Corticosterone

Identification

Generic Name
Corticosterone
DrugBank Accession Number
DB04652
Background

An adrenocortical steroid that has modest but significant activities as a mineralocorticoid and a glucocorticoid. (From Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed, p1437)

Type
Small Molecule
Groups
Experimental
Structure
Weight
Average: 346.4605
Monoisotopic: 346.214409448
Chemical Formula
C21H30O4
Synonyms
  • (11β)-11,21-dihydroxypregn-4-ene-3,20-dione
  • 11beta,21-Dihydroxy-4-pregnene-3,20-dione
  • 11β,21-dihydroxyprogesterone
  • 17-deoxycortisol
  • Kendall's compound B
  • Reichstein's substance H

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
ACorticosteroid 11-beta-dehydrogenase isozyme 1
substrate
product of
Humans
ANuclear receptor coactivator 1Not AvailableHumans
AMineralocorticoid receptorNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
PathwayCategory
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAHDisease
11-beta-Hydroxylase Deficiency (CYP11B1)Disease
Apparent Mineralocorticoid Excess SyndromeDisease
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase DeficiencyDisease
Corticosterone Methyl Oxidase I Deficiency (CMO I)Disease
3-beta-Hydroxysteroid Dehydrogenase DeficiencyDisease
SteroidogenesisMetabolic
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase DeficiencyDisease
17-alpha-Hydroxylase Deficiency (CYP17)Disease
21-Hydroxylase Deficiency (CYP21)Disease
Corticosterone Methyl Oxidase II Deficiency (CMO II)Disease
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbametapirThe serum concentration of Corticosterone can be increased when it is combined with Abametapir.
AmiodaroneThe metabolism of Corticosterone can be decreased when combined with Amiodarone.
AmprenavirThe metabolism of Corticosterone can be decreased when combined with Amprenavir.
ApalutamideThe serum concentration of Corticosterone can be decreased when it is combined with Apalutamide.
AprepitantThe metabolism of Corticosterone can be decreased when combined with Aprepitant.
Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as 21-hydroxysteroids. These are steroids carrying a hydroxyl group at the 21-position of the steroid backbone.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Hydroxysteroids
Direct Parent
21-hydroxysteroids
Alternative Parents
Gluco/mineralocorticoids, progestogins and derivatives / 20-oxosteroids / 3-oxo delta-4-steroids / 11-beta-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Alpha-hydroxy ketones / Secondary alcohols / Cyclic alcohols and derivatives / Primary alcohols
show 2 more
Substituents
11-beta-hydroxysteroid / 11-hydroxysteroid / 20-oxosteroid / 21-hydroxysteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Alpha-hydroxy ketone / Carbonyl group
show 14 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3-oxo steroid, 11beta-hydroxy steroid, glucocorticoid, 20-oxo steroid, 21-hydroxy steroid, C21-steroid (CHEBI:16827) / Pregnane and derivatives [Fig], C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives, Mineralocorticoids (C02140) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030186)
Affected organisms
Not Available

Chemical Identifiers

UNII
W980KJ009P
CAS number
50-22-6
InChI Key
OMFXVFTZEKFJBZ-HJTSIMOOSA-N
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
IUPAC Name
(1S,3aS,3bS,9aR,9bS,10S,11aS)-10-hydroxy-1-(2-hydroxyacetyl)-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]1(CC[C@@]2([H])[C@]3([H])CCC4=CC(=O)CC[C@]4(C)[C@@]3([H])[C@@]([H])(O)C[C@]12C)C(=O)CO

References

General References
Not Available
Human Metabolome Database
HMDB0001547
KEGG Compound
C02140
PubChem Compound
5753
PubChem Substance
46504547
ChemSpider
5550
BindingDB
50170653
ChEBI
16827
ChEMBL
CHEMBL110739
ZINC
ZINC000013513592
PDBe Ligand
C0R
Wikipedia
Corticosterone
PDB Entries
1y5r / 2a3i / 4qf7 / 5l91 / 5l92 / 6hgi / 7zh6 / 8cbz

