U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C30H48O3
Molecular Weight 456.7003
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TESTOSTERONE UNDECANOATE

SMILES

[H][C@@]12CC[C@H](OC(=O)CCCCCCCCCC)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C

InChI

InChIKey=UDSFVOAUHKGBEK-CNQKSJKFSA-N
InChI=1S/C30H48O3/c1-4-5-6-7-8-9-10-11-12-28(32)33-27-16-15-25-24-14-13-22-21-23(31)17-19-29(22,2)26(24)18-20-30(25,27)3/h21,24-27H,4-20H2,1-3H3/t24-,25-,26-,27-,29-,30-/m0/s1

HIDE SMILES / InChI

Molecular Formula C30H48O3
Molecular Weight 456.7003
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: Description was created based on several sources, including

Testosterone is a steroid sex hormone found in both men and women. In men, testosterone is produced primarily by the Leydig (interstitial) cells of the testes when stimulated by luteinizing hormone (LH). It functions to stimulate spermatogenesis, promote physical and functional maturation of spermatozoa, maintain accessory organs of the male reproductive tract, support development of secondary sexual characteristics, stimulate growth and metabolism throughout the body and influence brain development by stimulating sexual behaviors and sexual drive. In women, testosterone is produced by the ovaries (25%), adrenals (25%) and via peripheral conversion from androstenedione (50%). Testerone in women functions to maintain libido and general wellbeing. Testosterone exerts a negative feedback mechanism on pituitary release of LH and follicle-stimulating hormone (FSH). Testosterone may be further converted to dihydrotestosterone or estradiol depending on the tissue. 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. Testosterone is used as hormone replacement or substitution of diminished or absent endogenous testosterone. Use in males: For management of congenital or acquired hypogonadism, hypogonadism associated with HIV infection, and male climacteric (andopause). Use in females: For palliative treatment of androgen-responsive, advanced, inoperable, metastatis (skeletal) carcinoma of the breast in women who are 1-5 years postmenopausal; testosterone esters may be used in combination with estrogens in the management of moderate to severe vasomotor symptoms associated with menopause in women who do not respond to adequately to estrogen therapy alone.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: P10275
Gene ID: 367.0
Gene Symbol: AR
Target Organism: Homo sapiens (Human)
3.16 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TESTOSTERONE

Approved Use

Testosterone is an androgen indicated for replacement therapy in males for conditions associated with a deficiency or absence of endogenous testosterone: • Primary Hypogonadism (Congenital or Acquired) (1) • Hypogonadotropic Hypogonadism (Congenital or Acquired)

Launch Date

2013
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
13.1 pg/mL
8.2 mg single, topical
dose: 8.2 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
TESTOSTERONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
214 ng/dL
30 mg single, topical
dose: 30 mg
route of administration: topical
experiment type: single
co-administered:
TESTOSTERONE unknown
Homo sapiens
population: healthy
age:
sex:
food status:
231 ng/dL
30 mg single, topical
dose: 30 mg
route of administration: topical
experiment type: single
co-administered:
TESTOSTERONE unknown
Homo sapiens
population: healthy
age:
sex:
food status:
930.1 ng/dL
5 g 1 times / day multiple, topical
dose: 5 g
route of administration: topical
experiment type: multiple
co-administered:
TESTOSTERONE unknown
Homo sapiens
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
948 pg × h/mL
8.2 mg single, topical
dose: 8.2 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
TESTOSTERONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
2120 ng*h/dL
30 mg single, topical
dose: 30 mg
route of administration: topical
experiment type: single
co-administered:
TESTOSTERONE unknown
Homo sapiens
population: healthy
age:
sex:
food status:
3110 ng*h/dL
30 mg single, topical
dose: 30 mg
route of administration: topical
experiment type: single
co-administered:
TESTOSTERONE unknown
Homo sapiens
population: healthy
age:
sex:
food status:
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
8.2 mg single, topical
dose: 8.2 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
TESTOSTERONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
13%
8.2 mg single, topical
dose: 8.2 mg
route of administration: Topical
experiment type: SINGLE
co-administered:
TESTOSTERONE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
75 mg 1 times / day steady, subcutaneous (median)
Recommended
Dose: 75 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 75 mg, 1 times / day
Sources:
unhealthy, adult
n = 150
Health Status: unhealthy
Condition: hypogonadism
Age Group: adult
Sex: M
Population Size: 150
Sources:
Disc. AE: Hypertension...
AEs leading to
discontinuation/dose reduction:
Hypertension (5.6%)
Sources:
100 mg 1 times / day steady, topical
Recommended
Dose: 100 mg, 1 times / day
Route: topical
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy, mean 74 years
n = 106
Health Status: unhealthy
Condition: with limitations in mobility
Age Group: mean 74 years
Sex: M
Population Size: 106
Sources:
Other AEs: Cardiac disorders, Atherosclerosis...
Other AEs:
Cardiac disorders (6.5%)
Atherosclerosis (6.4%)
Sources:
AEs

