(8S,10S)-10-[(2S,4S,5S,6S)-4-Amino-6-methyl-5-[(2S)-oxan-2-yl]oxy-oxan-2-yl]oxy-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione
Pirarubicin
CAS: 72496-41-4
Molecular Formula: C32H37NO12
(8S,10S)-10-[(2S,4S,5S,6S)-4-Amino-6-methyl-5-[(2S)-oxan-2-yl]oxy-oxan-2-yl]oxy-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione - Names and Identifiers
(8S,10S)-10-[(2S,4S,5S,6S)-4-Amino-6-methyl-5-[(2S)-oxan-2-yl]oxy-oxan-2-yl]oxy-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione - Physico-chemical Properties
| Molecular Formula | C32H37NO12 |
| Molar Mass | 627.64 |
| Density | 1.51±0.1 g/cm3(Predicted) |
| Melting Point | 188-192°C (dec.) |
| Boling Point | 834.7±65.0 °C(Predicted) |
| Specific Rotation(α) | D25 +175 ±25° (c = 0.2 in CHCl3) |
| Flash Point | 458.6°C |
| Solubility | ethanol: soluble25mg/mL |
| Vapor Presure | 1.51E-29mmHg at 25°C |
| Appearance | powder |
| Color | Orange to Red |
| pKa | 7.35±0.60(Predicted) |
| Storage Condition | 2-8°C |
| Stability | Hygroscopic |
| Refractive Index | 1.67 |
| Physical and Chemical Properties | Red solid, melting point 188~192 C (decomposition). [Α] D23 175 ° ± 25 °(C = 0.2, chloroform). UV and visible absorption maxima (methanol):234,252,290,498,531.5,580nm(E1 cm1h0, 350,110,140,100,45). Soluble in ethyl acetate, chloroform or ethanol, slightly soluble in water, hexane or petroleum ether. Acute toxicity LD50 mice (mg/kg):27.8 I. V. |
| Use | Pirarubicin is an anthracycline. |
| In vitro study | Pirarubicin was rapidly taken up by M5076 cells and reached an intracellular concentration of over 2.5 times that of doxorubicin. Pirarubicin was more effective than doxorubicin in inhibiting 50% of cell growth in vitro. In MG-63 cells, Pirarubicin causes cell cycle arrest at the G0/ G1 phase. In MG-63 cells, Pirarubicin inhibited the expression of PCNA, cyclin D1,cyclin E and Bcl-2, and increased Bax protein expression. In MG-63 cells, Pirarubicin markedly relaxed noradrenaline (0.1 μm)-induced contraction of the endothelial aorta, but had no effect on cells without endothelium. Pirarubicin-induced relaxation was induced by methylene blue (5 μm), hydroquinone (100 μm), phenidone (50 μm), hemoglobin (1 μm) and p-bromobenzoylmethyl bromide (50 μm) but not by indomethacin (25 μm). In SKUT1B,HEC1A and BG1 cell lines, Pirarubicin is about 2-5 times more potent than adriacin. Pirarubicin also showed a reverse dose-response pattern of G2 hindrance, such that at high doses, cell cycle dynamics would mimic those of untreated controls. |
| In vivo study | In mice with M5076 solid tumors, Pirarubicin reduced tumor weight to 60% of control levels, although doxorubicin had no effect. When Pirarubicin and Epirubicin are injected via the hepatic intra-arterial (HIA) route, effective against V × 2 tumors, Pirarubicin is more active than Epirubicin. |
(8S,10S)-10-[(2S,4S,5S,6S)-4-Amino-6-methyl-5-[(2S)-oxan-2-yl]oxy-oxan-2-yl]oxy-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione - Risk and Safety
| Hazard Symbols | Xi - Irritant |
| Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
| Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| RTECS | QI9296000 |
| Toxicity | LD50 i.v. in mice: 27.8 mg/kg (Umezawa, 1979) |
(8S,10S)-10-[(2S,4S,5S,6S)-4-Amino-6-methyl-5-[(2S)-oxan-2-yl]oxy-oxan-2-yl]oxy-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione - Preparation solution concentration reference
| 1mg | 5mg | 10mg | |
|---|---|---|---|
| 1 mM | 1.593 ml | 7.966 ml | 15.933 ml |
| 5 mM | 0.319 ml | 1.593 ml | 3.187 ml |
| 10 mM | 0.159 ml | 0.797 ml | 1.593 ml |
| 5 mM | 0.032 ml | 0.159 ml | 0.319 ml |
Last Update：2024-01-02 23:10:35
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View History
(8S,10S)-10-[(2S,4S,5S,6S)-4-Amino-6-methyl-5-[(2S)-oxan-2-yl]oxy-oxan-2-yl]oxy-6,8,11-trihydroxy-8-(2-hydroxyacetyl)-1-methoxy-9,10-dihydro-7H-tetracene-5,12-dione
Hexahydro-1H-pyrrolo[1,2-a]azepin-5(6H)-one
4475-72-3
309282-21-1
2-(2,6-dimethyl-4-morpholinyl)-5-{3-nitrobenzylidene}-1,3-thiazol-4(5H)-one
Tripropionic acid 1,2,3-propanetriyl ester
2-ethyl-1-butano
30557-03-0
Acetamide,N-(4-butylcyclohexyl)-2,2-dichloro-
2-(4-{3-nitro-4-methylphenyl}-1-oxophthalazin-2(1H)-yl)-N-(4-methylphenyl)acetamide
Hexahydro-1H-pyrrolo[1,2-a]azepin-5(6H)-one
4475-72-3
309282-21-1
2-(2,6-dimethyl-4-morpholinyl)-5-{3-nitrobenzylidene}-1,3-thiazol-4(5H)-one
Tripropionic acid 1,2,3-propanetriyl ester
2-ethyl-1-butano
30557-03-0
Acetamide,N-(4-butylcyclohexyl)-2,2-dichloro-
2-(4-{3-nitro-4-methylphenyl}-1-oxophthalazin-2(1H)-yl)-N-(4-methylphenyl)acetamide