Daunorubicin EP Impurity D (Doxorubicin)

Category	Hepatitis B Virus (HBV)
CAS	23214-92-8
Description	Doxorubicin is an anthracycline antibiotic produced in Str. peucetius var. caesinus. Doxorubicin has anti-Gram-positive bacteria activity and has a broad anti-tumor spectrum. Doxorubicin is an antibiotic agent that inhibits DNA topoisomerase II and induces DNA damage and apoptosis.

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Product Information

Synonyms	(8S,10S)-10-[(3-amino-2,3,6-trideoxy-α-L-lyxohexopyranosyl)oxy]-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-7,8,9,10-tetrahydrotetracene-5,12-dione; Adriamycin; Doxil; Adriablastin; Doxorubicine; Adriblastina; 14-Hydroxydaunomycin; 14-Hydroxydaunorubicine; Caelyx; Hydroxydaunorubicin; NSC-759155; 5,12-Naphthacenedione, 10-((3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranosyl)oxy)-7,8,9,10-tetrahydro-6,8,11-trihydroxy-8-(hydroxyacetyl)-1-methoxy-, (8S-cis)-; NSC-123127; (1S,3S)-3,5,12-trihydroxy-3-(hydroxyacetyl)-10-(methyloxy)-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-1-yl 3-amino-2,3,6-trideoxy-alpha-L-lyxo-hexopyranoside; Epirubicin EP Impurity C
IUPAC Name	(7S,9S)-7-[(2R,4S,5S,6S)-4-amino-5-hydroxy-6-methyloxan-2-yl]oxy-6,9,11-trihydroxy-9-(2-hydroxyacetyl)-4-methoxy-8,10-dihydro-7H-tetracene-5,12-dione
Molecular Weight	543.52
Molecular Formula	C27H29NO11
Canonical SMILES	CC1C(C(CC(O1)OC2CC(CC3=C2C(=C4C(=C3O)C(=O)C5=C(C4=O)C(=CC=C5)OC)O)(C(=O)CO)O)N)O
InChI	InChI=1S/C27H29NO11/c1-10-22(31)13(28)6-17(38-10)39-15-8-27(36,16(30)9-29)7-12-19(15)26(35)21-20(24(12)33)23(32)11-4-3-5-14(37-2)18(11)25(21)34/h3-5,10,13,15,17,22,29,31,33,35-36H,6-9,28H2,1-2H3/t10-,13-,15-,17-,22+,27-/m0/s1
InChIKey	AOJJSUZBOXZQNB-TZSSRYMLSA-N
Boiling Point	810.3±65.0°C at 760 mmHg
Melting Point	204-205 °C
Flash Point	443.8°C
Purity	>98%
Density	1.61 g/cm3
Solubility	Soluble in DMF, DMSO, Ethanol, Methanol, Water (Poorly)
Appearance	Orange to Red Powder
Application	ADCs Cytotoxin
Shelf Life	Neutral aq soln are stable at room temp
Storage	Store at -20°C
Animal Admin	Thymic male nude mice (3-4 weeks old) are used. PC3 cells (4×106) are injected subcutaneously into the flank of mice. Tumor-bearing animals are randomly assigned to treatment groups (5 or 6 mice per group) and treatment is started when the xenograft reaches a volume of approximately 100 mm3. Use a combination of vehicle (PBS containing 0.1% BSA), doxorubicin (2-8 mg/kg), Apo2L/TRAIL (500 μg/animal) or 4 mg/kg doxorubicin as shown and then administer 500 μg Apo2L/. Lag. Doxorubicin is administered systemically, while Apo2L / TRAIL is administered intratumorously or systemically. Mice are monitored daily for signs of adverse reactions (listlessness and sloppy appearance). Calculate the mean ±SEM for each data point. When P < 0.05, the difference is considered significant. Thirty male Sprague-Dawley rats (body weight 250-300 g) are randomized to 1 of 3 experimental groups: doxorubicin protocol 1 (doxorubicin 1, n = 10), doxorubicin protocol 2 (doxorubicin 2, n = 10), or doxorubicin protocol 3 (doxorubicin 3, n = 10). For all doxorubicin treatment regimens, the cumulative dose of doxorubicin is 10 mg / kg. Blood pressure and cardiac function are assessed in all surviving animals before the first doxorubicin treatment and once a week after initiation of doxorubicin treatment, as long as there are at least 3 rats in each group.
Complexity	977
Exact Mass	543.17406074
Index Of Refraction	1.709
In Vitro	Peritoneal macrophages from BD IX rats collected 24 hr after an i.p. injection of Adriamycin (10 mg/kg) were cytotoxic to syngeneic cancer cells in culture. In contrast, incubation in vitro in Adriamycin solutions did not evoke tumoricidal activity in peritoneal macrophages, whatever the incubation time (from 1 to 24 hr) and the Adriamycin concentration (from 1 ng to 100 micrograms/ml).
In Vivo	Macrophages incubated with Adriamycin in vitro accumulated the drug in their nuclei, whereas macrophages from animals receiving Adriamycin in vivo accumulated it is cytoplasmic vacuoles. Early observation of peritoneal cells after in vivo exposure to Adriamycin shows that Adriamycin is concentrated in mast cell granules which are released and then phagocytosed by peritoneal macrophages. Adriamycin fluorescence appears in nuclei of cancer cells incubated with in vivo-labeled macrophages, suggesting that macrophages can directly transfer the drug into cancer cells and therefore play a role in the Adriamycin antitumor effect.
PSA	206.07000
Target	Topoisomerase I: 0.8 μM (IC50) Topoisomerase II: 2.67 μM (IC50) Daunorubicins/Doxorubicins HIV-1
Vapor Pressure	9.64E-28mmHg at 25°C
XLogP3-AA	1.3