30652-11-0
Deferiprone
CAS: 30652-11-0
Molecular Formula: C7H9NO2
30652-11-0 - Names and Identifiers
| Name | Deferiprone |
| Synonyms | L1 DMHP CP20 DEFERIPRON DEFERIDONE Deferiprone DEFERIPRONE 1,2-Dimethyl-3-hydroxy-4-pyridone 1,2-Dimethyl-3-hydroxypyridine-4-one 2-hydroxy-1,3-dimethyl-pyridin-4-one 3-HYDROXY-1,2-DIMETHYL-4(1H)-PYRIDONE 3-Hydroxy-1,2-Dimethyl-4(1H)-Pyridone 3-HYDROXY-1,2-DIMETHYL-4(1H)PYRIDINONE 3-hydroxy-1,2-dimethylpyridin-4(1H)-one |
| CAS | 30652-11-0 |
| EINECS | 212-783-8 |
| InChI | InChI=1/C7H9NO2/c1-5-6(9)3-4-8(2)7(5)10/h3-4,10H,1-2H3 |
| InChIKey | TZXKOCQBRNJULO-UHFFFAOYSA-N |
30652-11-0 - Physico-chemical Properties
| Molecular Formula | C7H9NO2 |
| Molar Mass | 139.15 |
| Density | 1.1997 (rough estimate) |
| Melting Point | 272-275 °C (lit.) |
| Boling Point | 255.1°C (rough estimate) |
| Flash Point | 94.7°C |
| Water Solubility | Soluble in hot water |
| Solubility | Soluble in hot water |
| Vapor Presure | 0.0107mmHg at 25°C |
| Appearance | white needle |
| Color | White to off-white |
| Merck | 14,2859 |
| pKa | pKa1 3.3, pKa2 9.7(at 25℃) |
| Storage Condition | 2-8°C |
| Stability | Stable for 1 year from date of purchase as supplied. Solutions are not stable and must be prepared fresh daily. |
| Refractive Index | 1.4800 (estimate) |
| MDL | MFCD00134497 |
| In vitro study | Deferiprone (100 μm) was able to protect myocytes under doxorubicin-induced release of lactate dehydrogenase. Deferiprone (300 μm) rapidly and efficiently cleared ferric ions (III) from the Doxorubicin complex. Deferiprone (300 μm) rapidly enters myocytes and displaces ferric ions from intracellular iron-calcein complexes captured by fluorescence quenching, indicating that in myocytes, deferiprone should also be able to displace the iron ions in its complex with doxorubicin. In The xanthine oxidase/xanthine superoxide generation system, Deferiprone (3 mM) was also able to greatly reduce the hydroxyl radical produced by the ferric ion (III)-Doxorubicin complex. Deferiprone (0.5 mM) increased the clearance of free iron from RBC membranes in a time-dose dependent manner. Deferiprone (0.3 mM) was able to effectively inhibit the transfer of radioactive iron from iron-loaded heart cells and to protect or restore mitochondrial respiratory enzyme activity. In iron-loaded heart cells, Deferiprone (1 mM) caused a sharp decrease in the I-III activity of the complex. Deferiprone showed cytotoxic effects on human tumor cell lines HSC-2,HSC-3 and HL-60 with IC50 of 13.5 μg/ml, 9.9 μg/ml and 10.6 μg/ml, the cytotoxicity of HK1 on HL-60 and HSC-2 cells was decreased in the presence of FeCl 3. Deferiprone (100 μg/ml) induced internucleosomal DNA fragmentation in HL-60 cells, but addition of FeCl 3 inhibited DNA fragmentation. Deferiprone (100 μg/ml) activates caspases 3,8 and 9 in HSC-2 cells. |
| In vivo study | In rabbits, Deferiprone (100 mg/kg) reduced the mean basilar artery cross-sectional area by 24%. In rabbits, Deferiprone (100 mg/kg) in combination with subarachnoid hemorrhage (SAH) showed a variable number of internal elastic membrane folds. |
30652-11-0 - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | R22 - Harmful if swallowed R36/37/38 - 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. S36 - Wear suitable protective clothing. S37/39 - Wear suitable gloves and eye/face protection |
| WGK Germany | 3 |
| RTECS | UU7785940 |
| HS Code | 29333990 |
| Toxicity | LD50 i.p. in rats, mice: 650 mg/kg, 0.8-1.0 g/kg; i.g. in rats: 2.0-3.0 g/kg (Kontoghiorghes, 1995) |
30652-11-0 - Reference Information
| Biological activity | Deferiprone (CP20) is a chelating agent that has affinity for iron ions (ferric ions) and combines with iron ions to form a neutral 3:1 (iron-removed copper: iron) complex. |
| production method | using 3-hydroxy -2-methyl -4-pyridone as raw material, through hydroxyl protection, N-methylation and deprotectant reaction to obtain the deferric ketone, the total yield is 4 9%. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 21:11:58
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