Nandrolone phenpropionate

Identification

Generic Name
Nandrolone phenpropionate
DrugBank Accession Number
DB00984
Background

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, Investigational
Structure
Thumb
Weight
Average: 406.5571
Monoisotopic: 406.250794954
Chemical Formula
C27H34O3
Synonyms
  • 19NTPP
  • Nadrolone phenylpropionate
  • Nandrolon phenylpropionate
  • Nandrolone phenpropionate
  • Nandrolone phenylpionate
  • Nandrolone phenylpropionate
  • Norandrolone phenyl propionate
  • Norandrostenolone phenylpropionate
  • Nortestosterone phenylpropionate
  • NPP
  • NTPP
External IDs
  • NSC-23162

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.

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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
Humans
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

Adverse Effects
Adverseeffects
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Toxicity

Not Available

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.
DrugInteraction
AcarboseNandrolone phenpropionate may increase the hypoglycemic activities of Acarbose.
AcenocoumarolNandrolone phenpropionate may increase the anticoagulant activities of Acenocoumarol.
AcetohexamideNandrolone phenpropionate may increase the hypoglycemic activities of Acetohexamide.
AlbiglutideNandrolone phenpropionate may increase the hypoglycemic activities of Albiglutide.
AllantoinThe therapeutic efficacy of Allantoin can be increased when used in combination with Nandrolone phenpropionate.
AlogliptinNandrolone phenpropionate may increase the hypoglycemic activities of Alogliptin.
Beclomethasone dipropionateThe risk or severity of edema formation can be increased when Nandrolone phenpropionate is combined with Beclomethasone dipropionate.
BetamethasoneThe risk or severity of edema formation can be increased when Nandrolone phenpropionate is combined with Betamethasone.
Betamethasone phosphateThe risk or severity of edema formation can be increased when Nandrolone phenpropionate is combined with Betamethasone phosphate.
BromocriptineNandrolone phenpropionate may increase the hypoglycemic activities of Bromocriptine.
Interactions
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Food Interactions
Not Available

Products

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Active Moieties
NameKindUNIICASInChI Key
Nandroloneprodrug6PG9VR430D434-22-0NPAGDVCDWIYMMC-IZPLOLCNSA-N
International/Other Brands
Durabolin

Categories

Drug Categories
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 / Benzene and substituted derivatives / Carboxylic acid esters / Monocarboxylic acids and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
3-oxo-delta-4-steroid / 3-oxosteroid / Aromatic homopolycyclic compound / Benzenoid / Carbonyl group / Carboxylic acid derivative / Carboxylic acid ester / Cyclic ketone / Cyclohexenone / Delta-4-steroid
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
3-phenylpropionate ester (CHEBI:7468)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
KF7Z9K2T3W
CAS number
62-90-8
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][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]

References

General References
  1. InChem Data Sheet [Link]
Human Metabolome Database
HMDB0015119
KEGG Drug
D00956
KEGG Compound
C08155
PubChem Compound
229455
PubChem Substance
46506276
ChemSpider
199761
RxNav
31495
ChEBI
7468
ChEMBL
CHEMBL1200412
ZINC
ZINC000003881613
Therapeutic Targets Database
DAP000903
PharmGKB
PA164746281
Drugs.com
Drugs.com Drug Page
Wikipedia
Nandrolone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Organon usa inc
  • Abraxis pharmaceutical products
  • Akorn inc
  • Watson laboratories inc
Packagers
  • C.O. Truxton Inc.
  • Darby Dental Supply Co. Inc.
  • Martin Surgical Supply
  • Organon Pharmaceuticals
  • Primedics Laboratories
  • Spectrum Pharmaceuticals
Dosage Forms
FormRouteStrength
Solution25 mg/1ml
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)
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

Targets

Drugtargets2
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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
  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. [Article]
  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. [Article]
  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. [Article]
  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. [Article]
  5. Yan W, Burns KH, Matzuk MM: Genetic engineering to study testicular tumorigenesis. APMIS. 2003 Jan;111(1):174-81; discussion 182-3. [Article]
  6. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]

Drug created on June 13, 2005 13:24 / Updated on October 21, 2021 04:41