Steroidogenesis inhibitor

Last updated
Steroidogenesis inhibitor
Drug class
Class identifiers
Synonyms Steroid biosynthesis inhibitor; Steroid synthesis inhibitor
UseVarious
Biological target Steroidogenic enzymes
Chemical class Steroidal; Nonsteroidal
In Wikidata

A steroidogenesis inhibitor, also known as a steroid biosynthesis inhibitor, is a type of drug which inhibits one or more of the enzymes that are involved in the process of steroidogenesis, the biosynthesis of endogenous steroids and steroid hormones. [1] They may inhibit the production of cholesterol and other sterols, sex steroids such as androgens, estrogens, and progestogens, corticosteroids such as glucocorticoids and mineralocorticoids, and neurosteroids. [1] [2] They are used in the treatment of a variety of medical conditions that depend on endogenous steroids. [1]

Contents

Steroidogenesis inhibitors are analogous in effect and use to antigonadotropins (which specifically inhibit gonadal sex steroid production), but work via a different mechanism of action; whereas antigonadotropins suppress gonadal production of sex steroids by effecting negative feedback on and thereby suppressing the hypothalamic–pituitary–gonadal axis, steroidogenesis inhibitors directly inhibit the enzymatic biosynthesis of steroids. [1]

Types, examples, and uses

Cholesterol synthesis inhibitors

Cholesterol biosynthesis from acetyl-CoA. HMG-CoA reductase pathway.svg
Cholesterol biosynthesis from acetyl-CoA.

Acetyl-CoA to lanosterol inhibitors

Lanosterol to cholesterol inhibitors

  • 24-Dehydrocholesterol reductase (24-DHCR) inhibitors such as azacosterol and triparanol inhibit the production of cholesterol from desmosterol, one of the last steps in cholesterol biosynthesis, and were formerly used to treat hypercholesterolemia, but were withdrawn from the market due to toxicity caused by accumulation of desmosterol in tissues. [12] [13]

Steroid hormone synthesis inhibitors

Steroidogenesis, biosynthesis of steroid hormones from cholesterol. Steroidogenesis.svg
Steroidogenesis, biosynthesis of steroid hormones from cholesterol.

