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Identification
NameNandrolone decanoate
Accession NumberDB08804
TypeSmall Molecule
GroupsApproved, Illicit
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.

Structure
Thumb
Synonyms
19-nortestosterone decanoate
Deca-durabolin
Nandrolone 17β-decanoate
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Deca Durabolin Inj 100mg/mlsolution100 mgintramuscularSchering Plough Canada Inc1973-12-312010-07-26Canada
Deca Durabolin Inj 50mg/mlliquid50 mgintramuscularOrganon Canada Ltd Ltee1973-12-311996-09-10Canada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Nandrolone Decanoateinjection, solution200 mg/mLintramuscularAmerican Regent, Inc.2000-01-01Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
Deca-DurabolNot Available
Deca-DurabolinNot Available
RetabolilNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIH45187T098
CAS number360-70-3
WeightAverage: 428.6472
Monoisotopic: 428.329045274
Chemical FormulaC28H44O3
InChI KeyInChIKey=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,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl decanoate
SMILES
CCCCCCCCCC(=O)O[[email protected]]1CC[[email protected]]2[C@@H]3CCC4=CC(=O)CC[C@@H]4[[email protected]]3CC[C@]12C
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassSteroid esters
Direct ParentSteroid esters
Alternative Parents
Substituents
  • Steroid ester
  • Estrogen-skeleton
  • Oxosteroid
  • Estrane-skeleton
  • 3-oxosteroid
  • 3-oxo-delta-4-steroid
  • Delta-4-steroid
  • Cyclic ketone
  • Ketone
  • Carboxylic acid ester
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor 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.
PharmacodynamicsNandrolone 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 actionNandrolone 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding58%
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 eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Solutionintramuscular100 mg
Liquidintramuscular50 mg
Injection, solutionintramuscular200 mg/mL
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.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point118 °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)19.28ChemAxon
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
Polarizability53.65 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesNot Available
AHFS Codes
  • 68:08.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (49.5 KB)
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
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 factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
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
Human
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
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
Human
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 tissues. MAOB preferentially degrades benzylamine and phenylethylamine.
Gene Name:
MAOB
Uniprot ID:
P27338
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
Human
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 tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:
MAOA
Uniprot ID:
P21397
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 ]
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 18:11