Identification

Name
Methyltestosterone
Accession Number
DB06710
Type
Small Molecule
Groups
Approved
Description

A synthetic anabolic steroid used for treating men with testosterone deficiency or similar androgen replacement therapies. Also, has antineoplastic properties and so has been used secondarily in women with advanced breast cancer. Methyltestosterone is a schedule III drug in the US.

Structure
Thumb
Synonyms
  • 17-beta-Hydroxy-17-methylandrost-4-en-3-one
  • 17-methyltestosterone
  • 17(alpha)-Methyl-delta(4)-androsten-17(beta)-ol-3-one
  • 17alpha-Methyl-3-oxo-4-androsten-17beta-ol
  • 17alpha-Methyl-delta(4)-androsten-17beta-ol-3-one
  • 17alpha-Methyltestosterone
  • 17beta-Hydroxy-17-methylandrost-4-en-3-one
  • 17α-methyl-Δ4-androsten-17β-ol-3-one
  • 17α-methyltestosterone
  • 4-Androstene-17alpha-methyl-17beta-ol-3-one
  • Methyltestosterone
  • Methyltestosteronum
  • Metiltestosterona
  • NSC-9701
External IDs
L 589.372 / NSC-139965 / RU 24400
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Metandren 10mgTablet10 mgOralNovartis1993-12-312001-04-05Canada
Metandren 25mgTablet25 mgOralNovartis1992-12-312001-04-05Canada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AndroidCapsule10 mg/1OralValeant Pharmaceuticals North America1973-12-032018-04-30Us
MethitestTablet10 mg/1OralImpax Generics1974-10-17Not applicableUs
MethylTESTOSTERoneCapsule10 mg/1OralImpax Generics2015-09-21Not applicableUs
Testred C-IIICapsule10 mg/1OralValeant Pharmaceuticals North America1973-12-03Not applicableUs
International/Other Brands
Android / Testred / Virilon
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
CovaryxMethyltestosterone (2.5 mg/1) + Estrogens, esterified (1.25 mg/1)Tablet, coatedOralCentrix Pharmaceutical2007-04-01Not applicableUs11528 0010 01 nlmimage10 5905aced
Covaryx HsMethyltestosterone (1.25 mg/1) + Estrogens, esterified (.625 mg/1)Tablet, coatedOralCentrix Pharmaceutical2007-04-01Not applicableUs
EemtMethyltestosterone (2.5 mg/1) + Estrogens, esterified (1.25 mg/1)Tablet, coatedOralCreekwood Pharmaceuticals, Inc.2011-09-01Not applicableUs
Eemt HsMethyltestosterone (1.25 mg/1) + Estrogens, esterified (.625 mg/1)Tablet, coatedOralCreekwood Pharmaceuticals, Inc.2011-09-01Not applicableUs
Esterified Estrogens and MethyltestosteroneMethyltestosterone (1.25 mg/1) + Conjugated estrogens (.625 mg/1)TabletOralAmneal Pharmaceuticals2010-09-22Not applicableUs53746 0077 01 nlmimage10 6605b34d
Esterified Estrogens and MethyltestosteroneMethyltestosterone (1.25 mg/1) + Estrogens, esterified (.625 mg/1)TabletOralANIP Acquisition Company2010-12-22Not applicableUs
Esterified Estrogens and MethyltestosteroneMethyltestosterone (2.5 mg/1) + Conjugated estrogens (1.25 mg/1)Tablet, film coatedOralSeton Pharmaceuticals2010-05-05Not applicableUs
Esterified Estrogens and MethyltestosteroneMethyltestosterone (2.5 mg/1) + Estrogens, esterified (1.25 mg/1)TabletOralMethod Pharmaceuticals2017-08-15Not applicableUs
Esterified Estrogens and MethyltestosteroneMethyltestosterone (2.5 mg/1) + Conjugated estrogens (1.25 mg/1)TabletOralAmneal Pharmaceuticals2010-09-22Not applicableUs53746 0078 01 nlmimage10 5f05afed
Esterified Estrogens and MethyltestosteroneMethyltestosterone (1.25 mg/1) + Estrone sodium sulfate (.625 mg/1)Tablet, film coatedOralTal Pharma Llc2010-09-17Not applicableUs50220 0001 01 nlmimage10 6005b07d
Categories
UNII
V9EFU16ZIF
CAS number
58-18-4
Weight
Average: 302.451
Monoisotopic: 302.224580204
Chemical Formula
C20H30O2
InChI Key
GCKMFJBGXUYNAG-HLXURNFRSA-N
InChI
InChI=1S/C20H30O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h12,15-17,22H,4-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1
IUPAC Name
(1S,2R,10R,11S,14S,15S)-14-hydroxy-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-5-one
SMILES

