nandrolone   

GtoPdb Ligand ID: 6949

Synonyms: 19-norandrostenolone | Deca-Durabolin® (decanoate ester) | Durabolin® (phenylpropionate ester)
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).
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2D Structure
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Physico-chemical Properties
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
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
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
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.