AEs

AESignificanceDosePopulation
Hypertension 5.6%
Disc. AE
75 mg 1 times / day steady, subcutaneous (median)
Recommended
Dose: 75 mg, 1 times / day
Route: subcutaneous
Route: steady
Dose: 75 mg, 1 times / day
Sources:
unhealthy, adult
n = 150
Health Status: unhealthy
Condition: hypogonadism
Age Group: adult
Sex: M
Population Size: 150
Sources:
Atherosclerosis 6.4%
100 mg 1 times / day steady, topical
Recommended
Dose: 100 mg, 1 times / day
Route: topical
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy, mean 74 years
n = 106
Health Status: unhealthy
Condition: with limitations in mobility
Age Group: mean 74 years
Sex: M
Population Size: 106
Sources:
Cardiac disorders 6.5%
100 mg 1 times / day steady, topical
Recommended
Dose: 100 mg, 1 times / day
Route: topical
Route: steady
Dose: 100 mg, 1 times / day
Sources:
unhealthy, mean 74 years
n = 106
Health Status: unhealthy
Condition: with limitations in mobility
Age Group: mean 74 years
Sex: M
Population Size: 106
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

Drug as perpetrator​Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
major [Km 10 uM]
major [Km 38.7 uM]
minor
minor
minor
minor
minor
minor
minor
minor
no
no
no
no
no
no
no
no
yes
yes
yes
yes
PubMed

PubMed

TitleDatePubMed
Effects of estrogenic (o,p'-DDT; octylphenol) and anti-androgenic (p,p'-DDE) chemicals on indicators of endocrine status in juvenile male summer flounder (Paralichthys dentatus).
2001 Apr
Psychophysiological responses to the Stroop Task after a maximal cycle ergometry in elite sportsmen and physically active subjects.
2001 Feb
Spz1, a novel bHLH-Zip protein, is specifically expressed in testis.
2001 Feb
Effects of the anti-androgen finasteride on the modulatory actions of oestradiol on androgen metabolism by human gingival fibroblasts.
2001 Feb
Androgens and the role of female "hyperaggressiveness" in spotted hyenas (Crocuta crocuta).
2001 Feb
Interactions among paternal behavior, steroid hormones, and parental experience in male marmosets (Callithrix kuhlii).
2001 Feb
Castration in Gambel's and Scaled Quail: ornate plumage and dominance persist, but courtship and threat behaviors do not.
2001 Feb
cDNA cloning and initial characterization of CYP3A43, a novel human cytochrome P450.
2001 Feb
Claudin-1 is not restricted to tight junctions in the rat epididymis.
2001 Feb
Relative enzymatic activity, protein stability, and tissue distribution of human steroid-metabolizing UGT2B subfamily members.
2001 Feb
Effects of organic solvents on the activities of cytochrome P450 isoforms, UDP-dependent glucuronyl transferase, and phenol sulfotransferase in human hepatocytes.
2001 Feb
Performance characteristics of a carbon isotope ratio method for detecting doping with testosterone based on urine diols: controls and athletes with elevated testosterone/epitestosterone ratios.
2001 Feb
Photoperiod-induced testicular apoptosis in European starlings (Sturnus vulgaris).
2001 Feb
Neuroendocrine regulation of sexually dimorphic brain structure and associated sexual behavior in male rats is genetically controlled.
2001 Feb
Influence of the degree of stimulation of the pituitary by gonadotropin-releasing hormone on the action of inhibin and testosterone to suppress the secretion of the gonadotropins in rams.
2001 Feb
Follicular-fluid factors and granulosa-cell gene expression associated with follicle deviation in cattle.
2001 Feb
Plasma melatonin concentration before and during testosterone replacement in Klinefelter's syndrome: relation to hepatic indolamine metabolism and sympathoadrenal activity.
2001 Feb
Longitudinal effects of aging on serum total and free testosterone levels in healthy men. Baltimore Longitudinal Study of Aging.
2001 Feb
Evidence that cyproterone acetate improves psychological symptoms and enhances the activity of the dopaminergic system in postmenopause.
2001 Feb
Androgen deficiency in women with hypopituitarism.
2001 Feb
Muting of androgen negative feedback unveils impoverished gonadotropin-releasing hormone/luteinizing hormone secretory reactivity in healthy older men.
2001 Feb
Polycystic ovary syndrome is associated with obstructive sleep apnea and daytime sleepiness: role of insulin resistance.
2001 Feb
Disparate response of wild-type and variant forms of LH to GnRH stimulation in individuals heterozygous for the LHbeta variant allele.
2001 Feb
Estrogen and androgen elicit growth hormone release via dissimilar patterns of hypothalamic neuropeptide secretion.
2001 Feb
Neuronal size in the spinal nucleus of the bulbocavernosus: direct modulation by androgen in rats with mosaic androgen insensitivity.
2001 Feb 1
Luteinizing hormone-dependent activity and luteinizing hormone-independent differentiation of rat fetal Leydig cells.
2001 Feb 14
Porcine gonadal and placental isozymes of aromatase cytochrome P450: sub-cellular distribution and support by NADPH-cytochrome P450 reductase.
2001 Feb 14
Changes in androgenic steroid profile due to urine contamination by microorganisms: a prospective study in the context of doping control.
2001 Feb 15
Progressive decrease in bone density over 10 years of androgen deprivation therapy in patients with prostate cancer.
2001 Jan
Long-term remission of ovarian hyperandrogenism after short-term treatment with a gonadotropin-releasing hormone agonist.
2001 Jan
Prevalence of polycystic ovary syndrome (PCOS) in first-degree relatives of patients with PCOS.
2001 Jan
Concentrations of steroid hormones in layers and biopsies of chelonian egg yolks.
2001 Jan
Insulin action and insulin secretion in polycystic ovary syndrome treated with ethinyl oestradiol/cyproterone acetate.
2001 Jan
Differential effects of dexamethasone treatment on lipopolysaccharide-induced testicular inflammation and reproductive hormone inhibition in adult rats.
2001 Jan
Testosterone-induced inhibition of spermatogenesis is more closely related to suppression of FSH than to testicular androgen levels in the cynomolgus monkey model (Macaca fascicularis).
2001 Jan
On call. I know that men have more heart disease than women and that athletes who use steroids can have heart attacks. Are male hormones responsible for heart disease in ordinary men like me?