Pharmacology

Indication

Methyltestosterone is an anabolic steroid hormone used to treat men with a testosterone deficiency. It is also used in women to treat breast cancer, breast pain, swelling due to pregnancy, and with the addition of estrogen it can treat symptoms of menopause.

Structured Indications
Pharmacodynamics

Testosterone is a steroid hormone from the androgen group. Testosterone is primarily secreted from the testes of males. In females, it is produced in the ovaries, adrenal glands and by conversion of adrostenedione in the periphery. It is the principal male sex hormone and an anabolic steroid. In both males and females, it plays key roles in health and well-being. Examples include enhanced libido, energy, immune function, and protection against osteoporosis. On average, the adult male body produces about twenty times the amount of testosterone than an adult female's body does.

Mechanism of action

The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.

TargetActionsOrganism
AAndrogen receptor
agonist
Human
UEstrogen receptor alphaNot AvailableHuman
Absorption

The methyl group aids to increase oral bioavailability.

Volume of distribution
Not Available
Protein binding

40% of testosterone in plasma is bound to sex hormone-binding globulin and 2% remains unbound and the rest is bound to albumin and other proteins.

Metabolism

Hepatic. Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).

Route of elimination

90% urine / 10% feces

Half life

6-8 hours

Clearance
Not Available
Toxicity

Side effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.

