General
Preferred name
TESTOSTERONE ENANTHATE
Synonyms
testosterone enantate ()
delta6-Testosterone Enanthate ()
Testosteroni enantas ()
Androtardyl ()
Testosterone enanthate component of ditate-ds ()
Primoteston Depot ()
Delatestryl ()
Xyosted (autoinjector) ()
NSC-17591 ()
Testosterone enanthate ciii ()
Xyosted ()
P&D ID
PD071733
CAS
315-37-7
11111-10-7
Tags
available
prodrug
drug
Approved by
FDA
First approval
1953
Drug Status
approved
Max Phase
4.0
Drug indication
metastatic prostate cancer
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
MOA 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 androgen effects.[A950]; ; Such activities are useful as endogenous androgens like testosterone and dihydrotestosterone are responsible for the normal growth and development of the male sex organs and for maintenance of secondary sex characteristics [F1941]. These effects include the growth and maturation of the prostate, seminal vesicles, penis, and scrotum; the development of male hair distribution, such as facial, pubic, chest, and axillary hair; laryngeal enlargement, vocal cord thickening, and alterations in body musculature and fat distribution [F1941].; ; Male hypogonadism, a clinical syndrome resulting from insufficient secretion of testosterone, has two main etiologies [F1941]. Primary hypogonadism is caused by defects of the gonads, such as Klinefelter’s syndrome or Leydig cell aplasia, whereas secondary hypogonadism is the failure of the hypothalamus (or pituitary) to produce sufficient gonadotropins (FSH, LH) [F1941].
INDICATION Testosterone enanthate in males is indicated as a replacement therapy in conditions associated with a deficiency or absence of endogenous testosterone. Some of the treated conditions are 1) primary hypogonadism, defined as testicular failure due to cryptorchidism, bilateral torsion, orchitis, vanishing testis syndrome or orchidectomy; 2) hypogonadotropic hypogonadism due to an idiopathic gonadotropin or luteinizing hormone-releasing hormone deficiency or due to a pituitary-hypothalamic injury from tumors, trauma or radiation, in this case it is important to accompany the treatment with adrenal cortical and thyroid hormone replacement therapy; 3) to stimulate puberty in patients with delayed puberty not secondary to a pathological disorder. If the conditions 1 and 2 occur prior to puberty, the androgen replacement therapy will be needed during adolescent years for the development of secondary sexual characteristics and prolonged androgen treatment might be needed it to maintain sexual characteristics after puberty.[FDA label]; ; In females, testosterone enanthate is indicated to be used secondarily in presence of advanced inoperable metastatic mammary cancer in women who are from one to five years postmenopausal. It has also been used in premenopausal women with breast cancer who have benefited from oophorectomy and are considered to have a hormone-responsive tumor.[FDA label]; ; Testosterone enanthate injections that are currently formulated for subcutaneous use are specifically indicated only for primary hypogonadism and hypogonadotropic hypogonadism [F1941]. The use of such formulations is limited because the safety and efficacy of these subcutaneous products in adult males with late-onset hypogonadism and males less than 18 years old have not yet been established [F1941]. Moreover, subcutaneously administered testosterone enanthate is indicated only for the treatment of men with hypogonadal conditions associated with structural or genetic etiologies, considering the medication could cause blood pressure increases that can raise the risk of major adverse cardiovascular events like non-fatal myocardial infarction, non-fatal stroke, and cardiovascular death [F1941].
TOXICITY Testosterone enanthate has been tested in preclinical carcinogenesis trials. In this studies, it is suggested that the exposure to this drug may increase the susceptibility to hematoma as well as the number of tumors and decrease the degree of differentiation of chemically induced carcinomas of the liver.[FDA label]; ; Testosterone enanthate is not indicated for use in females and is contraindicated in pregnant women. Testosterone is teratogenic and may cause fetal harm when administered to a pregnant woman based on data from animal studies and its mechanism of action. [F1941]; ; During treatment with large doses of exogenous androgens, including testosterone enanthate, spermatogenesis may be suppressed through feedback inhibition of the hypothalamic-pituitary-testicular axis [F1941]. Reduced fertility is observed in some men taking testosterone replacement therapy and the impact on fertility may be irreversible [F1941].; ; Safety and effectiveness of testosterone enanthate in pediatric patients less than 18 years old have not been established [F1941]. Improper use may result in the acceleration of bone age and premature closure of epiphyses [F1941].; ; Geriatric patients treated with androgens may also be at risk for worsening of signs and symptoms of Benign Prostatic Hyperplasia [F1941].
Compound Sets
8
Cayman Chemical Bioactives
22546
ChEMBL Approved Drugs
CHEMBL1200335
ChEMBL Drugs
CHEMBL1200335
DrugBank
DB13944
DrugBank Approved Drugs
DB13944
DrugCentral
4609
DrugCentral Approved Drugs
4609
ReFrame library
External IDs
37
Properties
(calculated by RDKit )
Molecular Weight
400.3
Hydrogen Bond Acceptors
3
Hydrogen Bond Donors
0
Rotatable Bonds
6
Ring Count
4
Aromatic Ring Count
0
cLogP
6.4
TPSA
43.37
Fraction CSP3
0.85
Chiral centers
6.0
Largest ring
6.0
QED
0.38
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Source data