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{{BioPsy}}
 
{{BioPsy}}
[[Image:Steroid-nomenclature.png|thumb|right|250px|Steroid skeleton. Carbons 18 and above can be absent.]]
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[[Image:Steroid numbering.png|thumb|right|400px|[[IUPAC nomenclature|IUPAC]] recommended ring (left) and atom numbering (right) of the steroid skeleton.<ref name="pmid2606099">{{cite journal | author = | title = IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989 | journal = Eur. J. Biochem. | volume = 186 | issue = 3 | pages = 429–58 | year = 1989 | month = December | pmid = 2606099 | doi = 10.1111/j.1432-1033.1989.tb15228.x | url = http://www.chem.qmul.ac.uk/iupac/steroid/ | issn = }}</ref><ref name="IUPAC">{{cite journal | journal = [[Pure & Appl. Chem.]] | volume = 61 | issue = 10 | pages = 1783–1822 | year = 1989 | title = Nomenclature of Steroids (Recommendations 1989) | author = G. P. Moss | doi = 10.1351/pac198961101783}}</ref>]]
{{dablink|This article is about the chemical family of steroids in general. For an article about the performance enhancing substance, please see [[Anabolic steroid]].}}
 
A '''steroid''' is a [[lipid]] characterized by a [[carbon]] skeleton with four fused rings. All steroids are derived from the [[acetyl CoA]] biosynthetic pathway. Different steroids vary in the [[functional group]]s attached to these rings. Hundreds of distinct steroids have been identified in plants, animals, and fungi.
 
   
==Physiology and medicine==
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[[Image:Lanosterol-skeletal.png|thumb|right|400px|Steroid skeleton of [[lanosterol]]. The total number of carbons (30) reflects its [[triterpenoid]] origin.]]
Their most important role in most living systems is as [[hormone]]s. Steroid hormones produce their physiological effects by binding to steroid hormone [[receptor (biochemistry)|receptor]] proteins. The binding of steroid hormones to their receptors causes changes in gene [[Transcription (genetics)|transcription]] and cell function.
 
   
In human physiology and medicine, the most important steroids are [[cholesterol]], the [[steroid hormone]]s, and their [[precursor]]s and [[metabolite]]s. In the bloodstream steroids are bound to carrier proteins.
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[[Image:Sterol synthesis.svg|thumb|right|400px|Simplified version of the steroid synthesis pathway with the intermediates [[isopentenyl pyrophosphate]](IPP),[[dimethylallyl pyrophosphate]] (DMAPP), [[geranyl pyrophosphate]] (GPP) and [[squalene]] shown. Some intermediates are omitted.]]
   
[[Cholesterol]] is an important [[sterol|steroid alcohol]], being a common component of animal cell membranes. However, a high level of it can cause various conditions and diseases, such as atherosclerosis. Most other steroids are synthesized from cholesterol. Also, various hormones, including vertebrate [[sex hormone]]s, are steroids created from cholesterol.
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A '''steroid''' is a [[terpenoid]] [[lipid]] characterized by a [[carbon]] skeleton with four fused rings, generally arranged in a 6-6-6-5 fashion.
  +
Steroids vary by the [[functional group]]s attached to these rings and the [[oxidation]] state of the rings. Hundreds of distinct steroids are found in plants, [[animal]]s, and fungi. All steroids are made in cells either from the [[sterol]] [[lanosterol]] (animals and fungi) or the sterol [[cycloartenol]] (plants). Both [[sterols]] are derived from the cyclization of the [[triterpene]] [[squalene]].<ref>[http://www.chem.qmul.ac.uk/iubmb/enzyme/reaction/terp/lanost.html Lanosterol biosynthesis<!-- Bot generated title -->]</ref>
   
==Classification==
 
===Functional===
 
Some of the common categories of steroids include:
 
*[[Anabolic steroid]]s are a class of steroids that interact with androgen receptors to increase muscle and bone synthesis. There are natural and synthetic anabolic steroids. These are the "steroids" used by [[athlete]]s to increase performance.
 
