Nandrolone decanoate

Identification

Name
Nandrolone decanoate
Accession Number
DB08804
Description

C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of estradiol to resemble testosterone but less one carbon at the 19 position. It is a schedule III drug in the U.S.

Type
Small Molecule
Groups
Approved, Illicit
Structure
Thumb
Weight
Average: 428.6472
Monoisotopic: 428.329045274
Chemical Formula
C28H44O3
Synonyms
  • 19-nortestosterone decanoate
  • Nandrolone 17β-decanoate
  • Nandrolone decanoate

Pharmacology

Indication

For the treatment of refractory deficient red cell production anemias, breast carcinoma, hereditary angioedema, antithrombin III deficiency, fibrinogen excess, growth failure and Turner's syndrome. It is also indicated in the prophylaxis of hereditary angioedema.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

Nandrolone is an anabolic steroid occurring naturally in the human body, albeit in small quantities. Nandrolone increases production and urinary excretion of erythropoietin. It may also have a direct action on bone marrow. Nandrolone binds to the androgen receptor to a greater degree than testosterone, but due to its inability to act on the muscle in ways unmediated by the receptor, has less overall effect on muscle growth.

Mechanism of action

Nandrolone is an androgen receptor agonist. The drug bound to the receptor complexes which allows it to enter the 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
Humans
Absorption
Not Available
Volume of distribution
Not Available
Protein binding

58%

Metabolism

Nandrolone is unusual in that unlike most anabolic steroids, it is not broken down into the more reactive DHT by the enzyme 5α-reductase, but rather into a less effective product known as Dihydronandrolone.

Route of elimination
Not Available
Half-life
Not Available
Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
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Toxicity
Not Available
Affected organisms
  • Humans and other mammals
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.
DrugInteraction
AcarboseNandrolone decanoate may increase the hypoglycemic activities of Acarbose.
AcenocoumarolNandrolone decanoate may increase the anticoagulant activities of Acenocoumarol.
AcetohexamideNandrolone decanoate may increase the hypoglycemic activities of Acetohexamide.
AlbiglutideNandrolone decanoate may increase the hypoglycemic activities of Albiglutide.
AllantoinThe therapeutic efficacy of Allantoin can be increased when used in combination with Nandrolone decanoate.
AlmotriptanThe metabolism of Almotriptan can be decreased when combined with Nandrolone decanoate.
AlogliptinNandrolone decanoate may increase the hypoglycemic activities of Alogliptin.
Beclomethasone dipropionateThe risk or severity of edema formation can be increased when Nandrolone decanoate is combined with Beclomethasone dipropionate.
BetamethasoneThe risk or severity of edema formation can be increased when Nandrolone decanoate is combined with Betamethasone.
Betamethasone phosphateThe risk or severity of edema formation can be increased when Nandrolone decanoate is combined with Betamethasone phosphate.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
No interactions found.

Products

Active Moieties
NameKindUNIICASInChI Key
Nandroloneprodrug6PG9VR430D434-22-0NPAGDVCDWIYMMC-IZPLOLCNSA-N
International/Other Brands
Deca-Durabol / Deca-Durabolin / Retabolil
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Nandrolone DecanoateInjection200 mg/1mLIntramuscularWatson Pharmaceuticals2007-02-08Not applicableUS flag
Nandrolone DecanoateInjection100 mg/1mLIntramuscularWatson Pharmaceuticals2007-02-08Not applicableUS flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Nandrolone DecanoateInjection, solution200 mg/1mLIntramuscularAMERICAN REGENT, INC.2010-09-012010-10-01US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as steroid esters. These are compounds containing a steroid moiety which bears a carboxylic acid ester group.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Steroid esters
Direct Parent
Steroid esters
Alternative Parents
Estrogens and derivatives / 3-oxo delta-4-steroids / Delta-4-steroids / Cyclohexenones / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
3-oxo-delta-4-steroid / 3-oxosteroid / Aliphatic homopolycyclic compound / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone / Cyclohexenone / Delta-4-steroid / Estrane-skeleton
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
steroid ester (CHEBI:7467)

Chemical Identifiers

UNII
H45187T098
CAS number
360-70-3
InChI Key
JKWKMORAXJQQSR-MOPIKTETSA-N
InChI
InChI=1S/C28H44O3/c1-3-4-5-6-7-8-9-10-27(30)31-26-16-15-25-24-13-11-20-19-21(29)12-14-22(20)23(24)17-18-28(25,26)2/h19,22-26H,3-18H2,1-2H3/t22-,23+,24+,25-,26-,28-/m0/s1
IUPAC Name
(1S,3aS,3bR,9aR,9bS,11aS)-11a-methyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl decanoate
SMILES
[H][[email protected]@]12CC[[email protected]](OC(=O)CCCCCCCCC)[[email protected]@]1(C)CC[[email protected]]1([H])[[email protected]@]3([H])CCC(=O)C=C3CC[[email protected]@]21[H]

