TESTOSTERONE

First marketed in 1937

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 Search

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CCC4=CC(=O)CC[C@]34C

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
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: 367.0 Gene Symbol: AR Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/17635942	Agonist 2637
Androgen Receptor 167 Target ID: CHEMBL1871 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19856921	Agonist 2637		3.16 nM [EC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypogonadism 28 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2015/203098s006lbl.pdf	Primary		Approved 8307	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 1.35950395E12

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 (median) 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 n = 150 Health Status: unhealthy Condition: hypogonadism Age Group: adult Sex: M Population Size: 150 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 n = 106 Health Status: unhealthy Condition: with limitations in mobility Age Group: mean 74 years Sex: M Population Size: 106 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 (median) 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 n = 150 Health Status: unhealthy Condition: hypogonadism Age Group: adult Sex: M Population Size: 150 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 n = 106 Health Status: unhealthy Condition: with limitations in mobility Age Group: mean 74 years Sex: M Population Size: 106 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 n = 106 Health Status: unhealthy Condition: with limitations in mobility Age Group: mean 74 years Sex: M Population Size: 106 Sources: https://pubmed.ncbi.nlm.nih.gov/20592293/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1670

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
BCRP 678 P-gp 1401 MRP2 363	UGT1A1 417 UGT1A3 421 UGT1A4 345 UGT1A5 55 UGT1A6 306 UGT1A7 235 UGT1A8 282 UGT1A9 378 UGT1A10 289 UGT2A1 32 UGT2A2 48 UGT2A3 48 UGT2B4 248 UGT2B7 387 UGT2B10 127 UGT2B15 202 UGT2B17 212 UGT2B28 63 CYP3A5 383 CYP3A7 110 P-gp 1491	MCT4 19 P-gp 252

Drug as perpetrator

Target	Modality	Activity
BCRP 751	inhibitor 3185 Sources: https://link.springer.com/article/10.1007/s11095-009-9896-0 Page: -	no
MRP2 452	inhibitor 3185 Sources: https://link.springer.com/article/10.1007/s11095-009-9896-0 Page: -	no
P-gp 1588	inhibitor 3185 Sources: https://link.springer.com/article/10.1007/s11095-009-9896-0 Page: -	no
MCT4 28	inducer 1515 Sources: https://physoc.onlinelibrary.wiley.com/doi/full/10.1113/jphysiol.2006.115436 Page: -	yes
P-gp 1588	inducer 1515 Sources: https://www.sciencedirect.com/science/article/pii/S0024320506000786 Page: -	yes

Drug as victim

Target	Modality	Activity
UGT2B17 212	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	major [Km 10 uM]
UGT2A1 32	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	major [Km 38.7 uM]
UGT1A10 289	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A3 421	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A4 345	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A8 282	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A9 378	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT2A2 48	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT2B15 202	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT2B7 387	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	minor
UGT1A1 417	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT1A5 55	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT1A6 306	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT1A7 235	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT2A3 48	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT2B10 127	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT2B28 63	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
UGT2B4 248	substrate 3264 Sources: https://dmd.aspetjournals.org/content/37/2/417.short Page: -	no
CYP3A4 1670	substrate 3264 Sources: https://jpet.aspetjournals.org/content/299/3/825.short Page: -	yes
CYP3A5 383	substrate 3264 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5697443/ Page: -	yes
CYP3A7 110	substrate 3264 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5697443/ Page: -	yes
P-gp 1491	substrate 3264 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
ChemicalBook	CB5380541	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB5380541
ZINC	ZINC000118912393	http://zinc15.docking.org/substances/ZINC000118912393
eMolecules	511977	https://www.emolecules.com/cgi-bin/more?vid=511977

PubMed

Title	Date	PubMed
Cross-talk between 2,3,7,8-tetrachlorodibenzo-p-dioxin and testosterone signal transduction pathways in LNCaP prostate cancer cells.	1999 Mar 24	10080920
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
Allelic variants of human cytochrome P450 1A1 (CYP1A1): effect of T461N and I462V substitutions on steroid hydroxylase specificity.	2000 Aug	10975606
Changes in serum and tissue zinc levels in sex hormone-induced prostatic carcinogenesis in the noble rat.	2000 Nov-Dec	11006573
Psychophysiological responses to the Stroop Task after a maximal cycle ergometry in elite sportsmen and physically active subjects.	2001 Feb	11166107
Castration in Gambel's and Scaled Quail: ornate plumage and dominance persist, but courtship and threat behaviors do not.	2001 Feb	11161878
Effects of organic solvents on the activities of cytochrome P450 isoforms, UDP-dependent glucuronyl transferase, and phenol sulfotransferase in human hepatocytes.	2001 Feb	11159803
Substitution mutation C268Y causes 17 beta-hydroxysteroid dehydrogenase 3 deficiency.	2001 Feb	11158067
Evidence that cyproterone acetate improves psychological symptoms and enhances the activity of the dopaminergic system in postmenopause.	2001 Feb	11158017
Muting of androgen negative feedback unveils impoverished gonadotropin-releasing hormone/luteinizing hormone secretory reactivity in healthy older men.	2001 Feb	11158004
Estrogen and androgen elicit growth hormone release via dissimilar patterns of hypothalamic neuropeptide secretion.	2001 Feb	11146085
Testosterone concentrations in women aged 25-50 years: associations with lifestyle, body composition, and ovarian status.	2001 Feb 1	11157413
Changes in androgenic steroid profile due to urine contamination by microorganisms: a prospective study in the context of doping control.	2001 Feb 15	11161304
Progressive decrease in bone density over 10 years of androgen deprivation therapy in patients with prostate cancer.	2001 Jan	11164157
Long-term remission of ovarian hyperandrogenism after short-term treatment with a gonadotropin-releasing hormone agonist.	2001 Jan	11163817
Prevalence of polycystic ovary syndrome (PCOS) in first-degree relatives of patients with PCOS.	2001 Jan	11163816
Targeted disruption of luteinizing hormone/human chorionic gonadotropin receptor gene.	2001 Jan	11145749
The female-to-male transsexual patient: a source of human ovarian cortical tissue for experimental use.	2001 Jan	11139553
Short-term 17beta-estradiol decreases glucose R(a) but not whole body metabolism during endurance exercise.	2001 Jan	11133904
Comparison of histological compositions and apoptosis in canine spontaneous benign prostatic hyperplasia treated with androgen suppressive agents chlormadinone acetate and finasteride.	2001 Jan	11125427
Sex steroid hormones enhance immune function in male and female Siberian hamsters.	2001 Jan	11124153
Rapid and reversible inhibition of brain aromatase activity.	2001 Jan	11123516
Anorexia, body composition, and ageing.	2001 Jan	11122553
Effects of hyperprolactinemia on rat prostate growth: evidence of androgeno-dependence.	2001 Jan	11120666
Novel approaches to female sexual dysfunction.	2001 Jan	11116282
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
Structure-function aspects and inhibitor design of type 5 17beta-hydroxysteroid dehydrogenase (AKR1C3).	2001 Jan 22	11165022
Reproductive effects of valproate, carbamazepine, and oxcarbazepine in men with epilepsy.	2001 Jan 9	11148232
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 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 `Fri Dec 16 16:41:59 UTC 2022` Edited by `admin` on `Fri Dec 16 16:41:59 UTC 2022`
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 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

TESTOSTERONE [INCI]

Common 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

TESTOSTERONE CIII

Common Name

English

Classification Tree Code System Code

FDA ORPHAN DRUG

52590