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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H34O7
Molecular Weight 446.5333
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CORTICOSTERONE-21-HEMISUCCINATE

SMILES

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

InChI

InChIKey=KEECMXYFGNWLEA-BIGDRKAKSA-N
InChI=1S/C25H34O7/c1-24-10-9-15(26)11-14(24)3-4-16-17-5-6-18(25(17,2)12-19(27)23(16)24)20(28)13-32-22(31)8-7-21(29)30/h11,16-19,23,27H,3-10,12-13H2,1-2H3,(H,29,30)/t16-,17-,18+,19-,23+,24-,25-/m0/s1

HIDE SMILES / InChI

Molecular Formula C25H34O7
Molecular Weight 446.5333
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
Quantitative analysis of human serum corticosterone by high-performance liquid chromatography coupled to electrospray ionization mass spectrometry.
1999 Apr 30
Molecular cloning and characterization of multispecific organic anion transporter 4 expressed in the placenta.
2000 Feb 11
The pregnane X receptor: a promiscuous xenobiotic receptor that has diverged during evolution.
2000 Jan
[Mineralocorticoids in cervical mucous and female blood serum: levels in the preovulatory phase of the menstrual cycle].
2000 Sep
Mild prenatal stress enhances learning performance in the non-adopted rat offspring.
2001
Mechanism of colchicine-induced steroidogenesis in rat adrenocortical cells.
2001
Effects of chronic stress on contextual fear conditioning and the hippocampal expression of the neural cell adhesion molecule, its polysialylation, and L1.
2001
Minireview: 11beta-hydroxysteroid dehydrogenase type 1- a tissue-specific amplifier of glucocorticoid action.
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
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
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
Vasopressin pressor receptor-mediated activation of HPA axis by acute ethanol stress in rats.
2001 Feb
Role of hypothalamic neuropeptide Y and orexigenic peptides in anorexia associated with experimental colitis in the rat.
2001 Feb
Central monoamine activity in genetically distinct strains of mice following a psychogenic stressor: effects of predator exposure.
2001 Feb 23
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
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
Bombesin-induced HPA and sympathetic activation requires CRH receptors.
2001 Jan
Dexamethasone, but not IL-1 alone, upregulates acute-phase serum amyloid A gene expression and production by cultured human aortic smooth muscle cells.
2001 Jan
Effect of acute and repeated restraint stress on glucose oxidation to CO2 in hippocampal and cerebral cortex slices.
2001 Jan
Distal tubular electrolyte transport during inhibition of renal 11beta-hydroxysteroid dehydrogenase.
2001 Jan
Acute stress rapidly and persistently enhances memory formation in the male rat.
2001 Jan
Deviant forms of aggression in glucocorticoid hyporeactive rats: a model for 'pathological' aggression?
2001 Jan
Buffering action of endogenous nitric oxide on the adrenocortical secretagogue effect of endothelins in the rat.
2001 Jan
Sexual diergism in rat hypothalamic-pituitary-adrenal axis responses to cholinergic stimulation and antagonism.
2001 Jan 1
Relationships between IFNgamma, IL-6, corticosterone, and Listeria monocytogenes pathogenesis in BALB/c mice.
2001 Jan 10
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
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
Stereotaxic delivery of corticosterone to the amygdala modulates colonic sensitivity in rats.
2001 Mar 2
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 Dec 16 09:08:29 GMT 2023
Edited
by admin
on Sat Dec 16 09:08:29 GMT 2023
Record UNII
IU50V885SP
Record Status Validated (UNII)
Record Version
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Name Type Language
CORTICOSTERONE-21-HEMISUCCINATE
Common Name English
CORTICOSTERONE HEMISUCCINATE
Common Name English
PREGN-4-ENE-3,20-DIONE, 21-(3-CARBOXY-1-OXOPROPOXY)-11-HYDROXY-, (11.BETA.)-
Systematic Name English
Code System Code Type Description
SMS_ID
100000128496
Created by admin on Sat Dec 16 09:08:29 GMT 2023 , Edited by admin on Sat Dec 16 09:08:29 GMT 2023
PRIMARY
EPA CompTox
DTXSID40907180
Created by admin on Sat Dec 16 09:08:29 GMT 2023 , Edited by admin on Sat Dec 16 09:08:29 GMT 2023
PRIMARY
PUBCHEM
159273
Created by admin on Sat Dec 16 09:08:29 GMT 2023 , Edited by admin on Sat Dec 16 09:08:29 GMT 2023
PRIMARY
FDA UNII
IU50V885SP
Created by admin on Sat Dec 16 09:08:29 GMT 2023 , Edited by admin on Sat Dec 16 09:08:29 GMT 2023
PRIMARY
EVMPD
SUB35577
Created by admin on Sat Dec 16 09:08:29 GMT 2023 , Edited by admin on Sat Dec 16 09:08:29 GMT 2023
PRIMARY
CAS
10215-77-7
Created by admin on Sat Dec 16 09:08:29 GMT 2023 , Edited by admin on Sat Dec 16 09:08:29 GMT 2023
PRIMARY
Related Record Type Details
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