Identification

Name
Stanolone
Accession Number
DB02901  (EXPT01199)
Type
Small Molecule
Groups
Illicit, Investigational
Description

A potent androgenic metabolite of testosterone. Dihydrotestosterone (DHT) is generated by a 5-alpha reduction of testosterone. Unlike testosterone, DHT cannot be aromatized to estradiol therefore DHT is considered a pure androgenic steroid.

Structure
Thumb
Synonyms
  • 17beta-Hydroxy-5alpha-androstan-3-one
  • 17beta-Hydroxy-5alpha-androstane-3-one
  • 17beta-Hydroxyandrostan-3-one
  • 17β-hydroxy-3-oxo-5α-androstanone
  • 17β-hydroxy-5α-androstan-3-one
  • 4-Dihydrotestosterone
  • 5alpha-Dihydrotestosterone
  • 5α-DHT
  • Androstanolone
  • DHT
  • Dihydrotestosteron
  • Dihydrotestostérone
  • Dihydrotestosterone
International/Other Brands
Anaboleen / Anabolex / Anaprotin / Andractim / Androlone / Cristerona MB / Neodrol / Proteina / Protona / Stanaprol
Categories
UNII
08J2K08A3Y
CAS number
521-18-6
Weight
Average: 290.4403
Monoisotopic: 290.224580204
Chemical Formula
C19H30O2
InChI Key
NVKAWKQGWWIWPM-ABEVXSGRSA-N
InChI
InChI=1S/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1
IUPAC Name
(1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[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)CC[C@]12C

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UEstradiol 17-beta-dehydrogenase 1Not AvailableHuman
UAndrogen receptorNot AvailableHuman
UEstrogen receptor alphaNot AvailableHuman
UMineralocorticoid receptorNot AvailableHuman
Absorption

Bioavailability is very low (0-2%) following oral administration.

Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity

Oral LD50 in rat is 7060 mg/kg. Oral LD50 in mouse is 3450 mg/kg.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
16-Bromoepiandrosterone16-Bromoepiandrosterone may increase the fluid retaining activities of Stanolone.Investigational
19-norandrostenedione19-norandrostenedione may increase the fluid retaining activities of Stanolone.Experimental, Illicit
5-androstenedione5-androstenedione may increase the fluid retaining activities of Stanolone.Experimental, Illicit
AcarboseStanolone may increase the hypoglycemic activities of Acarbose.Approved, Investigational
AcenocoumarolStanolone may increase the anticoagulant activities of Acenocoumarol.Approved, Investigational
AlbiglutideStanolone may increase the hypoglycemic activities of Albiglutide.Approved
AlclometasoneAlclometasone may increase the fluid retaining activities of Stanolone.Approved
AldosteroneAldosterone may increase the fluid retaining activities of Stanolone.Experimental, Investigational
AlogliptinStanolone may increase the hypoglycemic activities of Alogliptin.Approved
AmcinonideAmcinonide may increase the fluid retaining activities of Stanolone.Approved
AndrostenedioneAndrostenedione may increase the fluid retaining activities of Stanolone.Experimental, Illicit
AnecortaveAnecortave may increase the fluid retaining activities of Stanolone.Investigational
anecortave acetateanecortave acetate may increase the fluid retaining activities of Stanolone.Investigational
ApalutamideThe serum concentration of Stanolone can be decreased when it is combined with Apalutamide.Approved, Investigational
AtamestaneAtamestane may increase the fluid retaining activities of Stanolone.Investigational
Beclomethasone dipropionateBeclomethasone dipropionate may increase the fluid retaining activities of Stanolone.Approved, Investigational
BetamethasoneBetamethasone may increase the fluid retaining activities of Stanolone.Approved, Vet Approved
BromocriptineStanolone may increase the hypoglycemic activities of Bromocriptine.Approved, Investigational
BudesonideBudesonide may increase the fluid retaining activities of Stanolone.Approved
CanagliflozinStanolone may increase the hypoglycemic activities of Canagliflozin.Approved
ChlorpropamideStanolone may increase the hypoglycemic activities of Chlorpropamide.Approved, Investigational
CiclesonideCiclesonide may increase the fluid retaining activities of Stanolone.Approved, Investigational
ClobetasolClobetasol may increase the fluid retaining activities of Stanolone.Approved, Investigational
Clobetasol propionateClobetasol propionate may increase the fluid retaining activities of Stanolone.Approved
ClobetasoneClobetasone may increase the fluid retaining activities of Stanolone.Approved
ClocortoloneClocortolone may increase the fluid retaining activities of Stanolone.Approved
ClorindioneStanolone may increase the anticoagulant activities of Clorindione.Experimental
Conestat alfaStanolone may increase the thrombogenic activities of Conestat alfa.Approved, Investigational
Cortexolone 17α-propionateCortexolone 17α-propionate may increase the fluid retaining activities of Stanolone.Investigational
CorticosteroneCorticosterone may increase the fluid retaining activities of Stanolone.Experimental
Cortisone acetateCortisone acetate may increase the fluid retaining activities of Stanolone.Approved, Investigational
CyclosporineStanolone may increase the hepatotoxic activities of Cyclosporine.Approved, Investigational, Vet Approved
DapagliflozinStanolone may increase the hypoglycemic activities of Dapagliflozin.Approved
DeflazacortDeflazacort may increase the fluid retaining activities of Stanolone.Approved, Investigational
DesonideDesonide may increase the fluid retaining activities of Stanolone.Approved, Investigational
DesoximetasoneDesoximetasone may increase the fluid retaining activities of Stanolone.Approved
Desoxycorticosterone acetateDesoxycorticosterone acetate may increase the fluid retaining activities of Stanolone.Approved
Desoxycorticosterone PivalateDesoxycorticosterone Pivalate may increase the fluid retaining activities of Stanolone.Experimental, Vet Approved
DexamethasoneDexamethasone may increase the fluid retaining activities of Stanolone.Approved, Investigational, Vet Approved
Dexamethasone isonicotinateDexamethasone isonicotinate may increase the fluid retaining activities of Stanolone.Vet Approved
DicoumarolStanolone may increase the anticoagulant activities of Dicoumarol.Approved
DiflorasoneDiflorasone may increase the fluid retaining activities of Stanolone.Approved
