All You Need to Know About Steroids

Whatever organic chemical compound having sterane every bit a cadre structure

Structure of 24-ethyl-lanostane, a hypothetical steroid with 32 carbon atoms. Its core band system (ABCD), composed of 17 carbon atoms, is shown with IUPAC-approved ring lettering and atom numbering.^{[1] : 1785f}

A steroid is a biologically active organic compound with four rings arranged in a specific molecular configuration. Steroids have ii principal biological functions: as of import components of cell membranes which alter membrane fluidity; and as signaling molecules. Hundreds of steroids are institute 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.^[ii]

The steroid cadre structure is typically composed of seventeen carbon atoms, bonded in iv "fused" rings: three six-fellow member cyclohexane rings (rings A, B and C in the first illustration) and one five-member cyclopentane ring (the D ring). Steroids vary by the functional groups attached to this four-ring core and by the oxidation land of the rings. Sterols are forms of steroids with a hydroxy group at position 3 and a skeleton derived from cholestane.^{[i] : 1785f [3]} Steroids tin can besides exist more radically modified, such as by changes to the ring structure, for instance, cut 1 of the rings. Cutting Ring B produces secosteroids one of which is vitamin D_three.

Examples include the lipid cholesterol, the sex activity hormones estradiol and testosterone,^{[4] : 10–xix} and the anti-inflammatory drug dexamethasone.^[5]

Space-filling representation

Brawl-and-stick representation

5α-dihydroprogesterone (5α-DHP), a steroid. The shape of the four rings of most steroids is illustrated (carbon atoms in black, oxygens in ruby-red and hydrogens in grey). The nonpolar "slab" of hydrocarbon in the middle (gray, blackness) and the polar groups at opposing ends (red) are common features of natural steroids. 5α-DHP is an endogenous steroid hormone and a biosynthetic intermediate.

Nomenclature [edit]

Gonane, the simplest steroid, consisting only of the common steroid nucleus

Gonane, besides known every bit steran or cyclopentanoperhydrophenanthrene, the simplest steroid and the nucleus of all steroids and sterols,^{[6] [7]} is composed of seventeen carbon atoms in carbon-carbon bonds forming iv fused rings in a three-dimensional shape. The three cyclohexane rings (A, B, and C in the kickoff illustration) grade the skeleton of a perhydro derivative of phenanthrene. The D ring has a cyclopentane structure. When the two methyl groups and viii carbon side bondage (at C-17, as shown for cholesterol) are present, the steroid is said to accept a cholestane framework. The ii common 5α and 5β stereoisomeric forms of steroids be because of differences in the side of the largely planar ring system where the hydrogen (H) atom at carbon-five is fastened, which results in a change in steroid A-ring conformation. Isomerisation at the C-21 side concatenation produces a parallel series of compounds, referred to equally isosteroids.^[viii]

Examples of steroid structures are:

• 

• 

• 

• 

  Progesterone, a steroid hormone involved in the female menstrual cycle, pregnancy, and embryogenesis

• 

  Medrogestone, a constructed drug with effects like to progesterone

• 

  β-Sitosterol, a establish or phytosterol, with a fully branched hydrocarbon side chain at C-17 and an hydroxyl group at C-three

In addition to the ring scissions (cleavages), expansions and contractions (cleavage and reclosing to a larger or smaller rings)—all variations in the carbon-carbon bond framework—steroids tin likewise vary:

• in the bond orders within the rings,
• in the number of methyl groups attached to the ring (and, when present, on the prominent side chain at C17),
• in the functional groups fastened to the rings and side chain, and
• in the configuration of groups attached to the rings and chain.^{[4] : ii–9}

For example, sterols such every bit cholesterol and lanosterol accept a hydroxyl group attached at position C-iii, while testosterone and progesterone have a carbonyl (oxo substituent) at C-3; of these, lanosterol lone has two methyl groups at C-4 and cholesterol (with a C-5 to C-vi double bond) differs from testosterone and progesterone (which have a C-4 to C-v double bond).

Species distribution and function [edit]

This section needs attending from an skilful in pharmacology. The specific trouble is: to examine this and the following section (and throughout), and to remove redundancies of listed content, and to ensure sourcing for the listed content that remains in any section. WikiProject Pharmacology may be able to help recruit an expert. (March 2017)

In eukaryotes, steroids are institute in fungi, animals, and plants.

