testosterone decanoate   Click here for help

GtoPdb Ligand ID: 7630

Approved drug
testosterone decanoate is an approved drug
Compound class: Synthetic organic
Comment: Testosterone decanoate is a synthetic testosterone drug with improved bioavailability and metabolic half life compared to the endogenous hormone.
2D Structure
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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.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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.

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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 10
Topological polar surface area 43.37
Molecular weight 442.34
XLogP 8.61
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCCCCCCCCC(=O)OC1CCC2C1(C)CCC1C2CCC2=CC(=O)CCC12C
Isomeric SMILES CCCCCCCCCC(=O)O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C
InChI InChI=1S/C29H46O3/c1-4-5-6-7-8-9-10-11-27(31)32-26-15-14-24-23-13-12-21-20-22(30)16-18-28(21,2)25(23)17-19-29(24,26)3/h20,23-26H,4-19H2,1-3H3/t23-,24-,25-,26-,28-,29-/m0/s1
InChI Key LBERVHLCXUMDOT-MPZZESAYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
No information available.
Summary of Clinical Use Click here for help
Testosterone decanoate is one of the ingredients of the approved fixed-mixture drug Sustanon®, which contains four esterized testosterone compounds (testosterone phenylpropionate, testosterone propionate, testosterone isocaproate and testosterone decanoate) and is designed to provide sustained release of drug in to the bloodstream and more stable serum testosterone levels. This drug mixture is used for testosterone replacement therapy in males with conditions associated with primary and secondary hypogonadism, either congenital or acquired and may also be used as supportive therapy for female-to-male transsexuals. Sustanon® is an anabolic steroid product used illicitly by bodybuilders and athletes to build muscle mass. Sustanon® was first approved in the UK in 1973 (eMC link).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Testosterone binds to the androgen receptor (AR), and the ligand-receptor complex translocates to the nucleus and binds to androgen response elements (AREs) on chromosomal DNA, thereby modulating transcription of a set of androgen-responsive genes. Testosterone can also be converted to estrogen and has a similar regulatory action on genes containing estrogen response elements (EREs).