DifluocortoloneDifluocortolone may increase the fluid retaining activities of Stanolone.Approved, Investigational, Withdrawn
DifluprednateDifluprednate may increase the fluid retaining activities of Stanolone.Approved
DiphenadioneStanolone may increase the anticoagulant activities of Diphenadione.Experimental
DisopyramideStanolone may increase the hypoglycemic activities of Disopyramide.Approved
DulaglutideStanolone may increase the hypoglycemic activities of Dulaglutide.Approved, Investigational
EmpagliflozinStanolone may increase the hypoglycemic activities of Empagliflozin.Approved
EquileninEquilenin may increase the fluid retaining activities of Stanolone.Experimental
EquilinEquilin may increase the fluid retaining activities of Stanolone.Approved
EstroneEstrone may increase the fluid retaining activities of Stanolone.Approved
Estrone sulfateEstrone sulfate may increase the fluid retaining activities of Stanolone.Approved
Ethyl biscoumacetateStanolone may increase the anticoagulant activities of Ethyl biscoumacetate.Withdrawn
ExenatideStanolone may increase the hypoglycemic activities of Exenatide.Approved, Investigational
FluasteroneFluasterone may increase the fluid retaining activities of Stanolone.Investigational
FludrocortisoneFludrocortisone may increase the fluid retaining activities of Stanolone.Approved, Investigational
FluindioneStanolone may increase the anticoagulant activities of Fluindione.Approved, Investigational
FlumethasoneFlumethasone may increase the fluid retaining activities of Stanolone.Approved, Vet Approved
FlunisolideFlunisolide may increase the fluid retaining activities of Stanolone.Approved, Investigational
Fluocinolone AcetonideFluocinolone Acetonide may increase the fluid retaining activities of Stanolone.Approved, Investigational, Vet Approved
FluocinonideFluocinonide may increase the fluid retaining activities of Stanolone.Approved, Investigational
FluocortoloneFluocortolone may increase the fluid retaining activities of Stanolone.Approved, Withdrawn
FluorometholoneFluorometholone may increase the fluid retaining activities of Stanolone.Approved, Investigational
FluprednideneFluprednidene may increase the fluid retaining activities of Stanolone.Approved, Withdrawn
FluprednisoloneFluprednisolone may increase the fluid retaining activities of Stanolone.Approved
FlurandrenolideFlurandrenolide may increase the fluid retaining activities of Stanolone.Approved
FluticasoneFluticasone may increase the fluid retaining activities of Stanolone.Approved, Experimental, Investigational
Fluticasone furoateFluticasone furoate may increase the fluid retaining activities of Stanolone.Approved
Fluticasone propionateFluticasone propionate may increase the fluid retaining activities of Stanolone.Approved
FormestaneFormestane may increase the fluid retaining activities of Stanolone.Approved, Investigational, Withdrawn
GabexateStanolone may increase the thrombogenic activities of Gabexate.Investigational
GliclazideStanolone may increase the hypoglycemic activities of Gliclazide.Approved
GlimepirideStanolone may increase the hypoglycemic activities of Glimepiride.Approved
GlipizideStanolone may increase the hypoglycemic activities of Glipizide.Approved, Investigational
GlyburideStanolone may increase the hypoglycemic activities of Glyburide.Approved
HalcinonideHalcinonide may increase the fluid retaining activities of Stanolone.Approved, Investigational, Withdrawn
HE3286HE3286 may increase the fluid retaining activities of Stanolone.Investigational
Human C1-esterase inhibitorStanolone may increase the thrombogenic activities of Human C1-esterase inhibitor.Approved
HydrocortisoneHydrocortisone may increase the fluid retaining activities of Stanolone.Approved, Vet Approved
Insulin AspartStanolone may increase the hypoglycemic activities of Insulin Aspart.Approved
Insulin DetemirStanolone may increase the hypoglycemic activities of Insulin Detemir.Approved
Insulin GlargineStanolone may increase the hypoglycemic activities of Insulin Glargine.Approved
Insulin GlulisineStanolone may increase the hypoglycemic activities of Insulin Glulisine.Approved
Insulin HumanStanolone may increase the hypoglycemic activities of Insulin Human.Approved, Investigational
Insulin LisproStanolone may increase the hypoglycemic activities of Insulin Lispro.Approved
IsavuconazoleThe serum concentration of Stanolone can be increased when it is combined with Isavuconazole.Approved, Investigational
IstaroximeIstaroxime may increase the fluid retaining activities of Stanolone.Investigational
LiraglutideStanolone may increase the hypoglycemic activities of Liraglutide.Approved
LoteprednolLoteprednol may increase the fluid retaining activities of Stanolone.Approved
LumacaftorThe serum concentration of Stanolone can be decreased when it is combined with Lumacaftor.Approved
ME-609ME-609 may increase the fluid retaining activities of Stanolone.Investigational
MecaserminStanolone may increase the hypoglycemic activities of Mecasermin.Approved, Investigational
MedrysoneMedrysone may increase the fluid retaining activities of Stanolone.Approved
MelengestrolMelengestrol may increase the fluid retaining activities of Stanolone.Vet Approved
MetforminStanolone may increase the hypoglycemic activities of Metformin.Approved
MethylprednisoloneMethylprednisolone may increase the fluid retaining activities of Stanolone.Approved, Vet Approved
MifepristoneStanolone may increase the hypoglycemic activities of Mifepristone.Approved, Investigational
MiglitolStanolone may increase the hypoglycemic activities of Miglitol.Approved
MometasoneMometasone may increase the fluid retaining activities of Stanolone.Approved, Vet Approved
NateglinideStanolone may increase the hypoglycemic activities of Nateglinide.Approved, Investigational
NCX 1022NCX 1022 may increase the fluid retaining activities of Stanolone.Investigational
Oleoyl-estroneOleoyl-estrone may increase the fluid retaining activities of Stanolone.Investigational
ParamethasoneParamethasone may increase the fluid retaining activities of Stanolone.Approved
PentamidineStanolone may increase the hypoglycemic activities of Pentamidine.Approved, Investigational
PhenindioneStanolone may increase the anticoagulant activities of Phenindione.Approved, Investigational
PhenprocoumonStanolone may increase the anticoagulant activities of Phenprocoumon.Approved, Investigational
PioglitazoneStanolone may increase the hypoglycemic activities of Pioglitazone.Approved, Investigational
PitolisantThe serum concentration of Stanolone can be decreased when it is combined with Pitolisant.Approved, Investigational
PramlintideStanolone may increase the hypoglycemic activities of Pramlintide.Approved, Investigational
PrasteronePrasterone may increase the fluid retaining activities of Stanolone.Approved, Investigational, Nutraceutical
Prasterone sulfatePrasterone sulfate may increase the fluid retaining activities of Stanolone.Investigational
PrednicarbatePrednicarbate may increase the fluid retaining activities of Stanolone.Approved, Investigational
PrednisolonePrednisolone may increase the fluid retaining activities of Stanolone.Approved, Vet Approved
PrednisonePrednisone may increase the fluid retaining activities of Stanolone.Approved, Vet Approved
PregnenolonePregnenolone may increase the fluid retaining activities of Stanolone.Approved, Experimental, Investigational
QuinineStanolone may increase the hypoglycemic activities of Quinine.Approved
RanolazineThe serum concentration of Stanolone can be increased when it is combined with Ranolazine.Approved, Investigational
RepaglinideStanolone may increase the hypoglycemic activities of Repaglinide.Approved, Investigational
RimexoloneRimexolone may increase the fluid retaining activities of Stanolone.Approved
RosiglitazoneStanolone may increase the hypoglycemic activities of Rosiglitazone.Approved, Investigational
SaxagliptinStanolone may increase the hypoglycemic activities of Saxagliptin.Approved
SitagliptinStanolone may increase the hypoglycemic activities of Sitagliptin.Approved, Investigational
SulfadiazineStanolone may increase the hypoglycemic activities of Sulfadiazine.Approved, Investigational, Vet Approved
SulfamethoxazoleStanolone may increase the hypoglycemic activities of Sulfamethoxazole.Approved
SulfisoxazoleStanolone may increase the hypoglycemic activities of Sulfisoxazole.Approved, Vet Approved
SunitinibStanolone may increase the hypoglycemic activities of Sunitinib.Approved, Investigational
TioclomarolStanolone may increase the anticoagulant activities of Tioclomarol.Experimental
TixocortolTixocortol may increase the fluid retaining activities of Stanolone.Approved, Withdrawn
TolazamideStanolone may increase the hypoglycemic activities of Tolazamide.Approved, Investigational
TolbutamideStanolone may increase the hypoglycemic activities of Tolbutamide.Approved, Investigational
TriamcinoloneTriamcinolone may increase the fluid retaining activities of Stanolone.Approved, Vet Approved
UlobetasolUlobetasol may increase the fluid retaining activities of Stanolone.Approved
VemurafenibThe serum concentration of Stanolone can be increased when it is combined with Vemurafenib.Approved
WarfarinStanolone may increase the anticoagulant activities of Warfarin.Approved
Food Interactions
Not Available