Fungal steroids [edit]

Fungal steroids include the ergosterols, which are involved in maintaining the integrity of the fungal cellular membrane. Various antifungal drugs, such every bit amphotericin B and azole antifungals, use this information to kill pathogenic fungi.^[9] Fungi tin can change their ergosterol content (e.one thousand. through loss of function mutations in the enzymes ERG3 or ERG6, inducing depletion of ergosterol, or mutations that decrease the ergosterol content) to develop resistance to drugs that target ergosterol.^[x] Ergosterol is analogous to the cholesterol institute in the cellular membranes of animals (including humans), or the phytosterols plant in the cellular membranes of plants.^[10] All mushrooms contain large quantities of ergosterol, in the range of tens to hundreds of milligrams per 100 grams of dry out weight.^[10] Oxygen is necessary for the synthesis of ergosterol in fungi.^[10] Ergosterol is responsible for the vitamin D content found in mushrooms; ergosterol is chemically converted into provitamin D2 by exposure to ultraviolet lite.^[10] Provitamin D2 spontaneously forms vitamin D2.^[ten] However, not all fungi employ ergosterol in their cellular membranes; for example, the pathogenic fungal species Pneumocystis jirovecii does not, which has of import clinical implications (given the mechanism of action of many antifungal drugs).^[x] Using the fungus Saccharomyces cerevisiae as an example, other major steroids include ergosta‐v,seven,22,24(28)‐tetraen‐3β‐ol, zymosterol, and lanosterol.^[ten] S. cerevisiae utilizes 5,half-dozen‐dihydroergosterol in place of ergosterol in its cell membrane.^[10]

Animal steroids [edit]

Animal steroids include compounds of vertebrate and insect origin, the latter including ecdysteroids such as ecdysterone (controlling molting in some species). Vertebrate examples include the steroid hormones and cholesterol; the latter is a structural component of cell membranes which helps determine the fluidity of cell membranes and is a principal elective of plaque (implicated in atherosclerosis). Steroid hormones include:

• Sex hormones, which influence sex differences and support reproduction. These include androgens, estrogens, and progestogens.
• Corticosteroids, including most synthetic steroid drugs, with natural product classes the glucocorticoids (which regulate many aspects of metabolism and immune function) and the mineralocorticoids (which assist maintain claret book and control renal excretion of electrolytes)
• Anabolic steroids, natural and synthetic, which interact with androgen receptors to increase musculus and bone synthesis. In pop use, the term "steroids" ofttimes refers to anabolic steroids.

Plant steroids [edit]

Plant steroids include steroidal alkaloids found in Solanaceae^[11] and Melanthiaceae (especially the genus Veratrum),^[12] cardiac glycosides,^[thirteen] the phytosterols and the brassinosteroids (which include several plant hormones).

Prokaryotes [edit]

This section is missing data about non-eukaryotic type sterol framework – meet PMID 27446030, fig four/v, group 1 oxidosqualene cyclase. Please expand the section to include this data. Further details may exist on the talk folio. (November 2021)

In prokaryotes, biosynthetic pathways exist for the tetracyclic steroid framework (e.k. in mycobacteria)^[14] – where its origin from eukaryotes is conjectured^[15] – and the more-common pentacyclic triterpinoid hopanoid framework.^[16]

Types [edit]

By part [edit]

This department needs expansion with: This listing does non discuss lipid steroids. A more detailed explanation of function would also exist beneficial. You can help by adding to it. (January 2019)

The major classes of steroid hormones, with prominent members and examples of related functions, are:^{[ citation needed ]}

• Corticosteroids:
  • Glucocorticoids:
    • Cortisol, a glucocorticoid whose functions include immunosuppression
  • Mineralocorticoids:
    • Aldosterone, a mineralocorticoid which helps regulate blood pressure through h2o and electrolyte balance
• Sex activity steroids:
  • Progestogens:
    • Progesterone, which regulates cyclical changes in the endometrium of the uterus and maintains a pregnancy
  • Androgens:
    • Testosterone, which contributes to the development and maintenance of male secondary sex characteristics
  • Estrogens:
    • Estradiol, which contributes to the development and maintenance of female person secondary sex characteristics