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3Unknown StatusTreatmentOsteoarthritis in the Hip Joint1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.046 mg/mLALOGPS
logP2.09ALOGPS
logP2.02Chemaxon
logS-3.9ALOGPS
pKa (Strongest Acidic)13.86Chemaxon
pKa (Strongest Basic)-0.26Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count4Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area74.6 Å2Chemaxon
Rotatable Bond Count2Chemaxon
Refractivity96 m3·mol-1Chemaxon
Polarizability38.83 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9926
Blood Brain Barrier+0.9451
Caco-2 permeable+0.8867
P-glycoprotein substrateSubstrate0.771
P-glycoprotein inhibitor INon-inhibitor0.7124
P-glycoprotein inhibitor IINon-inhibitor0.7259
Renal organic cation transporterNon-inhibitor0.7122
CYP450 2C9 substrateNon-substrate0.8363
CYP450 2D6 substrateNon-substrate0.9143
CYP450 3A4 substrateSubstrate0.7636
CYP450 1A2 substrateNon-inhibitor0.9255
CYP450 2C9 inhibitorNon-inhibitor0.9211
CYP450 2D6 inhibitorNon-inhibitor0.9231
CYP450 2C19 inhibitorNon-inhibitor0.9593
CYP450 3A4 inhibitorNon-inhibitor0.8246
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8716
Ames testNon AMES toxic0.926
CarcinogenicityNon-carcinogens0.9497
BiodegradationNot ready biodegradable0.9454
Rat acute toxicity1.5110 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9403
hERG inhibition (predictor II)Non-inhibitor0.5206
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
GC-MS Spectrum - GC-MS (2 MEOX; 2 TMS)GC-MSsplash10-0f9l-4920000000-13c56138ef34befd6786
GC-MS Spectrum - GC-MS (2 MEOX; 2 TMS)GC-MSsplash10-0f7c-4921100000-1d2ace868fd94080c88e
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-000i-1968000000-377b49ad20a23591ce73
GC-MS Spectrum - EI-BGC-MSsplash10-014i-1798000000-b39fe3c8aaf8f09d7cde
GC-MS Spectrum - GC-MSGC-MSsplash10-0f9l-4920000000-13c56138ef34befd6786
GC-MS Spectrum - GC-MSGC-MSsplash10-0f7c-4921100000-1d2ace868fd94080c88e
Mass Spectrum (Electron Ionization)MSsplash10-014i-8953000000-cdd7d53a6012a6eb3f28
MS/MS Spectrum - Quattro_QQQ 10V, PositiveLC-MS/MSsplash10-0002-0009000000-81d0a5e41401c962645e
MS/MS Spectrum - Quattro_QQQ 25V, PositiveLC-MS/MSsplash10-05fs-2910000000-7a585bd042169de23cfe
MS/MS Spectrum - Quattro_QQQ 40V, PositiveLC-MS/MSsplash10-0597-6900000000-4c9bb40342921d7ff55e
MS/MS Spectrum - EI-B (HITACHI M-80) , PositiveLC-MS/MSsplash10-014i-1798000000-e8ef26b439701fc96537
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-0002-0759000000-8c04fadb6bd7d3e86c28
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSsplash10-05gi-3920000000-db0dc9413f5ca5cb69e3
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0009000000-362accabc0136898e549
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0002-0459000000-e31660ef75e29d9d9d78
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00fr-0941000000-1453953f7526fa9b8de6
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00e9-0920000000-da03f39d4590a6248157
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-00gi-0900000000-2ec9e62e392a282f6de4
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0002-0009000000-1db6d72ffc02b6efa63d
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00ba-1964000000-d35661aaf929a1609854
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00dj-2920000000-b29d21507e63bc379164
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-05fv-3900000000-8cd56447e4fa2da8c30b
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-0596-4900000000-0fdf5a6f27425f6540ba
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-052f-6900000000-d6cd49302b0991f7a681
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00mo-9800000000-fcf363e8a5a69914ad88
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-00mp-9600000000-493d479336ae32a15124
LC-MS/MS Spectrum - LC-ESI-QFT , positiveLC-MS/MSsplash10-016u-9500000000-5e6760693c17aadb3f80
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0169000000-f22e1aba4ac6510b7c67
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0002-0759000000-8c04fadb6bd7d3e86c28
MS/MS Spectrum - , positiveLC-MS/MSsplash10-05gi-3920000000-db0dc9413f5ca5cb69e3
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-002b-0009000000-84d2b6d8999f19f1c637
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0009000000-f17733331704f54e14ed
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-01tj-0449000000-7558e8bfd68d15fb8b0d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01ot-0009000000-c967fecef27f84260ceb
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00os-0039000000-57507170b1f559895ef5
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-044i-0920000000-7afddeffd2b609d3661c
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-193.4753726
predicted
DarkChem Lite v0.1.0
[M-H]-191.4263726
predicted
DarkChem Lite v0.1.0
[M-H]-194.6905726
predicted
DarkChem Lite v0.1.0
[M-H]-193.1920726
predicted
DarkChem Lite v0.1.0
[M-H]-170.16869
predicted
DeepCCS 1.0 (2019)
[M+H]+192.9493726
predicted
DarkChem Lite v0.1.0
[M+H]+191.1768726
predicted
DarkChem Lite v0.1.0
[M+H]+195.2125726
predicted
DarkChem Lite v0.1.0
[M+H]+195.4100726
predicted
DarkChem Lite v0.1.0
[M+H]+172.04268
predicted
DeepCCS 1.0 (2019)
[M+Na]+192.6111726
predicted
DarkChem Lite v0.1.0
[M+Na]+191.6441726
predicted
DarkChem Lite v0.1.0
[M+Na]+194.8765726
predicted
DarkChem Lite v0.1.0
[M+Na]+193.7631726
predicted
DarkChem Lite v0.1.0
[M+Na]+178.22136
predicted
DeepCCS 1.0 (2019)