References

Synthesis Reference

A. Glenn Braswell, Aftab J. Ahmed, "Composition for inhibiting production of dihydrotestosterone to treat benign prostate hyperplasia." U.S. Patent US6264996, issued October, 1996.

US6264996
General References
Not Available
External Links
Human Metabolome Database
HMDB0002961
KEGG Drug
D07456
KEGG Compound
C03917
PubChem Compound
10635
PubChem Substance
46506828
ChemSpider
10189
BindingDB
18161
ChEBI
16330
ChEMBL
CHEMBL27769
HET
DHT
Wikipedia
Dihydrotestosterone
ATC Codes
A14AA01 — AndrostanoloneG03BB02 — Androstanolone
PDB Entries
1d2s / 1dht / 1f5f / 1i37 / 1i38 / 1kdk / 1kdm / 1t5z / 1t63 / 1t65
show 34 more
MSDS
Download (111 KB)

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
Solid
Experimental Properties
PropertyValueSource
melting point (°C)181 °CPhysProp
water solubility525 mg/mL (at 25 °C)YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP3.55HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.00998 mg/mLALOGPS
logP3.37ALOGPS
logP3.41ChemAxon
logS-4.5ALOGPS
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
Refractivity83.6 m3·mol-1ChemAxon
Polarizability34.69 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+0.9818
Caco-2 permeable+0.8846
P-glycoprotein substrateSubstrate0.57
P-glycoprotein inhibitor INon-inhibitor0.5631
P-glycoprotein inhibitor IINon-inhibitor0.846
Renal organic cation transporterNon-inhibitor0.7884
CYP450 2C9 substrateNon-substrate0.7715
CYP450 2D6 substrateNon-substrate0.93
CYP450 3A4 substrateSubstrate0.7314
CYP450 1A2 substrateNon-inhibitor0.6853
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.971
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.8546
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9647
Ames testNon AMES toxic0.9414
CarcinogenicityNon-carcinogens0.9182
BiodegradationNot ready biodegradable0.9686
Rat acute toxicity1.9757 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9444
hERG inhibition (predictor II)Non-inhibitor0.576
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (11.2 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
GC-MS Spectrum - EI-BGC-MSsplash10-015c-8970000000-ef0c6a4fd9c52be30284
GC-MS Spectrum - EI-BGC-MSsplash10-001l-1790000000-60cff73adc796876d469
Mass Spectrum (Electron Ionization)MSsplash10-000x-9870000000-f6d80b2a53942c9af50b
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
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-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
3-oxo steroid, 17beta-hydroxy steroid, 17beta-hydroxyandrostan-3-one (CHEBI:16330) / C19 steroids (androgens) and derivatives, Androstane and derivatives, Androgens (C03917) / C19 steroids (androgens) and derivatives (LMST02020042)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Testosterone dehydrogenase (nad+) activity
Specific Function
Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
Gene Name
HSD17B1
Uniprot ID
P14061
Uniprot Name
Estradiol 17-beta-dehydrogenase 1
Molecular Weight
34949.715 Da
Details
2. Androgen receptor
Kind
Protein
Organism
Human
Pharmacological action
Unknown
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. Askew EB, Gampe RT Jr, Stanley TB, Faggart JL, Wilson EM: Modulation of androgen receptor activation function 2 by testosterone and dihydrotestosterone. J Biol Chem. 2007 Aug 31;282(35):25801-16. Epub 2007 Jun 25. [PubMed:17591767]
  2. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]
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. Kojima H, Iida M, Katsura E, Kanetoshi A, Hori Y, Kobayashi K: Effects of a diphenyl ether-type herbicide, chlornitrofen, and its amino derivative on androgen and estrogen receptor activities. Environ Health Perspect. 2003 Apr;111(4):497-502. [PubMed:12676605]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates targ...
Gene Name
NR3C2
Uniprot ID
P08235
Uniprot Name
Mineralocorticoid receptor
Molecular Weight
107066.575 Da
References
  1. Takeda AN, Pinon GM, Bens M, Fagart J, Rafestin-Oblin ME, Vandewalle A: The synthetic androgen methyltrienolone (r1881) acts as a potent antagonist of the mineralocorticoid receptor. Mol Pharmacol. 2007 Feb;71(2):473-82. Epub 2006 Nov 14. [PubMed:17105867]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function
Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name
CYP11A1
Uniprot ID
P05108
Uniprot Name
Cholesterol side-chain cleavage enzyme, mitochondrial
Molecular Weight
60101.87 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 17-alpha-monooxygenase activity
Specific Function
Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation ...
Gene Name
CYP17A1
Uniprot ID
P05093
Uniprot Name
Steroid 17-alpha-hydroxylase/17,20 lyase
Molecular Weight
57369.995 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]
Details
3. Cytochrome P450 19A1
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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]

Carriers

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. Metzger J, Schnitzbauer A, Meyer M, Soder M, Cuilleron CY, Hauptmann H, Huber E, Luppa PB: Binding analysis of 1alpha- and 17alpha-dihydrotestosterone derivatives to homodimeric sex hormone-binding globulin. Biochemistry. 2003 Nov 25;42(46):13735-45. [PubMed:14622020]
  2. Hauptmann H, Metzger J, Schnitzbauer A, Cuilleron CY, Mappus E, Luppa PB: Syntheses and ligand-binding studies of 1 alpha- and 17 alpha-aminoalkyl dihydrotestosterone derivatives to human sex hormone-binding globulin. Steroids. 2003 Sep;68(7-8):629-39. [PubMed:12957668]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Fedoruk MN, Gimenez-Bonafe P, Guns ES, Mayer LD, Nelson CC: P-glycoprotein increases the efflux of the androgen dihydrotestosterone and reduces androgen responsive gene activity in prostate tumor cells. Prostate. 2004 Apr 1;59(1):77-90. [PubMed:14991868]

Drug created on June 13, 2005 07:24 / Updated on June 02, 2018 07:09