Additional classes of steroids include:

• Neurosteroids such as DHEA and allopregnanolone
• Aminosteroid neuromuscular blocking agents such as pancuronium bromide

As well as the post-obit form of secosteroids (open-ring steroids):

• Vitamin D forms such every bit ergocalciferol, cholecalciferol, and calcitriol

By structure [edit]

Intact ring organization [edit]

This section needs expansion with: a more full discussion of this virtually prominent structural type. You can help past calculation to it. (March 2017)

Steroids tin be classified based on their chemical composition.^[17] One case of how MeSH performs this classification is available at the Wikipedia MeSH catalog. Examples of this nomenclature include:

Cyclopamine, an case of a complex C-nor-D-homosteroid

Course	Example	Number of carbon atoms
Cholestanes	Cholesterol	27
Cholanes	Cholic acid	24
Pregnanes	Progesterone	21
Androstanes	Testosterone	nineteen
Estranes	Estradiol	18

The gonane (steroid nucleus) is the parent 17-carbon tetracyclic hydrocarbon molecule with no alkyl sidechains.^[xviii]

Cleaved, contracted, and expanded rings [edit]

Secosteroids (Latin seco, "to cut") are a subclass of steroidal compounds resulting, biosynthetically or conceptually, from scission (cleavage) of parent steroid rings (generally one of the four). Major secosteroid subclasses are divers past the steroid carbon atoms where this scission has taken place. For example, the prototypical secosteroid cholecalciferol, vitamin D_iii (shown), is in the 9,x-secosteroid subclass and derives from the cleavage of carbon atoms C-ix and C-10 of the steroid B-ring; five,6-secosteroids and thirteen,14-steroids are similar.^[19]

Norsteroids (nor-, L. norma; "normal" in chemistry, indicating carbon removal)^[20] and homosteroids (homo-, Greek homos; "same", indicating carbon improver) are structural subclasses of steroids formed from biosynthetic steps. The old involves enzymic band expansion-contraction reactions, and the latter is achieved (biomimetically) or (more frequently) through ring closures of acyclic precursors with more (or fewer) ring atoms than the parent steroid framework.^[21]

Combinations of these ring alterations are known in nature. For instance, ewes who graze on corn lily ingest cyclopamine (shown) and veratramine, two of a sub-family of steroids where the C- and D-rings are contracted and expanded respectively via a biosynthetic migration of the original C-13 atom. Ingestion of these C-nor-D-homosteroids results in nascence defects in lambs: cyclopia from cyclopamine and leg deformity from veratramine.^[22] A farther C-nor-D-homosteroid (nakiterpiosin) is excreted by Okinawan cyanobacteriosponges. e.thou., Terpios hoshinota, leading to coral mortality from black coral disease.^[23] Nakiterpiosin-type steroids are active against the signaling pathway involving the smoothened and hedgehog proteins, a pathway which is hyperactive in a number of cancers.^{[ commendation needed ]}

Biological significance [edit]

Steroids and their metabolites often function equally signalling molecules (the virtually notable examples are steroid hormones), and steroids and phospholipids are components of jail cell membranes.^[24] Steroids such equally cholesterol decrease membrane fluidity.^[25] Similar to lipids, steroids are highly concentrated energy stores. Yet, they are non typically sources of energy; in mammals, they are normally metabolized and excreted.

Steroids play critical roles in a number of disorders, including malignancies like prostate cancer, where steroid product inside and exterior the tumour promotes cancer cell aggressiveness.^[26]

Biosynthesis and metabolism [edit]

The hundreds of steroids found in animals, fungi, and plants are made from lanosterol (in animals and fungi; see examples above) or cycloartenol (in other eukaryotes). Both lanosterol and cycloartenol derive from cyclization of the triterpenoid squalene.^[2] Lanosterol and cycloartenol are sometimes called protosterols considering they serve equally the starting compounds for all other steroids.

