U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS
This repository is under review for potential modification in compliance with Administration directives.

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 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
930.1 ng/dL
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
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
3110 ng*h/dL
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
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
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

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
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
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
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 Mon Mar 31 17:52:50 GMT 2025
Edited
by admin
on Mon Mar 31 17:52:50 GMT 2025
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 CIII
USP-RS  
Preferred Name English
TESTOSTERONE [JAN]
Common Name English
TESTOSTERONE [EP MONOGRAPH]
Common Name English
TESTOSTERONE [MART.]
Common Name English
ANDROST-4-EN-3-ONE, 17-HYDROXY-, (17.BETA.)-
Systematic Name English
TESTOSTERONE PROPIONATE IMPURITY C [EP IMPURITY]
Common Name English
INTRINSA
Brand Name English
ANDROGEL
Brand Name English
TESTOSTERONE [GREEN BOOK]
Common Name English
TESTOSTERONE [EP IMPURITY]
Common Name English
ANDROID-T
Brand Name English
TESTOSTERONE ENANTATE IMPURITY D [EP IMPURITY]
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
ANDROLAN
Brand Name English
17?-Hydroxyandrost-4-en-3-one
Systematic Name English
NATESTO
Brand Name English
Testosterone [WHO-DD]
Common Name English
TESTICULOSTERONE
Common Name English
MERTESTATE
Common Name English
TESTOSTERONE [USP MONOGRAPH]
Common Name English
VIROSTERONE
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
Classification Tree Code System Code
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 25987-9
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EMA ASSESSMENT REPORTS LIVENSA (SEXUAL DYSFUNCTIONS, PSYCHOLOGICAL )
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LOINC 26827-6
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LIVERTOX 944
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LOINC 26826-8
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CFR 21 CFR 862.1680
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LOINC 2987-6
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NCI_THESAURUS C2298
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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
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FDA ORPHAN DRUG 104197
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LOINC 35225-2
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LOINC 49042-5
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LOINC 59240-2
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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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LOINC 2984-3
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LOINC 15432-8
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LOINC 41018-3
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LOINC 35224-5
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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
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CFR 21 CFR 862.1430
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LOINC 70239-9
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CFR 21 CFR 310.528
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LOINC 2985-0
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LOINC 2989-2
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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
Created by admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
Code System Code Type Description
DAILYMED
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
PRIMARY
NSC
9700
Created by admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
PRIMARY
CHEBI
17347
Created by admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
PRIMARY
ECHA (EC/EINECS)
200-370-5
Created by admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
PRIMARY
WIKIPEDIA
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
PRIMARY
CAS
58-22-0
Created by admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
PRIMARY
MESH
D013739
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PRIMARY
HSDB
3398
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PRIMARY
IUPHAR
2858
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PRIMARY
DRUG BANK
DB00624
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PRIMARY
INN
1900
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PRIMARY
NCI_THESAURUS
C862
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PRIMARY
FDA UNII
3XMK78S47O
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PRIMARY
RS_ITEM_NUM
1646009
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PRIMARY
PUBCHEM
6013
Created by admin on Mon Mar 31 17:52:50 GMT 2025 , Edited by admin on Mon Mar 31 17:52:50 GMT 2025
PRIMARY
WIKIPEDIA
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
PRIMARY
SMS_ID
100000089191
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PRIMARY
ChEMBL
CHEMBL386630
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PRIMARY
LACTMED
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
PRIMARY
EPA CompTox
DTXSID8022371
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PRIMARY
RXCUI
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
PRIMARY RxNorm
EVMPD
SUB10937MIG
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PRIMARY
DRUG CENTRAL
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
PRIMARY
MERCK INDEX
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
PRIMARY Merck Index
Related Record Type Details
TRANSPORTER -> INHIBITOR
ENZYME->SUBSTRATE
Vmax
METABOLIC ENZYME -> SUBSTRATE
TARGET -> INHIBITOR
BINDING
IC50
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
METABOLITE -> PARENT
In reproductive tissues, dihydrotestosterone is further metabolized to 3-alpha and 3-beta androstanediol
PRODRUG -> METABOLITE ACTIVE
METABOLITE TOXIC -> PARENT
Metabolite shown to induce pyrogenic and inflammatory reactions in man.
PARENT -> METABOLITE
URINE
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
METABOLITE -> PARENT
PRODRUG -> METABOLITE ACTIVE
PRODRUG -> METABOLITE ACTIVE
PRODRUG -> METABOLITE ACTIVE
PRODRUG -> METABOLITE ACTIVE
METABOLITE ACTIVE -> PARENT
METABOLITE -> PARENT
URINE
METABOLITE -> PARENT
METABOLITE -> PARENT
By glucuronosyl transferase (UGT)
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ACTIVE MOIETY