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Glossary 4-azasteroid

synthetic compound mimicking steroids with a nitrogen atom

A 4-azasteroid is a type of synthetic compound that mimics the structure of steroids but includes a nitrogen atom at the fourth position in its chemical structure. These compounds are often used in medical treatments to inhibit enzymes like 5-alpha-reductase, which can help manage conditions such as benign prostatic hyperplasia and androgenic alopecia (hair loss).

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research Synthesis and 5α-Reductase Inhibitory Activity of C21 Steroids Having 1,4-diene or 4,6-diene 20-ones and 4-Azasteroid 20-Oximes

186 citations , December 2011 in “Molecules”

This study reported that while no synthesized compounds surpassed finasteride in 5α-reductase inhibitory activity, certain 4-azasteroid-2-oximes exhibited notable inhibition.

research 13C-NMR study of 4-azasteroids in solution and solid state

25 citations , June 2002 in “Steroids”

This study examined 4-azasteroids using 13C-NMR spectroscopy, detailing the NMR spectrum assignments and reporting a new molecular complex of finasteride with dioxane.

research Synthesis of a 4-azasteroid hormones compound

January 2009 in “Xiandai huagong”

This research outlines a chemical synthesis process for Finasteride, detailing the conversion of pregnadienolone acetate through various chemical reactions and modifications.

research Azasteroids as inhibitors of testosterone 5α-reductase in mammalian skin

34 citations , February 1993 in “Journal of steroid biochemistry and molecular biology/The Journal of steroid biochemistry and molecular biology”

This study found that 4-MA is a potent inhibitor of testosterone 5α-reductase in human tissues, promising potential for treating androgen-dependent skin conditions like male pattern baldness.

Synthesis and In Vitro Study of 17β-[N-Ureylene-N,N′-Disubstituted]-4-Methyl-4-Aza-5α-Androstan-3-Ones as Selective Inhibitors of Type I 5α-Reductase

research Synthesis and in vitro study of 17β-[N-ureylene-N,N′-disubstituted]-4-methyl-4-aza-5α-androstan-3-ones as selective inhibitors of type I 5α-reductase

5 citations , February 1997 in “Bioorganic & Medicinal Chemistry”

This study found that among 17 beta-(N-ureylene-N,N'-disubstituted)-4-azasteroids, those with an N'-phenyl moiety were the most effective inhibitors of human type I 5 alpha-reductase.

research An overview on 5α-reductase inhibitors

219 citations , October 2009 in “Steroids”

5α-reductase inhibitors, like Finasteride and Dutasteride, help manage benign prostatic hyperplasia.

research Steroid 5α-Reductase Inhibitors

42 citations , May 2003 in “Mini-reviews in Medicinal Chemistry”

This study found that newly synthesized steroidal trienones demonstrated stronger 5α-reductase inhibitory activity compared to dienones in various biological models, suggesting potential for developing enhanced antiandrogenic drugs.

research 12 Treatment of hirsutism with 5α-reductase inhibitors

28 citations , May 1986 in “Clinics in endocrinology and metabolism”

This review discusses the potential of 4-azasteroids as 5α-reductase inhibitors for treating hirsutism, reporting their promising effects in animal studies but noting no clinical trials have been conducted yet.

research 5α‐Reductase inhibitors and prostatic disease

21 citations , August 1994 in “Clinical endocrinology”

This article reviews the effects of 5 alpha-reductase inhibitors for treating conditions like male pattern baldness and benign prostatic hyperplasia, noting significant DHT reduction but reports no new clinical results.

research Novel inhibitors of 5α-reductase

20 citations , February 2002 in “Expert Opinion on Therapeutic Patents”

This review discusses the potential uses of 5α-reductase inhibitors for conditions ranging from benign prostatic hyperplasia to skin disorders like acne and male pattern baldness, but it reports no new clinical results.

research 5α-Reductase Inhibitors, Chemical and Clinical Models

17 citations , May 1998 in “Steroids”

This study constructed a model to predict finasteride's inhibitory activity on 5α-reductase type 2 and calculated that a 1 μM plasma concentration, after 50 mg administration, matches prostate inhibition levels.

research A Connection between the Mitochondrial Permeability Transition Pore, Autophagy, and Cerebral Amyloidogenesis

14 citations , May 2008 in “Journal of proteome research”

This study found that dutasteride reduced β-amyloid plaque load in a cerebral amyloidosis model, seemingly linked to mitochondrial apoptosis and autophagy processes.

research Recent Advances in Drug Design and Drug Discovery for Androgen- Dependent Diseases

11 citations , February 2016 in “Current Medicinal Chemistry”

This review discusses various targets for treating prostate cancer and benign prostatic hyperplasia and reports on recent studies of new compounds and 5α-reductase inhibitors, but provides no new experimental results.

research A concise review- Development of an analytical method and validation of dutasteride

January 2025 in “Current Trends in Pharmacy and Pharmaceutical Chemistry”

This review examines recent advancements in analytical techniques used to quantify dutasteride, a medication for enlarged prostate, in various biological samples and its commercial forms, emphasizing methods such as HPTLC, GC-MS, and HPLC.

research Dutasteride in Androgenetic Alopecia: An Update

27 citations , March 2017 in “Current Clinical Pharmacology”

In this review, the authors discuss the pharmacology of dutasteride and compare its efficacy to finasteride for treating androgenetic alopecia, highlighting dutasteride's effectiveness demonstrated in several clinical trials.

research Alopecia - the search for novel agents continues

11 citations , August 1997 in “Expert Opinion on Therapeutic Patents”

This review discusses nearly 70 patent applications for the treatment of androgenetic alopecia and other hair conditions, highlighting the mechanisms of action explored but reports no clinical results.

research Pharmacodynamic modeling of finasteride, a 5 alpha-reductase inhibitor.

