nandrolone   Click here for help

GtoPdb Ligand ID: 6949

Synonyms: 19-norandrostenolone | Deca-Durabolin® (decanoate ester) | Durabolin® (phenylpropionate ester)
Approved drug PDB Ligand
nandrolone is an approved drug (FDA (1959))
Compound class: Synthetic organic
Comment: An androgen receptor agonist with associated anabolic properties. The INN record for nandrolone is for the core compound without the decanoate side chain, but other national commissions use nandrolone decanoate to name nadrolone. The first US FDA nandrolone based drug approval was for nandrolone phenpropionate in 1959, since then many formulations have been approved but subsequently discontinued. Our record for nandrolone is intended to cover various fomulations of the compound including nandrolone phenpropionate (PubChem CID 229455) and nandrolone decanoate (PubChem CID 9677).
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: nandrolone

2D Structure
Click here for help

2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

✖
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 0
Topological polar surface area 37.3
Molecular weight 274.19
XLogP 3.22
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Click here for help

SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

✖
Canonical SMILES O=C1CCC2C(=C1)CCC1C2CCC2(C1CCC2O)C
Isomeric SMILES O=C1CC[C@H]2C(=C1)CC[C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@@H]2O)C
InChI InChI=1S/C18H26O2/c1-18-9-8-14-13-5-3-12(19)10-11(13)2-4-15(14)16(18)6-7-17(18)20/h10,13-17,20H,2-9H2,1H3/t13-,14+,15+,16-,17-,18-/m0/s1
InChI Key NPAGDVCDWIYMMC-IZPLOLCNSA-N
No information available.
Summary of Clinical Use Click here for help
Nandrolone increases production and urinary excretion of erythropoietin and for this property is used to manage refractory deficient red cell production anemias. Nandrolone is also used in the treatment of breast cancer, hereditary angioedema, antithrombin III deficiency, fibrinogen excess, growth failure and Turner's syndrome as well as in the prophylaxis of hereditary angioedema.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
The drug binds to the androgen receptor and the ligand bound complexes enter the nucleus and bind directly to specific androgen response elements in the promoters of androgen-responsive genes. This alters the transcriptional activity of these genes, the sequelae of which is the observed androgenic effects.