Steroid biosynthesis is an anabolic pathway which produces steroids from unproblematic precursors. A unique biosynthetic pathway is followed in animals (compared to many other organisms), making the pathway a common target for antibiotics and other anti-infection drugs. Steroid metabolism in humans is also the target of cholesterol-lowering drugs, such as statins. In humans and other animals the biosynthesis of steroids follows the mevalonate pathway, which uses acetyl-CoA equally building blocks for dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP).^{[27] [ better source needed ]}

In subsequent steps DMAPP and IPP conjugate to grade farnesyl diphosphate (FPP), which further conjugates with each other to form the linear triterpenoid squalene. Squalene biosynthesis is catalyzed past squalene synthase, which belongs to the squalene/phytoene synthase family unit. Subsequent epoxidation and cyclization of squalene generate lanosterol, which is the starting signal for additional modifications into other steroids (steroidogenesis).^[28] In other eukaryotes, the cyclization production of epoxidized squalene (oxidosqualene) is cycloartenol.

Mevalonate pathway [edit]

The mevalonate pathway (also chosen HMG-CoA reductase pathway) begins with acetyl-CoA and ends with dimethylallyl diphosphate (DMAPP) and isopentenyl diphosphate (IPP).

DMAPP and IPP donate isoprene units, which are assembled and modified to grade terpenes and isoprenoids^[29] (a large class of lipids, which include the carotenoids and form the largest form of institute natural products.^[30] Here, the isoprene units are joined to make squalene and folded into a set of rings to make lanosterol.^[31] Lanosterol tin and so be converted into other steroids, such as cholesterol and ergosterol.^{[31] [32]}

2 classes of drugs target the mevalonate pathway: statins (similar rosuvastatin), which are used to reduce elevated cholesterol levels,^[33] and bisphosphonates (similar zoledronate), which are used to treat a number of bone-degenerative diseases.^[34]

Steroidogenesis [edit]

Human steroidogenesis, with the major classes of steroid hormones, individual steroids and enzymatic pathways.^[35] Changes in molecular construction from a forerunner are highlighted in white.

Steroidogenesis is the biological process by which steroids are generated from cholesterol and changed into other steroids.^[36] The pathways of steroidogenesis differ among species. The major classes of steroid hormones, as noted above (with their prominent members and functions), are the Progestogen, Corticosteroids (corticoids), Androgens, and Estrogens.^{[37] [ citation needed ]} Human steroidogenesis of these classes occurs in a number of locations:

• Progestogens are the precursors of all other human steroids, and all human being tissues which produce steroids must first convert cholesterol to pregnenolone. This conversion is the rate-limiting step of steroid synthesis, which occurs inside the mitochondrion of the respective tissue.^{[38] [37] [ better source needed ]}
• Cortisol, corticosterone, aldosterone, and testosterone are produced in the adrenal cortex.^{[37] [ citation needed ]}
• Estradiol, estrone and progesterone are made primarily in the ovary, estriol in placenta during pregnancy, and testosterone primarily in the testes (some testosterone is also produced in the adrenal cortex).^{[37] [ citation needed ]}
• Estradiol is converted from testosterone directly (in males), or via the master pathway DHEA - androstenedione - estrone and secondarily via testosterone (in females).^{[37] [ citation needed ]}
• Stromal cells take been shown to produce steroids in response to signaling produced by androgen-starved prostate cancer cells.^{[39] [ non-chief source needed ] [ better source needed ]}
• Some neurons and glia in the primal nervous organization (CNS) express the enzymes required for the local synthesis of pregnenolone, progesterone, DHEA and DHEAS, de novo or from peripheral sources.^{[37] [ citation needed ]}

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• e

Production rates, secretion rates, clearance rates, and blood levels of major sex hormones

Sex	Sex hormone	Reproductive phase	Blood production rate	Gonadal secretion rate	Metabolic clearance charge per unit	Reference range (serum levels)
						SI units	Not-SI units
Men	Androstenedione	–	two.8 mg/day	1.half-dozen mg/day	2200 L/day	two.8–seven.iii nmol/L	80–210 ng/dL
	Testosterone	–	6.5 mg/24-hour interval	6.2 mg/24-hour interval	950 L/solar day	6.nine–34.vii nmol/Fifty	200–k ng/dL
	Estrone	–	150 μg/day	110 μg/mean solar day	2050 L/twenty-four hour period	37–250 pmol/50	10–70 pg/mL
	Estradiol	–	60 μg/day	50 μg/mean solar day	1600 L/day	<37–210 pmol/Fifty	ten–57 pg/mL
	Estrone sulfate	–	80 μg/solar day	Insignificant	167 L/day	600–2500 pmol/50	200–900 pg/mL
Women	Androstenedione	–	iii.ii mg/day	ii.8 mg/day	2000 L/day	3.i–12.2 nmol/L	89–350 ng/dL
	Testosterone	–	190 μg/solar day	60 μg/day	500 L/twenty-four hour period	0.7–2.8 nmol/L	20–81 ng/dL
	Estrone	Follicular stage	110 μg/twenty-four hours	eighty μg/solar day	2200 Fifty/twenty-four hours	110–400 pmol/L	30–110 pg/mL
		Luteal stage	260 μg/mean solar day	150 μg/day	2200 L/day	310–660 pmol/L	80–180 pg/mL
		Postmenopause	40 μg/twenty-four hour period	Insignificant	1610 L/day	22–230 pmol/50	6–sixty pg/mL
	Estradiol	Follicular phase	90 μg/24-hour interval	eighty μg/mean solar day	1200 L/day	<37–360 pmol/Fifty	x–98 pg/mL
		Luteal phase	250 μg/twenty-four hour period	240 μg/solar day	1200 50/day	699–1250 pmol/L	190–341 pg/mL
		Postmenopause	6 μg/mean solar day	Insignificant	910 L/day	<37–140 pmol/L	10–38 pg/mL
	Estrone sulfate	Follicular phase	100 μg/day	Insignificant	146 50/twenty-four hours	700–3600 pmol/L	250–1300 pg/mL
		Luteal stage	180 μg/day	Insignificant	146 L/day	1100–7300 pmol/L	400–2600 pg/mL
	Progesterone	Follicular phase	2 mg/24-hour interval	1.7 mg/day	2100 L/day	0.3–3 nmol/50	0.i–0.9 ng/mL
		Luteal phase	25 mg/day	24 mg/day	2100 Fifty/twenty-four hour period	19–45 nmol/L	6–fourteen ng/mL
Notes and sources Notes: "The concentration of a steroid in the circulation is adamant past the rate at which information technology is secreted from glands, the charge per unit of metabolism of precursor or prehormones into the steroid, and the charge per unit at which it is extracted by tissues and metabolized. The secretion charge per unit of a steroid refers to the total secretion of the compound from a gland per unit time. Secretion rates take been assessed past sampling the venous effluent from a gland over fourth dimension and subtracting out the arterial and peripheral venous hormone concentration. The metabolic clearance rate of a steroid is divers every bit the book of blood that has been completely cleared of the hormone per unit time. The production rate of a steroid hormone refers to entry into the blood of the compound from all possible sources, including secretion from glands and conversion of prohormones into the steroid of involvement. At steady country, the amount of hormone entering the claret from all sources will be equal to the rate at which it is existence cleared (metabolic clearance rate) multiplied by blood concentration (production rate = metabolic clearance rate × concentration). If there is little contribution of prohormone metabolism to the circulating puddle of steroid, then the production rate will judge the secretion rate." Sources: See template.

Alternative pathways [edit]

In plants and bacteria, the not-mevalonate pathway (MEP pathway) uses pyruvate and glyceraldehyde 3-phosphate as substrates to produce IPP and DMAPP.^{[29] [40]}

During diseases pathways otherwise not pregnant in healthy humans can go utilized. For example, in one form of built adrenal hyperplasia a deficiency in the 21-hydroxylase enzymatic pathway leads to an excess of 17α-Hydroxyprogesterone (17-OHP) – this pathological excess of 17-OHP in plow may be converted to dihydrotestosterone (DHT, a strong androgen) through among others 17,xx Lyase (a member of the cytochrome P450 family unit of enzymes), 5α-Reductase and 3α-Hydroxysteroid dehydrogenase.^[41]

Catabolism and excretion [edit]

Steroids are primarily oxidized past cytochrome P450 oxidase enzymes, such every bit CYP3A4. These reactions innovate oxygen into the steroid ring, allowing the cholesterol to be cleaved upwards by other enzymes into bile acids.^[42] These acids can and so be eliminated by secretion from the liver in bile.^[43] The expression of the oxidase cistron tin be upregulated by the steroid sensor PXR when at that place is a high blood concentration of steroids.^[44] Steroid hormones, lacking the side chain of cholesterol and bile acids, are typically hydroxylated at diverse ring positions or oxidized at the 17 position, conjugated with sulfate or glucuronic acrid and excreted in the urine.^[45]

Isolation, construction decision, and methods of analysis [edit]

Steroid isolation, depending on context, is the isolation of chemical matter required for chemical structure elucidation, derivitzation or degradation chemistry, biological testing, and other research needs (generally milligrams to grams, but often more^[46] or the isolation of "analytical quantities" of the substance of interest (where the focus is on identifying and quantifying the substance (for instance, in biological tissue or fluid). The amount isolated depends on the analytical method, but is generally less than one microgram.^{[47] [ page needed ]} The methods of isolation to attain the two scales of product are distinct, only include extraction, atmospheric precipitation, adsorption, chromatography, and crystallization. In both cases, the isolated substance is purified to chemic homogeneity; combined separation and belittling methods, such equally LC-MS, are called to be "orthogonal"—achieving their separations based on distinct modes of interaction betwixt substance and isolating matrix—to detect a single species in the pure sample. Construction determination refers to the methods to decide the chemical construction of an isolated pure steroid, using an evolving array of chemical and physical methods which have included NMR and small-molecule crystallography.^{[4] : 10–19} Methods of analysis overlap both of the above areas, emphasizing analytical methods to determining if a steroid is present in a mixture and determining its quantity.^[47]

Chemical synthesis [edit]

Microbial catabolism of phytosterol side chains yields C-19 steroids, C-22 steroids, and 17-ketosteroids (i.e. precursors to adrenocortical hormones and contraceptives).^{[48] [49] [50]} The improver and modification of functional groups is central when producing the wide multifariousness of medications bachelor inside this chemical classification. These modifications are performed using conventional organic synthesis and/or biotransformation techniques.^{[51] [52]}

Precursors [edit]

Semisynthesis [edit]

The semisynthesis of steroids ofttimes begins from precursors such as cholesterol,^[50] phytosterols,^[49] or sapogenins.^[53] The efforts of Syntex, a company involved in the Mexican barbasco merchandise, used Dioscorea mexicana to produce the sapogenin diosgenin in the early on days of the constructed steroid pharmaceutical industry.^[46]

Full synthesis [edit]

Some steroidal hormones are economically obtained only by total synthesis from petrochemicals (east.g. 13-alkyl steroids).^[50] For example, the pharmaceutical Norgestrel begins from methoxy-1-tetralone, a petrochemical derived from phenol.

Inquiry awards [edit]

A number of Nobel Prizes have been awarded for steroid enquiry, including:

• 1927 (Chemistry) Heinrich Otto Wieland — Constitution of bile acids and sterols and their connection to vitamins^[54]
• 1928 (Chemical science) Adolf Otto Reinhold Windaus — Constitution of sterols and their connectedness to vitamins^[55]
• 1939 (Chemical science) Adolf Butenandt and Leopold Ružička — Isolation and structural studies of steroid sexual activity hormones, and related studies on higher terpenes^[56]
• 1950 (Physiology or Medicine) Edward Calvin Kendall, Tadeus Reichstein, and Philip Hench — Structure and biological effects of adrenal hormones^[57]
• 1965 (Chemical science) Robert Burns Woodward — In office, for the synthesis of cholesterol, cortisone, and lanosterol^[58]
• 1969 (Chemistry) Derek Barton and Odd Hassel — Development of the concept of conformation in chemistry, emphasizing the steroid nucleus^[59]
• 1975 (Chemistry) Vladimir Prelog — In part, for developing methods to determine the stereochemical grade of cholesterol biosynthesis from mevalonic acid via squalene^[60]

See also [edit]

• Adrenal gland
• Batrachotoxin
• List of steroid abbreviations
• Listing of steroids
• Membrane steroid receptor
• Pheromone
• Contrary cholesterol transport
• Steroidogenesis inhibitor
• Steroidogenic astute regulatory protein
• Steroidogenic enzyme

References [edit]

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Source: https://en.wikipedia.org/wiki/Steroid

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