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Amcinonide

Amcinonide structure

Amcinonide 

structure
  • CAS No:

    51022-69-6

  • Formula:

    C28H35FO7

  • Chemical Name:

    Amcinonide

  • Synonyms:

    Pregna-1,4-diene-3,20-dione,21-(acetyloxy)-16,17-[cyclopentylidenebis(oxy)]-9-fluoro-11-hydroxy-,(11β,16α)-;Spiro[cyclopentane-1,8′-[2H]naphth[2′,1′:4,5]indeno[1,2-d][1,3]dioxole],pregna-1,4-diene-3,20-dione deriv.;(11β,16α)-21-(Acetyloxy)-16,17-[cyclopentylidenebis(oxy)]-9-fluoro-11-hydroxypregna-1,4-diene-3,20-dione;Amcinonide;Visderm;Cyclocort;CL 34699;Amciderm;Penticort;55588-50-6;55647-00-2;71507-73-8

  • Categories:

    Analytical Chemistry  >  Standard

Description

Amcinonide inhibit NO release from activated microglia with IC50 3.38 nM. Amcinonide has affinity for the glucocorticoid receptor.IC50 value: 3.38 nM [1]Target: NO releasein vitro: Simultaneous immunofluorescent staining for T6 and Ia antigenicity within human epidermis of Amcinonide treated skin detected reduced numbers of T6+/Ia+ cells with a concomitant increase in T6+/Ia- cells. [2]in vivo: Amcinonide is an anti-inflammatory agent, elicites whitening of a few hairs in both pheomelani


Solid


Amcinonide is a corticosteroid, an 11beta-hydroxy steroid, a fluorinated steroid, a 20-oxo steroid, an acetate ester, a spiroketal and a 3-oxo-Delta(1),Delta(4)-steroid. It has a role as an anti-inflammatory drug. It derives from a hydride of a pregnane.|Amcinonide is a corticosteroid.|Amcinonide is a Corticosteroid. The mechanism of action of amcinonide is as a Corticosteroid Hormone Receptor Agonist.|Amcinonide is a synthetic glucocorticoid receptor agonist that mimics the metabolic, anti-inflammatory, and immunosuppressive activity of the natural glucocorticoids. Amcinonide interacts with specific corticosteroid receptors and was internalized, which leads to binding of DNA and modification of gene expression. This results in synthesis of anti-inflammatory mediators while inhibiting synthesis of inflammatory mediators. Consequently, an overall reduction in chronic inflammation and autoimmune reactions are achieved.

Amcinonide Basic Attributes

502.57

502.57

256-915-2

423W026MA9

DTXSID6045905

C47389

D07AC11|D - Dermatologicals

2937220000

Characteristics

99.1

2.3

1.33 g/cm3

635.9ºC at 760 mmHg

338.4ºC

1.586

7.74e-03 g/L

214.9 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Safety Information

NONH for all modes of transport

2

TU3682500

P201, P202, P260, P261, P264, P271, P280, P281, P302+P352, P304+P340, P305+P351+P338, P308+P313, P312, P314, P321, P332+P313, P337+P313, P362, P403+P233, P405, P501

H315

|Warning|H361 (100%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]|P201, P202, P260, P281, P308+P313, P314, P405, and P501|Aggregated GHS information provided by 2 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Toxicity

Results from acute toxicity studies do not indicate that any risk of acute intoxication is to be expected following a single dermal application of an overdose (application over a large area under conditions favorable to absorption) or inadvertent oral ingestion.

Drug Information

For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.|FDA Label

Amcinonide is a topical corticosteroid. The topical corticosteroids constitute a class of primarily synthetic steroids used as anti-inflammatory and antipruritic agents. Amcinonide reduces or inhibits the actions of chemicals in the body that cause inflammation, redness, and swelling. The mechanism of anti-inflammatory activity of the topical corticosteroids is unclear. Various laboratory methods, including vasoconstrictor assays, are used to compare and predict potencies and/or clinical efficacies of the topical corticosteroids. There is some evidence to suggest that a recognizable correlation exists between vasoconstrictor potency and therapeutic efficacy in man. When in an ointment form, amcinonide also helps the skin maintain moisture.

A group of CORTICOSTEROIDS that affect carbohydrate metabolism (GLUCONEOGENESIS, liver glycogen deposition, elevation of BLOOD SUGAR), inhibit ADRENOCORTICOTROPIC HORMONE secretion, and possess pronounced anti-inflammatory activity. They also play a role in fat and protein metabolism, maintenance of arterial blood pressure, alteration of the connective tissue response to injury, reduction in the number of circulating lymphocytes, and functioning of the central nervous system. (See all compounds classified as Glucocorticoids.)

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.

Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys.

The mechanism of the anti-inflammatory activity of the topical steroids, in general, is unclear. However, corticosteroids are thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor, arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. Amcinonide has affinity for the glucocorticoid receptor. It has weak affinity for the progesterone receptor, and virtually no affinity for the mineralocorticoid, estrogen, or androgen receptors.

Amciderm

Amcinonide Use and Manufacturing

Uses

antiinflammatory

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:502.6
XLogP3:3.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:8
Rotatable Bond Count:4
Exact Mass:502.23668161
Monoisotopic Mass:502.23668161
Topological Polar Surface Area:99.1
Heavy Atom Count:36
Complexity:1090
Defined Atom Stereocenter Count:8
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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