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

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
Structure of TESTOSTERONE

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

HIDE SMILES / InChI

Molecular Formula C19H28O2
Molecular Weight 288.4244
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
3.16 nM [EC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TESTOSTERONE
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
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
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
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
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
Testosterone concentrations in women aged 25-50 years: associations with lifestyle, body composition, and ovarian status.
2001 Feb 1
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
Androgenic anabolic steroids and arterial structure and function in male bodybuilders.
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
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
Reproductive effects of valproate, carbamazepine, and oxcarbazepine in men with epilepsy.
2001 Jan 9
Patents

Sample Use Guides

In Vivo Use Guide
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
10 nM Testosterone significantly reduced secretion of BDNF in in human airway smooth muscle
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:19:19 UTC 2019
Edited
by admin
on Mon Oct 21 20:19:19 UTC 2019
Record UNII
3XMK78S47O
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TESTOSTERONE
EMA EPAR   EP   HSDB   INCI   INN   JAN   MART.   MI   ORANGE BOOK   USP   VANDF   WHO-DD  
INN   INCI  
Official Name English
TESTOSTERONE [JAN]
Common Name English
TESTOSTERONE [MART.]
Common Name English
ANDROST-4-EN-3-ONE, 17-HYDROXY-, (17.BETA.)-
Systematic Name English
TESTOSTERONE ENANTATE IMPURITY D [EP]
Common Name English
INTRINSA
Brand Name English
ANDROGEL
Brand Name English
TESTOSTERONE [GREEN BOOK]
Common Name English
TESTOSTERONE [WHO-DD]
Common Name English
ANDROID-T
Brand Name English
TESTOSTERONE [EP]
Common Name English
LIVENSA
Brand Name English
TESTOSTERONE [ORANGE BOOK]
Common Name English
TESTOSTERONE [HSDB]
Common Name English
TESTOSTERONE [EMA EPAR]
Common Name English
NSC-9700
Code English
TESTIM
Code English
VOGELXO
Brand Name English
TESTOSTERONE PROPIONATE IMPURITY C [EP]
Common Name English
TESTOSTERONE [INCI]
Common Name English
ANDROLAN
Brand Name English
17.BETA.-HYDROXYANDROST-4-EN-3-ONE
Systematic Name English
NATESTO
Brand Name English
TESTICULOSTERONE
Common Name English
MERTESTATE
Common Name English
VIROSTERONE
Common Name English
TESTOSTERONE [USP]
Common Name English
TESTOSTERONE [INN]
Common Name English
TESTOSTERONE [VANDF]
Common Name English
TESTOSTERONE [MI]
Common Name English
HOMOSTERONE
Common Name English
ANDRODERM
Brand Name English
TESTOSTERONE CIII
USP-RS  
Common Name English
TESTOSTERONE CIII [USP-RS]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 52590
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
NDF-RT N0000175824
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
WHO-VATC QG03EA02
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
EMA ASSESSMENT REPORTS LIVENSA (SEXUAL DYSFUNCTIONS, PSYCHOLOGICAL )
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
LIVERTOX 944
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
CFR 21 CFR 862.1680
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
NCI_THESAURUS C2298
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
NDF-RT N0000008241
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
FDA ORPHAN DRUG 104197
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
FDA ORPHAN DRUG 523916
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
WHO-VATC QG03BA03
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
WHO-ATC G03EA02
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
WHO-ATC G03BA03
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
EMA ASSESSMENT REPORTS INTRINSA (WITHDRAWN: SEXUAL DYSFUNCTIONS, PSYCHOLOGICAL)
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
FDA ORPHAN DRUG 94595
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
WHO-ESSENTIAL MEDICINES LIST 18.2
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
CFR 21 CFR 862.1430
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
CFR 21 CFR 310.528
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
DEA NO. 4000
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
NDF-RT N0000000146
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
Code System Code Type Description
ECHA (EC/EINECS)
200-370-5
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY
WIKIPEDIA
TESTOSTERONE
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY
CAS
58-22-0
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY
MESH
D013739
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY
HSDB
58-22-0
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY
IUPHAR
2858
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY
DRUG BANK
DB00624
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY
INN
1900
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY
NCI_THESAURUS
C862
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY
PUBCHEM
6013
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY
LactMed
58-22-0
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY
ChEMBL
CHEMBL386630
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY
EPA CompTox
58-22-0
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY
RXCUI
10379
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY RxNorm
EVMPD
SUB10937MIG
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY
MERCK INDEX
M10594
Created by admin on Mon Oct 21 20:19:19 UTC 2019 , Edited by admin on Mon Oct 21 20:19:19 UTC 2019
PRIMARY Merck Index
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
METABOLIC ENZYME -> SUBSTRATE
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
In reproductive tissues, dihydrotestosterone is further metabolized to 3-alpha and 3-beta androstanediol
METABOLITE TOXIC -> PARENT
Metabolite shown to induce pyrogenic and inflammatory reactions in man.
METABOLITE ACTIVE -> PARENT
DHT binds with greater affinity to SHBG than does testosterone
MAJOR
METABOLITE -> PARENT
In reproductive tissues, dihydrotestosterone is further metabolized to 3-alpha and 3-beta androstanediol
PRODRUG -> METABOLITE ACTIVE
METABOLITE ACTIVE -> PARENT
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (TLC)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY