Corticosterone
Star0
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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
- Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API
- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism ACorticosteroid 11-beta-dehydrogenase isozyme 1 substrateproduct ofHumans ANuclear receptor coactivator 1 Not Available Humans AMineralocorticoid receptor Not Available Humans - 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
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- Pathways
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbametapir The serum concentration of Corticosterone can be increased when it is combined with Abametapir. Amiodarone The metabolism of Corticosterone can be decreased when combined with Amiodarone. Amprenavir The metabolism of Corticosterone can be decreased when combined with Amprenavir. Apalutamide The serum concentration of Corticosterone can be decreased when it is combined with Apalutamide. Aprepitant The metabolism of Corticosterone can be decreased when combined with Aprepitant. - Food Interactions
- Not Available
Categories
- Drug Categories
- 11-Hydroxycorticosteroids
- Adrenal Cortex Hormones
- Anti-Inflammatory Agents
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Substrates
- Fused-Ring Compounds
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Hydroxycorticosteroids
- Pregnanes
- Pregnenediones
- Pregnenes
- Steroids
- 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
- External Links
- 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
Phase Status Purpose Conditions Count 3 Unknown Status Treatment Osteoarthritis in the Hip Joint 1
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
Property Value Source Water Solubility 0.046 mg/mL ALOGPS logP 2.09 ALOGPS logP 2.02 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 13.86 Chemaxon pKa (Strongest Basic) -0.26 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 74.6 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 96 m3·mol-1 Chemaxon Polarizability 38.83 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9926 Blood Brain Barrier + 0.9451 Caco-2 permeable + 0.8867 P-glycoprotein substrate Substrate 0.771 P-glycoprotein inhibitor I Non-inhibitor 0.7124 P-glycoprotein inhibitor II Non-inhibitor 0.7259 Renal organic cation transporter Non-inhibitor 0.7122 CYP450 2C9 substrate Non-substrate 0.8363 CYP450 2D6 substrate Non-substrate 0.9143 CYP450 3A4 substrate Substrate 0.7636 CYP450 1A2 substrate Non-inhibitor 0.9255 CYP450 2C9 inhibitor Non-inhibitor 0.9211 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9593 CYP450 3A4 inhibitor Non-inhibitor 0.8246 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8716 Ames test Non AMES toxic 0.926 Carcinogenicity Non-carcinogens 0.9497 Biodegradation Not ready biodegradable 0.9454 Rat acute toxicity 1.5110 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9403 hERG inhibition (predictor II) Non-inhibitor 0.5206
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 193.4753726 predictedDarkChem Lite v0.1.0 [M-H]- 191.4263726 predictedDarkChem Lite v0.1.0 [M-H]- 194.6905726 predictedDarkChem Lite v0.1.0 [M-H]- 193.1920726 predictedDarkChem Lite v0.1.0 [M-H]- 170.16869 predictedDeepCCS 1.0 (2019) [M+H]+ 192.9493726 predictedDarkChem Lite v0.1.0 [M+H]+ 191.1768726 predictedDarkChem Lite v0.1.0 [M+H]+ 195.2125726 predictedDarkChem Lite v0.1.0 [M+H]+ 195.4100726 predictedDarkChem Lite v0.1.0 [M+H]+ 172.04268 predictedDeepCCS 1.0 (2019) [M+Na]+ 192.6111726 predictedDarkChem Lite v0.1.0 [M+Na]+ 191.6441726 predictedDarkChem Lite v0.1.0 [M+Na]+ 194.8765726 predictedDarkChem Lite v0.1.0 [M+Na]+ 193.7631726 predictedDarkChem Lite v0.1.0 [M+Na]+ 178.22136 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- SubstrateProduct 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
- 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]
- 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]
2. DetailsNuclear receptor coactivator 1
- 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
- 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]
3. DetailsMineralocorticoid receptor
- 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
- 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
1. DetailsCytochrome P450 3A4
- 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
- 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]
- 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
- SubstrateProduct 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
- 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
- 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