Idarubicin

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Names

[ CAS No. ]:
58957-92-9

[ 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

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
  • 4-((Cyclohexylamino)methyl)benzoic acid hydrochloride
  • 1-[(2,4-Dichlorophenyl)methyl]-N-(1,1-dimethylethyl)-2-methyl-1H-indole-3-methanamine
  • rac-3-[(1R,5R)-bicyclo[3.1.0]hexan-1-yl]-1-methyl-1H-pyrazol-5-amine
  • 2-Methoxy-6-(pyrazol-1-yl)-benzonitrile
  • 1H-3-Benzazepin-7-ol, 8-chloro-2,3,4,5-tetrahydro-5-(3-iodophenyl)-3-methyl-, (S)-
  • (4-Methyl-tetrahydro-furan-2-yl)-methanol
  • N-(1-cyanocyclopentyl)-2-[4-(4-fluorobenzenesulfonyl)-1,4-diazepan-1-yl]acetamide
  • 4,5,6,7-Tetrahydrobenzo[d]isoxazole-3-carbaldehyde
  • tert-Butyl-DL-alanine
  • 4-amino-N-[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]-N-ethylbenzenesulfonamide