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Identification
NameMethyltestosterone
Accession NumberDB06710
TypeSmall Molecule
GroupsApproved
DescriptionA 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
Android
Methyltestosterone
Methyltestosteronum
Metiltestosterona
NSC-9701
Testred
Virilon
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Metandren 10mgTablet10 mgOralNovartis Pharmaceuticals Canada Inc1993-12-312001-04-05Canada
Metandren 25mgTablet25 mgOralNovartis Pharmaceuticals Canada Inc1992-12-312001-04-05Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AndroidCapsule10 mg/1OralValeant Pharmaceuticals North America LLC1973-12-03Not applicableUs
MethitestTablet10 mg/1OralImpax Generics1974-10-17Not applicableUs
MethyltestosteroneCapsule10 mg/1OralImpax Generics2015-09-21Not applicableUs
Testred C-IIICapsule10 mg/1OralValeant Pharmaceuticals North America LLC1973-12-03Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
TestredNot Available
VirilonNot Available
Brand mixtures
NameLabellerIngredients
CovaryxCentrix Pharmaceutical, Inc,
Covaryx HsCentrix Pharmaceutical, Inc,
EemtCreekwood Pharmaceutical, Inc,
Eemt HsCreekwood Pharmaceutical, Inc,
Esterified Estrogens and MethyltestosteroneSeton Pharmaceuticals
SaltsNot Available
Categories
UNIIV9EFU16ZIF
CAS number58-18-4
WeightAverage: 302.451
Monoisotopic: 302.224580204
Chemical FormulaC20H30O2
InChI KeyGCKMFJBGXUYNAG-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
[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Pharmacology
IndicationMethyltestosterone 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
PharmacodynamicsTestosterone 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 actionThe 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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Androgen receptorProteinyes
agonist
HumanP10275 details
Related Articles
AbsorptionThe methyl group aids to increase oral bioavailability.
Volume of distributionNot Available
Protein binding40% 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 elimination90% urine / 10% feces
Half life6-8 hours
ClearanceNot Available
ToxicitySide effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot 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
4-Androstenedione4-Androstenedione 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
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
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
AnecortaveAnecortave may increase the fluid retaining activities of Methyltestosterone.Investigational
AnvirzelAnvirzel may decrease the cardiotoxic activities of Methyltestosterone.Investigational
AprepitantThe serum concentration of Methyltestosterone can be increased when it is combined with Aprepitant.Approved, 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
BeclomethasoneBeclomethasone may increase the fluid retaining activities of Methyltestosterone.Investigational
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
BexaroteneThe serum concentration of Methyltestosterone can be decreased when it is combined with Bexarotene.Approved, Investigational
BoceprevirThe metabolism of Methyltestosterone can be decreased when combined with Boceprevir.Approved
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
C1 Esterase Inhibitor (Human)Methyltestosterone may increase the thrombogenic activities of C1 Esterase Inhibitor (Human).Approved
C1 Esterase Inhibitor (Recombinant)Methyltestosterone may increase the thrombogenic activities of C1 Esterase Inhibitor (Recombinant).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
ClocortoloneClocortolone may increase the fluid retaining activities of Methyltestosterone.Approved
ClopidogrelThe metabolism of Methyltestosterone can be decreased when combined with Clopidogrel.Approved, Nutraceutical
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
ConivaptanThe serum concentration of Methyltestosterone can be increased when it is combined with Conivaptan.Approved, Investigational
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
CyclosporineThe metabolism of Methyltestosterone can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
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
dehydroepiandrosterone sulfatedehydroepiandrosterone sulfate may increase the fluid retaining activities of Methyltestosterone.Investigational
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
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
DexamethasoneThe serum concentration of Methyltestosterone can be decreased when it is combined with Dexamethasone.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
DifluprednateDifluprednate may increase the fluid retaining activities of Methyltestosterone.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Methyltestosterone.Approved
DigoxinDigoxin 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
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
EfavirenzThe serum concentration of Methyltestosterone can be decreased when it is combined with Efavirenz.Approved, Investigational
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
Eslicarbazepine acetateThe serum concentration of Methyltestosterone can be decreased when it is combined with Eslicarbazepine acetate.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
EtravirineThe serum concentration of Methyltestosterone can be decreased when it is combined with Etravirine.Approved
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
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
HE3286HE3286 may increase the fluid retaining activities of Methyltestosterone.Investigational
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
LanreotideMethyltestosterone may increase the hypoglycemic activities of Lanreotide.Approved
LiraglutideMethyltestosterone may increase the hypoglycemic activities of Liraglutide.Approved
LopinavirThe metabolism of Methyltestosterone can be decreased when combined with Lopinavir.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
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
ModafinilThe serum concentration of Methyltestosterone can be decreased when it is combined with Modafinil.Approved, Investigational
MometasoneMometasone may increase the fluid retaining activities of Methyltestosterone.Approved, Vet Approved
NafcillinThe serum concentration of Methyltestosterone can be decreased when it is combined with Nafcillin.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
OctreotideMethyltestosterone may increase the hypoglycemic activities of Octreotide.Approved, Investigational
OlaparibThe metabolism of Methyltestosterone can be decreased when combined with Olaparib.Approved
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
PasireotideMethyltestosterone may increase the hypoglycemic activities of Pasireotide.Approved
PentamidineMethyltestosterone may increase the hypoglycemic activities of Pentamidine.Approved
PentobarbitalThe metabolism of Methyltestosterone can be increased when combined with Pentobarbital.Approved, Vet Approved
PhenindioneMethyltestosterone may increase the anticoagulant activities of Phenindione.Approved
PhenobarbitalThe metabolism of Methyltestosterone can be increased when combined with Phenobarbital.Approved
PhenprocoumonMethyltestosterone may increase the anticoagulant activities of Phenprocoumon.Approved
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
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
PrimidoneThe metabolism of Methyltestosterone can be increased when combined with Primidone.Approved, Vet Approved
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
RitonavirThe metabolism of Methyltestosterone can be decreased when combined with Ritonavir.Approved, Investigational
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.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
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
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
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 InteractionsNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesG03EA01G03BA02G03EK01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Tablet, coatedOral
TabletOral
Tablet, film coatedOral
TabletOral10 mg
TabletOral25 mg
TabletOral10 mg/1
CapsuleOral10 mg/1
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point163 °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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
MSMass Spectrum (Electron Ionization)splash10-006x-7921000000-0e8f2747a2f3c8166048View in MoNA
1D NMR1H NMR SpectrumNot Available
1D NMR13C NMR SpectrumNot Available
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens and derivatives
Alternative Parents
Substituents
  • Androgen-skeleton
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Tertiary alcohol
  • Cyclic alcohol
  • Cyclic ketone
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors

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 factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
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 ]

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
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 unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
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 colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
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, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration.
Gene Name:
SHBG
Uniprot ID:
P04278
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
inhibitorinducer
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 inhibited by the grapefruit juice component naringin.
Gene Name:
SLCO1A2
Uniprot ID:
P46721
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, fexofenadine. Transports benzylpenicillin (PCG), estrone-3-sulfate (E1S), cimetidine (CMD), 2,4-dichloro-phenoxyacetate (2,4-D), p-amino-hippurate (PAH), acyclovir (ACV) and ochratoxin (OTA).
Gene Name:
SLC22A8
Uniprot ID:
Q8TCC7
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 ]
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Drug created on May 16, 2010 09:41 / Updated on August 17, 2016 12:24