CAS 57852-57-0|Idarubicin (hydrochloride)

Introduction：Basic information about CAS 57852-57-0|Idarubicin (hydrochloride), including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Idarubicin (hydrochloride) BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Articles57
7. Synonyms

Common Name	Idarubicin (hydrochloride)
CAS Number	57852-57-0	Molecular Weight	533.955
Density	/	Boiling Point	725.4ºC at 760 mmHg
Molecular Formula	C₂₆H₂₈ClNO₉	Melting Point	183-185ºC
MSDS	ChineseUSA	Flash Point	392.5ºC
Symbol	GHS06, GHS08	Signal Word	Danger

Names

Name	Idarubicin HCl
Synonym	More Synonyms

Idarubicin (hydrochloride) BiologicalActivity

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 >>AutophagySignaling Pathways >>Cell Cycle/DNA Damage >>TopoisomeraseResearch 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-

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
InChIKey	JVHPTYWUBOQMBP-RVFAQHLVSA-N
SMILES	CC(=O)C1(O)Cc2c(O)c3c(c(O)c2C(OC2CC(N)C(O)C(C)O2)C1)C(=O)c1ccccc1C3=O.Cl
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

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Synonyms

(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)

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