Idarubicin

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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

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

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

(+)-N-Trifluoroacetyl-4-demethoxydaunorubicin
Daunorubicin HCl
(7-METHOXY-CHROMAN-3-YL)-METHYLAMINE
1-chloro-2,3,6-trideoxy-4-O-p-nitrobenzoyl-3-trifluoroacetamido-L-lyxohexopyranose
2,3,6-trideoxy-4-O-(p-nitrobenzoyl)-3-(trifluoroacetamido)-α-L-lyxo-hexopyranosyl p-nitrobenzoate
(-)-4'-O-p-Nitrobenzoyl-N-trifluoroacetyl-4-demethoxydaunorubicin

DownStream

Related Compounds

Idarubicin
IdarubicinHCl
N-[2-(2,4-dioxo-4aH-pyrido[2,3-d]pyrimidin-3-yl)ethyl]-1-benzothiophene-2-carboxamide
6-Phenyl-5-[4-[(3-propan-2-yl-1,2,4-oxadiazol-5-yl)methyl]piperazin-1-yl]diazinan-3-one
5-fluoro-6-propan-2-yl-2-[4-(quinoxaline-6-carbonyl)piperazin-1-yl]-5H-pyrimidin-4-one
[3-[(6-Phenylpyridazin-3-yl)oxymethyl]pyrrolidin-1-yl]-pyrazolidin-4-ylmethanone
1-[1-(1-Methylcyclohexyl)cyclopropyl]ethan-1-amine
2-[4-[[6-(3,5-dimethylpyrazol-1-yl)pyrimidin-4-yl]oxymethyl]piperidine-1-carbonyl]-2H-pyrazin-3-one
N-[[3-(2-oxopiperidin-4-yl)-1,2,4-oxadiazol-5-yl]methyl]pyrazolo[1,5-a]pyrimidine-3-carboxamide
5-[4-(Azepan-1-ylsulfonyl)piperazin-1-yl]-6-phenyldiazinan-3-one
4-chloro-N-[5-cyclopropyl-2-(4-methyl-5-methylidene-6-oxopyrimidin-2-yl)pyrazol-3-yl]benzamide
3-Methyl-6-[5-(quinoline-2-carbonyl)-1,3,3a,4,6,6a-hexahydropyrrolo[3,4-c]pyrrol-2-yl]-1,3-diazinane-2,4-dione

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