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).
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: nandrolone

2D Structure
Click here for structure editor
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
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1959))
IUPAC Name
(8R,9S,10R,13S,14S,17S)-17-hydroxy-13-methyl-2,6,7,8,9,10,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-3-one
International Nonproprietary Names
INN number INN
295 nandrolone
Synonyms
19-norandrostenolone | Deca-Durabolin® (decanoate ester) | Durabolin® (phenylpropionate ester)
Database Links
CAS Registry No. 434-22-0
ChEBI CHEBI:7466
ChEMBL Ligand CHEMBL757
DrugBank Ligand DB08804, DB00984
DrugCentral Ligand 1879
GtoPdb PubChem SID 178103531
NURSA Ligand 10.1621/BAXXFI2MIY
PubChem CID 9904
RCSB PDB Ligand 6VW
Search Google for chemical match using the InChIKey NPAGDVCDWIYMMC-IZPLOLCNSA-N
Search Google for chemicals with the same backbone NPAGDVCDWIYMMC
Search PubMed clinical trials nandrolone
Search PubMed titles nandrolone
Search PubMed titles/abstracts nandrolone
Search UniChem for chemical match using the InChIKey NPAGDVCDWIYMMC-IZPLOLCNSA-N
Search UniChem for chemicals with the same backbone NPAGDVCDWIYMMC
Wikipedia Nandrolone