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 Methyltestosterone.Investigational
19-norandrostenedione19-norandrostenedione may increase the fluid retaining activities of Methyltestosterone.Experimental, Illicit
5-androstenedione5-androstenedione may increase the fluid retaining activities of Methyltestosterone.Experimental, Illicit
AcarboseMethyltestosterone may increase the hypoglycemic activities of Acarbose.Approved, Investigational
AcenocoumarolMethyltestosterone may increase the anticoagulant activities of Acenocoumarol.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Methyltestosterone.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Methyltestosterone.Experimental
AlbiglutideMethyltestosterone may increase the hypoglycemic activities of Albiglutide.Approved
AlclometasoneAlclometasone may increase the fluid retaining activities of Methyltestosterone.Approved
AldosteroneAldosterone may increase the fluid retaining activities of Methyltestosterone.Experimental, Investigational
AlogliptinMethyltestosterone may increase the hypoglycemic activities of Alogliptin.Approved
AmcinonideAmcinonide may increase the fluid retaining activities of Methyltestosterone.Approved
AmiodaroneThe metabolism of Methyltestosterone can be decreased when combined with Amiodarone.Approved, Investigational
AndrostenedioneAndrostenedione may increase the fluid retaining activities of Methyltestosterone.Experimental, Illicit
AnecortaveAnecortave may increase the fluid retaining activities of Methyltestosterone.Investigational
anecortave acetateanecortave acetate may increase the fluid retaining activities of Methyltestosterone.Investigational
AprepitantThe serum concentration of Methyltestosterone can be increased when it is combined with Aprepitant.Approved, Investigational
AtamestaneAtamestane may increase the fluid retaining activities of Methyltestosterone.Investigational
AtazanavirThe metabolism of Methyltestosterone can be decreased when combined with Atazanavir.Approved, Investigational
AtomoxetineThe metabolism of Methyltestosterone can be decreased when combined with Atomoxetine.Approved
Beclomethasone dipropionateBeclomethasone dipropionate may increase the fluid retaining activities of Methyltestosterone.Approved, Investigational
BetamethasoneBetamethasone may increase the fluid retaining activities of Methyltestosterone.Approved, Vet Approved
BevacizumabBevacizumab may increase the cardiotoxic activities of Methyltestosterone.Approved, Investigational
BoceprevirThe metabolism of Methyltestosterone can be decreased when combined with Boceprevir.Approved, Withdrawn
BortezomibThe metabolism of Methyltestosterone can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Methyltestosterone can be decreased when it is combined with Bosentan.Approved, Investigational
BromocriptineMethyltestosterone may increase the hypoglycemic activities of Bromocriptine.Approved, Investigational
BudesonideBudesonide may increase the fluid retaining activities of Methyltestosterone.Approved
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Methyltestosterone.Approved
CanagliflozinMethyltestosterone may increase the hypoglycemic activities of Canagliflozin.Approved
CarbamazepineThe metabolism of Methyltestosterone can be increased when combined with Carbamazepine.Approved, Investigational
CeritinibThe serum concentration of Methyltestosterone can be increased when it is combined with Ceritinib.Approved
ChlorpropamideMethyltestosterone may increase the hypoglycemic activities of Chlorpropamide.Approved
CiclesonideCiclesonide may increase the fluid retaining activities of Methyltestosterone.Approved, Investigational
CitalopramThe metabolism of Methyltestosterone can be decreased when combined with Citalopram.Approved
ClarithromycinThe metabolism of Methyltestosterone can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Methyltestosterone can be decreased when combined with Clemastine.Approved
ClobetasolClobetasol may increase the fluid retaining activities of Methyltestosterone.Investigational
Clobetasol propionateClobetasol propionate may increase the fluid retaining activities of Methyltestosterone.Approved
ClobetasoneClobetasone may increase the fluid retaining activities of Methyltestosterone.Approved
ClocortoloneClocortolone may increase the fluid retaining activities of Methyltestosterone.Approved
ClopidogrelThe metabolism of Methyltestosterone can be decreased when combined with Clopidogrel.Approved, Nutraceutical
ClorindioneMethyltestosterone may increase the anticoagulant activities of Clorindione.Experimental
ClotrimazoleThe metabolism of Methyltestosterone can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Methyltestosterone can be decreased when combined with Cobicistat.Approved
Conestat alfaMethyltestosterone may increase the thrombogenic activities of Conestat alfa.Approved
ConivaptanThe serum concentration of Methyltestosterone can be increased when it is combined with Conivaptan.Approved, Investigational
Cortexolone 17α-propionateCortexolone 17α-propionate may increase the fluid retaining activities of Methyltestosterone.Investigational
CorticosteroneCorticosterone may increase the fluid retaining activities of Methyltestosterone.Experimental
Cortisone acetateCortisone acetate may increase the fluid retaining activities of Methyltestosterone.Approved
CrizotinibThe metabolism of Methyltestosterone can be decreased when combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Methyltestosterone.Approved, Investigational
CyclosporineMethyltestosterone may increase the hepatotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
CymarinCymarin may decrease the cardiotoxic activities of Methyltestosterone.Experimental
DabrafenibThe serum concentration of Methyltestosterone can be decreased when it is combined with Dabrafenib.Approved
DapagliflozinMethyltestosterone may increase the hypoglycemic activities of Dapagliflozin.Approved
DarunavirThe metabolism of Methyltestosterone can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Methyltestosterone can be increased when it is combined with Dasatinib.Approved, Investigational
DeferasiroxThe serum concentration of Methyltestosterone can be decreased when it is combined with Deferasirox.Approved, Investigational
DeflazacortDeflazacort may increase the fluid retaining activities of Methyltestosterone.Approved
DelavirdineThe metabolism of Methyltestosterone can be decreased when combined with Delavirdine.Approved
DesipramineThe metabolism of Methyltestosterone can be decreased when combined with Desipramine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Methyltestosterone.Approved
DesonideDesonide may increase the fluid retaining activities of Methyltestosterone.Approved, Investigational
DesoximetasoneDesoximetasone may increase the fluid retaining activities of Methyltestosterone.Approved
Desoxycorticosterone acetateDesoxycorticosterone acetate may increase the fluid retaining activities of Methyltestosterone.Approved
Desoxycorticosterone PivalateDesoxycorticosterone Pivalate may increase the fluid retaining activities of Methyltestosterone.Experimental, Vet Approved
DexamethasoneDexamethasone may increase the fluid retaining activities of Methyltestosterone.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateDexamethasone isonicotinate may increase the fluid retaining activities of Methyltestosterone.Vet Approved
DicoumarolMethyltestosterone may increase the anticoagulant activities of Dicoumarol.Approved
DiflorasoneDiflorasone may increase the fluid retaining activities of Methyltestosterone.Approved
DifluocortoloneDifluocortolone may increase the fluid retaining activities of Methyltestosterone.Approved, Investigational
DifluprednateDifluprednate may increase the fluid retaining activities of Methyltestosterone.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Methyltestosterone.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Methyltestosterone.Approved
Digoxin Immune Fab (Ovine)Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Methyltestosterone.Approved
DihydroergotamineThe metabolism of Methyltestosterone can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Methyltestosterone can be decreased when combined with Diltiazem.Approved
