TESTOSTERONE

First marketed in 1937

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H28O2
Molecular Weight	288.4251
Optical Activity	UNSPECIFIED
Defined Stereocenters	6 / 6
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@]12CCC(=O)C=C2CC[C@@]3([H])[C@]4([H])CC[C@@]([H])([C@@]4(C)CC[C@@]31[H])O

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	288.4251
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	6 / 6
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Androgen receptor 42 Target ID: P10275 Gene ID: 367 Gene Symbol: AR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17635942	Agonist 2456
Androgen Receptor 163 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19856921	Agonist 2456	Hypogonadism	3.16000000000000014 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypogonadism 28 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/203098s006lbl.pdf	Primary	Androgen Receptor	Approved 7997	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 1359504000000

C_max

Value	Dose	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	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:

T_1/2

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

F_unbound

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 Recommended Dose: 75 mg, 1 times / day Route: subcutaneous Route: steady Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30296416/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/30296416/	Disc. AE: Hypertension... AEs leading to discontinuation/dose reduction: Hypertension (5.6%) Sources: https://pubmed.ncbi.nlm.nih.gov/30296416/
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: https://pubmed.ncbi.nlm.nih.gov/20592293/	unhealthy, mean 74 years Health Status: unhealthy Age Group: mean 74 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/20592293/	Other AEs: Cardiac disorders, Atherosclerosis... Other AEs: Cardiac disorders (6.5%) Atherosclerosis (6.4%) Sources: https://pubmed.ncbi.nlm.nih.gov/20592293/

AEs

AE	Significance	Dose	Population
Hypertension	5.6% Disc. AE	75 mg 1 times / day steady, subcutaneous Recommended Dose: 75 mg, 1 times / day Route: subcutaneous Route: steady Dose: 75 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/30296416/	unhealthy, adult Health Status: unhealthy Age Group: adult Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/30296416/
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: https://pubmed.ncbi.nlm.nih.gov/20592293/	unhealthy, mean 74 years Health Status: unhealthy Age Group: mean 74 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/20592293/
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: https://pubmed.ncbi.nlm.nih.gov/20592293/	unhealthy, mean 74 years Health Status: unhealthy Age Group: mean 74 years Sex: M Sources: https://pubmed.ncbi.nlm.nih.gov/20592293/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1470

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BCRP 574 P-gp 1089 MRP2 341	UGT1A10 247 UGT1A1 358 UGT1A3 358 UGT1A4 295 UGT1A5 51 UGT1A6 258 UGT1A7 197 UGT1A8 242 UGT1A9 327 UGT2A1 29 UGT2A2 46 UGT2A3 46 UGT2B4 213 UGT2B7 329 UGT2B10 112 UGT2B15 165 UGT2B17 184 UGT2B28 57 CYP3A5 346 CYP3A7 104 P-gp 1223	MCT4 19 P-gp 225

Drug as perpetrator

Target	Modality	Activity
BCRP 639	inhibitor 2614 Sources: https://link.springer.com/article/10.1007/s11095-009-9896-0 Page: -	no
MRP2 421	inhibitor 2614 Sources: https://link.springer.com/article/10.1007/s11095-009-9896-0 Page: -	no
P-gp 1255	inhibitor 2614 Sources: https://link.springer.com/article/10.1007/s11095-009-9896-0 Page: -	no
MCT4 28	inducer 1333 Sources: https://physoc.onlinelibrary.wiley.com/doi/full/10.1113/jphysiol.2006.115436 Page: -	yes
P-gp 1255	inducer 1333 Sources: https://www.sciencedirect.com/science/article/pii/S0024320506000786 Page: -	yes

Drug as victim

Target	Modality	Activity
UGT2B17 184	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	major [Km 10 uM]
UGT2A1 29	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	major [Km 38.7 uM]
UGT1A10 247	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A3 358	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A4 295	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A8 242	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A9 327	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT2A2 46	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT2B15 165	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT2B7 329	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A1 358	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT1A5 51	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT1A6 258	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT1A7 197	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT2A3 46	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT2B10 112	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT2B28 57	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT2B4 213	substrate 2752 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
CYP3A4 1470	substrate 2752 Sources: https://jpet.aspetjournals.org/content/299/3/825.short Page: -	yes
CYP3A5 346	substrate 2752 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5697443/ Page: -	yes
CYP3A7 104	substrate 2752 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5697443/ Page: -	yes
P-gp 1223	substrate 2752 Sources: https://www.sciencedirect.com/science/article/pii/S0006291X19317887 Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:17347	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:17347
ZINC	ZINC000118912393	http://zinc15.docking.org/substances/ZINC000118912393

