4-Hydroxytestosterone

Identification

Name
4-Hydroxytestosterone
Accession Number
DB01485
Type
Small Molecule
Groups
Experimental, 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.

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
  • 4-Androstene-7alpha-17beta-diol-3-one
  • 4,17beta-Dihydroxy-4-androstene-3-one
  • 7alpha-Hydroxytestosterone
International/Other Brands
Testobol
Categories
UNII
912GOZ167T
CAS number
2141-17-5
Weight
Average: 304.43
Monoisotopic: 304.203844762
Chemical Formula
C19H28O3
InChI Key
BQOIJSIMMIDHMO-FBPKJDBXSA-N
InChI
InChI=1S/C19H28O3/c1-18-10-8-15(20)17(22)14(18)4-3-11-12-5-6-16(21)19(12,2)9-7-13(11)18/h11-13,16,21-22H,3-10H2,1-2H3/t11-,12-,13-,16-,18+,19-/m0/s1
IUPAC Name
(1S,2R,10R,11S,14S,15S)-6,14-dihydroxy-2,15-dimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one
SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=C(O)C(=O)CC[C@]34C)[C@@H]1CC[C@@H]2O

Pharmacology

Indication
Not Available
Pharmacodynamics

Aanabolic 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 action

4-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]

Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

Hepatic.

Route of elimination

Renal elimination following hepatic metabolism.

Half life
Not 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.

Toxicity

Excessive 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 organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe therapeutic efficacy of (R)-warfarin can be increased when used in combination with 4-Hydroxytestosterone.
(S)-WarfarinThe therapeutic efficacy of (S)-Warfarin can be increased when used in combination with 4-Hydroxytestosterone.
4-hydroxycoumarinThe therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with 4-Hydroxytestosterone.
AbciximabThe therapeutic efficacy of Abciximab can be increased when used in combination with 4-Hydroxytestosterone.
AcenocoumarolThe therapeutic efficacy of Acenocoumarol can be increased when used in combination with 4-Hydroxytestosterone.
Acetylsalicylic acidThe therapeutic efficacy of Acetylsalicylic acid can be increased when used in combination with 4-Hydroxytestosterone.
AldosteroneThe risk or severity of edema formation can be increased when 4-Hydroxytestosterone is combined with Aldosterone.
AlteplaseThe therapeutic efficacy of Alteplase can be increased when used in combination with 4-Hydroxytestosterone.
AmediplaseThe therapeutic efficacy of Amediplase can be increased when used in combination with 4-Hydroxytestosterone.
AnagrelideThe therapeutic efficacy of Anagrelide can be increased when used in combination with 4-Hydroxytestosterone.
Food Interactions
Not 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 References
  1. Kohler M, Parr MK, Opfermann G, Thevis M, Schlorer N, Marner FJ, Schanzer W: Metabolism of 4-hydroxyandrostenedione and 4-hydroxytestosterone: Mass spectrometric identification of urinary metabolites. Steroids. 2007 Mar;72(3):278-86. Epub 2007 Jan 17. [PubMed:17207827]
External Links
PubChem Compound
160615
PubChem Substance
46508337
ChemSpider
141138
ChEMBL
CHEMBL2431525
Wikipedia
4-Hydroxytestosterone

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
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.068 mg/mLALOGPS
logP2.48ALOGPS
logP2.85ChemAxon
logS-3.6ALOGPS
pKa (Strongest Acidic)9.28ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity86.4 m3·mol-1ChemAxon
Polarizability34.88 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Androstane steroids
Direct Parent
Androgens and derivatives
Alternative Parents
3-oxo delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Secondary alcohols / Cyclic alcohols and derivatives / Enols / Organic oxides / Hydrocarbon derivatives
Substituents
Androgen-skeleton / 3-oxo-delta-4-steroid / 3-oxosteroid / 4-hydroxysteroid / Hydroxysteroid / Oxosteroid / 17-hydroxysteroid / Delta-4-steroid / Cyclohexenone / Cyclic alcohol
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
C19 steroids (androgens) and derivatives (LMST02020102)

Drug created on July 31, 2007 07:09 / Updated on November 02, 2018 05:01