Non-specific steroid hormone synthesis inhibitors

Corticosteroid-specific synthesis inhibitors

Sex steroid-specific synthesis inhibitors

Other steroid synthesis inhibitors

List of steroid metabolism modulators

Enzyme Substrates→Products Inhibitors Inducers
HMG-CoA reductase
(HMGCR)		 HMG-CoA→Mevalonic acid Atorvastatin • Cerivastatin • Colestolone • Fluvastatin • Lovastatin • Mevastatin • Pitavastatin • Pravastatin • Rosuvastatin • Simvastatin
FPPS Dimethylallyl pyrophosphate (isoprenyl pyrophosphate)→Farnesyl pyrophosphate • Isopentenyl pyrophosphate→Farnesyl pyrophosphate Alendronic acid • Ibandronic acid • Incadronic acid • Pamidronic acid • Risedronic acid • Zoledronic acid
7-DHCR 7-Dehydrocholesterol→Cholesterol AY-9944 • BM-15766 • Triparanol
24-DHCR Desmosterol→Cholesterol Azacosterol • Clomifene • Triparanol • WY-3457
P450scc
(CYP11A1)		 Cholesterol→22R-Hydroxycholesterol • 22R-Hydroxycholesterol→20α,22R-Dihydroxycholesterol • 20α,22R-Dihydroxycholesterol→Pregnenolone 22-ABC • 3,3′-Dimethoxybenzidine • 3-Methoxybenzidine • Aminoglutethimide • Amphenone B • Canrenone • Cyanoketone • Danazol • Etomidate • Ketoconazole • Levoketoconazole • Mitotane • Spironolactone • Trilostane
3β-HSD
(HSD3B)		 Pregnenolone→Progesterone • 17α-Hydroxypregnenolone→17α-Hydroxyprogesterone • Dehydroepiandrosterone→Androstenedione • 5-Androstenediol→Testosterone • Androstadienol→Androstadienone 4-MA • Δ4-Abiraterone • Abiraterone • Abiraterone acetate • Amphenone B • Azastene • Cyanoketone • Cyproterone acetate • Danazol • Epostane • Genistein • Gestrinone • Medrogestone • Medroxyprogesterone acetate • Metribolone • Metyrapone • Norethisterone • Oxymetholone • Pioglitazone • Rosiglitazone • Trilostane • Troglitazone
17α-Hydroxylase,
17,20-lyase (CYP17A1)		 Pregnenolone→17α-Hydroxypregnenolone • Progesterone→17α-Hydroxyprogesterone • 17α-Hydroxypregnenolone→Dehydroepiandrosterone • 17α-Hydroxyprogesterone→Androstenedione 22-ABC • 22-Oxime • Δ4-Abiraterone • Abiraterone • Abiraterone acetate • Amphenone B • Bifluranol • Bifonazole • Canrenone • CFG-920 • Clotrimazole • Cyanoketone • Cyproterone acetate • Danazol • Econazole • Etomidate • Flutamide • Galeterone • Gestrinone • Isoconazole • Ketoconazole • L-39 • Levoketoconazole • Liarozole • LY-207,320 • MDL-27,302 • Miconazole • Mifepristone • Nilutamide • Orteronel • Pioglitazone • Prochloraz • Rosiglitazone • Seviteronel • Spironolactone • Stanozolol • SU-9055 • SU-10603 • TGF-β • Tioconazole • Troglitazone • VN/87-1 • YM116
11β-HSD
(HSD11B)		 Cortisol↔Cortisone 11-Ketoprogesterone • 11α-Hydroxyprogesterone • 11β-Hydroxyprogesterone • 18α-Glycyrrhizic acid • ABT-384 • Acetoxolone • Amphenone B • Carbenoxolone • Enoxolone (glycyrrhetinic acid) • Epigallocatechin gallate • Glycyrrhizin (glycyrrhizic acid) (licorice) • Progesterone
21-Hydroxylase
(CYP21A2)		 Progesterone→11-Deoxycorticosterone • 17α-Hydroxyprogesterone→11-Deoxycortisol Aminoglutethimide • Amphenone B • Bifonazole • Canrenone • Clotrimazole • Diazepam • Econazole • Genistein • Isoconazole • Ketoconazole • Levoketoconazole • Metyrapone • Miconazole • Midazolam • Spironolactone • Abiraterone • Abiraterone acetate • Tioconazole
11β-Hydroxylase
(CYP11B1)		 11-Deoxycorticosterone→Corticosterone • 11-Deoxycortisol→Cortisol Δ4-Abiraterone • Abiraterone • Abiraterone acetate • Aminoglutethimide • Canrenone • Etomidate • Fadrozole • FETO • Ketoconazole • Levoketoconazole • Metomidate • Metyrapol • Metyrapone • Mitotane • Potassium canrenoate • Spironolactone • Trilostane• Osilodrostat
Aldosterone
synthase (CYP11B2)		 Corticosterone→Aldosterone 18-Ethynylprogesterone (18-ethinylprogesterone) • 18-Vinylprogesterone • Aminoglutethimide • Azelnidipine • Benidipine • Canrenone • Cilnidipine • Efonidipine • FAD286 • Fadrozole • Ketoconazole • Metyrapone • Mespirenone • Osilodrostat • Potassium canrenoate • Spironolactone
17β-HSD
(HSD17B)		 Dehydroepiandrosterone↔5-Androstenediol • Androstenedione↔Testosterone • Estrone↔Estradiol Danazol • Ethanol • Fisetin • RM-532-105 • Simvastatin • STX-2171 • STX-2622 • STX-2624
5α-Reductase
(SRD5A)		 Cholestenone→5α-Cholestanone • Progesterone→5α-Dihydroprogesterone • 3α-Dihydroprogesterone→Allopregnanolone • 3β-Dihydroprogesterone→Isopregnanolone • Deoxycorticosterone→5α-Dihydrodeoxycorticosterone • Corticosterone→5α-Dihydrocorticosterone • Cortisol→5α-Dihydrocortisol • Aldosterone→5α-Dihydroaldosterone • Androstenedione→5α-Androstanedione • Testosterone→5α-Dihydrotestosterone • Androstadienone→Androstenone 22-Oxime • Δ4-Abiraterone • Abiraterone • Abiraterone acetate • Alfatradiol • Azelaic acid • β-Sitosterol • Bexlosteride • Chlormadinone acetate • Cl-4AS-1 • Dutasteride • Epitestosterone • Epristeride • Fatty acids (α-linolenic acid, linoleic acid, γ-linolenic acid, monolinolein, oleic acid) • Finasteride • Ganoderic acid • Gestodene • Izonsteride • L-39 • Lapisteride • Oxendolone • Saw palmetto extract • TFM-4AS-1 • Turosteride • Vitamin B6 • Zinc
