Corticosterone

Corticosterone: Corticosterone

IUPAC name

(11β)-11,21-dihydroxypregn-4-ene-3,20-dione

Identifiers

CAS number 50-22-6^Y

PubChem 5753

ChemSpider 5550^Y

UNII W980KJ009P^N

DrugBank DB04652

MeSH Corticosterone

ChEBI CHEBI:16827^N

ChEMBL CHEMBL110739^N

Jmol-3D images Image 1

SMILES

O=C4\C=C2/[C@]([C@H]1[C@@H](O)C[C@@]3([C@@H](C(=O)CO)CC[C@H]3[C@@H]1CC2)C)(C)CC4

InChI

InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1^Y
Key: OMFXVFTZEKFJBZ-HJTSIMOOSA-N^Y
InChI=1/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1
Key: OMFXVFTZEKFJBZ-HJTSIMOOBD

Properties

Molecular formula C₂₁H₃₀O₄

Molar mass 346.46 g mol⁻¹

N (verify) (what is: Y/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)

Infobox references

Corticosterone (CORT) is a 21-carbon steroid hormone of the corticosteroid type produced in the cortex of the adrenal glands.

Contents

1 Roles

2 Release or generation mechanisms

3 References

4 Additional images

Roles

In many species, including amphibians, reptiles, rodents and birds, corticosterone is a main glucocorticoid,^[1] involved in regulation of fuel, immune reactions, and stress responses.

However, in humans, corticosterone is produced primarily in the zona fasciculata of the adrenal cortex. It has only weak glucocorticoid and mineralocorticoid potencies in humans and is important mainly as an intermediate in the steroidogenic pathway from pregnenolone to aldosterone. Corticosterone is converted to aldosterone by aldosterone synthase, found only in the mitochondria of glomerulosa cells. Glomerulosa cells are found in the Zona glomerulosa, which is the most superficial region of endocrine cells in the adrenal cortex.

Release or generation mechanisms

One example of a release pathway relates to UV-B stimulation on the skins of certain amphibians such as the Rough-skinned Newt, Taricha granulosa; this trigger seems to cause the internal generation of corticosterone in that species.^[2]

References

^ "e.hormone | The Hormones : Corticoids". http://e.hormone.tulane.edu/learning/corticoids.html. Retrieved 2009-04-09.

^ C. Michael Hogan (2008) Rough-skinned Newt (Taricha granulosa), Globaltwitcher, ed. Nicklas Stromberg [1]

Additional images

Steroidogenesis

Deoxycorticosterone

Aldosterone

v · d · eCholesterol and steroid metabolic intermediates

Mevalonate pathway

to HMG-CoA

Acetyl-CoA · Acetoacetyl-CoA · HMG-CoA

Ketone bodies

Acetone · Acetoacetic acid · beta-Hydroxybutyric acid

to DMAPP

Mevalonic acid · Phosphomevalonic acid · 5-Diphosphomevalonic acid · Isopentenyl pyrophosphate · Dimethylallyl pyrophosphate

Geranyl-

Geranyl pyrophosphate · Geranylgeranyl pyrophosphate

Carotenoid

Prephytoene diphosphate · Phytoene

Non-mevalonate pathway

DOXP · MEP · CDP-ME · CDP-MEP · MEcPP · HMB-PP · IPP · DMAPP

To Cholesterol

Farnesyl pyrophosphate · Squalene · 2,3-Oxidosqualene · Lanosterol

Lanosterol · Lathosterol · 7-Dehydrocholesterol · Cholesterol
Lanosterol · Zymosterol · 7-Dehydrodesmosterol · Desmosterol · Cholesterol

Steroid

Corticosteroids
(C21 pregnane)

Mineralocorticoids

Pregnenolone · Progesterone · Cortodoxone · Corticosterone · Aldosterone

Glucocorticoids

Pregnenolone · 17-Hydroxypregnenolone · 17-Hydroxyprogesterone · Cortisol
Cortisol · Cortisone

Sex steroids

Androgens
(C19 androstane)

DHEA · Androstenedione/5-Androstenediol · Testosterone · Dihydrotestosterone
DHEA sulfate · Epitestosterone

Estrogens
(C18 estrane)

Estrone · Estradiol · Estriol

Nonhuman

Phytosterols

Stigmasterol · Brassicasterol

Ergosterols

Ergosterol · Ergocalciferol

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m(A16/C10),i(k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

M: END

anat/phys/devp/horm

noco(d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i

v · d · eCorticosteroids – glucocorticoids and mineralocorticoids (H02)
(also A07EA, C05AA, D07, D10AA, R01AD, R03BA, S01BA, S02B, and S03B)

Mineralocorticoids
(3-one, 4-ene,
no FG at 16)
Pregnenedione: ALDOSTERONE • 11-DEOXYCORTICOSTERONE • HALOGENATED AT 9: Fludrocortisone

Glucocorticoids
(3-one, 4-ene,
11-FG,
17-hydroxy)

Pregnene

CORTISONE

Pregnenedione
(+20-one)

HYDROCORTISONE/CORTISOL^# (Hydrocortisone aceponate, Hydrocortisone buteprate, Hydrocortisone butyrate) • Budesonide • Ciclesonide • Deflazacort • Medrysone • Tixocortol • HALOGENATED AT 6: Cloprednol • HALOGENATED, WITH FG AT 16: Halcinonide

Pregnadiene (+1-ene)

Rimexolone • HALOGENATED, WITH FG AT 16: Flunisolide • Triamcinolone • Amcinonide • Fluocinolone acetonide (Fluocinonide)

Pregnadienediol
(+21-hydroxy)

