Identification

Name
Corticosterone
Accession Number
DB04652
Type
Small Molecule
Groups
Experimental
Description

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)

Structure
Thumb
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
Categories
UNII
W980KJ009P
CAS number
50-22-6
Weight
Average: 346.4605
Monoisotopic: 346.214409448
Chemical Formula
C21H30O4
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,2R,10S,11S,14S,15S,17S)-17-hydroxy-14-(2-hydroxyacetyl)-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-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

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UMineralocorticoid receptorNot AvailableHuman
UCorticosteroid 11-beta-dehydrogenase isozyme 1Not AvailableHuman
UNuclear receptor coactivator 1Not AvailableHuman
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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
PathwayCategory
Corticosterone Methyl Oxidase II Deficiency (CMO II)Disease
Adrenal Hyperplasia Type 5 or Congenital Adrenal Hyperplasia Due to 17 alpha-Hydroxylase DeficiencyDisease
17-alpha-Hydroxylase Deficiency (CYP17)Disease
Adrenal Hyperplasia Type 3 or Congenital Adrenal Hyperplasia Due to 21-Hydroxylase DeficiencyDisease
Corticosterone Methyl Oxidase I Deficiency (CMO I)Disease
11-beta-Hydroxylase Deficiency (CYP11B1)Disease
21-Hydroxylase Deficiency (CYP21)Disease
3-beta-Hydroxysteroid Dehydrogenase DeficiencyDisease
SteroidogenesisMetabolic
Congenital Lipoid Adrenal Hyperplasia (CLAH) or Lipoid CAHDisease
Apparent Mineralocorticoid Excess SyndromeDisease
SteroidogenesisMetabolic
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be decreased when combined with Corticosterone.
(S)-WarfarinThe metabolism of (S)-Warfarin can be decreased when combined with Corticosterone.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Corticosterone.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Corticosterone.
5-androstenedioneThe metabolism of Corticosterone can be decreased when combined with 5-androstenedione.
6-Deoxyerythronolide BThe metabolism of Corticosterone can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Corticosterone.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Corticosterone.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Corticosterone.
AbirateroneThe metabolism of Abiraterone can be decreased when combined with Corticosterone.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0001547
KEGG Compound
C02140
PubChem Compound
5753
PubChem Substance
46504547
ChemSpider
5550
BindingDB
50170653
ChEBI
16827
ChEMBL
CHEMBL110739
HET
C0R
Wikipedia
Corticosterone
PDB Entries
1y5r / 2a3i / 4qf7 / 5l91 / 5l92

Clinical Trials

Clinical Trials
Not Available

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
Polarizability38.79 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-MSNot Available
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
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
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
1H NMR Spectrum1D NMRNot Applicable
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable
[1H,13C] 2D NMR Spectrum2D NMRNot Applicable

Taxonomy

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
Progestogin-skeleton / 21-hydroxysteroid / Pregnane-skeleton / 20-oxosteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / 11-hydroxysteroid / 11-beta-hydroxysteroid / Oxosteroid / Delta-4-steroid
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)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. [PubMed:10592235]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. [PubMed:10592235]

Enzymes

Kind
Protein
Organism
Human
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. [PubMed:28930203]
  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. [PubMed:10950859]

Drug created on September 11, 2007 11:49 / Updated on November 02, 2018 06:03