Drug/Small Molecule:

testosterone

Overview

Generic Names:	Dea No. 4000; TES; Testosteron; Testosterona [INN-Spanish]; Testosterone Cypionate; Testosterone Enanthate; Testosterone Hydrate; Testosteronum [INN-Latin]; Testostosterone; Trans-Testosterone; testosterone
IUPAC Name:	(8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one
Trade Names:	Andriol; Andro; Andro 100; Andro L.A. 200; Androderm; Androgel; Android 10; Android 25; Android 5; Androlin; Andronaq; Andronate 100; Andronate 200; Andropatch; Andropository 200; Androsorb; Andrusol; Andryl 200; Beta Testosterone; CDB 111C; Cristerona T; Cristerone T; Delatest; Delatestryl; Depo-Testosterone; Depo-Testosterone Cypionate; Depotest; Everone 200; Geno-Cristaux Gremy; Homosteron; Homosterone; Libigel; Malerone; Malestrone; Malogen in Oil; Malogen, Aquaspension Injection; Mertestate; Metandren; Methyltestosterone; Neo-Hombreol F; Neo-Testis; Neotestis; Oreton; Oreton F; Oreton Methyl; Oreton-F; Orquisteron; Perandren; Percutacrine Androgenique; Primotest; Primoteston; Relibra; Scheinpharm Testone-Cyp; Striant; Sustanon; Sustanone; Sustason 250; Synandrol F; T-Cypionate; Teslen; Testamone 100; Testandrone; Testaqua; Testiculosterone; Testim; Testobase; Testoderm; Testoderm Tts; Testogel; Testoject-50; Testolin; Testopel Pellets; Testopropon; Testosteroid; Testoviron; Testoviron Schering; Testoviron T; Testred; Testred Cypionate 200; Testrin-P.A; Testro Aq; Testrone; Testryl; Virilon; Virilon IM; Virormone; Virosterone
Brand Mixtures:	Anadiol Inj Liq (Estradiol Benzoate + Estradiol Enanthate + Testosterone Enanthate); Climacteron Liq Im (Estradiol Benzoate + Estradiol Dienanthate + Testosterone Enanthate Benzilic Acid Hydrazone); Component E-H Implants (Estradiol Benzoate + Testosterone Propionate); Component E-H Implants with Tylan (Estradiol Benzoate + Testosterone Propionate + Tylosin Tartrate); Neo Pause Injection (Estradiol Valerate + Testosterone Enanthate); Synovex H (Heifer Implants) (Estradiol Benzoate + Testosterone Propionate); Uni-Bol (Estradiol Benzoate + Estradiol Enanthate + Testosterone Enanthate)
PharmGKB Accession Id:	PA451627

Description

A potent androgenic steroid and major product secreted by the leydig cells of the testis. Its production is stimulated by luteinizing hormone from the pituitary gland. In turn, testosterone exerts feedback control of the pituitary LH and FSH secretion. Depending on the tissues, testosterone can be further converted to dihydrotestosterone or estradiol. [PubChem]

Indication

For replacement therapy in males for conditions associated with a deficiency or absence of endogenous testosterone.

ATC Therapeutic Categories

• G03BA:3-oxoandrosten (4) derivatives
• G03EK:Androgens and female sex hormones in combination with other drugs

Pharmacology and Interactions

Mechanism Of Action

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.

Pharmacology

Testosterone is a steroid hormone from the androgen group. Testosterone is primarily secreted in the testes of males and the ovaries of females although small amounts are secreted by the adrenal glands. It is the principal male sex hormone and an anabolic steroid. In both males and females, it plays key roles in health and well-being. Examples include enhanced libido, energy, immune function, and protection against osteoporosis. On average, the adult male body produces about twenty times the amount of testosterone than an adult female's body does.

Absorption, Distribution, Metabolism, Elimination & Toxicity

Biotransformation

Testosterone is metabolized to 17-keto steroids through two different pathways. The major active metabolites are estradiol and dihydrotestosterone (DHT).

Protein Binding

40% of testosterone in plasma is bound to sex hormone-binding globulin and 2% remains unbound and the rest is bound to albumin and other proteins.

Absorption

Approximately 10% of the testosterone dose applied on the skin surface is absorbed into systemic circulation

Half Life

10-100 minutes

Toxicity

Side effects include amnesia, anxiety, discolored hair, dizziness, dry skin, hirsutism, hostility, impaired urination, paresthesia, penis disorder, peripheral edema, sweating, and vasodilation.

Chemical Properties

Chemical Formula:

C₁₉H₂₈O₂

SMILES Code:

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

(Format: OpenEye Isomeric)

Molecular Weight ( average / monoisotopic )

288.4244 / 288.2089

Curated Information

The following genes are in curated knowledge about this drug.

	Gene	Relationship	Evidence
	ABCB1		Publications
	APOA1	PD	Publications
	AR	CO PD       GN	Publications
	CYP3A4	PD PK FA GN	Publications
	CYP3A5	PK FA	Publications
	UGT1A1	PD PK FA GN	Publications
	UGT2B17	CO          GN	Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other genes is available.

Metabolizing Enzymes

• CYP3A4
• CYP19A1
• CYP11A1
• MAOA

Drug Targets

• ALB
• SHBG
• AR
• NPPB

Reactome Pathways†

• Androgen biosynthesis - (Reactome via Pathway Interaction Database)
• Estrogen biosynthesis - (Reactome via Pathway Interaction Database)
• P450 Dehydrogenation of alkanes to form alkenes - (Reactome via Pathway Interaction Database)
• Unknown - (Reactome via Pathway Interaction Database)
• Xenobiotics - (Reactome via Pathway Interaction Database)

Non-Curated Information

A list of non-curated publications that mention this drug along with other drugs is available.

Drug Interactions

acenocoumarol	The androgen increases the anticoagulant effect
anisindione	The androgen increases the anticoagulant effect
dicumarol	The androgen increases the anticoagulant effect
docetaxel	The agent increases the serum levels and toxicity of docetaxel
warfarin	The androgen increases the anticoagulant effect

Curated Information

The following diseases are in curated knowledge about this drug.

	Disease	Relationship	Evidence
	Colorectal Neoplasms	PD PK FA GN	Publications
	Diarrhea	PD PK FA GN	Publications
	Klinefelter Syndrome	CO PD       GN	Publications
	Prostatic Neoplasms	PD       GN	Publications

Non-Curated Information

A list of non-curated publications that mention this drug along with other diseases is available.

Additional Datasets

These datasets are minimally curated and are sorted alphabetically by title.

1. The Connectivity Map: using gene-expression signatures to connect small molecules, genes, and disease

LinkOuts

Common Searches

Search PubMed
Search Medline Plus
Search PubChem
Search CTD

Non-Curated Publications

A list of non-curated publications that mention this drug is available.