U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30O4
Molecular Weight 346.4613
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CORTICOSTERONE

SMILES

C[C@@]12CCC(=O)C=C2CC[C@@]3([H])[C@]4([H])CC[C@]([H])(C(=O)CO)[C@@]4(C)C[C@@]([H])([C@@]31[H])O

InChI

InChIKey=OMFXVFTZEKFJBZ-HJTSIMOOSA-N
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

HIDE SMILES / InChI

Molecular Formula C21H30O4
Molecular Weight 346.4613
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Corticosterone is an adrenocortical steroid, the major glucocorticoid that has modest but significant activities as a mineralocorticoid and a glucocorticoid. Corticosterone is of minor importance in humans but is known, that it has a profound effect on the structure and function of the hippocampus. Brain corticosterone may involve memory storage and emotional stress might cause increases in plasma corticosterone.

CNS Activity

Curator's Comment:: Known to be CNS penetrant in rat. Human data not available

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Diagnostic
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Baboon cytochrome P450c11 is encoded by more than one gene.
2000 Nov
Mild prenatal stress enhances learning performance in the non-adopted rat offspring.
2001
Nociceptin/orphanin FQ regulates neuroendocrine function of the limbic-hypothalamic-pituitary-adrenal axis.
2001
Mechanism of colchicine-induced steroidogenesis in rat adrenocortical cells.
2001
Light and electron microscopy localization of the 11beta-hydroxysteroid dehydrogenase type I enzyme in the rat.
2001 Apr
Minireview: 11beta-hydroxysteroid dehydrogenase type 1- a tissue-specific amplifier of glucocorticoid action.
2001 Apr
Endomorphins and activation of the hypothalamo-pituitary-adrenal axis.
2001 Apr
Early growth retardation induced by excessive exposure to glucocorticoids in utero selectively increases cardiac GLUT1 protein expression and Akt/protein kinase B activity in adulthood.
2001 Apr
Parabrachial nucleus modulates cardiovascular responses to blood loss.
2001 Apr
Neuroendocrine and behavioral effects of repetitive transcranial magnetic stimulation in a psychopathological animal model are suggestive of antidepressant-like effects.
2001 Apr
Reversal of acute effects of high dose morphine on lymphocyte activity by chlorisondamine.
2001 Apr 1
Sex differences in plasma corticosterone in desert tortoises, Gopherus agassizii, during the reproductive cycle.
2001 Apr 15
Apolipoprotein E deficiency effects on learning in mice are dependent upon the background strain.
2001 Apr 8
Bidirectional effects of corticosterone on splenic T-cell activation: critical role of cell density and culture time.
2001 Feb
Corticosterone responses in 5-HT1B receptor knockout mice to stress or 5-HT1A receptor activation are normal.
2001 Feb
Acute changes in the response to peripheral leptin with alteration in the diet composition.
2001 Feb
Vasopressin pressor receptor-mediated activation of HPA axis by acute ethanol stress in rats.
2001 Feb
Influence of glucocorticoids on dopaminergic transmission in the rat dorsolateral striatum.
2001 Feb
GRKO mice express an aberrant dexamethasone-binding glucocorticoid receptor, but are profoundly glucocorticoid resistant.
2001 Feb 28
Quantitative modeling of suppression of IgG1, IgG2a, IL-2, and IL-4 responses to antigen in mice treated with exogenous corticosterone or restraint stress.
2001 Feb 9
Alterations in chromatin structure are implicated in the activation of the steroid hormone response unit of the ovalbumin gene.
