testosterone phenylpropionate   Click here for help

GtoPdb Ligand ID: 7628

Synonyms: testosterone 17-phenylpropionate | testosterone hydrocinnamate
Approved drug
testosterone phenylpropionate is an approved drug
Compound class: Synthetic organic
Comment: Testosterone phenylpropionate is a testosterone ester 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 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.

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Hydrogen bond acceptors 3
Hydrogen bond donors 0
Rotatable bonds 5
Topological polar surface area 43.37
Molecular weight 420.27
XLogP 6.07
No. Lipinski's rules broken 1
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.

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Canonical SMILES O=C(OC1CCC2C1(C)CCC1C2CCC2=CC(=O)CCC12C)CCc1ccccc1
Isomeric SMILES O=C(O[C@H]1CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2CCC2=CC(=O)CC[C@]12C)CCc1ccccc1
InChI InChI=1S/C28H36O3/c1-27-16-14-21(29)18-20(27)9-10-22-23-11-12-25(28(23,2)17-15-24(22)27)31-26(30)13-8-19-6-4-3-5-7-19/h3-7,18,22-25H,8-17H2,1-2H3/t22-,23-,24-,25-,27-,28-/m0/s1
InChI Key HHSXYDOROIURIP-FEZCWRLCSA-N
No information available.
Summary of Clinical Use Click here for help
Testosterone phenylpropionate 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).