Flurandrenolide Chemical Properties

Melting point:

247-255°

alpha 

D +140-150° (CHCl3)

Boiling point:

578.7±50.0 °C(Predicted)

Density 

1.0796 (rough estimate)

refractive index 

1.5980 (estimate)

storage temp. 

-20°C Freezer, Under inert atmosphere

solubility 

Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)

pka

12.87±0.10(Predicted)

form 

Solid

color 

White to Off-White

Water Solubility 

295mg/L(25 ºC)

EPA Substance Registry System

Fluradrenolide (1524-88-5)

Safety Information

WGK Germany 

3

RTECS 

TU5024800

HS Code 

2937220000

Hazardous Substances Data

1524-88-5(Hazardous Substances Data)

MSDS

• Language:English Provider:Flurandrenolide
• Language:English Provider:SigmaAldrich

Flurandrenolide Usage And Synthesis

Originator

Haelan ,Lilly ,UK ,1962

Uses

Flurandrenolide (Cordran, Cordran SP) is a synthetic fluorinated corticosteroid.

Uses

antiinflammatory; Glucocorticoid; antipsoriatic.

Indications

Flurandrenolide (Cordran, Cordran SP) is a synthetic fluorinated corticosteroid.

Definition

ChEBI: Flurandrenolide is a 21-hydroxy steroid.

brand name

Cordran (Oclassen); Cordran (Watson).

Therapeutic Function

Glucocorticoid, Antiinflammatory

Biological Functions

Corticosteroids influence all tissues of the body and produce numerous and varying effects in cells. These steroids regulate carbohydrate, lipid, and protein biosynthesis and metabolism (glucocorticoid effects), and they influence water and electrolyte balance (mineralocorticoid effects). Cortisol is the most potent glucocorticoid secreted by the adrenal gland, and aldosterone is the most potent endogenous mineralocorticoid. Both naturally occurring glucocorticoids and related, semisynthetic analogues can be evaluated in terms of their ability to sustain life, to stimulate an increase in blood glucose concentrations and a deposition of liver glycogen, to decrease circulating eosinophils, and to cause thymus involution in adrenalectomized animals. In addition, corticosteroids can affect immune system functions, inflammatory responses, and cell growth. The primary physiologic function of glucocorticoids is to maintain blood glucose levels and, thus, ensure glucose-dependent processes critical to life, particularly brain functions. Cortisol and related steroids accomplish this by stimulating the formation of glucose, by diminishing glucose use by peripheral tissues, and by promoting glycogen synthesis in the liver to increase carbohydrate stores for later release of glucose.

General Description

Flurandrenolide, 6α-fluoro-11β,21-dihydroxy-16α,17-[(1-methylethylidene)bis(oxy)]pregn-4-ene-3,20-dione, although available as a tape product,can stick to and remove damaged skin, so it should beavoided with vesicular or weeping dermatoses.

Mechanism of action

Glucocorticoid action is mediated through the glucocorticoid receptor, which is found primarily in the cytosol of the cell when not bound to glucocorticoids. The GR is stabilized in the cytosol by complexation with phosphorylated proteins, including a 90-kDa protein referred to as a heat shock protein 90. The steroid molecule binds to the GR, resulting in a conformational change of the receptor to dissociate the other proteins and initiate translocation of the steroid–receptor complex into the nucleus. The steroid–nuclear GR complex interacts with particular HRE regions of the cellular DNA, referred to as glucocorticoid-responsive elements and initiates transcription of the DNA sequence to produce mRNA. Finally, the elevated levels of mRNA lead to increased protein synthesis in the endoplasmic reticulum. These proteins then mediate glucocorticoid effects on carbohydrate, lipid, and protein metabolism. An alternative isoform of the GR has been identified. This isoform of the receptor does not bind known glucocorticoids, and its function remains to be determined.

Clinical Use

Two major uses of glucocorticoids are in the treatment of rheumatoid diseases and allergic manifestations. Their use in the treatment of severe asthma is well documented, as is the utility of glucocorticoids in sepsis and acute respiratory distress syndrome. They are effective in the treatment of rheumatoid arthritis, acute rheumatic fever, bursitis, spontaneous hypoglycemia in children, gout, rheumatoid carditis, sprue, allergy (including contact dermatitis), and other conditions. The treatment of chronic rheumatic diseases and allergic conditions with glucocorticoids is symptomatic and continuous. Symptoms return after withdrawal of the drug.

Side effects

Although side effects and toxicities vary with the drug and, sometimes, with the patient, facial mooning, flushing, sweating, acne, thinning of the scalp hair, abdominal distention, and weight gain are observed with most glucocorticoids. Protein depletion (with osteoporosis and spontaneous fractures), myopathy (with weakness of muscles of the thighs, pelvis, and lower back), and aseptic necrosis of the hip and humerus are other side effects.

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