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Identification
NameNandrolone phenpropionate
Accession NumberDB00984  (APRD00134)
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
SynonymLanguageCode
19NTPPNot AvailableNot Available
DurabolinNot AvailableNot Available
Nadrolone phenylpropionateNot AvailableNot Available
Nandrolon phenylpropionateNot AvailableNot Available
Nandrolone phenpropionateNot AvailableNot Available
Nandrolone phenylpionateNot AvailableNot Available
Nandrolone phenylpropionateNot AvailableJAN
Norandrolone phenyl propionateNot AvailableNot Available
Norandrostenolone phenylpropionateNot AvailableNot Available
Nortestosterone phenylpropionateNot AvailableNot Available
NPPNot AvailableNot Available
NTPPNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
DurabolinNot Available
Brand mixturesNot Available
Categories
CAS number434-22-0
WeightAverage: 406.5571
Monoisotopic: 406.250794954
Chemical FormulaC27H34O3
InChI KeyUBWXUGDQUBIEIZ-QNTYDACNSA-N
InChI
InChI=1S/C27H34O3/c1-27-16-15-22-21-11-9-20(28)17-19(21)8-10-23(22)24(27)12-13-25(27)30-26(29)14-7-18-5-3-2-4-6-18/h2-6,17,21-25H,7-16H2,1H3/t21-,22+,23+,24-,25-,27-/m0/s1
IUPAC Name
(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl 3-phenylpropanoate
SMILES
[H][C@@]12CC[C@H](OC(=O)CCC3=CC=CC=C3)[C@@]1(C)CC[C@]1([H])[C@@]3([H])CCC(=O)C=C3CC[C@@]21[H]
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassSteroid Esters
Direct parentSteroid Esters
Alternative parentsEstrogens and Derivatives; Ketosteroids; Benzene and Substituted Derivatives; Carboxylic Acid Esters; Ketones; Ethers; Enolates; Polyamines
Substituents3-keto-steroid; benzene; carboxylic acid ester; ketone; enolate; ether; polyamine; carboxylic acid derivative; carbonyl group
Classification descriptionThis compound belongs to the steroid esters. These are compounds containing a steroid moeity which bears a carboxylic acid ester group.
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.
AbsorptionThe absorption after oral dosing is rapid for testosterone and probably for other anabolic steroids, but there is extensive first-pass hepatic metabolism for all anabolic steroids except those that are substituted at the 17-alpha position. The rate of absorption from subcutaneous or intramuscular depots depends on the product and its formulation. Absorption is slow for the lipid-soluble esters such as the cypionate or enanthate, and for oily suspensions.
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 lifeThe elimination half-life from plasma is very short.
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
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9543
Caco-2 permeable + 0.6714
P-glycoprotein substrate Substrate 0.6529
P-glycoprotein inhibitor I Inhibitor 0.7951
P-glycoprotein inhibitor II Inhibitor 0.6657
Renal organic cation transporter Non-inhibitor 0.6836
CYP450 2C9 substrate Non-substrate 0.8112
CYP450 2D6 substrate Non-substrate 0.9213
CYP450 3A4 substrate Substrate 0.6889
CYP450 1A2 substrate Non-inhibitor 0.8333
CYP450 2C9 substrate Non-inhibitor 0.8469
CYP450 2D6 substrate Non-inhibitor 0.9277
CYP450 2C19 substrate Inhibitor 0.6153
CYP450 3A4 substrate Non-inhibitor 0.7091
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5453
Ames test Non AMES toxic 0.911
Carcinogenicity Non-carcinogens 0.9399
Biodegradation Not ready biodegradable 0.9685
Rat acute toxicity 1.8785 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.7552
hERG inhibition (predictor II) Non-inhibitor 0.737
Pharmacoeconomics
Manufacturers
  • Organon usa inc
  • Abraxis pharmaceutical products
  • Akorn inc
  • Watson laboratories inc
Packagers
Dosage forms
FormRouteStrength
LiquidIntramuscular
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point118 °CPhysProp
water solubility3090 mg/L (at 25 °C)YALKOWSKY,SH & HE,Y (2003)
logP2.62HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility4.58e-04 g/lALOGPS
logP4.22ALOGPS
logP5.79ChemAxon
logS-6ALOGPS
pKa (strongest acidic)19.28ChemAxon
pKa (strongest basic)-4.7ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count0ChemAxon
polar surface area43.37ChemAxon
rotatable bond count5ChemAxon
refractivity118.43ChemAxon
polarizability47.83ChemAxon
number of rings5ChemAxon
bioavailability1ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General Reference
  1. InChem Data Sheet
External Links
ResourceLink
KEGG DrugD00956
KEGG CompoundC08155
PubChem Compound229455
PubChem Substance46506276
ChemSpider199761
ChEBI7468
ChEMBLCHEMBL1200412
Therapeutic Targets DatabaseDAP000903
PharmGKBPA164746281
Drug Product Database270687
Drugs.comhttp://www.drugs.com/cdi/nandrolone.html
WikipediaNandrolone
ATC CodesA14AB01S01XA11
AHFS Codes
  • 68:08.00
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
WarfarinNandrolone may increase the serum concentration and anticoagulant effect of warfarin. Monitor for changes in prothrombin time and therapeutic effects of warfarin if nandrolone is initiated, discontinued or dose changed.
Food InteractionsNot Available

Targets

1. Androgen receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Androgen receptor P10275 Details

References:

  1. Cen Y, Li K, Liu XX: [Effect of nandrolone phenylpropionate on expression of hepatic albumin-mRNA and androgen receptor in burned rats] Zhongguo Xiu Fu Chong Jian Wai Ke Za Zhi. 2003 Nov;17(6):439-41. Pubmed
  2. Li K, Cen Y, Liu X, Luo X: [The effects of nandrolone phenylpropionate on androgen receptor of liver and sexual glands in burned rats] Sichuan Da Xue Xue Bao Yi Xue Ban. 2003 Oct;34(4):708-10. Pubmed
  3. Burger LL, Haisenleder DJ, Wotton GM, Aylor KW, Dalkin AC, Marshall JC: The regulation of FSHbeta transcription by gonadal steroids: testosterone and estradiol modulation of the activin intracellular signaling pathway. Am J Physiol Endocrinol Metab. 2007 Jul;293(1):E277-85. Epub 2007 Apr 3. Pubmed
  4. Fujii Y, Kawakami S, Okada Y, Kageyama Y, Kihara K: Regulation of prostate-specific antigen by activin A in prostate cancer LNCaP cells. Am J Physiol Endocrinol Metab. 2004 Jun;286(6):E927-31. Epub 2004 Feb 3. Pubmed
  5. Yan W, Burns KH, Matzuk MM: Genetic engineering to study testicular tumorigenesis. APMIS. 2003 Jan;111(1):174-81; discussion 182-3. Pubmed
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Enzymes

1. Cytochrome P450 19A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: substrate

Components

Name UniProt ID Details
Cytochrome P450 19A1 P11511 Details

References:

  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. Epub 2009 Nov 24. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on January 29, 2014 08:45