Metribolone
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Identification
- Generic Name
- Metribolone
- DrugBank Accession Number
- DB02998
- Background
A synthetic non-aromatizable androgen and anabolic steroid. It binds strongly to the androgen receptor and has therefore also been used as an affinity label for this receptor in the prostate and in prostatic tumors.
- Type
- Small Molecule
- Groups
- Experimental
- Structure
- Weight
- Average: 284.3927
Monoisotopic: 284.177630012 - Chemical Formula
- C19H24O2
- Synonyms
- 17-beta-Hydroxy-17-methylestra-4,9,11-trien-3-one
- 17alpha-Methyltrienolone
- Methyltrienolone
- Metribolona
- Metribolone
- Metribolonum
- External IDs
- R 1881
- R1881
- RU 1881
- Ru-1881
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UAndrogen receptor activatorHumans UNuclear receptor coactivator 2 Not Available Humans UMineralocorticoid receptor Not Available Humans UProgesterone receptor Not Available Humans UProstate-specific antigen activatorHumans - 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
- Not Available
- 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.Not Available
- Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Steroids and steroid derivatives
- Sub Class
- Estrane steroids
- Direct Parent
- Estrogens and derivatives
- Alternative Parents
- 3-oxosteroids / 17-hydroxysteroids / Cyclohexenones / Tertiary alcohols / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
- Substituents
- 17-hydroxysteroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic alcohol / Cyclic ketone / Cyclohexenone / Estrogen-skeleton / Hydrocarbon derivative
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- 3-oxo steroid, 17beta-hydroxy steroid, anabolic androgenic steroid (CHEBI:379896) / Estrane and derivatives (C14257)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 2C323EGI97
- CAS number
- 965-93-5
- InChI Key
- CCCIJQPRIXGQOE-XWSJACJDSA-N
- InChI
- InChI=1S/C19H24O2/c1-18-9-7-15-14-6-4-13(20)11-12(14)3-5-16(15)17(18)8-10-19(18,2)21/h7,9,11,16-17,21H,3-6,8,10H2,1-2H3/t16-,17+,18+,19+/m1/s1
- IUPAC Name
- (1S,3aS,3bS,11aS)-1-hydroxy-1,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,11aH-cyclopenta[a]phenanthren-7-one
- SMILES
- [H][C@@]12CC[C@](C)(O)[C@@]1(C)C=CC1=C3CCC(=O)C=C3CC[C@@]21[H]
References
- General References
- Not Available
- External Links
- KEGG Compound
- C14257
- PubChem Compound
- 261000
- PubChem Substance
- 46505539
- ChemSpider
- 229099
- BindingDB
- 50367916
- ChEBI
- 379896
- ChEMBL
- CHEMBL166444
- ZINC
- ZINC000003814420
- Guide to Pharmacology
- GtP Drug Page
- PDBe Ligand
- R18
- Wikipedia
- Metribolone
- PDB Entries
- 1e3g / 1e3k / 1xow / 1xq3 / 2ao6
Clinical Trials
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 0.0332 mg/mL ALOGPS logP 3.11 ALOGPS logP 2.53 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 18.4 Chemaxon pKa (Strongest Basic) -0.53 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 86.29 m3·mol-1 Chemaxon Polarizability 33.01 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.973 Caco-2 permeable + 0.8984 P-glycoprotein substrate Substrate 0.6498 P-glycoprotein inhibitor I Inhibitor 0.5489 P-glycoprotein inhibitor II Non-inhibitor 0.8923 Renal organic cation transporter Non-inhibitor 0.7324 CYP450 2C9 substrate Non-substrate 0.8167 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.7739 CYP450 1A2 substrate Non-inhibitor 0.9005 CYP450 2C9 inhibitor Non-inhibitor 0.95 CYP450 2D6 inhibitor Non-inhibitor 0.9452 CYP450 2C19 inhibitor Non-inhibitor 0.6668 CYP450 3A4 inhibitor Non-inhibitor 0.8812 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8683 Ames test Non AMES toxic 0.9382 Carcinogenicity Non-carcinogens 0.9483 Biodegradation Not ready biodegradable 0.9174 Rat acute toxicity 1.6259 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8938 hERG inhibition (predictor II) Non-inhibitor 0.7163
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-014i-0090000000-fac42149b49ba5114242 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-00kg-6490000000-9e0c8a4c4563e5d5b611 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0090000000-a145f407400b0cb9143c Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-022a-3940000000-57a706079b75134a723f Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0090000000-24bcd4fa19775dd1b0ff Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-06dl-1390000000-f88d2d7bdfdb2df2ef88 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 176.8895156 predictedDarkChem Lite v0.1.0 [M-H]- 166.37909 predictedDeepCCS 1.0 (2019) [M+H]+ 178.0102156 predictedDarkChem Lite v0.1.0 [M+H]+ 168.73708 predictedDeepCCS 1.0 (2019) [M+Na]+ 175.57088 predictedDeepCCS 1.0 (2019)
Targets
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1. DetailsAndrogen receptor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Activator
- General Function
- Zinc ion binding
- Specific Function
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
- Gene Name
- AR
- Uniprot ID
- P10275
- Uniprot Name
- Androgen receptor
- Molecular Weight
- 98987.9 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]
- Siddique HR, Mishra SK, Karnes RJ, Saleem M: Lupeol, a novel androgen receptor inhibitor: implications in prostate cancer therapy. Clin Cancer Res. 2011 Aug 15;17(16):5379-91. doi: 10.1158/1078-0432.CCR-11-0916. Epub 2011 Jun 28. [Article]
2. DetailsNuclear receptor coactivator 2
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Transcription coactivator activity
- Specific Function
- Transcriptional coactivator for steroid receptors and nuclear receptors. Coactivator of the steroid binding domain (AF-2) but not of the modulating N-terminal domain (AF-1). Required with NCOA1 to ...
- Gene Name
- NCOA2
- Uniprot ID
- Q15596
- Uniprot Name
- Nuclear receptor coactivator 2
- Molecular Weight
- 159155.645 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
- 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
- Takeda AN, Pinon GM, Bens M, Fagart J, Rafestin-Oblin ME, Vandewalle A: The synthetic androgen methyltrienolone (r1881) acts as a potent antagonist of the mineralocorticoid receptor. Mol Pharmacol. 2007 Feb;71(2):473-82. Epub 2006 Nov 14. [Article]
4. DetailsProgesterone receptor
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Progesterone receptor ...
- Gene Name
- PGR
- Uniprot ID
- P06401
- Uniprot Name
- Progesterone receptor
- Molecular Weight
- 98979.96 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- 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]
5. DetailsProstate-specific antigen
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Activator
- General Function
- Hydrolyzes semenogelin-1 thus leading to the liquefaction of the seminal coagulum.
- Specific Function
- Endopeptidase activity
- Gene Name
- KLK3
- Uniprot ID
- P07288
- Uniprot Name
- Prostate-specific antigen
- Molecular Weight
- 28741.1 Da
References
- Siddique HR, Mishra SK, Karnes RJ, Saleem M: Lupeol, a novel androgen receptor inhibitor: implications in prostate cancer therapy. Clin Cancer Res. 2011 Aug 15;17(16):5379-91. doi: 10.1158/1078-0432.CCR-11-0916. Epub 2011 Jun 28. [Article]
Drug created at June 13, 2005 13:24 / Updated at June 24, 2022 16:38