Prednisone (Meprednisone) • HALOGENATED AT 9: Fluorometholone • HALOGENATED, WITH FG AT 16: Fluocortolone (Clocortolone, Diflucortolone, Fluocortin) • Desoximetasone

Pregnadienetriol
(+11-hydroxy)

Prednisolone^# (Methylprednisolone, Methylprednisolone aceponate, Prednicarbate, Prednylidene) • Desonide • HALOGENATED: Fluprednisolone (Difluprednate, Fluperolone) • HALOGENATED, WITH FG AT 16: Dexamethasone^# • Betamethasone (Clobetasol, Clobetasone, Diflorasone, Halometasone, Ulobetasol) • Beclometasone • Paramethasone • Alclometasone • Fluclorolone • Flumetasone • Fluprednidene

Pregnatriene
(+2-ene)

Cortivazol

Androstene

HALOGENATED, WITH FG AT 16: Fluticasone (Fluticasone propionate, Fluticasone furoate)

Other/ungrouped

HALOGENATED: Loteprednol • HALOGENATED, WITH FG AT 16: Fludroxycortide • Formocortal • Mometasone furoate

Aldosterone antagonists
Spironolactone • Eplerenone • Potassium canrenoate • Canrenone

Synthesis modifiers
Trilostane • Carbenoxolone • Aminoglutethimide • Metyrapone

^#WHO-EM. ^‡Withdrawn from market. Clinical trials: ^†Phase III. ^§Never to phase III

M: END

anat/phys/devp/horm

noco(d)/cong/tumr, sysi/epon

proc, drug (A10/H1/H2/H3/H5)

Categories:
Corticosteroids

Corticosterone


IUPAC name (11β)-11,21-dihydroxypregn-4-ene-3,20-dione
Identifiers
CAS number	50-22-6^Y
PubChem	5753
ChemSpider	5550^Y
UNII	W980KJ009P^N
DrugBank	DB04652
MeSH	Corticosterone
ChEBI	CHEBI:16827^N
ChEMBL	CHEMBL110739^N
Jmol-3D images	Image 1
SMILES O=C4\C=C2/[C@]([C@H]1[C@@H](O)C[C@@]3([C@@H](C(=O)CO)CC[C@H]3[C@@H]1CC2)C)(C)CC4
InChI InChI=1S/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1^Y Key: OMFXVFTZEKFJBZ-HJTSIMOOSA-N^Y InChI=1/C21H30O4/c1-20-8-7-13(23)9-12(20)3-4-14-15-5-6-16(18(25)11-22)21(15,2)10-17(24)19(14)20/h9,14-17,19,22,24H,3-8,10-11H2,1-2H3/t14-,15-,16+,17-,19+,20-,21-/m0/s1 Key: OMFXVFTZEKFJBZ-HJTSIMOOBD
Properties
Molecular formula	C₂₁H₃₀O₄
Molar mass	346.46 g mol⁻¹
N (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Игры ⚽ Поможем решить контрольную работу

Look at other dictionaries:

corticosterone — n. any of several steroid compounds secreted by the adrenal cortex; they are involved in regulating water and electrolyte balance in the body. [WordNet 1.5] … The Collaborative International Dictionary of English
Corticosterone — Corticostérone La corticostérone est une hormone corticostéroïde secrétée par le cortex (écorce) de la glande surrénale à partir du cholestérol et sous la dépendance de l ACTH hypophysaire. Portail de la médecine Ce document provient de «… … Wikipédia en Français
corticostérone — ● corticostérone nom féminin Hormone du groupe des glucocorticoïdes sécrétée par la corticosurrénale … Encyclopédie Universelle
corticosterone — [kôr΄ti kō΄stir′ōn΄, kôr΄tikäs′tə rōn΄] n. [ CORTICO + STER(OL) + ONE] a corticosteroid, C21H30O4, that aids muscle efficiency, carbohydrate metabolism, etc … English World dictionary
Corticostérone — La corticostérone est une hormone corticostéroïde secrétée par le cortex (écorce) de la glande surrénale à partir du cholestérol et sous la dépendance de l ACTH hypophysaire. Portail de la médecine … Wikipédia en Français
Corticosterone 18-monooxygenase — Identifiers EC number 1.14.15.5 CAS number 37256 75 0 … Wikipedia
corticosterone methyl oxidase — cor·ti·cos·ter·one meth·yl ox·i·dase (kor″tĭ kosґtər ōn methґəl okґsĭ dās) corticosterone 18 monooxygenase … Medical dictionary
corticosterone 18-monooxygenase — cor·ti·cos·ter·one 18 mono·oxy·ge·nase (kor″tĭ kosґtər ōn mon″o okґsə jən ās) [EC 1.14.15.5] an enzyme of the oxidoreductase class that catalyzes hydroxylation of corticosteroids at the 18 position… … Medical dictionary
corticosterone — noun Date: 1937 a colorless crystalline corticosteroid C21H30O4 that is important in protein and carbohydrate metabolism … New Collegiate Dictionary
corticosterone — /kawr ti kos teuh rohn , koh steuh rohn /, n. Biochem. a steroid hormone, secreted by the adrenal cortex, that is involved in regulation of the water and electrolyte balance of the body. [1935 40; CORTICO + STER(OL) + ONE] * * * … Universalium

Academic Dictionaries and Encyclopedias

Corticosterone

Contents

Roles

Release or generation mechanisms

References

Additional images

Look at other dictionaries:

Share the article and excerpts

Academic Dictionaries and Encyclopedias

Wikipedia

Corticosterone

Contents

Roles

Release or generation mechanisms

References

Additional images

Look at other dictionaries:

Share the article and excerpts

Direct link