leukemias. cell cycle. 2009, 8(11): 1720–1724.
[2] haydar çelik and emel arinç. evaluation of the protective effects of quercetin, rutin, resveratrol, naringenin and trolox against idarubicin-induced dna damage. j pharm pharmaceut sci. 2010, 13(2): 231 – 241.
[3] ching-hon pui, siebold s. n. de graaf, lois w. dow, john h. rodman, william e. evans, bruce s. alpert and sharon b. murphy. phase i clinical trial of orally administered 4-demethoxydaunorubicin (idarubicin) with pharmacokinetic and in vitro drug sensitivity testing in children with refractory leukemia. cancer research. 1988, 48: 5348-5352.

58957-92-9
57852-57-0
Synthesis of Idarubicin hydrochloride from Idarubicin
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View Lastest Price from Idarubicin hydrochloride manufacturers

Image Update time Product Price Min. Order Purity Supply Ability Manufacturer
Idarubicin Hydrochloride pictures 2024-03-12 Idarubicin Hydrochloride
57852-57-0
US $0.00 / KG 1KG 98% HPLC 5000kgs shandong perfect biotechnology co.ltd
Idarubicin hydrochloride pictures 2022-02-23 Idarubicin hydrochloride
57852-57-0
US $9.90-7.70 / g 10g 99.99%HPLC.USP42 1000kgs Shanghai Biolang Biotechnology Co., Ltd.
Idarubicin hydrochloride pictures 2021-11-17 Idarubicin hydrochloride
57852-57-0
US $0.00 / g 1g 99%min 1000g WUHAN FORTUNA CHEMICAL CO., LTD

Idarubicin hydrochloride Spectrum

IDARUBICIN HYDROCHLORIDE 4-demethoxy-daunomycihydrochloride 4-demethoxydaunorubicinhydrochloride (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 4-DMD HCl 5,12-Naphthacenedione, 9-acetyl-7-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-, hydrochloride, (7S,9S)- Idarubicin hydrochloride, >=98% DMDR, Idamycin, IMI-30, (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 Idarubicin HCL for research (7S,9S)-9-Acetyl-7-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione Hydrochloride (7S-cis)-9-acetyl-7-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxynaphthacene-5,12-dione hydrochloride 5,12-Naphthacenedione, 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)- Daunomycin, 4-demethoxy-, hydrochloride Idarubicin Hydrochloride (50 mg) (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 (7S,9S)- Idarubicin HCl API 5,12-Naphthacenedione, 9-acetyl-7-[(3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-, hydrochloride, (7S-cis)- Zavedos (7S-cis)-9-Acetyl-7-[(3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-5,12-naphthacenedione hydrochloride Idarubicin Hydrochloride(NSC-256439, IdaMycin) Idarubicin hcl USP/EP Idarubicin HCI 5,12-Naphthacenedione,9-acetyl-7-[(3-aMino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,9,11-trihydroxy-,hydrochloride (1:1), (7S,9S)- (7S,9S)-9-acetyl-7-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-2H-pyran-2-yloxy)-6,9,11-trihydroxy-7,8,9,10-tetrahydrotetracene-5,12-dione hydrochloride 4-demethoxydaunorubicin (NSC256439 4-DMDR) HCl Idarubicin hydrochloride,Idarubicin HCl CS-1673 Idarubicin hydrochloride salt Idarubicin hydrochloride USP/EP/BP Ida Bixing ketone Edabixing hydrochloride impurity 4-demethoxydaunorubicin (NSC256439, 4-DMDR) HCl Idarubicin Hydrochloride (1335701) IDARUBICIN HCL Idabicin hydrochloride 57852-57-0 7852-57-0 C26H27NO9xHCL C26H27NO9ClH C26H28ClNO9 C26H27NO9HCl Apoptosis and Cell Cycle BioChemical Cell Biology Cell Signaling and Neuroscience DNA metabolism DNA Synthesis Inhibitors Idamycin, Zavedos, 4-demethoxydaunorubicin Drug Analogues Intermediates & Fine Chemicals Pharmaceuticals API Anti-cancer&immunity Inhibitors