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
Structure for Nandrolone decanoate (DB08804)
- 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.
Learn More- 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.
Target Actions Organism AAndrogen receptor agonistHumans - 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.
Learn More- 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.
Drug Interaction Unlock Additional DataAcarbose Nandrolone decanoate may increase the hypoglycemic activities of Acarbose. Acenocoumarol Nandrolone decanoate may increase the anticoagulant activities of Acenocoumarol. Acetohexamide Nandrolone decanoate may increase the hypoglycemic activities of Acetohexamide. Albiglutide Nandrolone decanoate may increase the hypoglycemic activities of Albiglutide. Allantoin The therapeutic efficacy of Allantoin can be increased when used in combination with Nandrolone decanoate. Almotriptan The metabolism of Almotriptan can be decreased when combined with Nandrolone decanoate. Alogliptin Nandrolone decanoate may increase the hypoglycemic activities of Alogliptin. Beclomethasone dipropionate The risk or severity of edema formation can be increased when Nandrolone decanoate is combined with Beclomethasone dipropionate. Betamethasone The risk or severity of edema formation can be increased when Nandrolone decanoate is combined with Betamethasone. Betamethasone phosphate The risk or severity of edema formation can be increased when Nandrolone decanoate is combined with Betamethasone phosphate. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- No interactions found.
Products
- Active Moieties
Name Kind UNII CAS InChI Key Nandrolone prodrug 6PG9VR430D 434-22-0 NPAGDVCDWIYMMC-IZPLOLCNSA-N - International/Other Brands
- Deca-Durabol / Deca-Durabolin / Retabolil
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataNandrolone Decanoate Injection 200 mg/1mL Intramuscular Watson Pharmaceuticals 2007-02-08 Not applicable US 
Nandrolone Decanoate Injection 100 mg/1mL Intramuscular Watson Pharmaceuticals 2007-02-08 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataNandrolone Decanoate Injection, solution 200 mg/1mL Intramuscular AMERICAN REGENT, INC. 2010-09-01 2010-10-01 US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
Categories
- Drug Categories
- Anabolic Agents
- Androgens
- Bone Density Conservation Agents
- Estranes
- Estrenes
- Fused-Ring Compounds
- Gonadal Hormones
- Gonadal Steroid Hormones
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- Monoamine Oxidase A Inhibitors for interaction with Monoamine Oxidase A substrates
- Nandrolone and esters
- Steroids
- Testosterone Congeners
- Thyroxine-binding globulin inhibitors
- 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
- External Links
- Human Metabolome Database
- HMDB0015694
- KEGG Drug
- D00955
- KEGG Compound
- C08154
- PubChem Compound
- 9677
- PubChem Substance
- 99445274
- ChemSpider
- 9296
- 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
Phase Status Purpose Conditions Count 2 Active Not Recruiting Supportive Care Hip Fracture 1 1 Completed Treatment HIV Wasting Syndrome / Human Immunodeficiency Virus (HIV) Infections 1 1, 2 Unknown Status Treatment Aplastic Anemia / Bone Marrow Failure Syndromes / Idiopathic Pulmonary Fibrosis (IPF) / Telomere Shortening 1 Not Available Completed Supportive Care Cachexia; Cancer 1 Not Available Completed Treatment End Stage Renal Disease (ESRD) / Muscle Weakness 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Solution Intramuscular 50 mg Solution Intramuscular Liquid Intramuscular Injection, solution Parenteral 25 mg/ml Injection, solution Parenteral 50 mg/ml Injection Intramuscular 100 mg/1mL Injection Intramuscular 200 mg/1mL Injection, solution Intramuscular 200 mg/1mL Injection Intramuscular; Subcutaneous 25 mg Injection Intramuscular; Subcutaneous 5 mg - Prices
Unit description Cost Unit Deca-Durabolin 100 mg/ml 97.16USD ml Nandrolone decanoate powder 79.88USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 118 °C Not Available water solubility 3.09 mg/mL at 25 °C YALKOWSKY,SH & HE,Y (2003) logP 2.62 HANSCH,C ET AL. (1995) - Predicted Properties
Property Value Source Water Solubility 0.000157 mg/mL ALOGPS logP 5.96 ALOGPS logP 7.32 ChemAxon logS -6.4 ALOGPS pKa (Strongest Acidic) 18.25 ChemAxon pKa (Strongest Basic) -4.7 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 0 ChemAxon Polar Surface Area 43.37 Å2 ChemAxon Rotatable Bond Count 10 ChemAxon Refractivity 125.94 m3·mol-1 ChemAxon Polarizability 53.64 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule Yes ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.97 Caco-2 permeable + 0.6718 P-glycoprotein substrate Substrate 0.6327 P-glycoprotein inhibitor I Inhibitor 0.8364 P-glycoprotein inhibitor II Inhibitor 0.5069 Renal organic cation transporter Non-inhibitor 0.7532 CYP450 2C9 substrate Non-substrate 0.8741 CYP450 2D6 substrate Non-substrate 0.9285 CYP450 3A4 substrate Substrate 0.72 CYP450 1A2 substrate Non-inhibitor 0.94 CYP450 2C9 inhibitor Non-inhibitor 0.8841 CYP450 2D6 inhibitor Non-inhibitor 0.9111 CYP450 2C19 inhibitor Non-inhibitor 0.5353 CYP450 3A4 inhibitor Non-inhibitor 0.7896 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5493 Ames test Non AMES toxic 0.9431 Carcinogenicity Non-carcinogens 0.9215 Biodegradation Not ready biodegradable 0.9625 Rat acute toxicity 1.8804 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8573 hERG inhibition (predictor II) Non-inhibitor 0.7636
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not 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
- 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
- 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
- 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
- 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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