Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C35H58O3 |
Molecular Weight | 526.8332 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCCC(=O)O[C@H]1CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3CC[C@]12C
InChI
InChIKey=OKFBXYQPCPWWRP-SHDAAXGTSA-N
InChI=1S/C35H58O3/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-33(37)38-32-21-20-30-29-19-18-27-26-28(36)22-24-34(27,2)31(29)23-25-35(30,32)3/h26,29-32H,4-25H2,1-3H3/t29-,30-,31-,32-,34-,35-/m0/s1
Molecular Formula | C35H58O3 |
Molecular Weight | 526.8332 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB00624Curator's Comment: Description was created based on several sources, including
Sources: http://www.drugbank.ca/drugs/DB00624
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.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: P10275 Gene ID: 367.0 Gene Symbol: AR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17635942 |
|||
Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19856921 |
3.16 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | TESTOSTERONE Approved UseTestosterone 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 Date2013 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
930.1 ng/dL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01386606 |
5 g 1 times / day multiple, topical dose: 5 g route of administration: topical experiment type: multiple co-administered: |
TESTOSTERONE plasma | Homo sapiens |
|
231 ng/dL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01725451 |
30 mg single, topical dose: 30 mg route of administration: topical experiment type: single co-administered: |
TESTOSTERONE serum | Homo sapiens population: healthy age: sex: food status: |
|
214 ng/dL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01725451 |
30 mg single, topical dose: 30 mg route of administration: topical experiment type: single co-administered: |
TESTOSTERONE serum | Homo sapiens population: healthy age: sex: food status: |
|
13.1 pg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10902784/ |
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 |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3110 ng*h/dL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01725451 |
30 mg single, topical dose: 30 mg route of administration: topical experiment type: single co-administered: |
TESTOSTERONE serum | Homo sapiens population: healthy age: sex: food status: |
|
2120 ng*h/dL Clinical Trial https://clinicaltrials.gov/ct2/show/NCT01725451 |
30 mg single, topical dose: 30 mg route of administration: topical experiment type: single co-administered: |
TESTOSTERONE serum | Homo sapiens population: healthy age: sex: food status: |
|
948 pg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10902784/ |
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 |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10902784/ |
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
13% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/10902784/ |
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 |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
no | |||
Page: - |
no | |||
Page: - |
no | |||
Page: - |
yes | |||
Page: - |
yes |
Drug as victim
PubMed
Title | Date | PubMed |
---|---|---|
Allelic variants of human cytochrome P450 1A1 (CYP1A1): effect of T461N and I462V substitutions on steroid hydroxylase specificity. | 2000 Aug |
|
Low-dose transdermal testosterone therapy improves angina threshold in men with chronic stable angina: A randomized, double-blind, placebo-controlled study. | 2000 Oct 17 |
|
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 |
|
Androgens and the role of female "hyperaggressiveness" in spotted hyenas (Crocuta crocuta). | 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 |
|
Photoperiod-induced testicular apoptosis in European starlings (Sturnus vulgaris). | 2001 Feb |
|
Substitution mutation C268Y causes 17 beta-hydroxysteroid dehydrogenase 3 deficiency. | 2001 Feb |
|
Sex differences in androgen receptors of the human mamillary bodies are related to endocrine status rather than to sexual orientation or transsexuality. | 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 |
|
Polycystic ovary syndrome is associated with obstructive sleep apnea and daytime sleepiness: role of insulin resistance. | 2001 Feb |
|
Luteinizing hormone-dependent activity and luteinizing hormone-independent differentiation of rat fetal Leydig cells. | 2001 Feb 14 |
|
Glucocorticoids regulate plasma membrane potential during rat thymocyte apoptosis in vivo and in vitro. | 2001 Jan |
|
Identification of twelve O-glycosylation sites in equine chorionic gonadotropin beta and equine luteinizing hormone ss by solid-phase Edman degradation. | 2001 Jan |
|
Androgen-dependent regulation of human angiotensinogen expression in KAP-hAGT transgenic mice. | 2001 Jan |
|
Influence of gender and sex hormones on nicotine acute pharmacological effects in mice. | 2001 Jan |
|
Heat-shock factor-1, steroid hormones, and regulation of heat-shock protein expression in the heart. | 2001 Jan |
|
Effects of hyperprolactinemia on rat prostate growth: evidence of androgeno-dependence. | 2001 Jan |
|
Signs of sexual behaviour are not increased after subchronic treatment with LHRH in young men. | 2001 Jan |
|
Structure-function aspects and inhibitor design of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3). | 2001 Jan 22 |
|
Pan1b (17betaHSD11)-enzymatic activity and distribution in the lung. | 2001 Jan 22 |
|
Regulation of the steroid-inducible 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase gene in Comamonas testosteroni. | 2001 Mar 30 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26566264
10 nM Testosterone significantly reduced secretion of BDNF in in human airway smooth muscle
Substance Class |
Chemical
Created
by
admin
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Edited
Mon Mar 31 18:10:52 GMT 2025
by
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Record UNII |
UV7U6AQ9KP
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Record Status |
Validated (UNII)
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DTXSID00912871
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METABOLITE ACTIVE -> PRODRUG |
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ACTIVE MOIETY |
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