(1S,2R,8S,10S,11S,13R,14R,15S,17S)-8-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one

• ChemBase ID: 1200
• Molecular Formular: C22H29FO5
• Molecular Mass: 392.4610632
• Monoisotopic Mass: 392.19990225
• SMILES: F[C@H]1C[C@H]2[C@H]3[C@@]([C@](O)([C@@H](C3)C)C(=O)CO)(C[C@H](O)[C@@H]2[C@@]2(C1=CC(=O)C=C2)C)C
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)F
• InChI: InChI=1S/C22H29FO5/c1-11-6-14-13-8-16(23)15-7-12(25)4-5-20(15,2)19(13)17(26)9-21(14,3)22(11,28)18(27)10-24/h4-5,7,11,13-14,16-17,19,24,26,28H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19-,20+,21+,22+/m1/s1
• InChIKey: MKPDWECBUAZOHP-AFYJWTTESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,8S,10S,11S,13R,14R,15S,17S)-8-fluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: paramethasone
• Brand Name: Haldrone
• Synonyms: Paramethasone

Database IDs

• CAS Number: 53-33-8
• PubChem SID: 46504651; 160964662
• PubChem CID: 5875

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.448742
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.2982434
• LogD (pH = 7.4): 1.2982396
• Log P: 1.2982434
• Molar Refractivity: 102.7883 cm^3
• Polarizability: 39.61838 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 1.51
• LOG S: -3.43
• Solubility (Water): 1.45e-01 g/l

DETAILS

DrugBank - DB01384

• Drug Groups: approved
• Description: A glucocorticoid with the general properties of corticosteroids. It has been used by mouth in the treatment of all conditions in which corticosteroid therapy is indicated except adrenal-deficiency states for which its lack of sodium-retaining properties makes it less suitable than hydrocortisone with supplementary fludrocortisone. (From Martindale, The Extra Pharmacopoeia, 30th ed, p737)
• Indication: For the treatment of all conditions in which corticosteroid therapy is indicated except adrenal-deficiency states for which its lack of sodium-retaining properties makes it less suitable than hydrocortisone with supplementary fludrocortisone.
• Pharmacology: Paramethasone is a glucocorticoid with the general properties of corticosteroids. Glucocorticoids are a class of steroid hormones characterised by an ability to bind with the cortisol receptor and trigger a variety of important cardiovascular, metabolic, immunologic and homeostatic effects. Glucocorticoids are distinguished from mineralocorticoids and sex steroids by having different receptors, target cells, and effects. Technically, the term corticosteroid refers to both glucocorticoids and mineralocorticoids, but is often used as a synonym for glucocorticoid. Glucocorticoids suppress cell-mediated immunity. They act by inhibiting genes that code for the cytokines IL-1, IL-2, IL-3, IL-4, IL-5, IL-6, IL-8 and TNF-alpha, the most important of which is the IL-2. Reduced cytokine production limits T cell proliferation. Glucocorticoids also suppress humoral immunity, causing B cells to express lower amounts of IL-2 and IL-2 receptors. This diminishes both B cell clonal expansion and antibody synthesis. The diminished amounts of IL-2 also leads to fewer T lymphocyte cells being activated.
• Toxicity: Side effects include inhibition of bone formation, suppression of calcium absorption delayed wound healing, immune suppression, and hyperglycemia.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic.
• Protein Binding: 80%
• Elimination: Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.
• External Links: Wikipedia