General
Preferred name
TESTOSTERONE UNDECANOATE
Synonyms
Restandol ()
TSX-011 ()
Jatenzo ()
Undestor ()
Aveed ()
Testosterone 17.beta.-undecylate ()
Kyzatrex ()
Testosterone undecylate ()
Tlando ()
MK-3033 ()
ORG-538 ()
Nebido ()
Andriol ()
Restandol Testocap ()
Testosterone, undecanoate (ester) ()
ORG 538 ()
P&D ID
PD012116
CAS
5949-44-0
Tags
prodrug
natural product
drug
available
Approved by
FDA
First approval
2014
Drug Status
investigational
approved
Drug indication
Hypogonadism
Max Phase
Phase 4
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
PHARMACODYNAMICS Testosterone plays a key role in male sexual differentiation and is involved in regulation of hematopoiesis, body composition, and bone metabolism. As a result, testosterone replacement therapy in males with hypogonadism can result in improved sexual function, increased lean body mass, bone density, erythropoiesis, prostate size, and changes in lipid profiles. [A176753]
MOA Testosterone is produced by Leydig cells and exerts it's effects by binding to androgen receptors throughout the body. [A176735] Testosterone affects the voice, genitalia, mood, and influences muscle growth and protein expression. [A176735] Accordingly, males with low levels of testosterone often experience decreased libido, fatigue, mood changes and dysphoria. [A176735] Exogenous sources of testosterone are designed to mimic the effects of endogenous testosterone.
INDICATION Testosterone undecanoate is indicated for replacement therapy in adult males with conditions that are linked with an absence or deficiency in endogenous testosterone production. [F4247][FDA Label]
ROE The majority (~90%) of an intramuscularly administered dose of testosterone is conjugated and eliminated in the urine. ; Approximately 6% of the dose is eliminated primarily unconjugated in the feces. [FDA Label]
TOXICITY There is evidence that in adolescent users, testosterone at supra-therapeutic levels may contribute to aggressive behaviour and increased rates of suicide. [A35939] However, testosterone does not appear to negatively affect cognition in adult men receiving testosterone replacement therapy and may in fact benefit cognitive function.[A35939] Administration of exogenous testosterone affects normal physiological hormonal regulation, and ultimately depresses the release of follicle-stimulating hormone and luteinizing hormone resulting in reduced sperm production.[A35939] This should be considered before initiating testosterone in males who wish to start or grow a family.[A35939] Increased levels of testosterone can also cause increased sebum production, therefore acne may be observed in patients taking exogenous testosterone.[A35939] Since testosterone is converted to estrogen in the body by aromatization, males taking testosterone replacement may experience gynecomastia and/or breast pain. [A35939]
METABOLISM The side chain of testosterone undecanoate is cleaved by non specific esterases when it enters circulation and the undecanoic acid side chain is metabolized by the beta-oxidation pathway. [A176882][FDA Label] The resulting Testosterone molecule is then metabolized to dihydrotestosterone (DHT) by the enzyme 5-alpha reductase. [F4307] DHT is reduced by 3-alpha-hydroxysteroid dehydrogenase (major) and 3-beta-hydroxysteroid dehydrogenase prior to being glucuronidated and cleared by the kidneys. [F4307] It should be noted that testosterone is metabolized to several other 17-keto steroids in the body. [FDA Label]
ABSORPTION The absorption of testosterone undecanoate varies based on the formulation. The intramuscular formulation of testosterone esters is suspended in oil and is absorbed from the lipid phase. Testosterone is released when tissue esterases cleave the undecanoic acid side chain. [F4247] ; The oral formulation of testosterone undecanoate is also formulated as a prodrug, is best absorbed with food and ideal absorption occurs when taken with a meal containing at least 30 g of fat. [FDA Label]
HALF-LIFE Based on one source, Testosterone undecanoate in castor oil (for intramuscular injection) has a half life of 33.9 days, allowing it to maintain serum levels in the normal range for over 6 weeks. [A176954] It should be noted that the half life of testosterone reported in the literature is inconsistent. [F4247]
Compound Sets
9
ChEMBL Approved Drugs
CHEMBL2107067
ChEMBL Drugs
CHEMBL2107067
DrugBank
DB13946
DrugBank Approved Drugs
DB13946
DrugCentral
2608
DrugCentral Approved Drugs
2608
DrugMAP
DMZO10Y
DrugMAP Approved Drugs
DMZO10Y
Natural product-based probes and drugs
External IDs
33
Properties
(calculated by RDKit )
Molecular Weight
456.36
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
0
Rotatable Bonds
10
Ring Count
4
Aromatic Ring Count
0
cLogP
7.96
TPSA
43.37
Fraction CSP3
0.87
Chiral centers
6.0
Largest ring
6.0
QED
0.25
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Biosynthetic Origin
Terpenoid (Steroid)
Therapeutic Indication
Hypogonadism
Therapeutic Class
Hormone Therapy
Source data