NAV

Nandrolone

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Summary

Nandrolone is an anabolic steroid indicated to increase bone density and muscle mass in patients with osteoporosis.

Generic Name
Nandrolone
DrugBank Accession Number
DB13169
Background

Nandrolone, also known as 19-nortestosterone or 19-norandrostenolone, is a synthetic anabolic-androgenic steroid (AAS) derived from testosterone.

Type
Small Molecule
Groups
Experimental, Investigational
Structure
3D
Similar Structures
Weight
Average: 274.3978
Monoisotopic: 274.193280076
Chemical Formula
C18H26O2
Synonyms
  • (17β)-17-hydroxyestr-4-en-3-one
  • 19-norandrostenolone
  • 19-nortestosterone
  • Nandrolona
  • Nandrolone
  • Nandrolonum
External IDs
  • NSC-3351
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Pharmacology

Indication

Not Available

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Management ofOsteoporosis (senile)•••••••••••••••••• ••••••••••••••••• ••••••••
Management ofOsteoporosis caused by glucocorticoid•••••••••••••••••• ••••••••••••••••• ••••••••
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.
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AcarboseNandrolone may increase the hypoglycemic activities of Acarbose.
AcenocoumarolNandrolone may increase the anticoagulant activities of Acenocoumarol.
AcetohexamideNandrolone may increase the hypoglycemic activities of Acetohexamide.
AlbiglutideNandrolone may increase the hypoglycemic activities of Albiglutide.
AllantoinThe therapeutic efficacy of Allantoin can be increased when used in combination with Nandrolone.
Food Interactions
Not Available

Products

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International/Other Brands
Menidrabol

Categories

ATC Codes
S01XA11 — NandroloneA14AB01 — Nandrolone
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as estrogens and derivatives. These are steroids with a structure containing a 3-hydroxylated estrane.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Estrane steroids
Direct Parent
Estrogens and derivatives
Alternative Parents
3-oxo delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Secondary alcohols / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
17-hydroxysteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Carbonyl group / Cyclic alcohol / Cyclic ketone / Cyclohexenone / Delta-4-steroid
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
3-oxo Delta(4)-steroid, 17beta-hydroxy steroid, anabolic androgenic steroid (CHEBI:7466) / Estrane and derivatives (C07254) / C18 steroids (estrogens) and derivatives (LMST02010044)
Affected organisms
Not Available

Chemical Identifiers

UNII
6PG9VR430D
CAS number
434-22-0
InChI Key
NPAGDVCDWIYMMC-IZPLOLCNSA-N
InChI
InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1
IUPAC Name
(1S,3aS,3bR,9aR,9bS,11aS)-1-hydroxy-11a-methyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-one
SMILES
[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]

References

General References
Not Available
Human Metabolome Database
HMDB0002725
KEGG Compound
C07254
PubChem Compound
9904
PubChem Substance
347829275
ChemSpider
9520
BindingDB
50080092
RxNav
7244
ChEBI
7466
ChEMBL
CHEMBL757
ZINC
ZINC000003814379
PharmGKB
PA164746281
PDBe Ligand
6VW
Wikipedia
Nandrolone
PDB Entries
5kp4

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAplastic Anemia / Blood Diseases / Hematologic Disease and Disorders / Pancytopenia1
2RecruitingTreatmentSarcopenia1
2TerminatedTreatmentCritically Ill Patients / Malnutrition1
2, 3CompletedTreatmentBurns1
2, 3TerminatedTreatmentBurns1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
Injection, solutionIntramuscular
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0561 mg/mLALOGPS
logP2.6ALOGPS
logP3.07Chemaxon
logS-3.7ALOGPS
pKa (Strongest Acidic)18.25Chemaxon
pKa (Strongest Basic)-0.88Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity79.95 m3·mol-1Chemaxon
Polarizability32.27 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-MSsplash10-0002-1390000000-ccec1d79f2682b0d6bcd
GC-MS Spectrum - EI-BGC-MSsplash10-05i3-8950000000-2aca1e24a2ef4acf545f
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-004i-0090000000-494e848349f5e9b86582
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0570-1980000000-e03a1bc79e9f4e2d8260
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a4i-2900000000-e8dd93d5cf0dff8b90e4
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0a5c-7900000000-71f3c599cf3161ab0eb7
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-057l-9500000000-ab3f2a34ef86ef591844
MS/MS Spectrum - , positiveLC-MS/MSsplash10-004i-0490000000-ef50b9f0fd0a9e2b7c03
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-056r-0090000000-dea300bdd769644d8c14
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-3229f56e1d20d17ec104
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0691-0920000000-bf64d53f324fa9c83357
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-00di-0090000000-05bbd78b08d3618f1f12
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ab9-0090000000-3de15442fc69f2e872ce
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0bta-0900000000-26031b9f3a6505e0de15
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]-174.796874
predicted
DarkChem Lite v0.1.0
[M-H]-175.246774
predicted
DarkChem Lite v0.1.0
[M-H]-171.0099
predicted
DeepCCS 1.0 (2019)
[M+H]+175.610474
predicted
DarkChem Lite v0.1.0
[M+H]+174.993774
predicted
DarkChem Lite v0.1.0
[M+H]+173.15211
predicted
DeepCCS 1.0 (2019)
[M+Na]+175.106674
predicted
DarkChem Lite v0.1.0
[M+Na]+179.45888
predicted
DeepCCS 1.0 (2019)

Drug created at February 15, 2017 19:13 / Updated at June 05, 2021 09:12