Identification
- Summary
Oxymetholone is an anabolic steroid used for the treatment of types of anemia, such as acquired aplastic anemia, congenital aplastic anemia, myelofibrosis, and the hypoplastic anemias.
- Brand Names
- Anadrol-50
- Generic Name
- Oxymetholone
- DrugBank Accession Number
- DB06412
- Background
Oxymetholone is a synthetic anabolic steroid marketed under the brand name Anapolon by Hoffmann La Roche Limitedand used in the treatment of osteoporosis, anaemia, and as an agent to stimulate muscle growth in malnourished or underdeveloped patients. Anabolic-androgenic steroids (AAS), such as oxymetholone, have been abused by bodybuilders and athletes. The uncontrolled misuse of oxymetholone can lead to a large variety of detrimental effects, the most often reported of which are cardiovascular events. In 2009, no producers of oxymetholone were identified worldwide (SRI 2009), but it was available from 14 suppliers, including 8 U.S. suppliers (ChemSources 2009).
- Type
- Small Molecule
- Groups
- Approved, Illicit
- Structure
Structure for Oxymetholone (DB06412)
- Weight
- Average: 332.484
Monoisotopic: 332.23514489 - Chemical Formula
- C21H32O3
- Synonyms
- 17β-Hydroxy-2-hydroxymethylidene-17α-methyl-3-androstanone
- Oximetolona
- Oxymetholon
- Oxymétholone
- Oxymetholone
- Oxymetholonum
- External IDs
- CI 406
- CI-406
Pharmacology
- Indication
Indicated in the treatment of anemias caused by deficient red cell production. Acquired aplastic anemia, congenital aplastic anemia, myelofibrosis and the hypoplastic anemias due to the administration of myelotoxic drugs often respond. Oxymetholone should not replace other supportive measures such as transfusion, correction of iron, folic acid, vitamin B12 or pyridoxine deficiency, antibacterial therapy and the appropriate use of corticosteroids.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Acquired aplastic anemia •••••••••••• Management of Congenital aplastic anemia •••••••••••• Management of Hypoplastic anemia •••••••••••• Management of Myelofibrosis •••••••••••• - Contraindications & Blackbox Warnings
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
Not Available
- Mechanism of action
Oxymethalone is a 17 alpha-alkylated anabolic-androgenic steroid and a synthetic derivative of testosterone, whose anabolic effects are used to treat muscle wasting in HIV patients. The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.
Target Actions Organism AAndrogen receptor agonistactivatorHumans UNatriuretic peptides B Not Available Humans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
May cause cancer. The uncontrolled misuse of oxymetholone can lead to a large variety of detrimental effects, the most often reported of which are cardiovascular events.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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 softwareAcarbose Oxymetholone may increase the hypoglycemic activities of Acarbose. Acenocoumarol The serum concentration of Acenocoumarol can be increased when it is combined with Oxymetholone. Acetohexamide Oxymetholone may increase the hypoglycemic activities of Acetohexamide. Albiglutide Oxymetholone may increase the hypoglycemic activities of Albiglutide. Alfuzosin The metabolism of Alfuzosin can be decreased when combined with Oxymetholone. - Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Anapolon (Abdi Ibrahim) / Androlic (British Dispensary) / Hemogenin (Sanofi Aventis)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Anadrol Tablet 50 mg/1 Oral Unimed Pharmaceuticals, Inc. 2006-06-12 2006-06-12 US 
Anadrol-50 Tablet 50 mg/1 Oral Alaven Pharmaceutical LLC 1972-06-01 Not applicable US
Categories
- ATC Codes
- A14AA05 — Oxymetholone
- Drug Categories
- Alimentary Tract and Metabolism
- Anabolic Agents
- Anabolic Agents for Systemic Use
- Anabolic Steroids
- Androgens
- Androstan Derivatives
- Androstanes
- Androstanols
- Cytochrome P-450 CYP2D6 Inhibitors
- Cytochrome P-450 CYP2D6 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors
- Cytochrome P-450 CYP3A4 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A5 Inhibitors
- Cytochrome P-450 CYP3A5 Inhibitors (strength unknown)
- Cytochrome P-450 CYP3A7 Inhibitors
- Cytochrome P-450 CYP3A7 Inhibitors (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Fused-Ring Compounds
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Steroids
- Thyroxine-binding globulin inhibitors
- 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-5-alpha-steroids / 17-hydroxysteroids / Vinylogous acids / Tertiary alcohols / Cyclic ketones / Cyclic alcohols and derivatives / Enols / Organic oxides / Hydrocarbon derivatives
- Substituents
- 17-hydroxysteroid / 3-oxo-5-alpha-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Androgen-skeleton / Carbonyl group / Cyclic alcohol / Cyclic ketone / Enol
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- Androstane and derivatives (C07393)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- L76T0ZCA8K
- CAS number
- 434-07-1
- InChI Key
- ICMWWNHDUZJFDW-DHODBPELSA-N
- InChI
- InChI=1S/C21H32O3/c1-19-11-13(12-22)18(23)10-14(19)4-5-15-16(19)6-8-20(2)17(15)7-9-21(20,3)24/h12,14-17,22,24H,4-11H2,1-3H3/b13-12-/t14-,15+,16-,17-,19-,20-,21-/m0/s1
- IUPAC Name
- (1S,2S,4Z,7S,10R,11S,14S,15S)-14-hydroxy-4-(hydroxymethylidene)-2,14,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one
- SMILES
- [H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CC[C@@]2([H])CC(=O)\C(C[C@]12C)=C/O
References
- General References
- Pavlatos AM, Fultz O, Monberg MJ, Vootkur A, Pharmd: Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid. Clin Ther. 2001 Jun;23(6):789-801; discussion 771. [Article]
- Authors unspecified: Oxymetholone. Rep Carcinog. 2011;12:338-40. [Article]
- Vergel N: Building your body to survive: the use of anabolic steroids for HIV therapy. Posit Aware. 1998 Mar-Apr;9(2):37-41. [Article]
- Davison SL, Bell R: Androgen physiology. Semin Reprod Med. 2006 Apr;24(2):71-7. [Article]
- Report on Carcinogens, Thirteenth Edition [Link]
- External Links
- KEGG Drug
- D00490
- KEGG Compound
- C07393
- PubChem Compound
- 5281034
- PubChem Substance
- 310264869
- ChemSpider
- 4444502
- 7813
- ChEBI
- 7864
- ChEMBL
- CHEMBL1200585
- ZINC
- ZINC000118912450
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Oxymetholone
- FDA label
- Download (172 KB)
- MSDS
- Download (490 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet Oral 50 mg/1 Tablet Oral 50 mg / tab Tablet Oral Tablet Oral 50 mg Tablet Oral 100 mg Capsule 50 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 178°C to 180°C Report on Carcinogens, Thirteenth Edition water solubility 5.21 mg/L Report on Carcinogens, Thirteenth Edition - Predicted Properties
Property Value Source Water Solubility 0.0349 mg/mL ALOGPS logP 3.17 ALOGPS logP 3.55 Chemaxon logS -4 ALOGPS pKa (Strongest Acidic) 8.87 Chemaxon pKa (Strongest Basic) -0.53 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 94.6 m3·mol-1 Chemaxon Polarizability 38.84 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 splash10-014i-0019000000-5eaab0deb82bc37a3096 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0009000000-83ce5838c158d692020e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-001i-0009000000-26266fbd258b45de1209 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-05o0-3597000000-5adb0aafa2f271e2f880 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0039000000-7c99d1293e888262e220 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0006-4920000000-2e629847380605a08d20 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]- 192.5666187 predictedDarkChem Lite v0.1.0 [M-H]- 190.9198187 predictedDarkChem Lite v0.1.0 [M-H]- 174.95236 predictedDeepCCS 1.0 (2019) [M+H]+ 191.5286187 predictedDarkChem Lite v0.1.0 [M+H]+ 189.3220187 predictedDarkChem Lite v0.1.0 [M+H]+ 176.77725 predictedDeepCCS 1.0 (2019) [M+Na]+ 191.2136187 predictedDarkChem Lite v0.1.0 [M+Na]+ 188.9688187 predictedDarkChem Lite v0.1.0 [M+Na]+ 182.48917 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AgonistActivator
- 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
- Davison SL, Bell R: Androgen physiology. Semin Reprod Med. 2006 Apr;24(2):71-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Receptor binding
- Specific Function
- Cardiac hormone which may function as a paracrine antifibrotic factor in the heart. Also plays a key role in cardiovascular homeostasis through natriuresis, diuresis, vasorelaxation, and inhibition...
- Gene Name
- NPPB
- Uniprot ID
- P16860
- Uniprot Name
- Natriuretic peptides B
- Molecular Weight
- 14725.825 Da
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inducer
- General Function
- Serotonin binding
- Specific Function
- Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral...
- Gene Name
- MAOA
- Uniprot ID
- P21397
- Uniprot Name
- Amine oxidase [flavin-containing] A
- Molecular Weight
- 59681.27 Da
References
- Thiblin I, Finn A, Ross SB, Stenfors C: Increased dopaminergic and 5-hydroxytryptaminergic activities in male rat brain following long-term treatment with anabolic androgenic steroids. Br J Pharmacol. 1999 Mar;126(6):1301-6. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Steroid hydroxylase activity
- Specific Function
- Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
- Gene Name
- CYP2D6
- Uniprot ID
- P10635
- Uniprot Name
- Cytochrome P450 2D6
- Molecular Weight
- 55768.94 Da
References
- Pavlatos AM, Fultz O, Monberg MJ, Vootkur A, Pharmd: Review of oxymetholone: a 17alpha-alkylated anabolic-androgenic steroid. Clin Ther. 2001 Jun;23(6):789-801; discussion 771. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateActivator
- General Function
- Electron carrier activity
- Specific Function
- Converts testosterone into 5-alpha-dihydrotestosterone and progesterone or corticosterone into their corresponding 5-alpha-3-oxosteroids. It plays a central role in sexual differentiation and andro...
- Gene Name
- SRD5A1
- Uniprot ID
- P18405
- Uniprot Name
- 3-oxo-5-alpha-steroid 4-dehydrogenase 1
- Molecular Weight
- 29458.18 Da
References
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Vitamin d3 25-hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- Thacker DL, Wainer IW, Lerch C, Fried K, Flockhart DA: Metabolism of An Anabolic Androgenic Steroid Oxymetholone by Human Cytochrome P450s Clinical Pharmacology&Therapeutics. 1999 Feb 1;65(2):136-137. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A5
- Uniprot ID
- P20815
- Uniprot Name
- Cytochrome P450 3A5
- Molecular Weight
- 57108.065 Da
References
- Thacker DL, Wainer IW, Lerch C, Fried K, Flockhart DA: Metabolism of An Anabolic Androgenic Steroid Oxymetholone by Human Cytochrome P450s Clinical Pharmacology&Therapeutics. 1999 Feb 1;65(2):136-137. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Oxygen binding
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP3A7
- Uniprot ID
- P24462
- Uniprot Name
- Cytochrome P450 3A7
- Molecular Weight
- 57525.03 Da
References
- Thacker DL, Wainer IW, Lerch C, Fried K, Flockhart DA: Metabolism of An Anabolic Androgenic Steroid Oxymetholone by Human Cytochrome P450s Clinical Pharmacology&Therapeutics. 1999 Feb 1;65(2):136-137. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Monooxygenase activity
- Specific Function
- Exhibits low testosterone 6-beta-hydroxylase activity.
- Gene Name
- CYP3A43
- Uniprot ID
- Q9HB55
- Uniprot Name
- Cytochrome P450 3A43
- Molecular Weight
- 57669.21 Da
References
- Thacker DL, Wainer IW, Lerch C, Fried K, Flockhart DA: Metabolism of An Anabolic Androgenic Steroid Oxymetholone by Human Cytochrome P450s Clinical Pharmacology&Therapeutics. 1999 Feb 1;65(2):136-137. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
- Kind
- Protein
- Organism
- Humans
- 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
Drug created at March 19, 2008 16:31 / Updated at October 09, 2021 02:48