3α-HSD
(AKR1C4)		 5α-Dihydroprogesterone↔Allopregnanolone • DHDOC↔THDOC • Dihydrotestosterone↔3α-Androstanediol Coumestrol • Daidzein • Genistein • Indometacin • Medroxyprogesterone acetate Fluoxetine • Fluvoxamine • Mirtazapine • Paroxetine • Sertraline • Venlafaxine
Aromatase
(CYP19A1)		 16α-Hydroxyandrostenedione→16α-Hydroxyestrone • Androstenedione→Estrone • Nandrolone→Estradiol • Metandienone→Methylestradiol • Methyltestosterone→Methylestradiol • Testosterone→Estradiol 4-AT • 4-Cyclohexylaniline • 4'-Hydroxynorendoxifen • 4-Hydroxytestosterone • 5α-DHNET • 20α-Dihydroprogesterone • Abyssinone II • alpha-Naphthoflavone • Aminoglutethimide • Anastrozole • Ascorbic acid (vitamin C) • Atamestane • ATD • Bifonazole • CGP-45,688 • CGS-47,645 • Chalconoids (e.g., isoliquiritigenin) • Clotrimazole • Corynesidone A • Coumestrol • DHT • Difeconazole • Econazole • Ellagitannins • Endosulfan • Exemestane • Fadrozole • Fatty acids (e.g., conjugated linoleic acid, linoleic acid, linolenic acid, palmitic acid) • Fenarimol • Finrozole • Flavonoids (e.g., 7-hydroxyflavone, 7-hydroxyflavanone, 7,8-DHF, acacetin, apigenin, baicalein, biochanin A, chrysin, EGCG, gossypetin, hesperetin, liquiritigenin, myricetin, naringenin, pinocembrin, rotenone, quercetin,sakuranetin, tectochrysin) • Formestane • Imazalil • Isoconazole • Ketoconazole • Leflutrozole • Letrozole • Liarozole • Melatonin • MEN-11066 • Miconazole • Minamestane • Nimorazole • NKS01 • Norendoxifen • ORG-33,201 • Penconazole • Phenytoin • PGE2 (dinoprostone) • Plomestane • Prochloraz • Propiconazole • Quinolinoids (e.g., berberine, casimiroin, triptoquinone A, XHN22, XHN26, XHN27) • Resorcylic acid lactones (e.g., zearalenone) • Rogletimide (pyridoglutethimide) • Stilbenoids (e.g., resveratrol) • Terpenoids (e.g., dehydroabietic acid, (–)-dehydrololiolide, retinol (vitamin A), Δ9-THC,tretinoin) • Testolactone • Tioconazole • Triadimefon • Triadimenol • Troglitazone • Valproic acid • Vorozole • Xanthones (e.g., garcinone D, garcinone E, α-mangostin, γ-mangostin, monodictyochrome A, monodictyochrome B) • YM-511 • Zinc Atrazine • Flavonoids (e.g., genistein, quercetin)
SST/EST Dehydroepiandrosterone→Dehydroepiandrosterone sulfate • Estrone→Estrone sulfate 4′OH-CB79 • 6-Hydroxyflavone • 2,6-Dichloro-4-nitrophenol (DCNP) • 7,8-Dihydroxyflavone • Equol • Galangin • Genistein • Parabens (e.g., butylparaben) • Pentachlorophenol (PCP) • Triclosan
STS Cholesterol sulfate→Cholesterol • Dehydroepiandrosterone sulfate→Dehydroepiandrosterone • Estrone sulfate→Estrone • Pregnenolone sulfate→Pregnenolone AHBS • Danazol • Estradiol sulfamate (E2MATE) • Estrone sulfamate (EMATE) • Irosustat (STX64, 667 Coumate, BN-83495) • KW-2581 • SR-16157 • STX213 • STX681 • STX1938
Sterol
27-hydroxylase
(CYP27A1)		 Cholesterol→27-Hydroxycholesterol Anastrozole • Bicalutamide • Dexmedetomidine • Fadrozole • Posaconazole • Ravuconazole
Cholesterol
7α-hydroxylase (CYP7A1)		 Cholesterol→7α-Hydroxycholesterol (intermediate to bile acids) Ketoconazole • Levoketoconazole
Lanosterol
14α-demethylase (CYP51A1)		 Lanosterol→4,4-Dimethylcholesta-8(9),14,24-trien-3β-ol (intermediate to ergosterol) Albaconazole • Aliconazole • Alteconazole • Arasertaconazole • Azaconazole • Azalanstat • Becliconazole • Bifonazole • Brolaconazole • Butoconazole • Chlormidazole • Cisconazole • Clotrimazole • Croconazole • Cyproconazole • Democonazole • Diniconazole • Doconazole • Eberconazole • Econazole • Econazole/triamcinolone • Efinaconazole • Embeconazole • Enilconazole • Etaconazole • Fenticonazole • Fluconazole • Flutrimazole • Fosfluconazole • Furconazole • Hexaconazole • Isavuconazole • Isavuconazonium chloride • Isavuconazonium sulfate • Isoconazole • Itraconazole • Ketoconazole • Lanoconazole • Levoketoconazole • Luliconazole • Miconazole • Neticonazole • Omoconazole • Orconazole • Oxiconazole • Parconazole • Penconazole • Posaconazole • Propiconazole • Pramiconazole • Quilseconazole • Ravuconazole • Saperconazole • Sertaconazole • Sulconazole • Tebuconazole • Terconazole (triaconazole) • Tioconazole • Uniconazole • Valconazole • Voriconazole • Zinoconazole • Zoficonazole


