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Hydrocortamate

Hydrocortamate structure

Hydrocortamate 

structure
  • CAS No:

    76-47-1

  • Formula:

    C27H41NO6

  • Chemical Name:

    Hydrocortamate

  • Synonyms:

    Glycine,N,N-diethyl-,(11β)-11,17-dihydroxy-3,20-dioxopregn-4-en-21-yl ester;Cortisol,21-ester with N,N-diethylglycine;Glycine,N,N-diethyl-,21-ester with cortisol;Pregnane,glycine deriv.;Ethamicort;17-Hydroxycorticosterone 21-(diethylamino)acetate;Magnacort;Hydrocortisone 21-(diethylamino)acetate;Hydrocortamate

Description

Solid


Solid


Hydrocortamate is a glycinyl ester, an 11beta-hydroxy steroid, a 17alpha-hydroxy steroid, a glucocorticoid, a 3-oxo-Delta(4) steroid and a tertiary alpha-hydroxy ketone. It has a role as an anti-inflammatory drug and an immunosuppressive agent. It derives from a cortisone.|Hydrocortamate is a synthetic glucocorticoid used for its anti-inflammatory or immunosuppressive properties to treat inflammation due to corticosteroid-responsive dermatoses. 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.

Hydrocortamate Basic Attributes

475.626

475.62

200-963-9

Y3N00BK5WK

DTXSID1057824

Characteristics

104

1.2

Solid

1.21g/cm3

162.5 °C

627.2ºC at 760 mmHg

333.1ºC

1.567

8.55e-02 g/L

Toxicity

Side effects include burning, itching, irritation, dryness, folliculitis, hypertrichosis, acneiform eruptions, hypopigmentation, perioral dermatitis, allergic contact dermatitis, maceration of the skin, secondary infection, skin atrophy, striae, miliaria.

Drug Information

Used topically as an antiinflammatory in the treatment of steroid-responsive dermatoses

Hydrocortamate is a synthetic glucocorticoid used for its anti-inflammatory or immunosuppressive properties to treat inflammation due to corticosteroid-responsive dermatoses. 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.

Primarily hepatic via CYP3A4

Hydrocortamate binds to the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. The immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding.

Computed Properties

Molecular Weight:475.6
XLogP3:3.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:8
Exact Mass:475.29338803
Monoisotopic Mass:475.29338803
Topological Polar Surface Area:104
Heavy Atom Count:34
Complexity:880
Defined Atom Stereocenter Count:7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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