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CAS No.: | 20830-81-3 |
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Name: | Daunorubicin |
Article Data: | 25 |
Molecular Structure: | |
Formula: | C27H29NO10 |
Molecular Weight: | 527.528 |
Synonyms: | (+)-Daunomycin;AI3-52942;Acetyladriamycin;BRN 1445583;CCRIS 914;Daunarubicinum;Daunamycin;Cerubidin;DaunoXome;Daunomycin;Daunorrubicina;UNII-ZS7284E0ZP; |
EINECS: | 244-069-7 |
Density: | 1.554 g/cm3 |
Melting Point: | 155 °C |
Boiling Point: | 769.977 °C at 760 mmHg |
Flash Point: | 419.467 °C |
Solubility: | Soluble |
Appearance: | Orange-red powder. |
Hazard Symbols: | 3249:; |
Risk Codes: | R3249 |
Transport Information: | UN 3249 |
PSA: | 185.84000 |
LogP: | 1.72920 |
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%.
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. |