Metandienone
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This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Summary
Metandienone is an anabolic steroid indicated for appetite stimulation in patients with anorexia.
- Generic Name
- Metandienone
- DrugBank Accession Number
- DB13586
- Background
Metandienone is an orally active anabolic androgenic steroid. It was introduced to the market in the 1960s but later discontinued and withdrawn from the market. Although it is prohibited in and outside competition by the World Anti-Doping Agency, metandienone continues to be marketed and misused as a performance-enhancing drug in sports.1 In the US, metandienone is a controlled substance under the Controlled Substances Act.3
- Type
- Small Molecule
- Groups
- Experimental, Withdrawn
- Structure
- Weight
- Average: 300.4351
Monoisotopic: 300.20893014 - Chemical Formula
- C20H28O2
- Synonyms
- Metandienone
- Methandrostenolone
- External IDs
- NSC-42722
Pharmacology
- Indication
Not Available
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 Therapies
- Contraindications & Blackbox Warnings
- Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.
- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- 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.Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Not Available
- 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.Not Available
- Food Interactions
- Not Available
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.
Categories
- ATC Codes
- A14AA03 — Metandienone
- A14AA — Androstan derivatives
- A14A — ANABOLIC STEROIDS
- A14 — ANABOLIC AGENTS FOR SYSTEMIC USE
- A — ALIMENTARY TRACT AND METABOLISM
- 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-1,4-steroids / 17-hydroxysteroids / Delta-1,4-steroids / Tertiary alcohols / Cyclic ketones / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
- Substituents
- 17-hydroxysteroid / 3-oxo-delta-1,4-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Androgen-skeleton / Carbonyl group / Cyclic alcohol / Cyclic ketone / Delta-1,4-steroid
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- C19 steroids (androgens) and derivatives (LMST02020013)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- COZ1R7EOCC
- CAS number
- 72-63-9
- InChI Key
- XWALNWXLMVGSFR-HLXURNFRSA-N
- InChI
- InChI=1S/C20H28O2/c1-18-9-6-14(21)12-13(18)4-5-15-16(18)7-10-19(2)17(15)8-11-20(19,3)22/h6,9,12,15-17,22H,4-5,7-8,10-11H2,1-3H3/t15-,16+,17+,18+,19+,20+/m1/s1
- IUPAC Name
- (1S,3aS,3bR,9aR,9bS,11aS)-1-hydroxy-1,9a,11a-trimethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
- SMILES
- [H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)C=C[C@]12C
References
- General References
- Loke S, Liu L, Wenzel M, Scheffler H, Iannone M, de la Torre X, Schlorer N, Botre F, Keiler AM, Bureik M, Parr MK: New Insights into the Metabolism of Methyltestosterone and Metandienone: Detection of Novel A-Ring Reduced Metabolites. Molecules. 2021 Mar 3;26(5). pii: molecules26051354. doi: 10.3390/molecules26051354. [Article]
- FDA Thailand Product Information: Anapromine (methanedione/cyproheptadine hydrochloride) oral capsules [Link]
- Code of Federal Regulations Title 21 Sec. 1300.01: Definitions relating to controlled substances. [Link]
- External Links
- Human Metabolome Database
- HMDB0041925
- ChemSpider
- 6061
- 6818
- ChEBI
- 6810
- ChEMBL
- CHEMBL1418176
- ZINC
- ZINC000003875469
- Wikipedia
- Metandienone
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Syrup 120 ml Tablet 10 mg Tablet 5 mg Capsule 20 mg Capsule 5 mg Capsule 10 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Not Available
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0161 mg/mL ALOGPS logP 3.55 ALOGPS logP 3.64 Chemaxon logS -4.3 ALOGPS pKa (Strongest Acidic) 18.39 Chemaxon pKa (Strongest Basic) -0.53 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 37.3 Å2 Chemaxon Rotatable Bond Count 0 Chemaxon Refractivity 90.16 m3·mol-1 Chemaxon Polarizability 35.09 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available 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 June 23, 2017 20:44 / Updated at December 01, 2022 11:28