Dexamethasone
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| Chemical formula | C22H29FO5 |
|---|---|
| Molar Mass(g/mol) | 392.461 |
| Melting Point(°C) | 262 |
| NFPA 704 |  0
0
0
|
Uses
Primary
- Pharm: WHO LEM component
- Pharm: DHS AMF component
Natural occurrence
Hazards
Character
Production
Synthesis
To synthesize dexamethasone, 16β-methylprednisolone acetate is dehydrated to the 9,11-dehydro derivative.[1][2] This is then reacted with a source of hypobromite, such as basic N-Bromosuccinimide, to form the 9α-bromo-11β-hydrin derivative, which is then ring-closed to an epoxide. A ring-opening reaction with hydrogen fluoride in tetrahydrofuran gives dexamethasone.
Testing
Purification
Storage
Disposal
See Also
References
- ↑ Arth, GE; Fried, J; Hoff, DR; et al (1958) "16-Methylated steroids. II. 16α-Methyl analogs of cortisone, a new group of anti-inflammatory steroids. 9α-Halo derivatives".
Journal of the American Chemical Society 80(12); pp3161–3163.
DOI:10.1021/ja01545a063 - ↑ Taub, D; Hoffsommer, RD; Slates, HL; lWendler, NL (1958) "16β-Methyl cortical steroids".
Journal of the American Chemical Society 80(16); pp4435.
DOI:10.1021/ja01549a095