*[[Corticosteroid]]s include [[glucocorticoid]] and [[mineralocorticoid]]s:
 
**[[Glucocorticoid]]s regulate many aspects of [[metabolism]] and [[immune system|immune function]], and are often prescribed by doctors to reduce [[inflammation|inflammatory conditions]] like [[asthma]] and [[arthritis]].
 
**[[Mineralocorticoid]]s are corticosteroids that help maintain blood volume and control [[kidney|renal]] excretion of [[electrolyte]]s.
 
*[[Sex steroid]]s are a subset of [[sex hormone]]s that produce [[sexual differentiation|sex differences]] or support [[reproduction]]. They include [[androgen]]s, [[estrogen]]s, and [[progestagen]]s.
 
*[[Phytosterol]]s - steroids naturally occurring in plants.
 
*[[Ergosterol]]s - steroids occuring in fungi. This includes some [[Vitamin D]] supplements.
 
   
In [[Anatomical Therapeutic Chemical Classification System]] system, anabolic steroids are classified under [[ATC code A14|A14]], sex hormones under [[ATC_code_G03|G03]] and [[ATC code L02|L02]], and corticosteroids under [[ATC_code_A07#A07EA_Corticosteroids_acting_locally|A07EA]],
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==Origin==
[[ATC_code_C05#C05AA_Products_containing_corticosteroids|C05AA]],
 
[[ATC code D07|D07]],
 
[[ATC_code_D10#D10AA_Corticosteroids.2C_combinations_for_treatment_of_acne|D10AA]],
 
[[ATC code H02|H02]],
 
[[ATC_code_R01#R01AD_Corticosteroids|R01AD]],
 
[[ATC_code_R03#R03BA_Glucocorticoids|R03BA]],
 
[[ATC_code_S01#S01BA_Corticosteroids.2C_plain|S01BA]],
 
[[ATC_code_S02#S02B_Corticosteroids|S02B]], and
 
[[ATC_code_S03#S03B_Corticosteroids|S03B]].
 
   
===Structural===
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Steroids include [[estrogen]], [[cortisol]], [[progesterone]] and [[testosterone]]. Estrogen and progesterone are made primarily in the [[ovary]] and in the [[placenta]] during pregnancy and [[testosterone]] in the [[testes]]. Testosterone is also converted into estrogen to regulate the supply of each, in the bodies of both females and males. Certain [[neurons]] and [[glia]] in the [[central nervous system]] (CNS) express the [[enzymes]] that are required for the local synthesis of [[pregnane]] [[neurosteroids]], either [[de novo synthesis|''de novo'']] or from peripherally derived sources. The rate limiting step of steroid synthesis is the conversion of [[cholesterol]] to [[pregnenolone]] which occurs inside the [[mitochondrion]].<ref name=Rossier>{{cite journal | title=T channels and steroid biosynthesis: in search of a link with mitochondria | author=Rossier MF | journal=Cell Calcium. | date=2006 | volume=40 | issue=2 | pages=155–64 | pmid=16759697 | doi=10.1016/j.ceca.2006.04.020 }}</ref>
It is also possible to classify steroids based upon their chemical composition. One example of how [[MeSH]] performs this classification is available at [[Wikipedia:MeSH_D04#MeSH_D04.808_---_steroids]].
 