See also

Related Research Articles

<span class="mw-page-title-main">Dehydroepiandrosterone</span> Chemical compound

Dehydroepiandrosterone (DHEA), also known as androstenolone, is an endogenous steroid hormone precursor. It is one of the most abundant circulating steroids in humans. DHEA is produced in the adrenal glands, the gonads, and the brain. It functions as a metabolic intermediate in the biosynthesis of the androgen and estrogen sex steroids both in the gonads and in various other tissues. However, DHEA also has a variety of potential biological effects in its own right, binding to an array of nuclear and cell surface receptors, and acting as a neurosteroid and modulator of neurotrophic factor receptors.

<span class="mw-page-title-main">Steroid</span> Any organic compound having sterane as a core structure

A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have two principal biological functions: as important components of cell membranes that alter membrane fluidity; and as signaling molecules. Hundreds of steroids are found in plants, animals and fungi. All steroids are manufactured in cells from the sterols lanosterol (opisthokonts) or cycloartenol (plants). Lanosterol and cycloartenol are derived from the cyclization of the triterpene squalene.

<span class="mw-page-title-main">Progestogen</span> Steroid hormone that activates the progesterone receptor

Progestogens, also sometimes written progestagens or gestagens, are a class of natural or synthetic steroid hormones that bind to and activate the progesterone receptors (PR). Progesterone is the major and most important progestogen in the body. The progestogens are named for their function in maintaining pregnancy, although they are also present at other phases of the estrous and menstrual cycles.

<span class="mw-page-title-main">Dihydrotestosterone</span> Human hormone

Dihydrotestosterone is an endogenous androgen sex steroid and hormone. The enzyme 5α-reductase catalyzes the formation of DHT from testosterone in certain tissues including the prostate gland, seminal vesicles, epididymides, skin, hair follicles, liver, and brain. This enzyme mediates reduction of the C4-5 double bond of testosterone. Relative to testosterone, DHT is considerably more potent as an agonist of the androgen receptor (AR).

<span class="mw-page-title-main">Estriol</span> Chemical compound

Estriol (E3), also spelled oestriol, is a steroid, a weak estrogen, and a minor female sex hormone. It is one of three major endogenous estrogens, the others being estradiol and estrone. Levels of estriol in women who are not pregnant are almost undetectable. However, during pregnancy, estriol is synthesized in very high quantities by the placenta and is the most produced estrogen in the body by far, although circulating levels of estriol are similar to those of other estrogens due to a relatively high rate of metabolism and excretion. Relative to estradiol, both estriol and estrone have far weaker activity as estrogens.

<span class="mw-page-title-main">Ketoconazole</span> Antifungal chemical compound

Ketoconazole, sold under the brand name Nizoral among others, is an antiandrogen and antifungal medication used to treat a number of fungal infections. Applied to the skin it is used for fungal skin infections such as tinea, cutaneous candidiasis, pityriasis versicolor, dandruff, and seborrheic dermatitis. Taken by mouth it is a less preferred option and only recommended for severe infections when other agents cannot be used. Other uses include treatment of excessive hair growth and Cushing's syndrome.

<span class="mw-page-title-main">Pregnenolone</span> Chemical compound

Pregnenolone (P5), or pregn-5-en-3β-ol-20-one, is an endogenous steroid and precursor/metabolic intermediate in the biosynthesis of most of the steroid hormones, including the progestogens, androgens, estrogens, glucocorticoids, and mineralocorticoids. In addition, pregnenolone is biologically active in its own right, acting as a neurosteroid.

<span class="mw-page-title-main">Aminoglutethimide</span> Group of stereoisomers

Aminoglutethimide (AG), sold under the brand names Elipten, Cytadren, and Orimeten among others, is a medication which has been used in the treatment of seizures, Cushing's syndrome, breast cancer, and prostate cancer, among other indications. It has also been used by bodybuilders, athletes, and other men for muscle-building and performance- and physique-enhancing purposes. AG is taken by mouth three or four times per day.