PubMed

Title	Date	PubMed
Acute anti-ischemic effect of testosterone in men with coronary artery disease.	1999 Apr 6	10190874
A report on alterations to the speaking and singing voices of four women following hormonal therapy with virilizing agents.	1999 Dec	10622516
Steroid feedback on gonadotropin release and pituitary gonadotropin subunit mRNA in mice lacking a functional estrogen receptor alpha.	1999 Oct	10709760
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	10490589
Profiling neurosteroids in cerebrospinal fluids and plasma by gas chromatography/electron capture negative chemical ionization mass spectrometry.	2000 Jan 15	10625505
Estrogen activation of the nuclear orphan receptor CAR (constitutive active receptor) in induction of the mouse Cyp2b10 gene.	2000 Nov	11075820
Effects of hyperprolactinemia on testosterone production in rat Leydig cells.	2001	11135360
Psychophysiological responses to the Stroop Task after a maximal cycle ergometry in elite sportsmen and physically active subjects.	2001 Feb	11166107
Spz1, a novel bHLH-Zip protein, is specifically expressed in testis.	2001 Feb	11165476
Relative enzymatic activity, protein stability, and tissue distribution of human steroid-metabolizing UGT2B subfamily members.	2001 Feb	11159850
Effects of organic solvents on the activities of cytochrome P450 isoforms, UDP-dependent glucuronyl transferase, and phenol sulfotransferase in human hepatocytes.	2001 Feb	11159803
Photoperiod-induced testicular apoptosis in European starlings (Sturnus vulgaris).	2001 Feb	11159376
Neuroendocrine regulation of sexually dimorphic brain structure and associated sexual behavior in male rats is genetically controlled.	2001 Feb	11159360
Follicular-fluid factors and granulosa-cell gene expression associated with follicle deviation in cattle.	2001 Feb	11159344
Sex differences in androgen receptors of the human mamillary bodies are related to endocrine status rather than to sexual orientation or transsexuality.	2001 Feb	11158052
Androgen deficiency in women with hypopituitarism.	2001 Feb	11158009
Disparate response of wild-type and variant forms of LH to GnRH stimulation in individuals heterozygous for the LHbeta variant allele.	2001 Feb	11157812
Estrogen and androgen elicit growth hormone release via dissimilar patterns of hypothalamic neuropeptide secretion.	2001 Feb	11146085
Neuronal size in the spinal nucleus of the bulbocavernosus: direct modulation by androgen in rats with mosaic androgen insensitivity.	2001 Feb 1	11157092
Concentrations of steroid hormones in layers and biopsies of chelonian egg yolks.	2001 Jan	11161774
Androgenic anabolic steroids and arterial structure and function in male bodybuilders.	2001 Jan	11153743
Effects of testosterone on production of perivitelline membrane glycoprotein ZPC by granulosa cells of Japanese quail (Coturnix japonica).	2001 Jan	11133688
Identification of twelve O-glycosylation sites in equine chorionic gonadotropin beta and equine luteinizing hormone ss by solid-phase Edman degradation.	2001 Jan	11133668
Androgen-dependent regulation of human angiotensinogen expression in KAP-hAGT transgenic mice.	2001 Jan	11133514
Comparison of histological compositions and apoptosis in canine spontaneous benign prostatic hyperplasia treated with androgen suppressive agents chlormadinone acetate and finasteride.	2001 Jan	11125427
Manipulation of androgens causes different energetic responses to cold in 60- and 40-day-old male rats.	2001 Jan	11124160
Sex steroid hormones enhance immune function in male and female Siberian hamsters.	2001 Jan	11124153
Influence of gender and sex hormones on nicotine acute pharmacological effects in mice.	2001 Jan	11123373
17beta-oestradiol acutely regulates Cl- secretion in rat distal colonic epithelium.	2001 Jan 1	11136857
Cross-talk between steroid-receptor-mediated and cell-membrane-receptor-mediated signalling pathways results in the in vivo modulation of c-Met and ornithine decarboxylase gene expression in mouse kidney.	2001 Jan 15	11139396
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase.	2001 Jan 22	11165020
Pan1b (17betaHSD11)-enzymatic activity and distribution in the lung.	2001 Jan 22	11165019
Sex difference in the phosphorylation of cAMP response element binding protein (CREB) in neonatal rat brain.	2001 Jan 26	11164773
Regulation of the steroid-inducible 3alpha-hydroxysteroid dehydrogenase/carbonyl reductase gene in Comamonas testosteroni.	2001 Mar 30	11139589

Patents

Sample Use Guides

In Vivo Use Guide

Starting dose of testosterone gel is 50 mg of testosterone (4 pump

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 `Fri Jun 25 21:10:15 UTC 2021` Edited by `admin` on `Fri Jun 25 21:10:15 UTC 2021`
Record UNII	3XMK78S47O
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

TESTOSTERONE

Official 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 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

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

52590