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Identification
Name Testosterone Propionate
Accession Number DB01420
Type small molecule
Groups approved
Description

An ester of testosterone with a propionate substitution at the 17-beta position. [PubChem]
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms Not Available
Brand names
  • Agovirin
  • Testex
Brand name mixtures Not Available
Categories
  • Androgens
CAS number 57-85-2
Weight Average: 344.4877
Monoisotopic: 344.235144890
Chemical Formula C22H32O3
InChI Key InChIKey=PDMMFKSKQVNJMI-BLQWBTBKSA-N
InChI
InChI=1S/C22H32O3/c1-4-20(24)25-19-8-7-17-16-6-5-14-13-15(23)9-11-21(14,2)18(16)10-12-22(17,19)3/h13,16-19H,4-12H2,1-3H3/t16-,17-,18-,19-,21-,22-/m0/s1
Plain Text
IUPAC Name
(1S,2R,10R,11S,14S,15S)-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl propanoate
SMILES
[H][C@@]12CC[C@H](OC(=O)CC)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
Plain Text
Mass Spec show (9.5 KB)
Taxonomy
Kingdom Organic
Classes
  • Steroids and Steroid Derivatives
Substructures
  • Steroids and Steroid Derivatives
  • Carboxylic Acids and Derivatives
  • Alkanes and Alkenes
  • Acetates
  • Ethers
  • Cyclohexenes and Derivatives
  • Ketones
Pharmacology
Indication Testosterone propionate is an anabolic steroid and a short ester form of testosterone that becomes active in the body. It is often used for muscle mass building.
Pharmacodynamics Testosterone is a steroid hormone from the androgen group. Testosterone is primarily secreted from the testes of males. In females, it is produced in the ovaries, adrenal glands and by conversion of adrostenedione in the periphery. It is the principal male sex hormone and an anabolic steroid. In both males and females, it plays key roles in health and well-being. Examples include enhanced libido, energy, immune function, and protection against osteoporosis. On average, the adult male body produces about twenty times the amount of testosterone than an adult female's body does. In the body, this ester form of testosterone is hydrolyzed rapidly and become actively available as testosterone.
Mechanism of action The effects of testosterone in humans and other vertebrates occur by way of two main mechanisms: by activation of the androgen receptor (directly or as DHT), and by conversion to estradiol and activation of certain estrogen receptors. Free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.
Absorption Not Available
Volume of distribution Not Available
Protein binding 40% of testosterone in plasma is bound to sex hormone-binding globulin and 2% remains unbound and the rest is bound to albumin and other proteins.
Metabolism

Testosterone propionate is rapidly hydrolysed into testosterone. Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).
Route of elimination About 90% of a dose of testosterone given intramuscularly is excreted in the urine as glucuronic and sulfuric acid conjugates of testosterone and its metabolites; about 6% of a dose is excreted in the feces, mostly in the unconjugated form.
Half life Not Available
Clearance Not Available
Toxicity Side effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Bel mar laboratories inc
  • Elkins sinn div ah robins co inc
  • Eli lilly and co
  • Watson laboratories inc
Packagers
Dosage forms
Form Route Strength
Capsule Oral
Gel Topical
Liquid Intramuscular
Patch Transdermal
Solution Intramuscular
Prices
Unit description Cost Unit
Testosterone propionate powder 6.25 USD g
First-testosterone mc 2% cr 0.91 USD g
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logS -5.37 [ADME Research, USCD] PhysProp
Predicted Properties
Property Value Source
water solubility 5.02e-03 g/l ALOGPS
logP 3.65 ALOGPS
logP 4.51 ChemAxon Molconvert
logS -4.84 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 43.37 ChemAxon Molconvert
rotatable bond count 3 ChemAxon Molconvert
refractivity 98.21 ChemAxon Molconvert
polarizability 40.43 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00959 Link_out
KEGG Compound C08158 Link_out
PubChem Compound 5995 Link_out
PubChem Substance 46508693 Link_out
ChemSpider 5774 Link_out
BindingDB 50215709 Link_out
Drug Product Database 0 Link_out
Drugs.com http://www.drugs.com/testosterone.html Link_out
ATC Codes
  • G03BA03
AHFS Codes
  • 68:08.00
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Not Available
Food Interactions Not Available
Targets

1. Androgen receptor

Pharmacological action: yes
Actions: agonist

The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Activated, but not phosphorylated, by HIPK3

Organism class: human
UniProt ID: P10275 Link_out
Gene: AR Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Small EJ, Ryan CJ: The case for secondary hormonal therapies in the chemotherapy age. J Urol. 2006 Dec;176(6 Pt 2):S66-71. Pubmed
  2. Omwancha J, Brown TR: Selective androgen receptor modulators: in pursuit of tissue-selective androgens. Curr Opin Investig Drugs. 2006 Oct;7(10):873-81. Pubmed
  3. Petraki CD, Sfikas CP: Histopathological changes induced by therapies in the benign prostate and prostate adenocarcinoma. Histol Histopathol. 2007 Jan;22(1):107-18. Pubmed
  4. Maudsley S, Davidson L, Pawson AJ, Freestone SH, Lopez de Maturana R, Thomson AA, Millar RP: Gonadotropin-releasing hormone functionally antagonizes testosterone activation of the human androgen receptor in prostate cells through focal adhesion complexes involving Hic-5. Neuroendocrinology. 2006;84(5):285-300. Epub 2007 Jan 4. Pubmed
  5. Lapauw B, Goemaere S, Crabbe P, Kaufman JM, Ruige JB: Is the effect of testosterone on body composition modulated by the androgen receptor gene CAG repeat polymorphism in elderly men? Eur J Endocrinol. 2007 Mar;156(3):395-401. Pubmed
  6. Yin D, Gao W, Kearbey JD, Xu H, Chung K, He Y, Marhefka CA, Veverka KA, Miller DD, Dalton JT: Pharmacodynamics of selective androgen receptor modulators. J Pharmacol Exp Ther. 2003 Mar;304(3):1334-40. Pubmed
Comments
Drug created on July 24, 2007 03:23 / Updated on December 27, 2010 10:22

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.