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Identification
Name4-Hydroxytestosterone
Accession NumberDB01485
TypeSmall Molecule
GroupsExperimental, Illicit
Description

4-Hydroxytestosterone is testosterone substituted with a hydroxy group on the fourth carbon atom. It is an anabolic steroid with no therapeutic indications, which is prohibited from use in sports by the World Anti-Doping Agency. 1

Formestane (Lentaron) acts as a prohormone of 4-Hydroxytestosterone, as 4-Hydroxytestosterone is one of the many byproducts of formestane metabolism. It is specifically the 17-hydroxylated analog to formestane. 1 Like formestane, 4-hydroxytesterone has been patented for use in decreasing estrogen production in the body, but no such indication currently exists. 4-Hydroxytestosterone was first patented in 1955 by G.D Searle & Company.

Structure
Thumb
Synonyms
SynonymLanguageCode
(17β)-4,17-dihydroxyandrost-4-en-3-oneNot AvailableNot Available
4,17-Dihydroxy-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-cyclopenta[a]phenanthren-3-oneNot AvailableNot Available
4,17beta-dihydroxy-4-androstene-3-oneNot AvailableNot Available
4,17β-Dihydroxy-4-androstene-3-oneNot AvailableNot Available
4OH-TNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
TestobolTMNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
CAS number2141-17-5
WeightNot Available
Chemical FormulaNot Available
InChI KeyNot Available
InChINot Available
IUPAC NameNot Available
SMILESNot Available
Taxonomy
ClassificationNot classified
Pharmacology
IndicationNot Available
PharmacodynamicsAanabolic steroids have a similar effect to testosterone in the body. Effects include an increase in protein production within cells, (ie. skeletal muscle cells) and well as the development and maintenance of masculine characteristics.
Mechanism of action4-hydroxytestosterone is a fat soluble compound which can cross the lipid bilayers of cell membranes to enter the cytoplasm of cells. In the cytoplasm, 4-hydroxytestosterone can bind to an androgen receptor, which then gets transported to the nucleus of the cell to alter protein transcription and translation. Ananolic steroids are believed to increase muscle mass by increasing the production of proteins, as well as by reducing the effects of the stress hormone cortisol, which is known to promote muscle breakdown. It is postulated that other steroid hormones (glucocorticoids) may also be inhibited by anabolic steroids in order to prevent muscle catabolism. [wiki]
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic.

Route of eliminationRenal elimination following hepatic metabolism.
Half lifeNot Available
Clearance

Clearance is via the urine. Excretion studies were performed using 200mg of 4-hydroxytestosterone administered to healthy male volunteers. Urine samples were then analyzed for metabolic products using conventional gas chromatography-mass spectrometry approaches.

One metabolite, 3-beta,4-alpha-dihydroxy-5alpha-androstan-17-one was identified as a long term metabolite which can be detected for 90 hours. Longer detection times are possible with the use of alternative monitoring technique in sports drug testing.

ToxicityExcessive doses of anabolic steroids can induce harmful changes in cholesterol, acne, hypertension, liver damage, and damage to the heart. Hormonal imbalances caused by the use of anabolic steriods may result in gynecomastia and testicular atrophy. Anabolic steroids are known to increase harmful LDL, while decreasing beneficial HDL cholesterol. Their ability to stimulate sebaceous glands may increase acne. Additionally, the elevation in blood pressure caused by anabolic steroids, is particularly pronounced and harmful in those with pre-existing hypertension.
Affected organismsNot Available
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal AbsorptionNot AvailableNot Available
Blood Brain BarrierNot AvailableNot Available
Caco-2 permeableNot AvailableNot Available
P-glycoprotein substrateNot AvailableNot Available
P-glycoprotein inhibitor INot AvailableNot Available
P-glycoprotein inhibitor IINot AvailableNot Available
Renal organic cation transporterNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 1A2 substrateNot AvailableNot Available
CYP450 2C9 substrateNot AvailableNot Available
CYP450 2D6 substrateNot AvailableNot Available
CYP450 2C19 substrateNot AvailableNot Available
CYP450 3A4 substrateNot AvailableNot Available
CYP450 inhibitory promiscuityNot AvailableNot Available
Ames testNot AvailableNot Available
CarcinogenicityNot AvailableNot Available
BiodegradationNot AvailableNot Available
Rat acute toxicityNot AvailableNot applicable
hERG inhibition (predictor I)Not AvailableNot Available
hERG inhibition (predictor II)Not AvailableNot Available
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot Available
Predicted PropertiesNot Available
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Kohler, Maxie, et al. “Metabolism of 4-hydroxyandrostenedione and 4-hydroxytestosterone: Mass spectrometric identification of urinary metabolites.” Steroids 72.3 (2007): 278-286.

General Reference

Kohler, Maxie, et al. “Metabolism of 4-hydroxyandrostenedione and 4-hydroxytestosterone: Mass spectrometric identification of urinary metabolites.” Steroids 72.3 (2007): 278-286.

W. Schanzer, H. Geyer, A. Gotzmann, U. Mareck. “Recent advances in doping analysis.” Cologne: Sport und Buch Strauss 129-138 (2004).

External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available
Comments
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Drug created on July 31, 2007 07:09 / Updated on July 02, 2013 12:09