2001 Jan
Altered responsiveness to stress and NMDA following prenatal exposure to cocaine.
2001 Jan
Interactions between effects of adrenalectomy and diet on insulin secretion in fa/fa Zucker rats.
2001 Jan
The impact of reduced frequency of cage changes on the health of mice housed in ventilated cages.
2001 Jan
Glycyrrhetinic acid induced apoptosis in murine splenocytes.
2001 Jan
Apical uptake of organic cations by human intestinal Caco-2 cells: putative involvement of ASF transporters.
2001 Jan
Transport of [3H]MPP+ in an immortalized rat brain microvessel endothelial cell line (RBE 4).
2001 Jan
Bombesin-induced HPA and sympathetic activation requires CRH receptors.
2001 Jan
Sexual diergism in rat hypothalamic-pituitary-adrenal axis responses to cholinergic stimulation and antagonism.
2001 Jan 1
Vendor differences in cocaine-induced behavioral activity and hormonal interactions in ovariectomized Fischer rats.
2001 Jan 1
Effects of centrally administered orexin-B and orexin-A: a role for orexin-1 receptors in orexin-B-induced hyperactivity.
2001 Jan 1
Induction of hippocampal glial cells expressing basic fibroblast growth factor RNA by corticosterone.
2001 Jan 22
Binding of estrogen and progesterone-BSA conjugates to glyceraldehyde-3-phosphate dehydrogenase (GAPDH) and the effects of the free steroids on GAPDH enzyme activity: physiological implications.
2001 Jun
Maternal essential fatty acid deficiency depresses serum leptin levels in suckling rat pups.
2001 Mar
Long-term fasting and re-feeding in penguins.
2001 Mar
Endocrine regulation of G-protein subunit production in an animal model of type 2 diabetes mellitus.
2001 Mar
A mutation in the cofactor-binding domain of 11beta-hydroxysteroid dehydrogenase type 2 associated with mineralocorticoid hypertension.
2001 Mar
Dantrolene reduces serum TNFalpha and corticosterone levels and muscle calcium, calpain gene expression, and protein breakdown in septic rats.
2001 Mar
Inhibition of aldosterone production in rat adrenal mitochondria by 18-ethynyl-11-deoxycorticosterone: a simple model for kinetic interpretation of mechanism-based inhibitors.
2001 Mar
Corticosteroid effects on serotonin responses in granule cells of the rat dentate gyrus.
2001 Mar
Cloning and in vitro characterization of alpha 1(I)-collagen 11 beta-hydroxysteroid dehydrogenase type 2 transgenes as models for osteoblast-selective inactivation of natural glucocorticoids.
2001 Mar
Urocortin, corticotropin releasing factor-2 receptors and energy balance.
2001 Mar
Long-term colony housing in Long Evans rats: immunological, hormonal, and behavioral consequences.
2001 Mar 1
An experimental model of stress-induced immunosuppression produced by electrical stimulation of the brain in the rat.
2001 Mar 1
Endogenous glucocorticoids play a positive regulatory role in the anti-keyhole limpet hemocyanin in vivo antibody response.
2001 Mar 15
Actions of cocaine- and amphetamine-regulated transcript (CART) peptide on regulation of appetite and hypothalamo-pituitary axes in vitro and in vivo in male rats.
2001 Mar 2
Stereotaxic delivery of corticosterone to the amygdala modulates colonic sensitivity in rats.
2001 Mar 2
Alpha-helical-corticotropin-releasing hormone reverses anxiogenic effects of C-type natriuretic peptide in rats.
2001 Mar 2
Role of corticosterone in ethyl carbamate-induced immunosuppression in female BALB/c mice.
2001 Mar 8
Hypothalamo-pituitary-adrenocortical dysregulation in aging F344/Brown-Norway F1 hybrid rats.
2001 Mar-Apr
Patents

