Identification

Name
Nandrolone phenpropionate
Accession Number
DB00984  (APRD00134)
Type
Small Molecule
Groups
Approved, Illicit, Investigational
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
  • 19NTPP
  • Nadrolone phenylpropionate
  • Nandrolon phenylpropionate
  • Nandrolone phenylpionate
  • Nandrolone phenylpropionate
  • Norandrolone phenyl propionate
  • Norandrostenolone phenylpropionate
  • Nortestosterone phenylpropionate
  • NPP
  • NTPP
External IDs
NSC-23162
International/Other Brands
Durabolin
Categories
UNII
KF7Z9K2T3W
CAS number
62-90-8
Weight
Average: 406.5571
Monoisotopic: 406.250794954
Chemical Formula
C27H34O3
InChI Key
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
IUPAC Name
(1S,2R,10R,11S,14S,15S)-15-methyl-5-oxotetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadec-6-en-14-yl 3-phenylpropanoate
SMILES
[H][[email protected]@]12CC[[email protected]](OC(=O)CCC3=CC=CC=C3)[[email protected]@]1(C)CC[[email protected]]1([H])[[email protected]@]3([H])CCC(=O)C=C3CC[[email protected]@]21[H]

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.

Structured Indications
Not Available
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
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteractionDrug group
Darbepoetin alfaNandrolone phenpropionate may increase the stimulatory activities of Darbepoetin alfa.Approved, Investigational
ErythropoietinNandrolone phenpropionate may increase the stimulatory activities of Erythropoietin.Approved
Methoxy polyethylene glycol-epoetin betaNandrolone phenpropionate may increase the stimulatory activities of Methoxy polyethylene glycol-epoetin beta.Approved
Food Interactions
Not Available

References

General References
  1. InChem Data Sheet [Link]
External Links
Human Metabolome Database
HMDB15119
KEGG Drug
D00956
KEGG Compound
C08155
PubChem Compound
229455
PubChem Substance
46506276
ChemSpider
199761
ChEBI
7468
ChEMBL
CHEMBL1200412
Therapeutic Targets Database
DAP000903
PharmGKB
PA164746281
Drugs.com
Drugs.com Drug Page
Wikipedia
Nandrolone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentAplastic Anaemia (AA) / Blood Diseases / Hematologic Diseases / Pancytopenia1
Not AvailableCompletedTreatmentMuscle Wasting1

Pharmacoeconomics

Manufacturers
  • Organon usa inc
  • Abraxis pharmaceutical products
  • Akorn inc
  • Watson laboratories inc
Packagers
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)118 °CPhysProp
water solubility3090 mg/L (at 25 °C)YALKOWSKY,SH & HE,Y (2003)
logP2.62HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.000458 mg/mLALOGPS
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 Area43.37 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity118.43 m3·mol-1ChemAxon
Polarizability47.83 Å3ChemAxon
Number of Rings5ChemAxon
Bioavailability1ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9543
Caco-2 permeable+0.6714
P-glycoprotein substrateSubstrate0.6529
P-glycoprotein inhibitor IInhibitor0.7951
P-glycoprotein inhibitor IIInhibitor0.6657
Renal organic cation transporterNon-inhibitor0.6836
CYP450 2C9 substrateNon-substrate0.8112
CYP450 2D6 substrateNon-substrate0.9213
CYP450 3A4 substrateSubstrate0.6889
CYP450 1A2 substrateNon-inhibitor0.8333
CYP450 2C9 inhibitorNon-inhibitor0.8469
CYP450 2D6 inhibitorNon-inhibitor0.9277
CYP450 2C19 inhibitorInhibitor0.6153
CYP450 3A4 inhibitorNon-inhibitor0.7091
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5453
Ames testNon AMES toxic0.911
CarcinogenicityNon-carcinogens0.9399
BiodegradationNot ready biodegradable0.9685
Rat acute toxicity1.8785 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.7552
hERG inhibition (predictor II)Non-inhibitor0.737
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

Taxonomy

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 / Benzene and substituted derivatives / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
Steroid ester / Estrogen-skeleton / 3-oxo-delta-4-steroid / 3-oxosteroid / Oxosteroid / Estrane-skeleton / Delta-4-steroid / Cyclohexenone / Monocyclic benzene moiety / Benzenoid
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
3-phenylpropionate ester (CHEBI:7468)

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 ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
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:14663936]
  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:14619588]
  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:17405825]
  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:14761877]
  5. Yan W, Burns KH, Matzuk MM: Genetic engineering to study testicular tumorigenesis. APMIS. 2003 Jan;111(1):174-81; discussion 182-3. [PubMed:12760377]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Substrate
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. 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. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Drug created on June 13, 2005 07:24 / Updated on November 07, 2017 01:45