   
==Terminology==
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==Classification==
The term ''steroid'' is often used more restrictively in specific contexts:
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===Taxonomical/Functional===
* For instance, ''steroid'' in common medical usage by non-endocrinologists usually refers to [[corticosteroid]]s, nearly always [[glucocorticoid]]s.
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Some of the common categories of steroids:
* In an athletic or body-building context, ''steroid'' commonly refers to [[anabolic steroid]]s.
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*Animal steroids
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**[[Insect]] steroids
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***Ecdysteroids such as [[ecdysterone]]
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**[[Vertebrate]] steroids
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***[[Steroid hormone]]s
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****[[Sex steroid]]s are a subset of [[sex hormone]]s that produce [[sexual differentiation|sex differences]] or support [[reproduction]]. They include [[androgen]]s, [[estrogen]]s, and [[progestagen]]s.
  +
****[[Corticosteroid]]s include [[glucocorticoid]]s and [[mineralocorticoid]]s. [[Glucocorticoid]]s regulate many aspects of [[metabolism]] and [[immune system|immune function]], whereas [[mineralocorticoid]]s help maintain blood volume and control [[kidney|renal]] excretion of [[electrolyte]]s. Many/most medical 'steroid' [[drug]]s are corticosteroids.
  +
****[[Anabolic steroid]]s are a class of steroids that interact with androgen receptors to increase muscle and bone synthesis. There are natural and synthetic anabolic steroids. In popular language the word "steroids" usually refers to anabolic steroids.
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***[[Cholesterol]] which modulates the fluidity of [[cell membranes]] and is the principal constituent of the plaques implicated in [[atherosclerosis]].
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*Plant steroids
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**[[Phytosterol]]s
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**[[Brassinosteroid]]s
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*Fungus steroids
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**[[Ergosterol]]s
   
==Origin==
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===Structural===
[[Sex steroids]] include [[estrogen]] (U.S spelling) or [[oestrogen]] (UK spelling), [[progesterone]] and [[androgen]]. Oestrogen and progesterone are made primarily in the [[ovary]] and in the [[placenta]] during pregnancy and [[testosterone]] in the [[testis]].
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It is also possible to classify steroids based upon their chemical composition. One example of how [[MeSH]] performs this classification is available at [[Wikipedia:MeSH D04#MeSH D04.808 --- steroids|the Wikipedia MeSH catalog]]. Examples from this classification include:
   
== External links ==
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{| class="wikitable"
* [http://www.indstate.edu/thcme/mwking/steroid-hormones.html Michael W. King's Medical Biochemistry]. Steroids and retinoids are both [[terpene]]s which are [[hydrophobic]], pass through [[cell membrane]]s and bind to [[Signal transduction# Nuclear receptors|intracellular receptors]]. However, retinoic acid is not a steroid because is does not have the defining ring structure. See: [http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Search&db=books&doptcmdl=GenBookHL&term=retinoids+AND+stryer%5Bbook%5D+AND+217301%5Buid%5D&rid=stryer.section.4466#4467 Steroids and Related Hydrophobic Molecules].
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|-
* "[http://www.ncbi.nlm.nih.gov/books/bv.fcgi?call=bv.View..ShowTOC&rid=stryer.TOC&depth=2 Biochemistry]" by Jeremy M. Berg, John L. Tymoczko and Lubert Stryer (2002) W. H. Freeman and Co. [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=Books&cmd=Search&term=steroid+AND+stryer%5Bbook%5D&doptcmdl=TOCView steroid topics in this]
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! align="center" | Class
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! align="center" | Examples
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! align="center" | Number of carbon atoms
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|-
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| align="center" | Cholstanes
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| align="center" | [[cholesterol]]
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| align="center" | 27
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|-
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| align="center" | Cholanes
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| align="center" | [[cholic acid]]
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| align="center" | 24
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|-
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| align="center" | Pregnanes
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| align="center" | [[progesterone]]
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| align="center" | 21
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|-
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| align="center" | Androstanes
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| align="center" | [[testosterone]]
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| align="center" | 19
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|-
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| align="center" | Estranes
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| align="center" | [[estradiol]]
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| align="center" | 18
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|-
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|}
   
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==See also==
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*[[Antiandrogens]]
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*[[Antiestrogens]]
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*[[Antieoplastic drugs]]
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*[[Anti inflammatory drugs]]
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*[[Batrachotoxin]]
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*[[Hormones]]
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*[[List of steroid abbreviations]]
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*[[Lipids]]
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*[[Steroid biosynthesis]]
   
