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
- 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.
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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.
Target Actions Organism AAndrogen receptor agonistHumans - 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
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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.
Drug Interaction Integrate drug-drug
interactions in your softwareAcarbose Nandrolone phenpropionate may increase the hypoglycemic activities of Acarbose. Acenocoumarol Nandrolone phenpropionate may increase the anticoagulant activities of Acenocoumarol. Acetohexamide Nandrolone phenpropionate may increase the hypoglycemic activities of Acetohexamide. Albiglutide Nandrolone phenpropionate may increase the hypoglycemic activities of Albiglutide. Allantoin The therapeutic efficacy of Allantoin can be increased when used in combination with Nandrolone phenpropionate. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- Active Moieties
Name Kind UNII CAS InChI Key Nandrolone prodrug 6PG9VR430D 434-22-0 NPAGDVCDWIYMMC-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,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 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
- InChem Data Sheet [Link]
- External Links
- Human Metabolome Database
- HMDB0015119
- KEGG Drug
- D00956
- KEGG Compound
- C08155
- PubChem Compound
- 229455
- PubChem Substance
- 46506276
- ChemSpider
- 199761
- 31495
- ChEBI
- 7468
- ChEMBL
- CHEMBL1200412
- ZINC
- ZINC000003881613
- Therapeutic Targets Database
- DAP000903
- PharmGKB
- PA164746281
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Nandrolone
Clinical Trials
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
Form Route Strength Solution 25 mg/1ml - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 118 °C PhysProp water solubility 3090 mg/L (at 25 °C) YALKOWSKY,SH & HE,Y (2003) - Predicted Properties
Property Value Source Water Solubility 0.000458 mg/mL ALOGPS logP 4.22 ALOGPS logP 5.79 Chemaxon logS -6 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 5 Chemaxon Refractivity 118.43 m3·mol-1 Chemaxon Polarizability 47.83 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - 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 inhibitor Non-inhibitor 0.8469 CYP450 2D6 inhibitor Non-inhibitor 0.9277 CYP450 2C19 inhibitor Inhibitor 0.6153 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-056u-2794000000-8a406f2131925f7d78d7 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-4281900000-fcabfc2e276122bfc798 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0000900000-b81bcdc10b6683c34ab8 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4j-0390100000-295d82aedb697a2976ec Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-4840900000-98b98379a18441c74181 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-2911300000-3841003aeaa3afbb4955 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-2490000000-0d9b6c2de98112348197 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 220.0184384 predictedDarkChem Lite v0.1.0 [M-H]- 218.5167384 predictedDarkChem Lite v0.1.0 [M-H]- 199.2855 predictedDeepCCS 1.0 (2019) [M+H]+ 220.3689384 predictedDarkChem Lite v0.1.0 [M+H]+ 219.6366384 predictedDarkChem Lite v0.1.0 [M+H]+ 202.35158 predictedDeepCCS 1.0 (2019) [M+Na]+ 220.4248384 predictedDarkChem Lite v0.1.0 [M+Na]+ 218.3430384 predictedDarkChem Lite v0.1.0 [M+Na]+ 209.59416 predictedDeepCCS 1.0 (2019)
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
- 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]
- 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]
- 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]
- 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]
- Yan W, Burns KH, Matzuk MM: Genetic engineering to study testicular tumorigenesis. APMIS. 2003 Jan;111(1):174-81; discussion 182-3. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
Drug created at June 13, 2005 13:24 / Updated at April 22, 2024 18:20