Idarubicin

Names

[ Name ]:
Idarubicin

[Synonym ]:
(7S-cis)-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
(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
Daunomycin, 4-demethoxy-
Idarubicine
Idarubicina
EINECS 260-990-7
4-Demethoxydaunomycin
Idarubicine [INN-French]
5,12-naphthacenedione
Idamycin
Idarubicinum
4-Demethoxydaunorubicin
Idarubicinum [INN-Latin]
Idarubicin
MFCD00866457
5,12-Naphthacenedione, 7,8,9,10-tetrahydro-9-acetyl-7-((3-amino-2,3,6-trideoxy-α-L-lyxo-hexopyranosyl)oxy)-6,9,11-trihydroxy-, (7S-cis)-
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)-
(7S,9S)-9-acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-8,10-dihydro-7H-tetracene-5,12-dione
(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

Biological Activity

[Description]:

Idarubicin is an orally active and potent anthracycline antileukemic agent. Idarubicin inhibits the topoisomerase II interfering with the replication of DNA and RNA transcription. Idarubicin shows induction of DNA damage. Idarubicin inhibits DNA synthesis and of c-myc expression. Idarubicin inhibits the growth of bacteria and yeasts[1][2][3][4][5].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase

Research Areas >> Infection

Signaling Pathways >> Cell Cycle/DNA Damage >> DNA/RNA Synthesis

Signaling Pathways >> Anti-infection >> Fungal

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Apoptosis >> c-Myc

Signaling Pathways >> Anti-infection >> Bacterial

[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 shows 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 MCF-7 cell growth, with an IC50 of approximately 0.01 μM. Idarubicin produces a concentration-dependent inhibition of DNA synthesis and a time- and concentration-dependent suppression of c-myc expression[4].

[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-

[5]. Kinnunen U, et al. Idarubicin inhibits the growth of bacteria and yeasts in an automated blood culture system. Eur J Clin Microbiol Infect Dis. 2009 Mar;28(3):301-3.

Chemical & Physical Properties

[ Density]:
1.6±0.1 g/cm3

[ Boiling Point ]:
725.4±60.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₆H₂₇NO₉

[ Molecular Weight ]:
497.494

[ Flash Point ]:
392.5±32.9 °C

[ Exact Mass ]:
497.168579

[ PSA ]:
176.61000

[ LogP ]:
2.95

[ Appearance of Characters ]:
solid

[ Vapour Pressure ]:
0.0±2.5 mmHg at 25°C

[ Index of Refraction ]:
1.706

[ Storage condition ]:
2-8°C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: QI9297700

CHEMICAL NAME :: 5,12-Naphthacenedione, 7,8,9,10-tetrahydro-9-acetyl-7-((3-amino-2,3,6-trideo xy-alpha-L-lyxo- hexopyranosyl)oxy)-6,9,11-trihydroxy-, (7S-cis)-

CAS REGISTRY NUMBER :: 58957-92-9

LAST UPDATED :: 199512

DATA ITEMS CITED :: 17

MOLECULAR FORMULA :: C26-H27-N-O9

MOLECULAR WEIGHT :: 497.54

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 16 mg/kg

TOXIC EFFECTS :: Blood - hemorrhage Blood - changes in spleen Tumorigenic - active as anti-cancer agent

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3 mg/kg

TOXIC EFFECTS :: Nutritional and Gross Metabolic - weight loss or decreased weight gain

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4 mg/kg

TOXIC EFFECTS :: Blood - hemorrhage Blood - changes in spleen Tumorigenic - active as anti-cancer agent

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 4900 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 5100 ug/kg/3D-I

TOXIC EFFECTS :: Lungs, Thorax, or Respiration - other changes Blood - hemorrhage Related to Chronic Data - death

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 3390 ug/kg/3D-I

TOXIC EFFECTS :: Related to Chronic Data - death

MUTATION DATA

TYPE OF TEST :: DNA adduct

TEST SYSTEM :: Mammal - species unspecified Lymphocyte

DOSE/DURATION :: 200 nmol/L

REFERENCE :: BBRCA9 Biochemical and Biophysical Research Communications. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 69,744,1976

Safety Information

[ Hazard Codes ]:
T+

[ Risk Phrases ]:
60-61-28-40

[ Safety Phrases ]:
S53-S45

[ RIDADR ]:
UN 2811 6.1/PG 2

[ WGK Germany ]:
3

[ RTECS ]:
HB7877000

[ Hazard Class ]:
6.1

Idarubicin

Names

Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

MUTATION DATA

Safety Information

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds