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Home > Encyclopedia > Hydrocortisone buteprate

Hydrocortisone buteprate

pharmaceutical raw materials
Hydrocortisone buteprate structure

Hydrocortisone buteprate 

structure
  • CAS No:

    72590-77-3

  • Formula:

    C28H40O7

  • Chemical Name:

    Hydrocortisone buteprate

  • Synonyms:

    Pregn-4-ene-3,20-dione,11-hydroxy-17-(1-oxobutoxy)-21-(1-oxopropoxy)-,(11β)-;(11β)-11-Hydroxy-17-(1-oxobutoxy)-21-(1-oxopropoxy)pregn-4-ene-3,20-dione;17α-Butyryloxy-11β-hydroxy-21-propionyloxy-4-pregnene-3,20-dione;Hydrocortisone 17-butyrate 21-propionate;Pandel;TS 408;Hydrocortisone buteprate;Hydrocortisone probutate

Description

Hydrocortisone buteprate (Hydrocortisone probutate) is a medium potent, non-halogenated double-ester of hydrocortisone with a favorable benefit/risk ratio for the treatment of inflammatory skin disorders. Hydrocortisone buteprate (Hydrocortisone probutate) is available as a 0.1% cream or ointment formulation[1].


Hydrocortisone butyrate propionate is a corticosteroid hormone and a butyrate ester.|Hydrocortisone Probutate is the probutate salt form of hydrocortisone, a synthetic glucocorticoid receptor agonist with antiinflammatory, antipruritic and vasoconstrictive effects. Binding and activation of the glucocorticoid receptor results in the activation of lipocortin that in turn inhibits cytosolic phospholipase A2. Lack of phospholipase A2 prevents the release of arachidonic acid, precursor for inflammatory mediator prostaglandins and leukotrienes, from the cell membrane. Secondly, mitogen-activated protein kinase (MAPK) phosphatase 1 is induced, thereby leads to dephosphorylation and inactivation of Jun N-terminal kinase directly inhibiting c-Jun mediated transcription. Finally, transcriptional activity of nuclear factor (NF)-kappa-B is blocked, thereby inhibits the transcription of cyclooxygenase 2, which is essential for prostaglandin production.

Hydrocortisone buteprate Basic Attributes

488.613

488.61

276-726-9

O6550D6K3A

DTXSID3048603

C48023

D - Dermatologicals

Characteristics

107

4.09350

1.2g/cm3

122 °C

608.9ºC at 760 mmHg

194.7ºC

1.547

Safety Information

|Danger|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P260, P264, P280, P281, P302+P352, P305+P351+P338, P308+P313, P314, P321, P332+P313, P337+P313, P362, P405, and P501|The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

Toxicity

Side effects include inhibition of bone formation, suppression of calcium absorption and delayed wound healing

95%

Drug Information

For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Also used to treat endocrine (hormonal) disorders (adrenal insufficiency, Addisons disease). It is also used to treat many immune and allergic disorders, such as arthritis, lupus, severe psoriasis, severe asthma, ulcerative colitis, and Crohn's disease.

Hydrocortisone is the most important human glucocorticoid. It is essential for life and regulates or supports a variety of important cardiovascular, metabolic, immunologic and homeostatic functions. Topical hydrocortisone is 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.

Substances that reduce or suppress INFLAMMATION. (See all compounds classified as Anti-Inflammatory Agents.)

Topical corticosteroids can be absorbed from normal intact skin. Inflammation and/or other disease processes in the skin increase percutaneous absorption.|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.

Primarily hepatic via CYP3A4

6-8 hours

Hydrocortisone 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. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. The cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In other words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally 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.

hydrocortisone 17-butyrate 21-propionate

Hydrocortisone buteprate Use and Manufacturing

Methods of Manufacturing

Hydrocortisone butyrate reacts with propionic anhydride to obtain hydrocortisone butyrate propionate.

Uses

A synthetic adrenocorticosteroid that acts as an anti-inflammatory and anti-pruritic agents. It is used as a topical for the treatment of dermatologic disorders such as atopic dermatitis and psoriasis.

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Lipids -> Sterol Lipids [ST] -> Steroids [ST02] -> C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives [ST0203]

Computed Properties

Molecular Weight:488.6
XLogP3:4.2
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:9
Exact Mass:488.27740361
Monoisotopic Mass:488.27740361
Topological Polar Surface Area:107
Heavy Atom Count:35
Complexity:938
Defined Atom Stereocenter Count:7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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