103497-68-3

Usage

Structure

A synthetic steroid compound with a 4-aza steroid framework, a nor-21-carbon atom, and a methyl group at the 23rd position

Derivative

Of the hormone progesterone

Properties

Potent anti-inflammatory and immunosuppressive agent

Uses

Treatment of various inflammatory and autoimmune conditions

Mechanism of action

Binds to progesterone receptors and inhibits the production of inflammatory mediators

Potential applications

Hormone therapy, molecular probe in research studies involving steroid hormones

Upstream product

• 103335-58-6 23-methyl-4-aza-21-nor-5α-cholane-3,20-dione 
• 98319-27-8 22-methyl-4-aza-21-nor-5α-cholane-3,20-dione 
• 104239-97-6 3-Oxo-4-aza-5α-androst-1-ene-17β-carboxylic acid 
• 5674-02-2 2-methylpropylmagnesium chloride 
• 129273-17-2 (4aR,4bS,6aS,7S,9aS,9bS,11aR)-7-(Imidazole-1-carbonyl)-4a,6a-dimethyl-1,4a,4b,5,6,6a,7,8,9,9a,9b,10,11,11a-tetradecahydro-indeno[5,4-f]quinolin-2-one 

Relevant academic research and scientific papers

Method of treatment for prostatic cancer

Disclosed is a new treatment for men with prostatic cancer involving combination therapy of a 5α-reductase inhibitor, i.e., a 17β-substituted 4-azasteroid, a 17β-substituted non-azasteroid, 17β-acyl-3-carboxyandrost-3,5-diene, benzoylaminophenoxybutanoic acid derivative, fused benz(thio)amide or cinnamoylamide derivative, aromatic 1,2-diethers or thioethers, aromatic ortho acylaminophenoxy alkanoic acids, ortho thioalkylacylamino-phenoxy alkanoic acids, pharmaceutically acceptable salts and esters thereof, and particularly finasteride, in combination with an antiandrogen, i.e. flutamide. Pharmaceutical compositions useful for treatment are also disclosed.

Method of treatment for benign prostatic hyperplasia

Disclosed is an improved treatment for men with benign prostatic hyperplasia (BPH), involving combination therapy of a 5α-reductase inhibitor, e.g. a 17β-substituted 4-azasteroid, a 17β-substituted non-azasteroid, 17β-acyl-3-carboxy-androst-3,5-diene, benzoylaminophenoxybutanoic acid derivative, fused benz(thio)amide or cinnamoylamide derivative, aromatic 1,2-diethers or thioethers, aromatic ortho acylaminophenoxy alkanoic acids, ortho thioalkylacylaminophenoxy alkanoic acids, pharmaceutically acceptable salts and esters thereof, and particularly finasteride, in combination with an α1 -adrenergic receptor blocker, i.e., terazosin. The combination provides therapy at the molecular level for the underlying cause of the disease as well as providing symptomatic relief. Pharmaceutical compositions useful for treatment are also disclosed.

7β-substituted-4-aza-5α-androstan-3-ones as 5α-reductase inhibitors

Described are new 7β-substituted 4-aza-5α-androstan-3-ones and related compounds as 5α-reductase inhibitors.

Substituted 4-aza-5α-androstan-ones as 5α-reductase inhibitors

Described are new 16-substituted and 7,16-disubstituted 4-aza-5α-androstan-3-ones and related compounds as 5α-reductase inhibitors.

Use of 17beta-acyl-4-aza-5alpha-androst-1-en-3-ones for the preparation of a medicament for the prevention of prostatic carcinoma

17 beta -Acyl-4-aza-5 alpha -androst-1-ene-3-ones of the formula: wherein R is selected from hydrogen, methyl and ethyl and R is monocyclic aryl optionally containing 1 or more lower alkyl substituents of from 1-2 carbon atoms and/or 1 or more halo (Cl o

17β-acyl-4-aza-5α-androst-1-ene-3-ones as 5α-reductase inhibitors

17β-Acyl-4-aza-5α-androst-1-ene-3-ones of the formula STR1 wherein R is selected from hydrogen, methyl and ethyl and R2 is monocyclic aryl optionally containing 1 or more lower alkyl substituents of from 1-2 carbon atoms and/or 1 or more halo (

Acylimidazolides as Versatile Synthetic Intermediates for the Preparation of Sterically Congested Amides and Ketones: A Practical Synthesis of Proscar

Acylimidazolides react with magnesium amides to produce carboxamides in excellent yields, whereas Fe(III) catalyzed cross coupling between acylimidazolide and Grignard reagents produce ketones in high yields.These methods were utilized to prepare the α-reductase inhibitor Proscar as well as various 17β-amide and ketone analogs of Δ1-4-aza-5α-androsten-3-one.

Azasteroids: Structure-activity relationships for inhibition of 5α-reductase and of androgen receptor binding

A series of steroids, primarily 4-azasteroids, were prepared and tested in vitro as inhibitors of human and rat prostatic 5α-reductase and of binding of dihydrotestosterone to the rat androgen receptor. The primary structural modifications were changes of the A ring and of moieties attached at the C-17 position of the steroid nucleus. New A-ring modifications included 4-cyano-3-oxoΔ4 system in the carbocyclic series and 1α-CN, 1α-CH3, 1α,2α-CH2, 2β-F, 2-aza, 2-oxa, and A-homo changes in the 3-oxo-4-aza series. In addition, 4-azasteroids with a D-homo ring or methyl substitution at C-7 (α and β) or C-16 (α and β) were prepared. The majority of the C-17 substituents were prepared from reactive intermediates derived from the 17β-COOH. Enhanced 5α-reductase inhibition in both the human and rat enzyme assays is seen with 4-CN substitution on 3-oxo-Δ4 steroids and with a C-17 side chain incorporating a lipophilically substituted semipolar group on the 4-aza-3-oxo-5α-androstane nucleus. Fewer highly active compounds were found in the human enzyme assay than in the rat assay. Structural requirements for inhibition of the rat androgen receptor are much different from those for inhibition of the enzyme. The 17β-OH moiety enhances potency more than any other feature while introduction of double bonds at C-1 or C-5 in the azasteroid gives a small improvement. Azasteroids unsubstituted at the 4-position show greatly diminished receptor activity.