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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H30O4
Molecular Weight 346.4605
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CORTICOSTERONE

SMILES

[H][C@@]12CC[C@H](C(=O)CO)[C@@]1(C)C[C@H](O)[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C

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 346.4605
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
Glucocorticoid hypersecretion following intracerebroventricular injection of ethylcholine mustard aziridinium ion in rats.
2001
Effects of chronic stress on contextual fear conditioning and the hippocampal expression of the neural cell adhesion molecule, its polysialylation, and L1.
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
Reversal of acute effects of high dose morphine on lymphocyte activity by chlorisondamine.
2001 Apr 1
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
Role of hypothalamic neuropeptide Y and orexigenic peptides in anorexia associated with experimental colitis in the rat.
2001 Feb
Glucocorticoids, androgens, testis mass, and the energetics of vocalization in breeding male frogs.
2001 Feb
Neuroendocrine regulation of sexually dimorphic brain structure and associated sexual behavior in male rats is genetically controlled.
2001 Feb
Glucocorticoids modulate the NGF mRNA response in the rat hippocampus after traumatic brain injury.
2001 Feb 23
Central monoamine activity in genetically distinct strains of mice following a psychogenic stressor: effects of predator exposure.
2001 Feb 23
GRKO mice express an aberrant dexamethasone-binding glucocorticoid receptor, but are profoundly glucocorticoid resistant.
2001 Feb 28
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
Adrenalectomy enhances response of tumour necrosis factor-alpha (TNF-alpha) to haemorrhage in the conscious rat.
2001 Jan
Effect of acute and repeated restraint stress on glucose oxidation to CO2 in hippocampal and cerebral cortex slices.
2001 Jan
Differential effects of dexamethasone treatment on lipopolysaccharide-induced testicular inflammation and reproductive hormone inhibition in adult rats.
2001 Jan
Acute stress rapidly and persistently enhances memory formation in the male rat.
2001 Jan
Effects of centrally administered orexin-B and orexin-A: a role for orexin-1 receptors in orexin-B-induced hyperactivity.
2001 Jan 1
Heterogeneity of hippocampal GABA(A) receptors: regulation by corticosterone.
2001 Jan 1
Estradiol tends to improve inhibitory avoidance performance in adrenalectomized male rats and reduces pyknotic cells in the dentate gyrus of adrenalectomized male and female rats.
2001 Jan 19
Induction of hippocampal glial cells expressing basic fibroblast growth factor RNA by corticosterone.
2001 Jan 22
Phenotypic analysis of mice bearing targeted deletions of 11beta-hydroxysteroid dehydrogenases 1 and 2 genes.
2001 Jan 22
Functional effects of corticosterone on 5-HT(1A) and 5-HT(1B) receptor activity in rat brain: in vivo microdialysis studies.
2001 Jan 5
The effects of a mild stressor on spontaneous alternation in mice.
2001 Jan 8
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
A mutation in the cofactor-binding domain of 11beta-hydroxysteroid dehydrogenase type 2 associated with mineralocorticoid hypertension.
2001 Mar
Corticosteroid effects on serotonin responses in granule cells of the rat dentate gyrus.
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
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 Fri Dec 15 15:16:00 GMT 2023
Edited
by admin
on Fri Dec 15 15:16:00 GMT 2023
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 Fri Dec 15 15:16:00 GMT 2023 , Edited by admin on Fri Dec 15 15:16:00 GMT 2023
LOINC 55842-9
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LOINC 14042-6
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LOINC 25381-5
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LOINC 55843-7
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LOINC 2139-4
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NCI_THESAURUS C2323
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LOINC 55841-1
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Code System Code Type Description
NCI_THESAURUS
C393
Created by admin on Fri Dec 15 15:16:00 GMT 2023 , Edited by admin on Fri Dec 15 15:16:00 GMT 2023
PRIMARY NCIT
CAS
50-22-6
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PRIMARY
PUBCHEM
5753
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PRIMARY
DRUG BANK
DB04652
Created by admin on Fri Dec 15 15:16:00 GMT 2023 , Edited by admin on Fri Dec 15 15:16:00 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-019-6
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PRIMARY
NSC
9705
Created by admin on Fri Dec 15 15:16:00 GMT 2023 , Edited by admin on Fri Dec 15 15:16:00 GMT 2023
PRIMARY
MERCK INDEX
m3794
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PRIMARY Merck Index
MESH
D003345
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PRIMARY
EVMPD
SUB130501
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PRIMARY
SMS_ID
100000156517
Created by admin on Fri Dec 15 15:16:00 GMT 2023 , Edited by admin on Fri Dec 15 15:16:00 GMT 2023
PRIMARY
WIKIPEDIA
CORTICOSTERONE
Created by admin on Fri Dec 15 15:16:00 GMT 2023 , Edited by admin on Fri Dec 15 15:16:00 GMT 2023
PRIMARY
FDA UNII
W980KJ009P
Created by admin on Fri Dec 15 15:16:00 GMT 2023 , Edited by admin on Fri Dec 15 15:16:00 GMT 2023
PRIMARY
EPA CompTox
DTXSID6022474
Created by admin on Fri Dec 15 15:16:00 GMT 2023 , Edited by admin on Fri Dec 15 15:16:00 GMT 2023
PRIMARY
CHEBI
16827
Created by admin on Fri Dec 15 15:16:00 GMT 2023 , Edited by admin on Fri Dec 15 15:16:00 GMT 2023
PRIMARY
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