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23541-50-6

Basic Information
CAS No.: 23541-50-6
Name: 5,12-Naphthacenedione,8-acetyl-10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-,hydrochloride (1:1), (8S,10S)-
Article Data: 6
Cas Database
Molecular Structure:
Molecular Structure of 23541-50-6 (5,12-Naphthacenedione,8-acetyl-10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-,hydrochloride (1:1), (8S,10S)-)
Formula: C27H29NO10.HCl
Molecular Weight: 563.989
Synonyms: 5,12-Naphthacenedione,8-acetyl-10-[(3-amino-2,3,6-trideoxy-a-L-lyxo-hexopyranosyl)oxy]-7,8,9,10-tetrahydro-6,8,11-trihydroxy-1-methoxy-,hydrochloride, (8S,10S)- (9CI);Cerubidine;Daunoblastin;Daunomycin chlorohydrate;NDC0082-4155;Ondena;RP 13057 hydrochloride;Rubidomycin hydrochloride;
EINECS: 245-723-4
Density: 1.554 g/cm3
Melting Point: 190°C (dec)
Boiling Point: 770 °C at 760 mmHg
Flash Point: 419.5 °C
Solubility: N/A
Appearance: dark red crystals
Hazard Symbols: HarmfulXn,IrritantXi
Risk Codes: 22-40-42/43-36/37/38-20/21/22
Safety: 22-36/37-45-37/39-36-26
Transport Information: UN 2811 6.1/PG 3
PSA: 185.84000
LogP: 2.53120
Synthetic route
36508-71-1

Benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

A

23541-50-6

daunomycin hydrochloride

B

613-94-5

benzoic acid hydrazide

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, 0.01 M phosphate buffer;
110925-43-4

Nicotinic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

A

553-53-7

Nicotinic acid hydrazide

B

23541-50-6

daunomycin hydrochloride

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, pH 6.80, pH 7.35, 0.01 M phosphate buffer;
110925-39-8

Isonicotinic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

A

54-85-3

isoniazid

B

23541-50-6

daunomycin hydrochloride

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, pH 6.80, pH 7.35, 0.01 M phosphate buffer;
110925-32-1

4-Amino-benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

A

23541-50-6

daunomycin hydrochloride

B

5351-17-7

4-aminobenzohydrazide

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, 0.01 M phosphate buffer;
66996-57-4

4-Hydroxy-benzoic acid [1-[(2S,4S)-4-((2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene]-hydrazide; hydrochloride

A

23541-50-6

daunomycin hydrochloride

B

5351-23-5

4-hydroxybenzoic acid hydrazide

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, 0.01 M phosphate buffer;
110925-36-5

3-[1-[(2S,4S)-4-((2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene-hydrazinocarbonyl]-benzoic acid ethyl ester; hydrochloride

A

23541-50-6

daunomycin hydrochloride

B

110925-44-5

ethyl m-hydrazinecarbonyl benzoate

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, 0.01 M phosphate buffer;
110925-37-6

4-[1-[(2S,4S)-4-((2R,4S,5S,6S)-4-Amino-5-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydro-naphthacen-2-yl]-eth-(E)-ylidene-hydrazinocarbonyl]-benzoic acid ethyl ester; hydrochloride

A

19827-16-8

4-hydrazinocarbonyl-benzoic acid ethyl ester

B

23541-50-6

daunomycin hydrochloride

Conditions
ConditionsYield
With water at 37℃; Rate constant; also half-conversion period, pH 5.58, 0.01 M phosphate buffer;
193743-47-4

daunoform

23541-50-6

daunomycin hydrochloride

Conditions
ConditionsYield
Stage #1: daunoform In dimethylsulfoxide-d6; water-d2 for 24h;
Stage #2: With hydrogenchloride In dimethylsulfoxide-d6; water-d2
23541-50-6

daunomycin hydrochloride

407-25-0

trifluoroacetic anhydride

219921-59-2

3'-N,4'-O-di-trifluoroacetyldaunomycin

Conditions
ConditionsYield
In dichloromethane at -2 - 2℃; for 1h; Inert atmosphere;100%
In dichloromethane at -2 - 2℃; for 1h; Inert atmosphere;100%
In dichloromethane at 0℃; for 1.5h;

Pyr-His-Trp-Tyr-D-Lys(NH2-O-CH2-CO-Gly-Phe-Leu-Gly)Trp-Tyr-Pro-Gly-NH2

23541-50-6

daunomycin hydrochloride

[D-Lys6(Dau=Aoa-GFLG)]GnRH-II

Conditions
ConditionsYield
In aq. acetate buffer at 20℃; for 24h; pH=5.2;100%
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    Daunorubicin hydrochloride

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Chemistry

MF: C27H30ClNO10
MW: 563.98
EINECS: 245-723-4
mp:  190°C (dec)
storage temp:  20°C
form:  solid
Merck:  13,2852
Synonyms:WP900 HYDROCHLORIDE;daunoblastin;daunoblastina; daunomycinchlorohydrate; ndc00824155;ondena;rp13057hydrochloride; rubidomycinhydrochloride
The structure of Daunorubicin hydrochloride(23541-50-6) is:

 

Uses

Daunorubicin hydrochloride(23541-50-6) ia used as anthracycline antibiotic related to the rhodomycins. Antineoplastic.

Toxicity Data With Reference

1.   

mmo-sat 83 ng/plate

   CNREA8    Cancer Research. 38 (1978),2148.
2.   

mmo-asn 250 mg/L

   MUREAV    Mutation Research. 97 (1982),293.
3.   

orl-rat LD50:290 mg/kg

   NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),437.
4.   

ipr-rat LD50:14,300 µg/kg

   NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),437.
5.   

scu-rat LD50:33,200 µg/kg

   NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),437.
6.   

ivn-rat LD50:14,300 µg/kg

   NIIRDN    “Drugs in Japan. Ethical Drugs, 6th Edition 1982“ Edited by Japan Pharmaceutical Information Center. 6 (1982),437.
   

 

    
   

 

    
   

 

   

Consensus Reports

EPA Genetic Toxicology Program.

Safety Profile

Hazard Codes:  Xn,Xi
Risk Statements:  22-40-42/43-36/37/38-20/21/22
Safety Statements:  22-36/37-45-37/39-36-26
RIDADR:  UN 2811 6.1/PG 3
WGK Germany:  3
RTECS:  HB7878000
F:  3-10
HazardClass:  6.1(b)
PackingGroup:  III
Poison by ingestion, intraperitoneal, subcutaneous, and intravenous routes. Mutation data reported. An antineoplastic agent. When heated to decomposition it emits very toxic fumes of NOx and HCl.

Specification

Daunorubicin hydrochloride(23541-50-6) may emit toxic oxides of nitrogen when heated.