Desoxycorticosterone
From DrugPedia: A Wikipedia for Drug discovery
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| Desoxycorticosterone
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| Systematic (IUPAC) name | |
| (8S,9S,10R,13S,14S,17S)-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one | |
| Identifiers | |
| CAS number | |
| ATC code | ? |
| PubChem | |
| Chemical data | |
| Formula | C21H30O3 |
| Mol. mass | 330.46 |
| SMILES | & |
| Synonyms | 11-Deoxycorticosterone |
| Physical data | |
| Melt. point | 141.5(EXP) °C |
| Solubility in water | 59.5(EXP) at 37oC mg/mL |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | ? |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
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| Legal status | |
| Routes | ? |
Desoxycorticosterone (11-deoxycorticosterone) is a mineralocorticoid<ref>Template:DorlandsDict</ref> secreted from Zona reticularis and Zona fasciculata of the adrenal gland. 21-Hydroxypregn-4-ene-3,20-dione. Desoxycorticosterone acetate (DOCA) is used as replacement therapy in ADDISON DISEASE.
Contents |
[edit] General Properties
*Molecular Weight
330.46
*Molecular Formula
C21H30O3
*IUPAC NAME
(8S,9S,10R,13S,14S,17S)-17-(2-hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
*Canonical Smiles
CC12CCC3C(C1CCC2C(=O)CO)CCC4=CC(=O)CCC34C
*Isomeric Smiles
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2C(=O)CO)CCC4=CC(=O)CC[C@]34C
[edit] PhysioChemical Properties
*Melting Point
141.5(EXP)
*LogP
2.88(EXP)
*Water Solubility
59.5(EXP) at 37C
[edit] Synthesis
In the cytosol of the mitochondrion, pregnenolone is converted to either androgens or 11-deoxycorticosterone and 11-deoxycortisol by enzymes of the endoplasmic reticulum. Then, 11-deoxycorticosterone, along with 11-deoxycortisol, re-enters the mitochondrion, where the enzymes are located for tissue-specific conversion to mineralocorticoids or glucocorticoids, respectively.
[edit] Forms
Desoxycorticosterone is commonly found in two forms: the acetate salt (desoxycorticosterone acetate, or DOCA) and the pivalate salt (desoxycorticosterone pivalate).
[edit] Uses
Both forms are given as intramuscular injections as replacement therapy for Addison's disease. This disease is marked by insufficient adrenal function, including low mineralocorticoid levels.
Desoxycorticosterone pivalate is sold for veterinary use by Novartis under the brand name Percoten.
