NAV

4-Hydroxytestosterone

Identification

Generic Name
4-Hydroxytestosterone
DrugBank Accession Number
DB01485
Background

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.1Like 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.

Type
Small Molecule
Groups
Experimental, Illicit
Structure
 3D
Similar Structures
Weight
Average: 304.43
Monoisotopic: 304.203844762
Chemical Formula
C19H28O3
Synonyms
  • 4-Androstene-7alpha-17beta-diol-3-one
  • 4,17beta-Dihydroxy-4-androstene-3-one
  • 7alpha-Hydroxytestosterone

Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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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.

的作用机制

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

蛋白质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.

Adverse Effects
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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.

Pathways
Not Available
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction
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Abciximab 4-Hydroxytestosterone may increase the anticoagulant activities of Abciximab.
Acenocoumarol 4-Hydroxytestosterone may increase the anticoagulant activities of Acenocoumarol.
Alteplase 4-Hydroxytestosterone may increase the anticoagulant activities of Alteplase.
Ancrod 4-Hydroxytestosterone may increase the anticoagulant activities of Ancrod.
Anistreplase 4-Hydroxytestosterone may increase the anticoagulant activities of Anistreplase.
Antithrombin Alfa 4-Hydroxytestosterone may increase the anticoagulant activities of Antithrombin Alfa.
Antithrombin III human 4-Hydroxytestosterone may increase the anticoagulant activities of Antithrombin III human.
Apixaban 4-Hydroxytestosterone may increase the anticoagulant activities of Apixaban.
Ardeparin 4-Hydroxytestosterone may increase the anticoagulant activities of Ardeparin.
Argatroban 4-Hydroxytestosterone may increase the anticoagulant activities of Argatroban.
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Food Interactions
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided byClassyfire
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
雄烷类固醇
Direct Parent
Androgens and derivatives
Alternative Parents
3-oxo delta-4-steroids/17-hydroxysteroids/Delta-4-steroids/Cyclohexenones/二级醇/Cyclic alcohols and derivatives/Enols/Organic oxides/Hydrocarbon derivatives
Substituents
17-hydroxysteroid/3-oxo-delta-4-steroid/3-oxosteroid/4-hydroxysteroid/Alcohol/Aliphatic homopolycyclic compound/Androgen-skeleton/Carbonyl group/Cyclic alcohol/Cyclic ketone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
C19 steroids (androgens) and derivatives (LMST02020102)
Affected organisms
Not Available

Chemical Identifiers

UNII
912GOZ167T
CAS number
2141-17-5
InChI Key
BQOIJSIMMIDHMO-FBPKJDBXSA-N
InChI
InChI = 1 s / 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,3aS,3bR,9aR,9bS,11aS)-1,6-dihydroxy-9a,11a-dimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=C(O)C(=O)CC[C@]12C

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. [Article]
PubChem Compound
160615
PubChem Substance
46508337
ChemSpider
141138
ChEMBL
CHEMBL2431525
ZINC
ZINC000031460450
Wikipedia
4-Hydroxytestosterone

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count

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
Property Value Source
Water Solubility 0.068 mg/mL ALOGPS
logP 2.48 ALOGPS
logP 2.85 Chemaxon
logS -3.6 ALOGPS
pKa (Strongest Acidic) 9.28 Chemaxon
pKa (Strongest Basic) -0.88 Chemaxon
Physiological Charge 0 Chemaxon
Hydrogen Acceptor Count 3 Chemaxon
Hydrogen Donor Count 2 Chemaxon
Polar Surface Area 57.53 Å2 Chemaxon
Rotatable Bond Count 0 Chemaxon
Refractivity 86.4 m3·mol-1 Chemaxon
Polarizability 34.73 Å3 Chemaxon
Number of Rings 4 Chemaxon
Bioavailability 1 Chemaxon
Rule of Five Yes Chemaxon
Ghose Filter Yes Chemaxon
Veber's Rule No Chemaxon
MDDR-like Rule No Chemaxon
Predicted ADMET Features
Not Available

Spectra

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

Drug created at July 31, 2007 13:09 / Updated at June 12, 2020 16:51