Mesterolone

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

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Name
Mesterolone
Accession Number
DB13587
Type
Small Molecule
Groups
Experimental
Description

Mesterolone is a synthetic anabolic-androgenic steroid (AAS) and derivative of dihydrotestosterone (DHT). It is inactivated by 3α-hydroxysteroid dehydrogenase in skeleta muscules so it is considered a weak androgen. It is not a substrate for aromatase so it is not converted into estrogen. Mesterolone demonstrated to have minimal effect on sperm counts and levels of FSH or LH 1,2. Experiments of mesterolone serving as a potential treatment of depression are still undergoing.

Structure
Thumb
Synonyms
  • Mesterolona
External IDs
NSC-75054 / SH 723 / SH-723
Categories
UNII
0SRQ75X9I9
CAS number
1424-00-6
Weight
Average: 304.4669
Monoisotopic: 304.240230268
Chemical Formula
C20H32O2
InChI Key
UXYRZJKIQKRJCF-TZPFWLJSSA-N
InChI
InChI=1S/C20H32O2/c1-12-10-14(21)11-13-4-5-15-16-6-7-18(22)19(16,2)9-8-17(15)20(12,13)3/h12-13,15-18,22H,4-11H2,1-3H3/t12-,13-,15-,16-,17-,18-,19-,20-/m0/s1
IUPAC Name
(1S,2S,3S,7S,10R,11S,14S,15S)-14-hydroxy-2,3,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)C[C@H](C)[C@]12C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Additional Data Available
Adverse Effects

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinMesterolone may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinMesterolone may increase the anticoagulant activities of (S)-Warfarin.
2,4-thiazolidinedioneMesterolone may increase the hypoglycemic activities of 2,4-thiazolidinedione.
4-hydroxycoumarinMesterolone may increase the anticoagulant activities of 4-hydroxycoumarin.
AcarboseMesterolone may increase the hypoglycemic activities of Acarbose.
AcenocoumarolMesterolone may increase the anticoagulant activities of Acenocoumarol.
AcetohexamideMesterolone may increase the hypoglycemic activities of Acetohexamide.
AICA ribonucleotideMesterolone may increase the hypoglycemic activities of AICA ribonucleotide.
AlbiglutideMesterolone may increase the hypoglycemic activities of Albiglutide.
AldosteroneThe risk or severity of edema formation can be increased when Mesterolone is combined with Aldosterone.
Additional Data Available
  • Extended Description
    Extended Description

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  • Severity
    Severity

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  • Evidence Level
    Evidence Level

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  • Action
    Evidence Level

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Food Interactions
Not Available

References

General References
  1. Jackaman FR, Ansell ID, Ghanadian R, McLoughlin PV, Lewis JG, Chisholm GD: The hormone response to a synthetic androgen (mesterolone) in oligospermia. Clin Endocrinol (Oxf). 1977 May;6(5):339-45. [PubMed:872444]
  2. Varma TR, Patel RH: The effect of mesterolone on sperm count, on serum follicle stimulating hormone, luteinizing hormone, plasma testosterone and outcome in idiopathic oligospermic men. Int J Gynaecol Obstet. 1988 Feb;26(1):121-8. [PubMed:2892728]
External Links
Human Metabolome Database
HMDB0006036
PubChem Compound
15020
PubChem Substance
347829305
ChemSpider
14296
BindingDB
50423551
ChEBI
135293
ChEMBL
CHEMBL258918
Wikipedia
Mesterolone
ATC Codes
G03BB01 — Mesterolone

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
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00641 mg/mLALOGPS
logP3.75ALOGPS
logP3.7ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)19.38ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity88.15 m3·mol-1ChemAxon
Polarizability36.46 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Androstane steroids
Direct Parent
Androgens and derivatives
Alternative Parents
3-oxo-5-alpha-steroids / 17-hydroxysteroids / Secondary alcohols / Cyclic ketones / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
Androgen-skeleton / 3-oxosteroid / 3-oxo-5-alpha-steroid / 17-hydroxysteroid / Oxosteroid / Hydroxysteroid / Cyclic alcohol / Cyclic ketone / Secondary alcohol / Ketone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
C19 steroids (androgens) and derivatives (LMST02020107)

Drug created on June 23, 2017 14:44 / Updated on May 01, 2019 11:48