DiphenadioneMethyltestosterone may increase the anticoagulant activities of Diphenadione.Experimental
DisopyramideMethyltestosterone may increase the hypoglycemic activities of Disopyramide.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Methyltestosterone.Approved, Investigational
DoxorubicinThe metabolism of Methyltestosterone can be decreased when combined with Doxorubicin.Approved, Investigational
DoxycyclineThe metabolism of Methyltestosterone can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronedaroneThe metabolism of Methyltestosterone can be decreased when combined with Dronedarone.Approved
DulaglutideMethyltestosterone may increase the hypoglycemic activities of Dulaglutide.Approved
EmpagliflozinMethyltestosterone may increase the hypoglycemic activities of Empagliflozin.Approved
EnzalutamideThe serum concentration of Methyltestosterone can be decreased when it is combined with Enzalutamide.Approved
EquileninEquilenin may increase the fluid retaining activities of Methyltestosterone.Experimental
EquilinEquilin may increase the fluid retaining activities of Methyltestosterone.Approved
ErythromycinThe metabolism of Methyltestosterone can be decreased when combined with Erythromycin.Approved, Vet Approved
EstroneEstrone may increase the fluid retaining activities of Methyltestosterone.Approved
Estrone sulfateEstrone sulfate may increase the fluid retaining activities of Methyltestosterone.Approved
Ethyl biscoumacetateMethyltestosterone may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
ExenatideMethyltestosterone may increase the hypoglycemic activities of Exenatide.Approved, Investigational
fluasteronefluasterone may increase the fluid retaining activities of Methyltestosterone.Investigational
FluconazoleThe metabolism of Methyltestosterone can be decreased when combined with Fluconazole.Approved
FludrocortisoneFludrocortisone may increase the fluid retaining activities of Methyltestosterone.Approved
FluindioneMethyltestosterone may increase the anticoagulant activities of Fluindione.Investigational
FlumethasoneFlumethasone may increase the fluid retaining activities of Methyltestosterone.Approved, Vet Approved
FlunisolideFlunisolide may increase the fluid retaining activities of Methyltestosterone.Approved, Investigational
Fluocinolone AcetonideFluocinolone Acetonide may increase the fluid retaining activities of Methyltestosterone.Approved, Investigational, Vet Approved
FluocinonideFluocinonide may increase the fluid retaining activities of Methyltestosterone.Approved, Investigational
FluocortoloneFluocortolone may increase the fluid retaining activities of Methyltestosterone.Approved, Withdrawn
FluorometholoneFluorometholone may increase the fluid retaining activities of Methyltestosterone.Approved
FluprednideneFluprednidene may increase the fluid retaining activities of Methyltestosterone.Approved, Withdrawn
FluprednisoloneFluprednisolone may increase the fluid retaining activities of Methyltestosterone.Approved
FlurandrenolideFlurandrenolide may increase the fluid retaining activities of Methyltestosterone.Approved
Fluticasone furoateFluticasone furoate may increase the fluid retaining activities of Methyltestosterone.Approved
Fluticasone propionateFluticasone propionate may increase the fluid retaining activities of Methyltestosterone.Approved
FluvoxamineThe metabolism of Methyltestosterone can be decreased when combined with Fluvoxamine.Approved, Investigational
FormestaneFormestane may increase the fluid retaining activities of Methyltestosterone.Approved, Investigational, Withdrawn
FosamprenavirThe metabolism of Methyltestosterone can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Methyltestosterone can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Methyltestosterone can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Methyltestosterone can be increased when it is combined with Fusidic Acid.Approved
GitoformateGitoformate may decrease the cardiotoxic activities of Methyltestosterone.Experimental
GliclazideMethyltestosterone may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideMethyltestosterone may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideMethyltestosterone may increase the hypoglycemic activities of Glipizide.Approved
GlyburideMethyltestosterone may increase the hypoglycemic activities of Glyburide.Approved
HalcinonideHalcinonide may increase the fluid retaining activities of Methyltestosterone.Approved, Investigational, Withdrawn
HE3286HE3286 may increase the fluid retaining activities of Methyltestosterone.Investigational
Human C1-esterase inhibitorMethyltestosterone may increase the thrombogenic activities of Human C1-esterase inhibitor.Approved
HydrocortisoneHydrocortisone may increase the fluid retaining activities of Methyltestosterone.Approved, Vet Approved
IdelalisibThe serum concentration of Methyltestosterone can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Methyltestosterone can be decreased when combined with Imatinib.Approved
IndinavirThe metabolism of Methyltestosterone can be decreased when combined with Indinavir.Approved
Insulin AspartMethyltestosterone may increase the hypoglycemic activities of Insulin Aspart.Approved
Insulin DetemirMethyltestosterone may increase the hypoglycemic activities of Insulin Detemir.Approved
Insulin GlargineMethyltestosterone may increase the hypoglycemic activities of Insulin Glargine.Approved
Insulin GlulisineMethyltestosterone may increase the hypoglycemic activities of Insulin Glulisine.Approved
Insulin HumanMethyltestosterone may increase the hypoglycemic activities of Insulin Human.Approved, Investigational
Insulin LisproMethyltestosterone may increase the hypoglycemic activities of Insulin Lispro.Approved
IsavuconazoniumThe metabolism of Methyltestosterone can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Methyltestosterone can be decreased when combined with Isradipine.Approved
IstaroximeIstaroxime may increase the fluid retaining activities of Methyltestosterone.Investigational
ItraconazoleThe metabolism of Methyltestosterone can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Methyltestosterone can be increased when it is combined with Ivacaftor.Approved
KetoconazoleThe metabolism of Methyltestosterone can be decreased when combined with Ketoconazole.Approved, Investigational
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Methyltestosterone.Experimental
LiraglutideMethyltestosterone may increase the hypoglycemic activities of Liraglutide.Approved
LopinavirThe metabolism of Methyltestosterone can be decreased when combined with Lopinavir.Approved
LoteprednolLoteprednol may increase the fluid retaining activities of Methyltestosterone.Approved
LovastatinThe metabolism of Methyltestosterone can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Methyltestosterone can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Methyltestosterone can be decreased when it is combined with Lumacaftor.Approved
ME-609ME-609 may increase the fluid retaining activities of Methyltestosterone.Investigational
MecaserminMethyltestosterone may increase the hypoglycemic activities of Mecasermin.Approved, Investigational
MedrysoneMedrysone may increase the fluid retaining activities of Methyltestosterone.Approved
MelengestrolMelengestrol may increase the fluid retaining activities of Methyltestosterone.Vet Approved
MetforminMethyltestosterone may increase the hypoglycemic activities of Metformin.Approved
MethylprednisoloneMethylprednisolone may increase the fluid retaining activities of Methyltestosterone.Approved, Vet Approved
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Methyltestosterone.Experimental
MifepristoneThe serum concentration of Methyltestosterone can be increased when it is combined with Mifepristone.Approved, Investigational
MiglitolMethyltestosterone may increase the hypoglycemic activities of Miglitol.Approved
MitotaneThe serum concentration of Methyltestosterone can be decreased when it is combined with Mitotane.Approved
MometasoneMometasone may increase the fluid retaining activities of Methyltestosterone.Approved, Vet Approved
NateglinideMethyltestosterone may increase the hypoglycemic activities of Nateglinide.Approved, Investigational
NCX 1022NCX 1022 may increase the fluid retaining activities of Methyltestosterone.Investigational
NefazodoneThe metabolism of Methyltestosterone can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Methyltestosterone can be decreased when combined with Nelfinavir.Approved
NetupitantThe serum concentration of Methyltestosterone can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Methyltestosterone can be increased when combined with Nevirapine.Approved
NilotinibThe metabolism of Methyltestosterone can be decreased when combined with Nilotinib.Approved, Investigational
OlaparibThe metabolism of Methyltestosterone can be decreased when combined with Olaparib.Approved
OleandrinOleandrin may decrease the cardiotoxic activities of Methyltestosterone.Experimental, Investigational
Oleoyl-estroneOleoyl-estrone may increase the fluid retaining activities of Methyltestosterone.Investigational
OsimertinibThe serum concentration of Methyltestosterone can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Methyltestosterone.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Methyltestosterone.Approved, Vet Approved
PalbociclibThe serum concentration of Methyltestosterone can be increased when it is combined with Palbociclib.Approved
ParamethasoneParamethasone may increase the fluid retaining activities of Methyltestosterone.Approved
ParoxetineThe metabolism of Methyltestosterone can be decreased when combined with Paroxetine.Approved, Investigational
PentamidineMethyltestosterone may increase the hypoglycemic activities of Pentamidine.Approved
PentobarbitalThe metabolism of Methyltestosterone can be increased when combined with Pentobarbital.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Methyltestosterone.Experimental
PhenindioneMethyltestosterone may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenobarbitalThe metabolism of Methyltestosterone can be increased when combined with Phenobarbital.Approved
PhenprocoumonMethyltestosterone may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PhenytoinThe metabolism of Methyltestosterone can be increased when combined with Phenytoin.Approved, Vet Approved
PioglitazoneMethyltestosterone may increase the hypoglycemic activities of Pioglitazone.Approved, Investigational
PosaconazoleThe metabolism of Methyltestosterone can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PramlintideMethyltestosterone may increase the hypoglycemic activities of Pramlintide.Approved, Investigational
PrasteronePrasterone may increase the fluid retaining activities of Methyltestosterone.Approved, Nutraceutical
Prasterone sulfatePrasterone sulfate may increase the fluid retaining activities of Methyltestosterone.Investigational
PrednicarbatePrednicarbate may increase the fluid retaining activities of Methyltestosterone.Approved
PrednisolonePrednisolone may increase the fluid retaining activities of Methyltestosterone.Approved, Vet Approved
PrednisonePrednisone may increase the fluid retaining activities of Methyltestosterone.Approved, Vet Approved
PregnenolonePregnenolone may increase the fluid retaining activities of Methyltestosterone.Experimental, Investigational
PrimidoneThe metabolism of Methyltestosterone can be increased when combined with Primidone.Approved, Vet Approved
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Methyltestosterone.Experimental
QuazepamThe serum concentration of Methyltestosterone can be increased when it is combined with Quazepam.Approved, Illicit
QuinineMethyltestosterone may increase the hypoglycemic activities of Quinine.Approved
RanolazineThe metabolism of Methyltestosterone can be decreased when combined with Ranolazine.Approved, Investigational
RepaglinideMethyltestosterone may increase the hypoglycemic activities of Repaglinide.Approved, Investigational
RifabutinThe metabolism of Methyltestosterone can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Methyltestosterone can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Methyltestosterone can be increased when combined with Rifapentine.Approved
RimexoloneRimexolone may increase the fluid retaining activities of Methyltestosterone.Approved
RosiglitazoneMethyltestosterone may increase the hypoglycemic activities of Rosiglitazone.Approved, Investigational
SaquinavirThe metabolism of Methyltestosterone can be decreased when combined with Saquinavir.Approved, Investigational
SaxagliptinMethyltestosterone may increase the hypoglycemic activities of Saxagliptin.Approved
SertralineThe metabolism of Methyltestosterone can be decreased when combined with Sertraline.Approved
SildenafilThe metabolism of Methyltestosterone can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Methyltestosterone can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Methyltestosterone can be increased when it is combined with Simeprevir.Approved
SitagliptinMethyltestosterone may increase the hypoglycemic activities of Sitagliptin.Approved, Investigational
SorafenibThe metabolism of Methyltestosterone can be decreased when combined with Sorafenib.Approved, Investigational
St. John's WortThe serum concentration of Methyltestosterone can be decreased when it is combined with St. John's Wort.Investigational, Nutraceutical
StiripentolThe serum concentration of Methyltestosterone can be increased when it is combined with Stiripentol.Approved
SulfadiazineMethyltestosterone may increase the hypoglycemic activities of Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleMethyltestosterone may increase the hypoglycemic activities of Sulfamethoxazole.Approved
SulfisoxazoleThe metabolism of Methyltestosterone can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SunitinibMethyltestosterone may increase the hypoglycemic activities of Sunitinib.Approved, Investigational
TelaprevirThe metabolism of Methyltestosterone can be decreased when combined with Telaprevir.Approved, Withdrawn
TelithromycinThe metabolism of Methyltestosterone can be decreased when combined with Telithromycin.Approved
ThiotepaThe metabolism of Methyltestosterone can be decreased when combined with Thiotepa.Approved
TiclopidineThe metabolism of Methyltestosterone can be decreased when combined with Ticlopidine.Approved
TioclomarolMethyltestosterone may increase the anticoagulant activities of Tioclomarol.Experimental
TixocortolTixocortol may increase the fluid retaining activities of Methyltestosterone.Approved
TocilizumabThe serum concentration of Methyltestosterone can be decreased when it is combined with Tocilizumab.Approved
TolazamideMethyltestosterone may increase the hypoglycemic activities of Tolazamide.Approved
TolbutamideMethyltestosterone may increase the hypoglycemic activities of Tolbutamide.Approved
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Methyltestosterone.Approved, Investigational
TriamcinoloneTriamcinolone may increase the fluid retaining activities of Methyltestosterone.Approved, Vet Approved
UlobetasolUlobetasol may increase the fluid retaining activities of Methyltestosterone.Approved
VenlafaxineThe metabolism of Methyltestosterone can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Methyltestosterone can be decreased when combined with Verapamil.Approved
VoriconazoleThe metabolism of Methyltestosterone can be decreased when combined with Voriconazole.Approved, Investigational
WarfarinMethyltestosterone may increase the anticoagulant activities of Warfarin.Approved
ZiprasidoneThe metabolism of Methyltestosterone can be decreased when combined with Ziprasidone.Approved
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB15655
KEGG Drug
D00408
KEGG Compound
C07198
PubChem Compound
6010
PubChem Substance
99443262
ChemSpider
5788
BindingDB
50410531
ChEBI
27436
ChEMBL
CHEMBL1395
PharmGKB
PA165958383
Wikipedia
Methyltestosterone
ATC Codes
G03EA01 — Methyltestosterone and estrogenG03EK01 — MethyltestosteroneG03BA02 — Methyltestosterone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentHot Flushes, Menopause, Postmenopause1
2CompletedTreatmentMenopause1
2TerminatedTreatmentMenopause2