Sample Use Guides

for rats: effects of chronic exposure to corticosterone in drinking water on corticosterone kinetics, blood chemistry, and concentrations of catecholamines in parts of brain were studied in Long-Evans rats. Rats were randomly grouped into 3 x 2 treatments (n=4), with three treatments of drinking water (tap water, or 2.5% ethanol, or 400 microg/mL of corticosterone in 2.5% ethanol) for 28 days and two treatments of gavage with a single dose of either corn oil or corticosterone 20 mg/kg on day 28. Blood samples were collected at 0, 15, 30, 60, 120, 240, 480, and 720 min after dosing to determine plasma corticosterone concentrations.
Route of Administration: Oral
Fibroblast-like synovial cells of rat were stimulated with 10 ng/ml interleukin (IL)-1β for 24 h, and were subsequently, within the next 24 h, treated with or without 10-6 mmol/l corticosterone alone or with 100 nmol/l PF915275. At the end of the second 24 h, PGE2 levels in culture supernatants were assayed. Corticosterone was demonstrated to suppress the mRNA expression levels of inflammatory factors, such as TNF-α and PGE2, induced by IL-1β in vitro. Simultaneously, expression levels of 11β-HSD1 decreased significantly at the mRNA and protein levels (P<0.05).
Substance Class Chemical
Created
by admin
on Sat Jun 26 06:33:59 UTC 2021
Edited
by admin
on Sat Jun 26 06:33:59 UTC 2021
Record UNII
W980KJ009P
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
CORTICOSTERONE
MI  
Common Name English
NSC-9705
Code English
REICHSTEIN'S SUBSTANCE H
Common Name English
(11.BETA.)-11,21-DIHYDROXYPREGN-4-ENE-3,20-DIONE
Systematic Name English
CORTICOSTERONE [MI]
Common Name English
KENDALL'S COMPOUND B
Common Name English
4-PREGNENE-11.BETA.,21-DIOL-3,20-DIONE
Common Name English
Classification Tree Code System Code
CFR 21 CFR 862.1200
Created by admin on Sat Jun 26 06:33:59 UTC 2021 , Edited by admin on Sat Jun 26 06:33:59 UTC 2021
LOINC 55842-9
Created by admin on Sat Jun 26 06:34:00 UTC 2021 , Edited by admin on Sat Jun 26 06:34:00 UTC 2021
LOINC 14042-6
Created by admin on Sat Jun 26 06:33:59 UTC 2021 , Edited by admin on Sat Jun 26 06:33:59 UTC 2021
LOINC 25381-5
Created by admin on Sat Jun 26 06:34:00 UTC 2021 , Edited by admin on Sat Jun 26 06:34:00 UTC 2021
LOINC 55843-7
Created by admin on Sat Jun 26 06:34:00 UTC 2021 , Edited by admin on Sat Jun 26 06:34:00 UTC 2021
LOINC 2139-4
Created by admin on Sat Jun 26 06:34:00 UTC 2021 , Edited by admin on Sat Jun 26 06:34:00 UTC 2021
NCI_THESAURUS C2323
Created by admin on Sat Jun 26 06:34:00 UTC 2021 , Edited by admin on Sat Jun 26 06:34:00 UTC 2021
LOINC 55841-1
Created by admin on Sat Jun 26 06:34:00 UTC 2021 , Edited by admin on Sat Jun 26 06:34:00 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C393
Created by admin on Sat Jun 26 06:34:00 UTC 2021 , Edited by admin on Sat Jun 26 06:34:00 UTC 2021
PRIMARY NCIT
CAS
50-22-6
Created by admin on Sat Jun 26 06:33:59 UTC 2021 , Edited by admin on Sat Jun 26 06:33:59 UTC 2021
PRIMARY
PUBCHEM
5753
Created by admin on Sat Jun 26 06:34:00 UTC 2021 , Edited by admin on Sat Jun 26 06:34:00 UTC 2021
PRIMARY
DRUG BANK
DB04652
Created by admin on Sat Jun 26 06:33:59 UTC 2021 , Edited by admin on Sat Jun 26 06:33:59 UTC 2021
PRIMARY
ECHA (EC/EINECS)
200-019-6
Created by admin on Sat Jun 26 06:33:59 UTC 2021 , Edited by admin on Sat Jun 26 06:33:59 UTC 2021
PRIMARY
MERCK INDEX
M3794
Created by admin on Sat Jun 26 06:34:00 UTC 2021 , Edited by admin on Sat Jun 26 06:34:00 UTC 2021
PRIMARY Merck Index
MESH
D003345
Created by admin on Sat Jun 26 06:34:00 UTC 2021 , Edited by admin on Sat Jun 26 06:34:00 UTC 2021
PRIMARY
EVMPD
SUB130501
Created by admin on Sat Jun 26 06:33:59 UTC 2021 , Edited by admin on Sat Jun 26 06:33:59 UTC 2021
PRIMARY
WIKIPEDIA
CORTICOSTERONE
Created by admin on Sat Jun 26 06:34:00 UTC 2021 , Edited by admin on Sat Jun 26 06:34:00 UTC 2021
PRIMARY
FDA UNII
W980KJ009P
Created by admin on Sat Jun 26 06:33:59 UTC 2021 , Edited by admin on Sat Jun 26 06:33:59 UTC 2021
PRIMARY
EPA CompTox
50-22-6
Created by admin on Sat Jun 26 06:33:59 UTC 2021 , Edited by admin on Sat Jun 26 06:33:59 UTC 2021
PRIMARY
Related Record Type Details
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY