Identification

Name
Oxymetholone
Accession Number
DB06412
Type
Small Molecule
Groups
Approved, Illicit
Description

Oxymetholone is a synthetic anabolic steroid marketed under the brand name Anapolon by Hoffmann La Roche Limited. Its primary clinical applications include treatment of osteoporosis and anaemia, as well as stimulating 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).

Structure
Thumb
Synonyms
  • 17β-Hydroxy-2-hydroxymethylidene-17α-methyl-3-androstanone
  • Oximetolona
  • Oxymetholon
  • Oxymétholone
  • Oxymetholonum
External IDs
CI 406 / CI-406
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
AnadrolTablet50 mg/1OralUnimed Pharmaceuticals, Inc.2006-06-122006-06-12Us
Anadrol-50Tablet50 mg/1OralAlaven Pharmaceutical1972-06-01Not applicableUs
Anapolon 50Tablet50 mgOralSyntex Inc.1970-12-311997-08-26Canada
Anapolon 50 Tablets 50mgTablet50 mgOralHoffmann La Roche1997-07-291999-03-17Canada
International/Other Brands
Anapolon (Abdi Ibrahim) / Androlic (British Dispensary) / Hemogenin (Sanofi Aventis)
Categories
UNII
L76T0ZCA8K
CAS number
434-07-1
Weight
Average: 332.484
Monoisotopic: 332.23514489
Chemical Formula
C21H32O3
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

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.

Associated Conditions
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.

TargetActionsOrganism
AAndrogen receptor
agonist
activator
Human
UNatriuretic peptides BNot AvailableHuman
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
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.

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinOxymetholone may increase the anticoagulant activities of (R)-warfarin.
(S)-WarfarinOxymetholone may increase the anticoagulant activities of (S)-Warfarin.
2,4-thiazolidinedioneOxymetholone may increase the hypoglycemic activities of 2,4-thiazolidinedione.
3,5-diiodothyropropionic acidThe metabolism of 3,5-diiodothyropropionic acid can be decreased when combined with Oxymetholone.
4-hydroxycoumarinThe metabolism of 4-hydroxycoumarin can be decreased when combined with Oxymetholone.
4-MethoxyamphetamineThe metabolism of 4-Methoxyamphetamine can be decreased when combined with Oxymetholone.
5-androstenedioneThe metabolism of 5-androstenedione can be decreased when combined with Oxymetholone.
6-O-benzylguanineThe metabolism of 6-O-benzylguanine can be decreased when combined with Oxymetholone.
9-aminocamptothecinThe metabolism of 9-aminocamptothecin can be decreased when combined with Oxymetholone.
AbemaciclibThe metabolism of Abemaciclib can be decreased when combined with Oxymetholone.
Food Interactions
Not Available

References

General References
  1. 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. [PubMed:11440282]
  2. Authors unspecified: Oxymetholone. Rep Carcinog. 2011;12:338-40. [PubMed:21860526]
  3. Vergel N: Building your body to survive: the use of anabolic steroids for HIV therapy. Posit Aware. 1998 Mar-Apr;9(2):37-41. [PubMed:11365225]
  4. Davison SL, Bell R: Androgen physiology. Semin Reprod Med. 2006 Apr;24(2):71-7. [PubMed:16633980]
  5. Report on Carcinogens, Thirteenth Edition [Link]
External Links
KEGG Drug
D00490
KEGG Compound
C07393
PubChem Compound
5281034
PubChem Substance
310264869
ChemSpider
4444502
ChEBI
7864
ChEMBL
CHEMBL1200585
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Oxymetholone
ATC Codes
A14AA05 — Oxymetholone
FDA label
Download (172 KB)
MSDS
Download (490 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
TabletOral50 mg/1
TabletOral50 mg
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)178°C to 180°CReport on Carcinogens, Thirteenth Edition
water solubility5.21 mg/LReport on Carcinogens, Thirteenth Edition
Predicted Properties
PropertyValueSource
Water Solubility0.0349 mg/mLALOGPS
logP3.17ALOGPS
logP3.55ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)8.87ChemAxon
pKa (Strongest Basic)-0.53ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area57.53 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity94.6 m3·mol-1ChemAxon
Polarizability38.84 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-5-alpha-steroids / 17-hydroxysteroids / Vinylogous acids / Tertiary alcohols / Cyclic ketones / Cyclic alcohols and derivatives / Enols / Organic oxides / Hydrocarbon derivatives
Substituents
Androgen-skeleton / 3-oxosteroid / 3-oxo-5-alpha-steroid / 17-hydroxysteroid / Oxosteroid / Hydroxysteroid / Cyclic alcohol / Vinylogous acid / Tertiary alcohol / Cyclic ketone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Androstane and derivatives (C07393)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
Activator
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
  1. Davison SL, Bell R: Androgen physiology. Semin Reprod Med. 2006 Apr;24(2):71-7. [PubMed:16633980]
Kind
Protein
Organism
Human
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
Human
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
  1. 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. [PubMed:10217522]
Kind
Protein
Organism
Human
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
  1. 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. [PubMed:11440282]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Substrate
Activator
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
  1. 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. [PubMed:11440282]
  2. Davison SL, Bell R: Androgen physiology. Semin Reprod Med. 2006 Apr;24(2):71-7. [PubMed:16633980]
Kind
Protein
Organism
Human
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
  1. 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.
Kind
Protein
Organism
Human
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
  1. 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.
Kind
Protein
Organism
Human
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
  1. 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.
Kind
Protein
Organism
Human
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
  1. 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.

Carriers

Kind
Protein
Organism
Human
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
Human
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 on March 19, 2008 10:31 / Updated on November 02, 2018 06:16