Banner
targets (1) enzymes (1)
for drugs
Identification
Name Nandrolone phenpropionate
Accession Number DB00984 (APRD00134)
Type small molecule
Groups illicit, approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
19NTPP
Nadrolone phenylpropionate
Nandrolin
Nandrolon phenylpropionate
Nandrolone phenylpionate
Nandrolone phenylpropionate
Norandrolone phenyl propionate
Norandrostenolone phenylpropionate
Nortestosterone phenylpropionate
NTPP
Testosterone phenylpropionate
First Prev Next Last
Salts Not Available
Brand names
Name Company
Activin
Durabol
Durabolin
Fenobolin
Nandrobolic
Nerobil
Nerobiolil
Nerobolil
Phenobolin
Strabolene
Superanabolon
First Prev Next Last
Brand mixtures Not Available
Categories
  • Anabolic Agents
  • Androgens
CAS number 434-22-0
Weight Average: 406.5571
Monoisotopic: 406.250794954
Chemical Formula C27H34O3
InChI Key InChIKey=UBWXUGDQUBIEIZ-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
Plain Text
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]
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Carboxylic Acids and Derivatives
  • Alkanes and Alkenes
  • Acetates
  • Ethers
  • Benzene and Derivatives
  • Aromatic compounds
  • Cyclohexenes and Derivatives
  • Ketones
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.
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.
Absorption The 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 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 The elimination half-life from plasma is very short.
Clearance Not Available
Toxicity Not Available
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Organon usa inc
  • Abraxis pharmaceutical products
  • Akorn inc
  • Watson laboratories inc
Packagers
Dosage forms
Form Route Strength
Liquid Intramuscular
Prices Not Available
Patents Not Available
Properties
State solid
Experimental Properties
Property Value Source
melting point 118 °C PhysProp
water solubility 3090 mg/L (at 25 °C) YALKOWSKY,SH & HE,Y (2003)
logP 2.62 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 4.58e-04 g/l ALOGPS
logP 4.22 ALOGPS
logP 5.79 ChemAxon
logS -6 ALOGPS
pKa (strongest acidic) 19.28 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 ChemAxon
rotatable bond count 5 ChemAxon
refractivity 118.43 ChemAxon
polarizability 47.83 ChemAxon
References
Synthesis Reference Not Available
General Reference
  1. InChem Data Sheet
External Links
Resource Link
KEGG Drug D00956 Link_out
KEGG Compound C08155 Link_out
PubChem Compound 229455 Link_out
PubChem Substance 46506276 Link_out
ChemSpider 199761 Link_out
ChEBI 7468 Link_out
ChEMBL 7468 Link_out
Therapeutic Targets Database DAP000903 Link_out
PharmGKB PA164746281 Link_out
Drug Product Database 270687 Link_out
Drugs.com http://www.drugs.com/cdi/nandrolone.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Nandrolone Link_out
ATC Codes
  • A14AB01
  • S01XA11
AHFS Codes
  • 68:08.00
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Warfarin Nandrolone 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 Interactions Not Available
Targets

1. Androgen receptor

Pharmacological action: yes
Actions: agonist

The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Activated, but not phosphorylated, by HIPK3

Organism class: human
UniProt ID: P10275 Link_out
Gene: AR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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

Actions: substrate

Catalyzes the formation of aromatic C18 estrogens from C19 androgens

UniProt ID: P11511 Link_out
Gene: CYP19A1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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
Comments
Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19