Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C19H28O2 |
Molecular Weight | 288.4244 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)CC[C@]34C)[C@@H]1CC[C@@H]2O
InChI
InChIKey=MUMGGOZAMZWBJJ-DYKIIFRCSA-N
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1
Molecular Formula | C19H28O2 |
Molecular Weight | 288.4244 |
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 | |||
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no | |||
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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 |
|
Profiling neurosteroids in cerebrospinal fluids and plasma by gas chromatography/electron capture negative chemical ionization mass spectrometry. | 2000 Jan 15 |
|
Estrogen activation of the nuclear orphan receptor CAR (constitutive active receptor) in induction of the mouse Cyp2b10 gene. | 2000 Nov |
|
Psychophysiological responses to the Stroop Task after a maximal cycle ergometry in elite sportsmen and physically active subjects. | 2001 Feb |
|
Interactions among paternal behavior, steroid hormones, and parental experience in male marmosets (Callithrix kuhlii). | 2001 Feb |
|
cDNA cloning and initial characterization of CYP3A43, a novel human cytochrome P450. | 2001 Feb |
|
Modulation of P450 CYP3A4-dependent metabolism by P-glycoprotein: implications for P450 phenotyping. | 2001 Feb |
|
Claudin-1 is not restricted to tight junctions in the rat epididymis. | 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 |
|
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 |
|
Estrogen and androgen elicit growth hormone release via dissimilar patterns of hypothalamic neuropeptide secretion. | 2001 Feb |
|
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results. | 2001 Feb |
|
Luteinizing hormone-dependent activity and luteinizing hormone-independent differentiation of rat fetal Leydig cells. | 2001 Feb 14 |
|
Androgenic anabolic steroids and arterial structure and function in male bodybuilders. | 2001 Jan |
|
Targeted disruption of luteinizing hormone/human chorionic gonadotropin receptor gene. | 2001 Jan |
|
Glucocorticoids regulate plasma membrane potential during rat thymocyte apoptosis in vivo and in vitro. | 2001 Jan |
|
Differential effects of dexamethasone treatment on lipopolysaccharide-induced testicular inflammation and reproductive hormone inhibition in adult rats. | 2001 Jan |
|
Regulation of cytochrome P450 aromatase gene expression in adult rat Leydig cells: comparison with estradiol production. | 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 |
|
Side of ovulation, hormones and sex ratios. | 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 |
|
Effects of testosterone on production of perivitelline membrane glycoprotein ZPC by granulosa cells of Japanese quail (Coturnix japonica). | 2001 Jan |
|
Sex steroid hormones enhance immune function in male and female Siberian hamsters. | 2001 Jan |
|
Rapid and reversible inhibition of brain aromatase activity. | 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 |
|
Anorexia, body composition, and ageing. | 2001 Jan |
|
Effects of hyperprolactinemia on rat prostate growth: evidence of androgeno-dependence. | 2001 Jan |
|
Chlorinated hydrocarbons and biomarkers of exposure in wading birds and fish of the lower Rio Grande Valley, Texas. | 2001 Jan |
|
Novel approaches to female sexual dysfunction. | 2001 Jan |
|
Androgen receptors in cranial nerve motor nuclei of male and female rats. | 2001 Jan |
|
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase. | 2001 Jan 22 |
|
Testosterone modulates the dendritic architecture of arcuate neuroendocrine neurons in adult male rats. | 2001 Jan 26 |
|
Reproductive effects of valproate, carbamazepine, and oxcarbazepine in men with epilepsy. | 2001 Jan 9 |
|
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
on
Edited
Mon Mar 31 17:52:50 GMT 2025
by
admin
on
Mon Mar 31 17:52:50 GMT 2025
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Record UNII |
3XMK78S47O
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
52590
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LOINC |
49043-3
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NDF-RT |
N0000175824
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LOINC |
2990-0
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LOINC |
76352-4
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LOINC |
2986-8
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WHO-VATC |
QG03EA02
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LOINC |
34380-6
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LOINC |
83116-4
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LOINC |
59229-5
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LOINC |
25987-9
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EMA ASSESSMENT REPORTS |
LIVENSA (SEXUAL DYSFUNCTIONS, PSYCHOLOGICAL )
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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LOINC |
26827-6
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admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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LIVERTOX |
944
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LOINC |
26826-8
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CFR |
21 CFR 862.1680
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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LOINC |
2987-6
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admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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NCI_THESAURUS |
C2298
Created by
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NDF-RT |
N0000008241
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LOINC |
2993-4
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LOINC |
49041-7
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LOINC |
2994-2
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LOINC |
13486-6
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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FDA ORPHAN DRUG |
104197
Created by
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LOINC |
35225-2
Created by
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LOINC |
49042-5
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LOINC |
59240-2
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admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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FDA ORPHAN DRUG |
523916
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LOINC |
59233-7
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FDA ORPHAN DRUG |
855921
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WHO-VATC |
QG03BA03
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LOINC |
2988-4
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LOINC |
16286-7
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WIKIPEDIA |
Designer-drugs-Testosterone
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LOINC |
15095-3
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LOINC |
31030-0
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WHO-ATC |
G03EA02
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WHO-ATC |
G03BA03
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LOINC |
73570-4
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2984-3
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15432-8
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LOINC |
2991-8
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14914-6
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41018-3
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35224-5
