Mesterolone

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

Identification

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
Not Available
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
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
DrugInteractionDrug group
16-Bromoepiandrosterone16-Bromoepiandrosterone may increase the fluid retaining activities of Mesterolone.Investigational
19-norandrostenedione19-norandrostenedione may increase the fluid retaining activities of Mesterolone.Experimental, Illicit
5-androstenedione5-androstenedione may increase the fluid retaining activities of Mesterolone.Experimental, Illicit
AcarboseMesterolone may increase the hypoglycemic activities of Acarbose.Approved, Investigational
AcenocoumarolMesterolone may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
AlbiglutideMesterolone may increase the hypoglycemic activities of Albiglutide.Approved
AlclometasoneAlclometasone may increase the fluid retaining activities of Mesterolone.Approved
AldosteroneAldosterone may increase the fluid retaining activities of Mesterolone.Experimental, Investigational
AlogliptinMesterolone may increase the hypoglycemic activities of Alogliptin.Approved
AmcinonideAmcinonide may increase the fluid retaining activities of Mesterolone.Approved
AndrostenedioneAndrostenedione may increase the fluid retaining activities of Mesterolone.Experimental, Illicit
AnecortaveAnecortave may increase the fluid retaining activities of Mesterolone.Investigational
anecortave acetateanecortave acetate may increase the fluid retaining activities of Mesterolone.Investigational
AtamestaneAtamestane may increase the fluid retaining activities of Mesterolone.Investigational
Beclomethasone dipropionateThe risk or severity of edema formation can be increased when Mesterolone is combined with Beclomethasone dipropionate.Approved, Investigational
BetamethasoneBetamethasone may increase the fluid retaining activities of Mesterolone.Approved, Vet Approved
BromocriptineMesterolone may increase the hypoglycemic activities of Bromocriptine.Approved, Investigational
BudesonideThe risk or severity of edema formation can be increased when Mesterolone is combined with Budesonide.Approved
CanagliflozinMesterolone may increase the hypoglycemic activities of Canagliflozin.Approved
ChlorpropamideMesterolone may increase the hypoglycemic activities of Chlorpropamide.Approved, Investigational
CiclesonideCiclesonide may increase the fluid retaining activities of Mesterolone.Approved, Investigational
ClobetasolClobetasol may increase the fluid retaining activities of Mesterolone.Approved, Investigational
Clobetasol propionateClobetasol propionate may increase the fluid retaining activities of Mesterolone.Approved
ClobetasoneClobetasone may increase the fluid retaining activities of Mesterolone.Approved
ClocortoloneClocortolone may increase the fluid retaining activities of Mesterolone.Approved
ClorindioneMesterolone may increase the anticoagulant activities of Clorindione.Experimental
Conestat alfaMesterolone may increase the thrombogenic activities of Conestat alfa.Approved, Investigational
Cortexolone 17α-propionateCortexolone 17α-propionate may increase the fluid retaining activities of Mesterolone.Investigational
CorticosteroneCorticosterone may increase the fluid retaining activities of Mesterolone.Experimental
Cortisone acetateCortisone acetate may increase the fluid retaining activities of Mesterolone.Approved, Investigational
CyclosporineMesterolone may increase the hepatotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
DapagliflozinMesterolone may increase the hypoglycemic activities of Dapagliflozin.Approved
DeflazacortDeflazacort may increase the fluid retaining activities of Mesterolone.Approved, Investigational
DesonideDesonide may increase the fluid retaining activities of Mesterolone.Approved, Investigational
DesoximetasoneDesoximetasone may increase the fluid retaining activities of Mesterolone.Approved
Desoxycorticosterone acetateDesoxycorticosterone acetate may increase the fluid retaining activities of Mesterolone.Approved
Desoxycorticosterone PivalateDesoxycorticosterone Pivalate may increase the fluid retaining activities of Mesterolone.Experimental, Vet Approved
DexamethasoneThe risk or severity of edema formation can be increased when Mesterolone is combined with Dexamethasone.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateDexamethasone isonicotinate may increase the fluid retaining activities of Mesterolone.Vet Approved
DicoumarolMesterolone may increase the anticoagulant activities of Dicoumarol.Approved
DiflorasoneDiflorasone may increase the fluid retaining activities of Mesterolone.Approved
DifluocortoloneDifluocortolone may increase the fluid retaining activities of Mesterolone.Approved, Investigational, Withdrawn
DifluprednateDifluprednate may increase the fluid retaining activities of Mesterolone.Approved
DiphenadioneMesterolone may increase the anticoagulant activities of Diphenadione.Experimental
DisopyramideMesterolone may increase the hypoglycemic activities of Disopyramide.Approved
DulaglutideMesterolone may increase the hypoglycemic activities of Dulaglutide.Approved, Investigational
EmpagliflozinMesterolone may increase the hypoglycemic activities of Empagliflozin.Approved
EquileninEquilenin may increase the fluid retaining activities of Mesterolone.Experimental
EquilinEquilin may increase the fluid retaining activities of Mesterolone.Approved
EstroneEstrone may increase the fluid retaining activities of Mesterolone.Approved
Estrone sulfateEstrone sulfate may increase the fluid retaining activities of Mesterolone.Approved
Ethyl biscoumacetateMesterolone may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
ExenatideMesterolone may increase the hypoglycemic activities of Exenatide.Approved, Investigational
FluasteroneFluasterone may increase the fluid retaining activities of Mesterolone.Investigational
FludrocortisoneFludrocortisone may increase the fluid retaining activities of Mesterolone.Approved, Investigational
FluindioneMesterolone may increase the anticoagulant activities of Fluindione.Approved, Investigational
FlumethasoneFlumethasone may increase the fluid retaining activities of Mesterolone.Approved, Vet Approved
FlunisolideFlunisolide may increase the fluid retaining activities of Mesterolone.Approved, Investigational
Fluocinolone AcetonideFluocinolone Acetonide may increase the fluid retaining activities of Mesterolone.Approved, Investigational, Vet Approved
FluocinonideFluocinonide may increase the fluid retaining activities of Mesterolone.Approved, Investigational
FluocortoloneFluocortolone may increase the fluid retaining activities of Mesterolone.Approved, Withdrawn
FluorometholoneFluorometholone may increase the fluid retaining activities of Mesterolone.Approved, Investigational
FluprednideneFluprednidene may increase the fluid retaining activities of Mesterolone.Approved, Withdrawn
FluprednisoloneFluprednisolone may increase the fluid retaining activities of Mesterolone.Approved
FlurandrenolideFlurandrenolide may increase the fluid retaining activities of Mesterolone.Approved
FluticasoneFluticasone may increase the fluid retaining activities of Mesterolone.Approved, Experimental, Investigational
Fluticasone furoateFluticasone furoate may increase the fluid retaining activities of Mesterolone.Approved
Fluticasone propionateThe risk or severity of edema formation can be increased when Mesterolone is combined with Fluticasone propionate.Approved
FormestaneFormestane may increase the fluid retaining activities of Mesterolone.Approved, Investigational, Withdrawn
GabexateMesterolone may increase the thrombogenic activities of Gabexate.Investigational
GliclazideMesterolone may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideMesterolone may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideMesterolone may increase the hypoglycemic activities of Glipizide.Approved, Investigational
GlyburideMesterolone may increase the hypoglycemic activities of Glyburide.Approved
HalcinonideHalcinonide may increase the fluid retaining activities of Mesterolone.Approved, Investigational, Withdrawn
HE3286HE3286 may increase the fluid retaining activities of Mesterolone.Investigational
Human C1-esterase inhibitorMesterolone may increase the thrombogenic activities of Human C1-esterase inhibitor.Approved
HydrocortisoneThe risk or severity of edema formation can be increased when Mesterolone is combined with Hydrocortisone.Approved, Vet Approved
Hydrocortisone acetateThe risk or severity of edema formation can be increased when Mesterolone is combined with Hydrocortisone acetate.Approved, Vet Approved
Hydrocortisone butyrateThe risk or severity of edema formation can be increased when Mesterolone is combined with Hydrocortisone butyrate.Approved, Vet Approved
Insulin AspartMesterolone may increase the hypoglycemic activities of Insulin Aspart.Approved
Insulin DetemirMesterolone may increase the hypoglycemic activities of Insulin Detemir.Approved
Insulin GlargineMesterolone may increase the hypoglycemic activities of Insulin Glargine.Approved
Insulin GlulisineMesterolone may increase the hypoglycemic activities of Insulin Glulisine.Approved
Insulin HumanMesterolone may increase the hypoglycemic activities of Insulin Human.Approved, Investigational
Insulin LisproMesterolone may increase the hypoglycemic activities of Insulin Lispro.Approved
IstaroximeIstaroxime may increase the fluid retaining activities of Mesterolone.Investigational
LiraglutideMesterolone may increase the hypoglycemic activities of Liraglutide.Approved
LoteprednolLoteprednol may increase the fluid retaining activities of Mesterolone.Approved
ME-609ME-609 may increase the fluid retaining activities of Mesterolone.Investigational
MecaserminMesterolone may increase the hypoglycemic activities of Mecasermin.Approved, Investigational
MedrysoneMedrysone may increase the fluid retaining activities of Mesterolone.Approved
MelengestrolMelengestrol may increase the fluid retaining activities of Mesterolone.Vet Approved
MetforminMesterolone may increase the hypoglycemic activities of Metformin.Approved
MethylprednisoloneThe risk or severity of edema formation can be increased when Mesterolone is combined with Methylprednisolone.Approved, Vet Approved
MifepristoneMesterolone may increase the hypoglycemic activities of Mifepristone.Approved, Investigational
MiglitolMesterolone may increase the hypoglycemic activities of Miglitol.Approved
MometasoneMometasone may increase the fluid retaining activities of Mesterolone.Approved, Vet Approved
NateglinideMesterolone may increase the hypoglycemic activities of Nateglinide.Approved, Investigational
NCX 1022NCX 1022 may increase the fluid retaining activities of Mesterolone.Investigational
Oleoyl-estroneOleoyl-estrone may increase the fluid retaining activities of Mesterolone.Investigational
ParamethasoneParamethasone may increase the fluid retaining activities of Mesterolone.Approved
PentamidineMesterolone may increase the hypoglycemic activities of Pentamidine.Approved, Investigational
PhenindioneMesterolone may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonMesterolone may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PioglitazoneMesterolone may increase the hypoglycemic activities of Pioglitazone.Approved, Investigational
PramlintideMesterolone may increase the hypoglycemic activities of Pramlintide.Approved, Investigational
PrasteronePrasterone may increase the fluid retaining activities of Mesterolone.Approved, Investigational, Nutraceutical
Prasterone sulfatePrasterone sulfate may increase the fluid retaining activities of Mesterolone.Investigational
PrednicarbatePrednicarbate may increase the fluid retaining activities of Mesterolone.Approved, Investigational
PrednisoloneThe risk or severity of edema formation can be increased when Mesterolone is combined with Prednisolone.Approved, Vet Approved
PrednisonePrednisone may increase the fluid retaining activities of Mesterolone.Approved, Vet Approved
PregnenolonePregnenolone may increase the fluid retaining activities of Mesterolone.Approved, Experimental, Investigational
QuinineMesterolone may increase the hypoglycemic activities of Quinine.Approved
RepaglinideMesterolone may increase the hypoglycemic activities of Repaglinide.Approved, Investigational
RimexoloneRimexolone may increase the fluid retaining activities of Mesterolone.Approved
RosiglitazoneMesterolone may increase the hypoglycemic activities of Rosiglitazone.Approved, Investigational
SaxagliptinMesterolone may increase the hypoglycemic activities of Saxagliptin.Approved
SitagliptinMesterolone may increase the hypoglycemic activities of Sitagliptin.Approved, Investigational
SulfadiazineMesterolone may increase the hypoglycemic activities of Sulfadiazine.Approved, Investigational, Vet Approved
SulfamethoxazoleMesterolone may increase the hypoglycemic activities of Sulfamethoxazole.Approved
SulfisoxazoleMesterolone may increase the hypoglycemic activities of Sulfisoxazole.Approved, Vet Approved
SunitinibMesterolone may increase the hypoglycemic activities of Sunitinib.Approved, Investigational
TioclomarolMesterolone may increase the anticoagulant activities of Tioclomarol.Experimental
TixocortolTixocortol may increase the fluid retaining activities of Mesterolone.Approved, Withdrawn
TolazamideMesterolone may increase the hypoglycemic activities of Tolazamide.Approved, Investigational
TolbutamideMesterolone may increase the hypoglycemic activities of Tolbutamide.Approved, Investigational
TriamcinoloneTriamcinolone may increase the fluid retaining activities of Mesterolone.Approved, Vet Approved
UlobetasolUlobetasol may increase the fluid retaining activities of Mesterolone.Approved
WarfarinMesterolone may increase the anticoagulant activities of Warfarin.Approved
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 August 02, 2018 06:55