<Suppliers Price>

Idarubicin (hydrochloride)

Names

[ CAS No. ]:
57852-57-0

[ Name ]:
Idarubicin (hydrochloride)

[Synonym ]:
(1S,3S)-3-Acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-1-tetracenyl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside hydrochloride (1:1)
4-demethoxy-daunomycihydrochloride
4-DMD HCl
(1S,3S)-3-Acetyl-1,2,3,4,6,11-hexahydro-3,5,12-trihydroxy-6,11-dioxo-1-naphthacenyl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside, hydrochloride
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-, (7S,9S)-, hydrochloride
Idarubicin hcl USP/EP
IdarubicinHCl
4-demethoxydaunomycin hydrochloride
Idarubicin 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-, (7S,9S)-, hydrochloride (1:1)
(1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranoside hydrochloride (1:1)
(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
(1S,3S)-3-Acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside hydrochloride (1:1)
Idamycin
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-, (7S,9S)-, hydrochloride (1:1)
Zavedos
(7S-cis)-9-Acetyl-7-((3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,9,11-trihydroxynaphthacene-5,12-dione Hydrochloride
(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
Idarubicin HCL for research
IDARUBICIN HYDROCHLORIDE
4-Demethoxydaunorubicin hydrochloride
(1S,3S)-3-acetyl-3,5,12-trihydroxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranoside hydrochloride
Idarubicin (hydrochloride)

Biological Activity

[Description]:

Idarubicin hydrochloride is an anthracycline antileukemic drug. It inhibits the topoisomerase II interfering with the replication of DNA and RNA transcription.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy
Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase
Research Areas >> Cancer

[Target]

Topoisomerase II


[In Vitro]

The IC50 of idarubicin is 3.3±0.4 ng/mL on MCF-7 monolayers and 7.9±1.1 ng/mL in multicellular spheroids[1]. Idarubicin has shown a greater cytotoxicity than daunorubicin or doxorubicin in various in vitro systems. This has been attributed to a better ability of idarubicin to induce the formation of topoisomerase II -mediated DNA breaks[2].Idarubicin is about 57.5-fold and 25-fold more active than doxorubicin and epirubicin, respectively[3]. Idarubicin produces a concentration-dependent reduction in cell growth, with an IC50 value of approximately 0.01 μM. Idarubicin produced a concentration-dependent inhibition of DNA synthesis[4].

[Cell Assay]

Stock solutions of idarubicin hydrochloride is dissolved in distilled water (1 mg/mL). MCF-7 monolayer are exposed to idarubicin or its metabolite idarubicinol at 0.01, 0.1, 1, 10, 100, and 1000 ng/mL for 24 hours. Multicellular spheroids are exposed to the same range of idarubicin and idarubicinol concentration as monolayers (0.01-1000 ng/mL) for 24 h and, in separate experiments, at the drug concentration of 100 ng/mL for 6, 12, 24 and 48 h. The inhibition of cell proliferation is determined by counting the viable cells with an hemocytometer. Results are expressed as percentage of cell survival vs. control cultures[1].

[References]

[1]. Orlandi P, et al. Idarubicin and idarubicinol effects on breast cancer multicellular spheroids. J Chemother. 2005 Dec;17(6):663-7.

[2]. Robert J. Clinical pharmacokinetics of idarubicin. Clin Pharmacokinet. 1993 Apr;24(4):275-88.

[3]. Siegsmund MJ, et al. Enhanced in vitro cytotoxicity of idarubicin compared to epirubicin and doxorubicin in rat prostate carcinoma cells. Eur Urol. 1997;31(3):365-70.

[4]. Gewirtz DA, et al. Induction of DNA damage, inhibition of DNA synthesis and suppression of c-myc expression by the anthracycline analog, idarubicin (4-demethoxy-daunorubicin) in the MCF-7 breast tumor cell line. Cancer Chemother Pharmacol. 1998;41(5):361-


[Related Small Molecules]

Campathecin | 7-Ethyl-10-hydroxycamptothecin | Exatecan (Mesylate) | Daun02 | Beta-Lapachone | Betulinic acid | Teniposide | Amsacrine | TAS 103 | Genz-644282 | Amonafide | Ellipticine (hydrochloride) | Pirarubicin | Banoxantrone dihydrochloride | Voreloxin (Hydrochloride)

Chemical & Physical Properties

[ Boiling Point ]:
725.4ºC at 760 mmHg

[ Melting Point ]:
183-185ºC

[ Molecular Formula ]:
C26H28ClNO9

[ Molecular Weight ]:
533.955

[ Flash Point ]:
392.5ºC

[ Exact Mass ]:
533.145264

[ PSA ]:
176.61000

[ LogP ]:
2.52260

[ Storage condition ]:
-20℃

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HB7877000
CHEMICAL NAME :
Daunomycin, 4-demethoxy-, hydrochloride
CAS REGISTRY NUMBER :
57852-57-0
LAST UPDATED :
199612
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C26-H27-N-O9.Cl-H
MOLECULAR WEIGHT :
534.00
WISWESSER LINE NOTATION :
L E6 C666 BV MVT&&&J DQ FQ HV1 HQ KQ RQ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
5430 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,364,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2930 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,364,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3080 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,364,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
13980 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,364,1995
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
700 ug/kg
TOXIC EFFECTS :
Tumorigenic - active as anti-cancer agent
REFERENCE :
CTRRDO Cancer Treatment Reports. (Washington, DC) V.60-71, 1976-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 60,829,1976
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4690 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,364,1995
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4100 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,364,1995
TYPE OF TEST :
LD - Lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>500 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
IYKEDH Iyakuhin Kenkyu. Study of Medical Supplies. (Nippon Koteisho Kyokai, 12-15, 2-chome, Shibuya, Shibuya-ku, Tokyo 150, Japan) V.1- 1970- Volume(issue)/page/year: 26,364,1995

Safety Information

[ Symbol ]:

GHS06, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H300-H351-H360

[ 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

[ Hazard Codes ]:
T+:Verytoxic;

[ Risk Phrases ]:
R60;R61;R28;R40

[ Safety Phrases ]:
S53-S45

[ RIDADR ]:
UN 2811

[ RTECS ]:
HB7877000

Precursor & DownStream

Articles

Breakthrough Fusarium solani infection in a patient with acute myeloid leukemia receiving posaconazole prophylaxis.

Ann. Hematol. 93(6) , 1079-81, (2014)

A yeast-based assay identifies drugs that interfere with immune evasion of the Epstein-Barr virus.

Dis. Model Mech. 7(4) , 435-44, (2014)

Epstein-Barr virus (EBV) is tightly associated with certain human cancers, but there is as yet no specific treatment against EBV-related diseases. The EBV-encoded EBNA1 protein is essential to maintai...

Final report of phase II study of sorafenib, cytarabine and idarubicin for initial therapy in younger patients with acute myeloid leukemia.

Leukemia 28(7) , 1543-5, (2014)


More Articles


Related Compounds