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. 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.
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Structure
Structure for 4-Hydroxytestosterone (DB01485)
- 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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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
- Adverse Effects
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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/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" 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 Integrate drug-drug
interactions in your softwareAbciximab 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. - Food Interactions
- Not Available
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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
- 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=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,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
- 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]
- External Links
- PubChem Compound
- 160615
- PubChem Substance
- 46508337
- ChemSpider
- 141138
- ChEMBL
- CHEMBL2431525
- ZINC
- ZINC000031460450
- Wikipedia
- 4-Hydroxytestosterone
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" 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 splash10-0a4r-0079000000-639e6ddf0d7172f0c493 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0009000000-b323f7c2062bb948d94a Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-052r-1792000000-c97684b01178bd7f98a3 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0079000000-68395f09218e06781293 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0zia-1910000000-3d1d0818a66418d70c10 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0frl-0092000000-97cbb997a196647c9f9a Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 179.43053 predictedDeepCCS 1.0 (2019) [M+H]+ 181.78853 predictedDeepCCS 1.0 (2019) [M+Na]+ 188.92555 predictedDeepCCS 1.0 (2019)
Drug created at July 31, 2007 13:09 / Updated at June 12, 2020 16:51