<span class="mw-page-title-main">Danazol</span> Chemical compound

Danazol, sold as Danocrine and other brand names, is a medication used in the treatment of endometriosis, fibrocystic breast disease, hereditary angioedema and other conditions. It is taken by mouth.

<span class="mw-page-title-main">Dehydroepiandrosterone sulfate</span> Chemical compound

Dehydroepiandrosterone sulfate, abbreviated as DHEA sulfate or DHEA-S, also known as androstenolone sulfate, is an endogenous androstane steroid that is produced by the adrenal cortex. It is the 3β-sulfate ester and a metabolite of dehydroepiandrosterone (DHEA) and circulates in far greater relative concentrations than DHEA. The steroid is hormonally inert and is instead an important neurosteroid and neurotrophin.

17β-Hydroxysteroid dehydrogenases, also 17-ketosteroid reductases (17-KSR), are a group of alcohol oxidoreductases which catalyze the reduction of 17-ketosteroids and the dehydrogenation of 17β-hydroxysteroids in steroidogenesis and steroid metabolism. This includes interconversion of DHEA and androstenediol, androstenedione and testosterone, and estrone and estradiol.

<span class="mw-page-title-main">Inborn errors of steroid metabolism</span> Medical condition

An inborn error of steroid metabolism is an inborn error of metabolism due to defects in steroid metabolism.

A neurosteroidogenesis inhibitor is a drug that inhibits the production of endogenous neurosteroids. Neurosteroids include the excitatory neurosteroids pregnenolone sulfate, dehydroepiandrosterone (DHEA), and dehydroepiandrosterone sulfate (DHEA-S), and the inhibitory neurosteroids allopregnanolone, tetrahydrodeoxycorticosterone (THDOC), and 3α-androstanediol, among others. By inhibiting the synthesis of endogenous neurosteroids, neurosteroidogenesis inhibitors have effects in the central nervous system.

An androgen synthesis inhibitor is a type of drug which inhibits the enzymatic synthesis of androgens, such as testosterone and dihydrotestosterone (DHT). They include:

Adrenal steroids are steroids that are derived from the adrenal glands. They include corticosteroids, which consist of glucocorticoids like cortisol and mineralocorticoids like aldosterone, adrenal androgens like dehydroepiandrosterone (DHEA), DHEA sulfate (DHEA-S), and androstenedione (A4), and neurosteroids like DHEA and DHEA-S, as well as pregnenolone and pregnenolone sulfate (P5-S). Adrenal steroids are specifically produced in the adrenal cortex.

<span class="mw-page-title-main">Amphenone B</span>

Amphenone B, or simply amphenone, also known as 3,3-bis(p-aminophenyl)butan-2-one, is an inhibitor of steroid hormone and thyroid hormone biosynthesis which was never marketed but has been used as a tool in scientific research to study corticosteroids and the adrenal glands. It acts as competitive inhibitor of 11β-hydroxylase, 17α-hydroxylase, 17,20-lyase, 21-hydroxylase, and 3β-hydroxysteroid dehydrogenase, as well as of cholesterol side-chain cleavage enzyme, thereby inhibiting the production of steroid hormones including glucocorticoids, mineralocorticoids, androgens, and estrogens. In addition, amphenone B inhibits the production of thyroxine by a thiouracil-like mechanism, specifically via inhibition of organic binding of iodine and uptake of iodide by the thyroid gland.

<span class="mw-page-title-main">Steroidogenic enzyme</span>

Steroidogenic enzymes are enzymes that are involved in steroidogenesis and steroid biosynthesis. They are responsible for the biosynthesis of the steroid hormones, including sex steroids and corticosteroids, as well as neurosteroids, from cholesterol. Steroidogenic enzymes are most highly expressed in classical steroidogenic tissues, such as the testis, ovary, and adrenal cortex, but are also present in other tissues in the body.

An anticorticotropin, or anticorticotrophin, is a drug which opposes the actions of corticotropin-releasing hormone (CRH) and/or adrenocorticotropic hormone (ACTH) in relation to their stimulatory effects on the adrenal glands, or which otherwise suppresses steroid hormone production in the adrenal glands. They can be said to have anticorticotropic effects, and are used to treat Cushing's syndrome, prostate cancer, hyperandrogenism, and other conditions.

An estrogen synthesis inhibitor is a type of drug which inhibits the enzymatic synthesis of estrogens, such as estradiol. They include:

A progesterone synthesis inhibitor, or progestogen synthesis inhibitor, is a type of drug which inhibits the enzymatic synthesis of progesterone. They include:

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