This article is about the family of polycyclic chemical compounds.

For the drugs, also used as

performance-enhancing substances, see Anabolic steroid. For the scientific journal, see Steroids
(journal). For the Death Grips EP, see Steroids (Crouching Tiger Hidden Gabber Megamix).

Structure of 24-ethyl-lanostane, a hypothetical steroid with 32 carbon atoms. Its core ring 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 two principal biological functions: as important components of cell
membranes which 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.[2]
The steroid core structure is typically composed of seventeen carbon atoms, bonded in four "fused"
rings: three six-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 state of the rings. Sterols are forms of steroids with a hydroxy group at
position three and a skeleton derived from cholestane.[1]: 1785f [3] Steroids can also be more radically
modified, such as by changes to the ring structure, for example, cutting one of the rings. Cutting
Ring B produces secosteroids one of which is vitamin D3.
Examples include the lipid cholesterol, the sex hormones estradiol and testosterone,[4]: 10–19  and
the anti-inflammatory drug dexamethasone.[5]

Nomenclature[edit]
See also: Gonane and Sterane

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

Steroid 5α and 5β stereoisomers[1]: 1786f 

Gonane, also known as 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 four fused rings in a three-dimensional shape. The three cyclohexane rings (A, B, and
C in the first illustration) form the skeleton of a perhydro derivative of phenanthrene. The D ring has
a cyclopentane structure. When the two methyl groups and eight carbon side chains (at C-17, as
shown for cholesterol) are present, the steroid is said to have a cholestane framework. The two
common 5α and 5β stereoisomeric forms of steroids exist because of differences in the side of the
largely planar ring system where the hydrogen (H) atom at carbon-5 is attached, which results in a
change in steroid A-ring conformation. Isomerisation at the C-21 side chain produces a parallel
series of compounds, referred to as isosteroids.[8]
Examples of steroid structures are:

Testosterone, the principal male sex hormone and an anabolic steroid

Cholic acid, a bile acid, showing the carboxylic acid and additional hydroxyl groups often present

Dexamethasone, a synthetic corticosteroid drug

Lanosterol, the biosynthetic precursor to animal steroids. The number of carbons (30) indicates
its triterpenoid classification.
 

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

Medrogestone, a synthetic drug with effects similar to progesterone

β-Sitosterol, a plant or phytosterol, with a fully branched hydrocarbon side chain at C-17 and an
hydroxyl group at C-3
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 can also
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 attached to the rings and side chain, and
 in the configuration of groups attached to the rings and chain. [4]: 2–9 
For instance, sterols such as cholesterol and lanosterol have a hydroxyl group attached at position
C-3, while testosterone and progesterone have a carbonyl (oxo substituent) at C-3; of
these, lanosterol alone has two methyl groups at C-4 and cholesterol (with a C-5 to C-6 double
bond) differs from testosterone and progesterone (which have a C-4 to C-5 double bond).
Cholesterol, a prototypical animal sterol. This structural lipid and key
steroid biosynthetic precursor.[1]: 1785f 

5α-cholestane, a common steroid core

Species distribution and function[edit]

This section needs attention from an expert in pharmacology.
The specific problem 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 found 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 as amphotericin B and azole antifungals, utilize
this information to kill pathogenic fungi.[9] Fungi can alter their ergosterol content (e.g. 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.[10] Ergosterol is analogous to the cholesterol found in the cellular membranes of animals
(including humans), or the phytosterols found 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 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 light.[10] Provitamin D2 spontaneously forms vitamin D2. [10] However, not all
fungi utilize ergosterol in their cellular membranes; for example, the pathogenic fungal
species Pneumocystis jirovecii does not, which has important clinical implications (given the
mechanism of action of many antifungal drugs).[10] Using the fungus Saccharomyces cerevisiae as an
example, other major steroids include ergosta‐5,7,22,24(28)‐tetraen‐3β‐ol, zymosterol,
and lanosterol.[10] S. cerevisiae utilizes 5,6‐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 constituent
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 help maintain blood volume and control renal excretion
of electrolytes)
 Anabolic steroids, natural and synthetic, which interact with androgen receptors to increase
muscle and bone synthesis. In popular use, the term "steroids" often refers to anabolic steroids.
Plant steroids[edit]
Plant steroids include steroidal alkaloids found in Solanaceae[11] and Melanthiaceae (specially the
genus Veratrum),[12] cardiac glycosides,[13] the phytosterols and the brassinosteroids (which include
several plant hormones).