Targets

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Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Substrate
Product of
General Function
11-beta-hydroxysteroid dehydrogenase [nad(p)] activity
Specific Function
Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the rea...
Gene Name
HSD11B1
Uniprot ID
P28845
Uniprot Name
Corticosteroid 11-beta-dehydrogenase isozyme 1
Molecular Weight
32400.665 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
  2. Pacha J, Lisa V, Miksik I: Effect of cellular differentiation on 11beta-hydroxysteroid dehydrogenase activity in the intestine. Steroids. 2002 Feb;67(2):119-26. doi: 10.1016/s0039-128x(01)00143-x. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
General Function
Transcription coactivator activity
Specific Function
Nuclear receptor coactivator that directly binds nuclear receptors and stimulates the transcriptional activities in a hormone-dependent fashion. Involved in the coactivation of different nuclear re...
Gene Name
NCOA1
Uniprot ID
Q15788
Uniprot Name
Nuclear receptor coactivator 1
Molecular Weight
156755.44 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
General Function
Zinc ion binding
Specific Function
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates targ...
Gene Name
NR3C2
Uniprot ID
P08235
Uniprot Name
Mineralocorticoid receptor
Molecular Weight
107066.575 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [Article]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Manda VK, Avula B, Dale OR, Chittiboyina AG, Khan IA, Walker LA, Khan SI: Studies on Pharmacokinetic Drug Interaction Potential of Vinpocetine. Medicines (Basel). 2015 Jun 5;2(2):93-105. doi: 10.3390/medicines2020093. [Article]
  2. Kajita J, Kuwabara T, Kobayashi H, Kobayashi S: CYP3A4 is mainly responsibile for the metabolism of a new vinca alkaloid, vinorelbine, in human liver microsomes. Drug Metab Dispos. 2000 Sep;28(9):1121-7. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
Product of
General Function
11-beta-hydroxysteroid dehydrogenase [nad(p)] activity
Specific Function
Catalyzes reversibly the conversion of cortisol to the inactive metabolite cortisone. Catalyzes reversibly the conversion of 7-ketocholesterol to 7-beta-hydroxycholesterol. In intact cells, the rea...
Gene Name
HSD11B1
Uniprot ID
P28845
Uniprot Name
Corticosteroid 11-beta-dehydrogenase isozyme 1
Molecular Weight
32400.665 Da
References
  1. Pacha J, Lisa V, Miksik I: Effect of cellular differentiation on 11beta-hydroxysteroid dehydrogenase activity in the intestine. Steroids. 2002 Feb;67(2):119-26. doi: 10.1016/s0039-128x(01)00143-x. [Article]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Steroid binding
Specific Function
Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation...
Gene Name
HSD11B2
Uniprot ID
P80365
Uniprot Name
Corticosteroid 11-beta-dehydrogenase isozyme 2
Molecular Weight
44126.06 Da
References
  1. Pacha J, Lisa V, Miksik I: Effect of cellular differentiation on 11beta-hydroxysteroid dehydrogenase activity in the intestine. Steroids. 2002 Feb;67(2):119-26. doi: 10.1016/s0039-128x(01)00143-x. [Article]

Drug created at September 11, 2007 17:49 / Updated at May 06, 2022 00:44