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Daunorubicin
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Name

Daunorubicin

 EINECS 244-069-7
CAS No. 20830-81-3 Density 1.554 g/cm3
PSA 185.84000 LogP 1.72920
Solubility Soluble Melting Point 155 °C
Formula C27H29NO10 Boiling Point 769.977 °C at 760 mmHg
Molecular Weight 527.528 Flash Point 419.467 °C
Transport Information UN 3249 Appearance Orange-red powder.
Safety Risk Codes R3249
Molecular Structure Molecular Structure of 20830-81-3 (Daunorubicin) Hazard Symbols 3249:;
Synonyms

(+)-Daunomycin;AI3-52942;Acetyladriamycin;BRN 1445583;CCRIS 914;Daunarubicinum;Daunamycin;Cerubidin;DaunoXome;Daunomycin;Daunorrubicina;UNII-ZS7284E0ZP;

Article Data 25

Daunorubicin Specification

The 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-,(8S,10S)- with CAS registry number of 20830-81-3 is also known as Cerubidin. The IUPAC name is (7S,9S)-9-Acetyl-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione. Its EINECS registry number is 244-069-7. In addition, the formula is C27H29NO10 and the molecular weight is 527.52. This chemical should be stored in sealed containers away from atrong oxidants. Besides, it is isolated from Streptomyces peucetius.

Physical properties about 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-,(8S,10S)- are: (1)ACD/LogP: 0.54; (2)# of Rule of 5 Violations: 3; (3)ACD/BCF (pH 5.5): 1; (4)ACD/BCF (pH 7.4): 1; (5)ACD/KOC (pH 5.5): 1; (6)ACD/KOC (pH 7.4): 1; (7)#H bond acceptors: 11; (8)#H bond donors: 6; (9)#Freely Rotating Bonds: 9; (10)Index of Refraction: 1.692; (11)Molar Refractivity: 129.984 cm3; (12)Molar Volume: 339.426 cm3; (13)Surface Tension: 87.431 dyne/cm; (14)Density: 1.554 g/cm3; (15)Flash Point: 419.467 °C; (16)Enthalpy of Vaporization: 117.598 kJ/mol; (17)Boiling Point: 769.977 °C at 760 mmHg.

Uses of 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-,(8S,10S)-: it is mainly used in treating AML and used to treat neuroblastoma. What's more, It is also used as the starting material for semi-synthetic manufacturing of doxorubicin, epirubicin and idarubicin. It is used to produce N-(1-carboethoxypropen-1-yl-2)daunorubicin by reaction with acetoacetic acid ethyl ester. This reaction needs reagent CH2Cl2 at ambient temperature and the yield is about 66%.

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-,(8S,10S)- is used to produce N-(1-carboethoxypropen-1-yl-2)daunorubicin by reaction with acetoacetic acid ethyl ester.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CC1C(C(CC(O1)OC2CC(CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)C)O)N)O
2. Isomeric SMILES: C[C@H]1[C@H]([C@H](C[C@@H](O1)O[C@H]2C[C@@](CC3=C(C4=C(C(=C23)O)C(=O)C5=C(C4=O)C=CC=C5OC)O)(C(=O)C)O)N)O
3. InChI: InChI=1S/C27H29NO10/c1-10-22(30)14(28)7-17(37-10)38-16-9-27(35,11(2)29)8-13-19(16)26(34)21-20(24(13)32)23(31)12-5-4-6-15(36-3)18(12)25(21)33/h4-6,10,14,16-17,22,30,32,34-35H,7-9,28H2,1-3H3/t10-,14-,16-,17-,22+,27-/m0/s1
4. InChIKey: STQGQHZAVUOBTE-VGBVRHCVSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 10mg/kg/30D-I (10mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION British Journal of Clinical Practice. Vol. 44, Pg. 633, 1990.
dog LD50 intravenous 4mg/kg (4mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 948, 1967.
guinea pig LD50 intravenous 6mg/kg (6mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 948, 1967.
hamster LDLo intravenous 50mg/kg (50mg/kg)   Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 15, Pg. 1614, 1973.
human LDLo oral 6mg/kg (6mg/kg) CARDIAC: OTHER CHANGES "Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 521, 1969.
mouse LD50 intraperitoneal 2500ug/kg (2.5mg/kg) GASTROINTESTINAL: OTHER CHANGES National Cancer Institute Report. Vol. -, Pg. 304, 1967.
mouse LD50 intravenous 8600ug/kg (8.6mg/kg)   Cancer Research. Vol. 49, Pg. 4098, 1989.
mouse LD50 oral 205mg/kg (205mg/kg)   Yakkyoku. Pharmacy. Vol. 25, Pg. 573, 1974.
mouse LD50 unreported 24900ug/kg (24.9mg/kg)   Biochemical Pharmacology. Vol. 38, Pg. 167, 1989.
rabbit LD50 intravenous 5mg/kg (5mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) Arzneimittel-Forschung. Drug Research. Vol. 17, Pg. 948, 1967.
rat LD50 intraperitoneal 20mg/kg (20mg/kg)   Advances in Teratology. Vol. 3, Pg. 181, 1968.
rat LD50 intravenous 13mg/kg (13mg/kg) BLOOD: OTHER CHANGES

SKIN AND APPENDAGES (SKIN): HAIR: OTHER		 National Cancer Institute Report. Vol. -, Pg. 304, 1967.
rat LD50 oral 336mg/kg (336mg/kg)   Yakkyoku. Pharmacy. Vol. 25, Pg. 573, 1974.
rat LD50 subcutaneous 33200ug/kg (33.2mg/kg)   Yakkyoku. Pharmacy. Vol. 25, Pg. 573, 1974.

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