References

General References
Not Available
Human Metabolome Database
HMDB0015694
KEGG Drug
D00955
KEGG Compound
C08154
PubChem Compound
9677
PubChem Substance
99445274
ChemSpider
9296
RxNav
31494
ChEBI
7467
ChEMBL
CHEMBL1200946
ZINC
ZINC000008214619
Therapeutic Targets Database
DAP000903
PharmGKB
PA165958423
Drugs.com
Drugs.com Drug Page
Wikipedia
Nandrolone_decanoate
MSDS
Download (49.5 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Active Not RecruitingSupportive CareHip Fracture1
1CompletedTreatmentHIV Wasting Syndrome / Human Immunodeficiency Virus (HIV) Infections1
1, 2Unknown StatusTreatmentAplastic Anemia / Bone Marrow Failure Syndromes / Idiopathic Pulmonary Fibrosis (IPF) / Telomere Shortening1
Not AvailableCompletedSupportive CareCachexia; Cancer1
Not AvailableCompletedTreatmentEnd Stage Renal Disease (ESRD) / Muscle Weakness1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
SolutionIntramuscular50 mg
SolutionIntramuscular
LiquidIntramuscular
Injection, solutionParenteral25 mg/ml
Injection, solutionParenteral50 mg/ml
InjectionIntramuscular100 mg/1mL
InjectionIntramuscular200 mg/1mL
Injection, solutionIntramuscular200 mg/1mL
InjectionIntramuscular; Subcutaneous25 mg
InjectionIntramuscular; Subcutaneous5 mg
Prices
Unit descriptionCostUnit
Deca-Durabolin 100 mg/ml97.16USD ml
Nandrolone decanoate powder79.88USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)118 °CNot Available
water solubility3.09 mg/mL at 25 °CYALKOWSKY,SH & HE,Y (2003)
logP2.62HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.000157 mg/mLALOGPS
logP5.96ALOGPS
logP7.32ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)18.25ChemAxon
pKa (Strongest Basic)-4.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 Å2ChemAxon
Rotatable Bond Count10ChemAxon
Refractivity125.94 m3·mol-1ChemAxon
Polarizability53.64 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.97
Caco-2 permeable+0.6718
P-glycoprotein substrateSubstrate0.6327
P-glycoprotein inhibitor IInhibitor0.8364
P-glycoprotein inhibitor IIInhibitor0.5069
Renal organic cation transporterNon-inhibitor0.7532
CYP450 2C9 substrateNon-substrate0.8741
CYP450 2D6 substrateNon-substrate0.9285
CYP450 3A4 substrateSubstrate0.72
CYP450 1A2 substrateNon-inhibitor0.94
CYP450 2C9 inhibitorNon-inhibitor0.8841
CYP450 2D6 inhibitorNon-inhibitor0.9111
CYP450 2C19 inhibitorNon-inhibitor0.5353
CYP450 3A4 inhibitorNon-inhibitor0.7896
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5493
Ames testNon AMES toxic0.9431
CarcinogenicityNon-carcinogens0.9215
BiodegradationNot ready biodegradable0.9625
Rat acute toxicity1.8804 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8573
hERG inhibition (predictor II)Non-inhibitor0.7636
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
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

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
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. Birgner C, Kindlundh-Hogberg AM, Alsio J, Lindblom J, Schioth HB, Bergstrom L: The anabolic androgenic steroid nandrolone decanoate affects mRNA expression of dopaminergic but not serotonergic receptors. Brain Res. 2008 Nov 13;1240:221-8. doi: 10.1016/j.brainres.2008.09.003. Epub 2008 Sep 13. [PubMed:18809391]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Oxygen binding
Specific Function
Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name
CYP19A1
Uniprot ID
P11511
Uniprot Name
Aromatase
Molecular Weight
57882.48 Da
References
  1. Takahashi K, Hallberg M, Magnusson K, Nyberg F, Watanabe Y, Langstrom B, Bergstrom M: Increase in [11C]vorozole binding to aromatase in the hypothalamus in rats treated with anabolic androgenic steroids. Neuroreport. 2007 Jan 22;18(2):171-4. [PubMed:17301684]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Primary amine oxidase activity
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
MAOB
Uniprot ID
P27338
Uniprot Name
Amine oxidase [flavin-containing] B
Molecular Weight
58762.475 Da
References
  1. Birgner C, Kindlundh-Hogberg AM, Oreland L, Alsio J, Lindblom J, Schioth HB, Bergstrom L: Reduced activity of monoamine oxidase in the rat brain following repeated nandrolone decanoate administration. Brain Res. 2008 Jul 11;1219:103-10. doi: 10.1016/j.brainres.2008.05.014. Epub 2008 May 17. [PubMed:18539264]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
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. Birgner C, Kindlundh-Hogberg AM, Oreland L, Alsio J, Lindblom J, Schioth HB, Bergstrom L: Reduced activity of monoamine oxidase in the rat brain following repeated nandrolone decanoate administration. Brain Res. 2008 Jul 11;1219:103-10. doi: 10.1016/j.brainres.2008.05.014. Epub 2008 May 17. [PubMed:18539264]

Drug created on June 13, 2005 07:24 / Updated on June 12, 2020 10:52

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