Daunorubicin

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.