NAV

Mesterolone

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

Identification

Summary

Mesterolone is an anabolic steroid indicated in the treatment of low testosterone, hypogonadism, oligozoospermia, and Leydig cell failure.

Generic Name
Mesterolone
DrugBank Accession Number
DB13587
Background

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.

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 304.4669
Monoisotopic: 304.240230268
Chemical Formula
C20H32O2
Synonyms
  • Mesterolona
  • Mesterolone
External IDs
  • NSC-75054
  • SH 723
  • SH-723
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Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofAndrogen deficiency••••••••••••••••••
Treatment ofHypogonadism••••••••••••••••••
Treatment ofLeydig cell failure in adult••••••••••••••••••
Treatment ofOligozoospermia••••••••••••••••••
Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
Not Available
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
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.
DrugInteraction
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interactions in your software
AcarboseMesterolone may increase the hypoglycemic activities of Acarbose.
AcenocoumarolMesterolone may increase the anticoagulant activities of Acenocoumarol.
AcetohexamideMesterolone may increase the hypoglycemic activities of Acetohexamide.
AlbiglutideMesterolone may increase the hypoglycemic activities of Albiglutide.
AlogliptinMesterolone may increase the hypoglycemic activities of Alogliptin.
Food Interactions
Not Available

Products

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Categories

ATC Codes
G03BB01 — Mesterolone
Drug Categories
Chemical TaxonomyProvided by Classyfire
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
17-hydroxysteroid / 3-oxo-5-alpha-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Androgen-skeleton / Carbonyl group / Cyclic alcohol / Cyclic ketone / Hydrocarbon derivative
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
C19 steroids (androgens) and derivatives (LMST02020107)
Affected organisms
Not Available

Chemical Identifiers

UNII
0SRQ75X9I9
CAS number
1424-00-6
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,3aS,3bR,5aS,9S,9aS,9bS,11aS)-1-hydroxy-9,9a,11a-trimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-7-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

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. [Article]
  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. [Article]
  3. TITCK Product Information: Proviron (mesterolone) oral tablets [Link]
Human Metabolome Database
HMDB0006036
PubChem Compound
15020
PubChem Substance
347829305
ChemSpider
14296
BindingDB
50423551
RxNav
6781
ChEBI
135293
ChEMBL
CHEMBL258918
ZINC
ZINC000003881977
Wikipedia
Mesterolone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral
TabletOral10 MG
TabletOral25.000 mg
TabletOral50 MG
TabletOral25 mg
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
Polarizability36.3 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-MSsplash10-03g1-0290000000-6711f2fd4cedd8b8ebe9
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0570-0092000000-25359755e3d3cba38eaf
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0009000000-f3aee4de5277649910ee
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-1691000000-f9df21fb021cb2523cc9
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udi-0019000000-e301ae96559ee65daa0e
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0udr-0059000000-55c0705a1716b76be754
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-1920000000-dc9cbad7cd87588257ca
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-181.1513022
predicted
DarkChem Lite v0.1.0
[M-H]-173.29152
predicted
DeepCCS 1.0 (2019)
[M+H]+182.2412022
predicted
DarkChem Lite v0.1.0
[M+H]+175.28745
predicted
DeepCCS 1.0 (2019)
[M+Na]+181.3296022
predicted
DarkChem Lite v0.1.0
[M+Na]+181.02785
predicted
DeepCCS 1.0 (2019)

Drug created at June 23, 2017 20:44 / Updated at May 29, 2021 18:11