Prokaryotes[edit]
This section is missing information about non-eukaryotic type
sterol framework – see PMID 27446030, fig 4/5, group
1 oxidosqualene cyclase. Please expand the section to include this
information. Further details may exist on the talk page. (November
2021)

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

Types[edit]
By function[edit]
This section needs expansion with: A more detailed explanation of
function would also be 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:
o Glucocorticoids:
 Cortisol, a glucocorticoid whose functions include immunosuppression
o Mineralocorticoids:
 Aldosterone, a mineralocorticoid which helps regulate blood pressure through water and
electrolyte balance
 Sex steroids:
o Progestogens:
 Progesterone, which regulates cyclical changes in the endometrium of the uterus and
maintains a pregnancy
o Androgens:
 Testosterone, which contributes to the development and maintenance of
male secondary sex characteristics
o Estrogens:
  Estradiol, which contributes to the development and maintenance of female secondary
sex characteristics
Additional classes of steroids include:

 Neurosteroids such as DHEA and allopregnanolone

 Bile acids such as taurocholic acid
 Aminosteroid neuromuscular blocking agents (mainly synthetic) such as pancuronium bromide
 Steroidal antiandrogens (mainly synthetic) such as cyproterone acetate
 Steroidogenesis inhibitors (mainly exogenous) such as alfatradiol
 Membrane sterols such as cholesterol, ergosterol, and various phytosterols
 Toxins such as steroidal saponins and cardenolides/cardiac glycosides
As well as the following class of secosteroids (open-ring steroids):

 Vitamin D forms such as ergocalciferol, cholecalciferol, and calcitriol

By structure[edit]
Intact ring system[edit]
This section needs expansion with: a more full discussion of this
most prominent structural type. You can help by adding to it. (March
2017)

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

Cholecalciferol (vitamin D3), an example of a 9,10-secosteroid

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

Class Example Number of carbon atoms

Cholestanes Cholesterol 27

Cholanes Cholic acid 24

Pregnanes Progesterone 21

Androstanes Testosterone 19

Estranes Estradiol 18

In biology, it is common to name the above steroid classes by the number of carbon atoms present
when referring to hormones: C18-steroids for the estranes (mostly estrogens), C19-steroids for the
androstanes (mostly androgens), and C21-steroids for the pregnanes (mostly corticosteroids). [18] The
classification "17-ketosteroid" is also important in medicine.
The gonane (steroid nucleus) is the parent 17-carbon tetracyclic hydrocarbon molecule with
no alkyl sidechains.[19]
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 defined by the steroid carbon atoms where this
scission has taken place. For instance, the prototypical secosteroid cholecalciferol, vitamin
D3 (shown), is in the 9,10-secosteroid subclass and derives from the cleavage of carbon atoms C-9
and C-10 of the steroid B-ring; 5,6-secosteroids and 13,14-steroids are similar.[20]
Norsteroids (nor-, L. norma; "normal" in chemistry, indicating carbon removal) [21] and homosteroids
(homo-, Greek homos; "same", indicating carbon addition) are structural subclasses of steroids
formed from biosynthetic steps. The former involves enzymic ring expansion-contraction reactions,
and the latter is accomplished (biomimetically) or (more frequently) through ring
closures of acyclic precursors with more (or fewer) ring atoms than the parent steroid framework. [22]
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 birth defects in
lambs: cyclopia from cyclopamine and leg deformity from veratramine.[23] A further C-nor-D-
homosteroid (nakiterpiosin) is excreted by Okinawan cyanobacteriosponges. e.g., Terpios hoshinota,
leading to coral mortality from black coral disease.[24] 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.