7 citations , July 1995 in “PubMed”

Finasteride, a drug that changes testosterone to a different hormone, was studied and its effects over time were modeled successfully.

research Species Differences in Prostatic Steroid 5α-Reductases of Rat, Dog, and Human

193 citations , August 1985 in “Endocrinology”

This study found significant species differences in the enzyme activity and inhibitor affinities of prostatic 5α-reductases from rats, dogs, and humans, with variable potencies for different 3-oxo-4-azasteroid inhibitors across species.

research FORMULATION AND EVALUATION OF FINASTERIDE SUSTAINED-RELEASE MATRIX TABLETS USING DIFFERENT RATE CONTROLLING POLYMERS

3 citations , December 2016 in “Universal journal of pharmaceutical research”

This study concluded that Finasteride can be effectively delivered in matrix tablets using different polymer ratios for sustained release.

research FINASTERIDE AS A TREATMENT FOR MALE ANDROGENETIC ALOPECIA

April 2013 in “e-Jurnal Medika Udayana”

This abstract indicates that finasteride, at a dose of 1 mg per day, is effective in treating androgenetic alopecia in men by significantly reducing DHT levels.

research Synthesis of N-Substituted 3-Oxo-17b- carboxamide-4-aza-5a-androstanes and the Tautomerism of 3-Oxo-4-aza-5-androstenes

4 citations , January 1998 in “Heterocycles”

Researchers made two new compounds that could be used for medicine.

research Crystal Structure of 3-Oxo-4-Aza-5-Alpha-Androstone-17 β-Tert-Butyl Carboxamide with an O···H–(C, N) Acceptor Four-Center Hydrogen Bond

2 citations , December 2008 in “Journal of Chemical Crystallography”

This study reports the crystal structure and geometric parameters of a modified Finasteride derivative, highlighting significant differences in dihedral angles compared to its solvated analog and computational models.

Synthesis and In Vitro Evaluation of 4-Substituted N-(1,1-Dimethylethyl)-3-Oxo-4-Androstene-17β-Carboxamides as 5α-Reductase Inhibitors and Antiandrogens

research Synthesis and in Vitro Evaluation of 4-Substituted N-(1,1-Dimethylethyl)-3-oxo-4-androstene-17.beta.-carboxamides as 5.alpha.-Reductase Inhibitors and Antiandrogens

12 citations , April 1995 in “Journal of Medicinal Chemistry”

In this study, 4-substituted N-(1,1-dimethylethyl)-3-oxo-4-androstene-17.beta.-carboxamides were synthesized and evaluated in vitro as potential 5 alpha-reductase inhibitors and antiandrogens.

research New approach to 3-oxo-4-aza-5α-androst-1-ene-17β-(--butylcarboxamide)

14 citations , May 2005 in “Steroids”

This study describes the synthesis of finasteride from 4-androstene-3,17-dione in a seven-step process with an overall yield of 18.6%.

Evaluation of New Pregnane Derivatives as 5α-Reductase Inhibitors

research Evaluation of New Pregnane Derivatives as 5.ALPHA.-Reductase Inhibitor.

23 citations , January 2001 in “Chemical & Pharmaceutical Bulletin”

This study found that several synthesized pregnane derivatives exhibited significant inhibitory effects on testosterone conversion to dihydrotestosterone and reduced related androgenic parameters in multiple pharmacological models.

New Progesterone Esters as 5α-Reductase Inhibitors

research New Progesterone Esters as 5.ALPHA.-Reductase Inhibitors.

22 citations , January 2001 in “Chemical & Pharmaceutical Bulletin”

This study found that two new progesterone derivatives showed higher antiandrogenic effects and 5α-reductase inhibition than finasteride in hamsters, particularly reducing seminal vesicle weight and flank organ size.

research Recent advances in thiasteroids chemistry

37 citations , October 2006 in “Steroids”

This paper describes recent advancements in the synthesis of thiasteroids but reports no new experimental results, noting that introducing heteroatoms in steroidal structures has potential biological effects.

research Generation of comparative pharmacophoric model for steroidal 5α-reductase I and II inhibitors: A 3D-QSAR study on 6-azasteroids

13 citations , January 2015 in “Steroids”

This study generated a pharmacophoric model for both isoforms of steroidal 5α-reductase using 6-azasteroids, providing a structural framework for designing new inhibitors.

Experimental Assessment of 3-Meta-Pyridine-1,2,4-Oxadiazole Deoxycholic Acid Derivative as a Prototype of 5-Alpha-Reductase Inhibitors in Silico and in Vivo Models

research Experimental Assessment of 3-meta-Pyridine-1,2,4-Oxadiazole Deoxycholic Acid Derivative as a Prototype of 5-α-Reductase Inhibitors in silico and in vivo Models

January 2023 in “Bioorganičeskaâ himiâ”

This study found that a new deoxycholic acid derivative may offer a similar prostatoprotective effect to finasteride with lower toxicity in rat models.

Selective Induction of Apoptosis in the Hamster Flank Sebaceous Gland Organ by a Topical Liposome 5-Alpha-Reductase Inhibitor: A Treatment Strategy for Acne

research Selective induction of apoptosis in the hamster flank sebaceous gland organ by a topical liposome 5-α-reductase inhibitor: A treatment strategy for acne

8 citations , February 2010 in “Journal of Dermatology”

This study observed that a topical liposome formulation of a 5‐α‐reductase inhibitor effectively reduced the size of treated sebaceous glands and induced apoptosis in a hamster model, suggesting potential benefits for acne treatment.