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==References==
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{{reflist}}
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== External links ==
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* [http://www.indstate.edu/thcme/mwking/steroid-hormones.html Michael W. King's Medical Biochemistry]. Steroids and retinoids are both [[terpene]]s which are [[hydrophobic]], pass through [[cell membrane]]s and bind to [[Signal transduction# Nuclear receptors|intracellular receptors]]. However, retinoic acid is not a steroid because it does not have the defining ring structure. See: [http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Search&db=books&doptcmdl=GenBookHL&term=retinoids+AND+stryer%5Bbook%5D+AND+217301%5Buid%5D&rid=stryer.section.4466#4467 Steroids and Related Hydrophobic Molecules].
  +
* "[http://www.ncbi.nlm.nih.gov/books/bv.fcgi?call=bv.View..ShowTOC&rid=stryer.TOC&depth=2 Biochemistry]" by Jeremy M. Berg, John L. Tymoczko and Lubert Stryer (2002) W. H. Freeman and Co. [http://www.ncbi.nlm.nih.gov/entrez/query.fcgi?db=Books&cmd=Search&term=steroid+AND+stryer%5Bbook%5D&doptcmdl=TOCView steroid topics in this]
  +
*[http://www.insidermedicine.com/Archives/Steroids,_Rage_and_Criminal_Activity_316.aspx Steroids, Rage and Criminal Activity] -- Video: Insidermedicine.com's Maria Radina on Anabolic Androgenic Steroids, as presented in a study in ''Archives of General Psychiatry''.
  +
*[http://www.chem.qmul.ac.uk/iupac/steroid/ Nomenclature of Steroids Home Page] at Queen Mary University of London.
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*[http://web.archive.org/web/20061117030358/http://il-st-acad-sci.org/steroid0.html Steroid abbreviations] at ISAS (page now defunct, web archive version)
   
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{{Steroids}}
   
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[[Category:Drugs]]
 
[[Category:Steroids|*]]
 
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File:Steroid numbering.png
File:Lanosterol-skeletal.png
File:Sterol synthesis.svg

A steroid is a terpenoid lipid characterized by a carbon skeleton with four fused rings, generally arranged in a 6-6-6-5 fashion. Steroids vary by the functional groups attached to these rings and the oxidation state of the rings. Hundreds of distinct steroids are found in plants, animals, and fungi. All steroids are made in cells either from the sterol lanosterol (animals and fungi) or the sterol cycloartenol (plants). Both sterols are derived from the cyclization of the triterpene squalene.[3]


OriginEdit

Steroids include estrogen, cortisol, progesterone and testosterone. Estrogen and progesterone are made primarily in the ovary and in the placenta during pregnancy and testosterone in the testes. Testosterone is also converted into estrogen to regulate the supply of each, in the bodies of both females and males. Certain neurons and glia in the central nervous system (CNS) express the enzymes that are required for the local synthesis of pregnane neurosteroids, either de novo or from peripherally derived sources. The rate limiting step of steroid synthesis is the conversion of cholesterol to pregnenolone which occurs inside the mitochondrion.[4]

ClassificationEdit

Taxonomical/FunctionalEdit

Some of the common categories of steroids:

StructuralEdit

It is also possible to classify steroids based upon their chemical composition. One example of how MeSH performs this classification is available at the Wikipedia MeSH catalog. Examples from this classification include:

Class Examples Number of carbon atoms
Cholstanes cholesterol 27
Cholanes cholic acid 24
Pregnanes progesterone 21
Androstanes testosterone 19
Estranes estradiol 18

See alsoEdit

ReferencesEdit

  1. (December 1989)IUPAC-IUB Joint Commission on Biochemical Nomenclature (JCBN). The nomenclature of steroids. Recommendations 1989. Eur. J. Biochem. 186 (3): 429–58.
  2. G. P. Moss (1989). Nomenclature of Steroids (Recommendations 1989). Pure & Appl. Chem. 61 (10): 1783–1822.
  3. Lanosterol biosynthesis
  4. Rossier MF (2006). T channels and steroid biosynthesis: in search of a link with mitochondria. Cell Calcium. 40 (2): 155–64.

External links Edit

Template:Biochemical families
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