2001 Jan
Induction of nuclear transcription factors, cytochrome P450 monooxygenases, and glutathione S-transferase alpha gene expression in Aroclor 1254-treated rat hepatocyte cultures.
2001 Jan 15
Cross-talk between steroid-receptor-mediated and cell-membrane-receptor-mediated signalling pathways results in the in vivo modulation of c-Met and ornithine decarboxylase gene expression in mouse kidney.
2001 Jan 15
Expression of the 17beta-hydroxysteroid dehydrogenase type 5 mRNA in the human brain.
2001 Jan 22
Distribution of 17beta-hydroxysteroid dehydrogenases in human osteoblast-like cells.
2001 Jan 22
Phytoestrogens inhibit human 17beta-hydroxysteroid dehydrogenase type 5.
2001 Jan 22
Structure-function aspects and inhibitor design of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3).
2001 Jan 22
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase.
2001 Jan 22
Pan1b (17betaHSD11)-enzymatic activity and distribution in the lung.
2001 Jan 22
17beta-Hydroxysteroid dehydrogenase type 9 and other short-chain dehydrogenases/reductases that catalyze retinoid, 17beta- and 3alpha-hydroxysteroid metabolism.
2001 Jan 22
Type 5 17beta-hydroxysteroid dehydrogenase: its role in the formation of androgens in women.
2001 Jan 22
Sex difference in the phosphorylation of cAMP response element binding protein (CREB) in neonatal rat brain.
2001 Jan 26
Testosterone modulates the dendritic architecture of arcuate neuroendocrine neurons in adult male rats.
2001 Jan 26
Effects of low-frequency magnetic fields on implantation in rats.
2001 Jan-Feb
Testosterone influences libido and well being in women.
2001 Jan-Feb
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: can also be injected https://www.drugs.com/pro/testosterone.html
Starting dose of testosterone gel is 50 mg of testosterone (4 pump actuations, two 25 mg packets, or one 50 mg packet), applied once daily in the morning.
Route of Administration: Topical
10 nM Testosterone significantly reduced secretion of BDNF in in human airway smooth muscle
Substance Class Chemical
Created
by admin
on Sat Dec 16 05:14:20 GMT 2023
Edited
by admin
on Sat Dec 16 05:14:20 GMT 2023
Record UNII
H16A5VCT9C
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TESTOSTERONE UNDECANOATE
MI   USAN   VANDF   WHO-DD  
USAN  
Official Name English
TESTOSTERONE UNDECYLATE [MART.]
Common Name English
TLANDO
Brand Name English
TESTOSTERONE UNDECANOATE [VANDF]
Common Name English
ORG 538
Code English
ORG-538
Code English
Testosterone undecanoate [WHO-DD]
Common Name English
Androst-4-en-3-one, 17-[(1-oxoundecyl)oxy]-(17β)
Common Name English
TESTOSTERONE UNDECANOATE [MI]
Common Name English
3-OXOANDROST-4-EN-17.BETA.-YL UNDECANOATE
Systematic Name English
TESTOSTERONE, UNDECANOATE (ESTER)
Common Name English
TSX-011
Code English
TESTOSTERONE UNDECYLATE
MART.  
Common Name English
17.BETA.-HYDROXYANDROST-4-EN-3-ONE UNDECANOATE
Common Name English
ANDRIOL
Brand Name English
TESTOSTERONE 17.BETA.-UNDECYLATE
Common Name English
(17.BETA.)-17-HYDROXYANDROST-4-EN-3-ONE UNDECANOATE
Common Name English
.DELTA.(SUP 4)-ANDROSTEN-17.BETA.-OL-3-ONE UNDECANOATE
Common Name English
TESTOSTERONE UNDECANOATE [ORANGE BOOK]
Common Name English
AVEED
Brand Name English
TESTOSTERONE UNDECANOATE [USAN]
Common Name English
NEBIDO
Brand Name English
MK-3033
Code English
JATENZO
Brand Name English
KYZATREX
Brand Name English
Classification Tree Code System Code
NCI_THESAURUS C862
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
FDA ORPHAN DRUG 366012
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID90863661
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
RXCUI
37864
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY RxNorm
SMS_ID
100000089009
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
NCI_THESAURUS
C1249
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
MESH
C010792
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
EVMPD
SUB04744MIG
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
USAN
PP-70
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
DRUG CENTRAL
2608
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
FDA UNII
H16A5VCT9C
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
DRUG BANK
DB13946
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
MERCK INDEX
m10594
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY Merck Index
PUBCHEM
65157
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
ChEMBL
CHEMBL2107067
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
DAILYMED
H16A5VCT9C
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
ECHA (EC/EINECS)
227-712-6
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
CAS
5949-44-0
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
WIKIPEDIA
TESTOSTERONE UNDECANOATE
Created by admin on Sat Dec 16 05:14:20 GMT 2023 , Edited by admin on Sat Dec 16 05:14:20 GMT 2023
PRIMARY
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