NAV

Metandienone

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 It was introduced to the market in the 1960s but later discontinued and withdrawn from the market.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Experimental, Withdrawn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
3D
Similar Structures
Weight
Average: 300.4351
Monoisotopic: 300.20893014
Chemical Formula
C20H28O2
Synonyms
  • Metandienone
  • Methandrostenolone
External IDs
  • NSC-42722
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Pharmacology

Indication

Not Available

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Associated Therapies
Contraindications & Blackbox Warnings
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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
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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

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Categories

ATC Codes
A14AA03 — MetandienoneD11AE01 — Metandienone
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
  1. 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]
  2. FDA Thailand Product Information: Anapromine (methanedione/cyproheptadine hydrochloride) oral capsules [Link]
  3. Code of Federal Regulations Title 21 Sec. 1300.01: Definitions relating to controlled substances. [Link]
Human Metabolome Database
HMDB0041925
ChemSpider
6061
RxNav
6818
ChEBI
6810
ChEMBL
CHEMBL1418176
ZINC
ZINC000003875469
Wikipedia
Metandienone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Syrup120 ml
Tablet10 mg
Tablet5 mg
Capsule20 mg
Capsule5 mg
Capsule10 mg
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0161 mg/mLALOGPS
logP3.55ALOGPS
logP3.64Chemaxon
logS-4.3ALOGPS
pKa (Strongest Acidic)18.39Chemaxon
pKa (Strongest Basic)-0.53Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity90.16 m3·mol-1Chemaxon
Polarizability35.09 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSsplash10-00dr-0390000000-1e414c4eabc29414d0e6
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-001i-0091000000-a2ad6855df6eeb3bf154
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0kgo-0972000000-87ffb565093bf744ddd8
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-d7d2587339b1f3b7ba58
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0090000000-b420edcca5b7b6910333
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4l-2910000000-17a2b7d722271df28e63
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-001j-0490000000-760f5bb0955e887b1a4e
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-180.2587981
predicted
DarkChem Lite v0.1.0
[M-H]-180.9882981
predicted
DarkChem Lite v0.1.0
[M-H]-170.19914
predicted
DeepCCS 1.0 (2019)
[M+H]+181.3932981
predicted
DarkChem Lite v0.1.0
[M+H]+181.5996981
predicted
DarkChem Lite v0.1.0
[M+H]+172.30583
predicted
DeepCCS 1.0 (2019)
[M+Na]+180.8119981
predicted
DarkChem Lite v0.1.0
[M+Na]+181.3693981
predicted
DarkChem Lite v0.1.0
[M+Na]+178.22548
predicted
DeepCCS 1.0 (2019)

Drug created at June 23, 2017 20:44 / Updated at December 01, 2022 11:28