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CAS 10184-69-7

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17,21-Dihydroxypregna-1,4,9(11)-triene-3,20-dione

Description:
17,21-Dihydroxypregna-1,4,9(11)-triene-3,20-dione, commonly known as dexamethasone, is a synthetic glucocorticoid with anti-inflammatory and immunosuppressant properties. It is characterized by its steroidal structure, which includes a cyclopentanoperhydrophenanthrene core, modified with hydroxyl groups at the 17 and 21 positions and a double bond between the 1 and 4 positions. This compound is highly lipophilic, allowing it to easily penetrate cell membranes and bind to glucocorticoid receptors, thereby influencing gene expression and modulating various physiological responses. Dexamethasone is utilized in the treatment of a variety of conditions, including allergies, autoimmune diseases, and certain cancers, due to its ability to reduce inflammation and suppress the immune system. Its pharmacokinetics include a relatively long half-life and high oral bioavailability, making it effective in both systemic and localized therapies. However, its use can be associated with side effects, particularly with long-term administration, including metabolic disturbances and increased susceptibility to infections.
Formula:C21H26O4
InChI:InChI=1S/C21H26O4/c1-19-8-5-14(23)11-13(19)3-4-15-16(19)6-9-20(2)17(15)7-10-21(20,25)18(24)12-22/h5-6,8,11,15,17,22,25H,3-4,7,9-10,12H2,1-2H3/t15-,17+,19+,20+,21+/m1/s1
InChI key:InChIKey=MATJXMUQVASJHW-ONKRVSLGSA-N
SMILES:C[C@@]12[C@]([C@]3(C([C@]4(C)C(CC3)=CC(=O)C=C4)=CC1)[H])(CC[C@@]2(C(CO)=O)O)[H]
Synonyms:
  • 17,21-Dihydroxypregna-1,4,9(11)-triene-3,20-dione
  • Pregna-1,4,9(11)-triene-3,20-dione, 17,21-dihydroxy-
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