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
Tablet, coatedOral
TabletOral
Tablet, film coatedOral
TabletOral10 mg
TabletOral25 mg
TabletOral10 mg/1
CapsuleOral10 mg/1
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)163 °CPhysProp
water solubility33.9 mg/L (at 25 °C)YALKOWSKY,SH & HE,Y (2003)
logP3.36HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.0139 mg/mLALOGPS
logP3.61ALOGPS
logP3.65ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)19.09ChemAxon
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity89.07 m3·mol-1ChemAxon
Polarizability35.65 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9774
Caco-2 permeable+0.8737
P-glycoprotein substrateSubstrate0.6431
P-glycoprotein inhibitor IInhibitor0.5981
P-glycoprotein inhibitor IINon-inhibitor0.732
Renal organic cation transporterNon-inhibitor0.757
CYP450 2C9 substrateNon-substrate0.8075
CYP450 2D6 substrateNon-substrate0.8604
CYP450 3A4 substrateSubstrate0.7916
CYP450 1A2 substrateNon-inhibitor0.8619
CYP450 2C9 inhibitorNon-inhibitor0.8844
CYP450 2D6 inhibitorNon-inhibitor0.951
CYP450 2C19 inhibitorNon-inhibitor0.6629
CYP450 3A4 inhibitorNon-inhibitor0.8713
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8711
Ames testNon AMES toxic0.9429
CarcinogenicityNon-carcinogens0.9361
BiodegradationNot ready biodegradable0.9494
Rat acute toxicity2.0516 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.886
hERG inhibition (predictor II)Non-inhibitor0.7219
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-006x-7921000000-0e8f2747a2f3c8166048
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
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0udi-1329000000-c8db8c2a5d8403c476e1
1H NMR Spectrum1D NMRNot Applicable
13C NMR Spectrum1D NMRNot Applicable

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 delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Tertiary alcohols / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
Androgen-skeleton / 3-oxo-delta-4-steroid / 3-oxosteroid / Hydroxysteroid / Oxosteroid / 17-hydroxysteroid / Delta-4-steroid / Cyclohexenone / Tertiary alcohol / Cyclic alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
enone, 3-oxo Delta(4)-steroid, 17beta-hydroxy steroid (CHEBI:27436) / C19 steroids (androgens) and derivatives (C07198) / C19 steroids (androgens) and derivatives (LMST02020029)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
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
  1. Small EJ, Ryan CJ: The case for secondary hormonal therapies in the chemotherapy age. J Urol. 2006 Dec;176(6 Pt 2):S66-71. [PubMed:17084172]
  2. Omwancha J, Brown TR: Selective androgen receptor modulators: in pursuit of tissue-selective androgens. Curr Opin Investig Drugs. 2006 Oct;7(10):873-81. [PubMed:17086931]
  3. Petraki CD, Sfikas CP: Histopathological changes induced by therapies in the benign prostate and prostate adenocarcinoma. Histol Histopathol. 2007 Jan;22(1):107-18. [PubMed:17128417]
  4. Maudsley S, Davidson L, Pawson AJ, Freestone SH, Lopez de Maturana R, Thomson AA, Millar RP: Gonadotropin-releasing hormone functionally antagonizes testosterone activation of the human androgen receptor in prostate cells through focal adhesion complexes involving Hic-5. Neuroendocrinology. 2006;84(5):285-300. Epub 2007 Jan 4. [PubMed:17202804]
  5. Lapauw B, Goemaere S, Crabbe P, Kaufman JM, Ruige JB: Is the effect of testosterone on body composition modulated by the androgen receptor gene CAG repeat polymorphism in elderly men? Eur J Endocrinol. 2007 Mar;156(3):395-401. [PubMed:17322500]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name
ESR1
Uniprot ID
P03372
Uniprot Name
Estrogen receptor
Molecular Weight
66215.45 Da
References
  1. Huang R, Sakamuru S, Martin MT, Reif DM, Judson RS, Houck KA, Casey W, Hsieh JH, Shockley KR, Ceger P, Fostel J, Witt KL, Tong W, Rotroff DM, Zhao T, Shinn P, Simeonov A, Dix DJ, Austin CP, Kavlock RJ, Tice RR, Xia M: Profiling of the Tox21 10K compound library for agonists and antagonists of the estrogen receptor alpha signaling pathway. Sci Rep. 2014 Jul 11;4:5664. doi: 10.1038/srep05664. [PubMed:25012808]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid 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 oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Carriers

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Pardridge WM: Serum bioavailability of sex steroid hormones. Clin Endocrinol Metab. 1986 May;15(2):259-78. [PubMed:3521955]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Pardridge WM: Serum bioavailability of sex steroid hormones. Clin Endocrinol Metab. 1986 May;15(2):259-78. [PubMed:3521955]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
Inducer
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Lu R, Kanai N, Bao Y, Wolkoff AW, Schuster VL: Regulation of renal oatp mRNA expression by testosterone. Am J Physiol. 1996 Feb;270(2 Pt 2):F332-7. [PubMed:8779895]
  2. Kanai N, Lu R, Bao Y, Wolkoff AW, Vore M, Schuster VL: Estradiol 17 beta-D-glucuronide is a high-affinity substrate for oatp organic anion transporter. Am J Physiol. 1996 Feb;270(2 Pt 2):F326-31. [PubMed:8779894]
  3. Bossuyt X, Muller M, Hagenbuch B, Meier PJ: Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver. J Pharmacol Exp Ther. 1996 Mar;276(3):891-6. [PubMed:8786566]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inducer
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Kobayashi Y, Hirokawa N, Ohshiro N, Sekine T, Sasaki T, Tokuyama S, Endou H, Yamamoto T: Differential gene expression of organic anion transporters in male and female rats. Biochem Biophys Res Commun. 2002 Jan 11;290(1):482-7. [PubMed:11779196]

Drug created on May 16, 2010 09:41 / Updated on November 09, 2017 03:55