Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C40H52N2O4 |
Molecular Weight | 624.8519 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CC[C@H](OC(=O)CCCCCC)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(CC[C@]34C)=NNC(=O)C(O)(C5=CC=CC=C5)C6=CC=CC=C6
InChI
InChIKey=PTVXYACXDYZNID-CKORHOBASA-N
InChI=1S/C40H52N2O4/c1-4-5-6-13-18-36(43)46-35-22-21-33-32-20-19-30-27-31(23-25-38(30,2)34(32)24-26-39(33,35)3)41-42-37(44)40(45,28-14-9-7-10-15-28)29-16-11-8-12-17-29/h7-12,14-17,27,32-35,45H,4-6,13,18-26H2,1-3H3,(H,42,44)/b41-31-/t32-,33-,34-,35-,38-,39-/m0/s1
Molecular Formula | C40H52N2O4 |
Molecular Weight | 624.8519 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 1 |
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 |
---|---|---|---|---|
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 |
|
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 unknown | Homo sapiens population: healthy age: sex: food status: |
|
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 unknown | Homo sapiens population: healthy age: sex: food status: |
|
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 unknown | Homo sapiens |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
|
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 unknown | Homo sapiens population: healthy age: sex: food status: |
|
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 unknown | Homo sapiens population: healthy age: sex: food status: |
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 |
Doses
Dose | Population | Adverse 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%) Sources: Atherosclerosis (6.4%) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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
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 |
---|---|---|
Estradiol prevents and testosterone promotes Fas-dependent apoptosis in CD4+ Th2 cells by altering Bcl 2 expression. | 1999 |
|
Study on steroidal oximinoethers: synthesis and stereostructure by NMR spectroscopy. | 1999 Apr |
|
Antibody binding characteristics of geometrical isomers of testosterone 3-(O-carboxymethyl)oxime. | 1999 Mar |
|
Circadian expression of the steroid 15 alpha-hydroxylase (Cyp2a4) and coumarin 7-hydroxylase (Cyp2a5) genes in mouse liver is regulated by the PAR leucine zipper transcription factor DBP. | 1999 Oct |
|
Profiling neurosteroids in cerebrospinal fluids and plasma by gas chromatography/electron capture negative chemical ionization mass spectrometry. | 2000 Jan 15 |
|
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 |
|
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 |
|
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 |
|
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 |
|
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 |
|
Progressive decrease in bone density over 10 years of androgen deprivation therapy in patients with prostate cancer. | 2001 Jan |
|
Effects of hyperprolactinemia on rat prostate growth: evidence of androgeno-dependence. | 2001 Jan |
|
Effects of low-frequency magnetic fields on implantation in rats. | 2001 Jan-Feb |
|
Testosterone influences libido and well being in women. | 2001 Jan-Feb |
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
on
Edited
Sat Dec 16 00:17:02 GMT 2023
by
admin
on
Sat Dec 16 00:17:02 GMT 2023
|
Record UNII |
X8Z8A2G2Y4
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
SUB15494MIG
Created by
admin on Sat Dec 16 00:17:02 GMT 2023 , Edited by admin on Sat Dec 16 00:17:02 GMT 2023
|
PRIMARY | |||
|
76971566
Created by
admin on Sat Dec 16 00:17:02 GMT 2023 , Edited by admin on Sat Dec 16 00:17:02 GMT 2023
|
PRIMARY | |||
|
242-458-6
Created by
admin on Sat Dec 16 00:17:02 GMT 2023 , Edited by admin on Sat Dec 16 00:17:02 GMT 2023
|
PRIMARY | |||
|
100000077561
Created by
admin on Sat Dec 16 00:17:02 GMT 2023 , Edited by admin on Sat Dec 16 00:17:02 GMT 2023
|
PRIMARY | |||
|
X8Z8A2G2Y4
Created by
admin on Sat Dec 16 00:17:02 GMT 2023 , Edited by admin on Sat Dec 16 00:17:02 GMT 2023
|
PRIMARY | |||
|
DB13947
Created by
admin on Sat Dec 16 00:17:02 GMT 2023 , Edited by admin on Sat Dec 16 00:17:02 GMT 2023
|
PRIMARY | |||
|
18625-33-7
Created by
admin on Sat Dec 16 00:17:02 GMT 2023 , Edited by admin on Sat Dec 16 00:17:02 GMT 2023
|
PRIMARY | |||
|
Testosterone enantate benzilic acid hydrazone
Created by
admin on Sat Dec 16 00:17:02 GMT 2023 , Edited by admin on Sat Dec 16 00:17:02 GMT 2023
|
PRIMARY | |||
|
DTXSID001117610
Created by
admin on Sat Dec 16 00:17:02 GMT 2023 , Edited by admin on Sat Dec 16 00:17:02 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |