Helen Frankenthaler Foundation

Pasireotide

Metandienone

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 It was introduced to the market in the 1960s but later discontinued and withdrawn from the market.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. In the US, metandienone is a controlled substance under the Controlled Substances Act.

Modality

Small Molecule

Groups

Approved, Withdrawn

Structure

Weight

Average: 300.4351

Monoisotopic: 300.20893014

Chemical Formula

C 20 H 28 O 2

Synonyms

  • Metandienone
  • Methandrostenolone

External IDs

  • NSC-42722

Associated Conditions

Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form

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

Toxicity

Not Available

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

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

Drug Categories

  • Alimentary Tract and Metabolism
  • Anabolic Agents
  • Anabolic Agents for Systemic Use
  • Anabolic Steroids
  • Androgens for Topical Use
  • Androstadienes
  • Androstan Derivatives
  • Androstanes
  • Androstenes
  • Dermatologicals
  • Fused-Ring Compounds
  • Hormones
  • Hormones, Hormone Substitutes, and Hormone Antagonists
  • Steroids

Affected organisms

Not Available

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

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.

2. FDA Thailand Product Information: Anapromine (methanedione/cyproheptadine hydrochloride) oral capsules

3. Code of Federal Regulations Title 21 Sec. 1300.01: Definitions relating to controlled substances.

Clinical Trials

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PhaseStatusPurposeConditionsCountStart DateWhy Stopped100+ additional columns

Manufacturers

Not Available

Packagers

Not Available

Dosage Forms

FormRouteStrength
CapsuleOral10 mg
CapsuleOral20 mg
CapsuleOral5 mg
Syrup120 ml
TabletOral10 mg
TabletOral5 mg

Prices

Not Available

Patents

Not Available

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 Å 2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity90.16 m 3·mol-1Chemaxon
Polarizability35.09 Å 3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon

Predicted ADMET Features

Not Available

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 (Å 2)Source typeSource
[M-H]-180.2587981predictedDarkChem Lite v0.1.0
[M-H]-180.9882981predictedDarkChem Lite v0.1.0
[M-H]-170.19914predictedDeepCCS 1.0 (2019)
[M+H]+181.3932981predictedDarkChem Lite v0.1.0
[M+H]+181.5996981predictedDarkChem Lite v0.1.0
[M+H]+172.30583predictedDeepCCS 1.0 (2019)
[M+Na]+180.8119981predictedDarkChem Lite v0.1.0
[M+Na]+181.3693981predictedDarkChem Lite v0.1.0
[M+Na]+178.22548predictedDeepCCS 1.0 (2019)