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LOINC |
2992-6
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17685-9
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LOINC |
59219-6
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EMA ASSESSMENT REPORTS |
INTRINSA (WITHDRAWN: SEXUAL DYSFUNCTIONS, PSYCHOLOGICAL)
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LOINC |
48357-8
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FDA ORPHAN DRUG |
94595
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LOINC |
10631-0
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LOINC |
51005-7
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WHO-ESSENTIAL MEDICINES LIST |
18.2
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LOINC |
27306-0
Created by
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CFR |
21 CFR 862.1430
Created by
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LOINC |
70239-9
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CFR |
21 CFR 310.528
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LOINC |
70240-7
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LOINC |
15094-6
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LOINC |
2985-0
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LOINC |
2989-2
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LOINC |
6891-6
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LOINC |
83115-6
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LOINC |
14913-8
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LOINC |
17687-5
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DEA NO. |
4000
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LOINC |
25986-1
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NDF-RT |
N0000000146
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Code System | Code | Type | Description | ||
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3XMK78S47O
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PRIMARY | |||
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9700
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17347
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200-370-5
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TESTOSTERONE
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PRIMARY | |||
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58-22-0
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admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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D013739
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admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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3398
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admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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2858
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admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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DB00624
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admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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1900
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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C862
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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3XMK78S47O
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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1646009
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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6013
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admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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Testosterone (medication)
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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100000089191
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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CHEMBL386630
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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Testosterone
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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DTXSID8022371
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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10379
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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SUB10937MIG
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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2607
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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m10594
Created by
admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
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PRIMARY | Merck Index |
Related Record | Type | Details | ||
---|---|---|---|---|
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TRANSPORTER -> INHIBITOR | |||
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ENZYME->SUBSTRATE |
Vmax
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METABOLIC ENZYME -> SUBSTRATE | |||
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TARGET -> INHIBITOR |
BINDING
IC50
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METABOLIC ENZYME -> SUBSTRATE |
Related Record | Type | Details | ||
---|---|---|---|---|
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METABOLITE -> PARENT |
In reproductive tissues, dihydrotestosterone is further metabolized to 3-alpha and 3-beta androstanediol
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PRODRUG -> METABOLITE ACTIVE |
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METABOLITE TOXIC -> PARENT |
Metabolite shown to induce pyrogenic and inflammatory reactions in man.
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PARENT -> METABOLITE |
URINE
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METABOLITE ACTIVE -> PARENT |
DHT binds with greater affinity to SHBG than does testosterone
MAJOR
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METABOLITE -> PARENT |
In reproductive tissues, dihydrotestosterone is further metabolized to 3-alpha and 3-beta androstanediol
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METABOLITE -> PARENT |
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PRODRUG -> METABOLITE ACTIVE |
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PRODRUG -> METABOLITE ACTIVE | |||
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PRODRUG -> METABOLITE ACTIVE |
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||
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PRODRUG -> METABOLITE ACTIVE | |||
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METABOLITE ACTIVE -> PARENT | |||
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METABOLITE -> PARENT |
URINE
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METABOLITE -> PARENT |
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||
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METABOLITE -> PARENT |
By glucuronosyl transferase (UGT)
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Related Record | Type | Details | ||
---|---|---|---|---|
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
EP
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||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (TLC)
EP
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||
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
---|---|---|---|---|
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ACTIVE MOIETY |
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