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Details

Stereochemistry ABSOLUTE
Molecular Formula C22H32O3
Molecular Weight 344.4877
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Testosterone propionate

SMILES

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

InChI

InChIKey=PDMMFKSKQVNJMI-BLQWBTBKSA-N
InChI=1S/C22H32O3/c1-4-20(24)25-19-8-7-17-16-6-5-14-13-15(23)9-11-21(14,2)18(16)10-12-22(17,19)3/h13,16-19H,4-12H2,1-3H3/t16-,17-,18-,19-,21-,22-/m0/s1

HIDE SMILES / InChI

Molecular Formula C22H32O3
Molecular Weight 344.4877
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
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

Primary TargetPharmacologyConditionPotency
3.16 nM [EC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TESTOSTERONE

Cmax

ValueDoseCo-administeredAnalytePopulation
13.1 pg/mL
8.2 mg single, topical
TESTOSTERONE plasma
Homo sapiens
214 ng/dL
30 mg single, topical
TESTOSTERONE unknown
Homo sapiens
231 ng/dL
30 mg single, topical
TESTOSTERONE unknown
Homo sapiens
930.1 ng/dL
5 g 1 times / day multiple, topical
TESTOSTERONE unknown
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
948 pg × h/mL
8.2 mg single, topical
TESTOSTERONE plasma
Homo sapiens
2120 ng*h/dL
30 mg single, topical
TESTOSTERONE unknown
Homo sapiens
3110 ng*h/dL
30 mg single, topical
TESTOSTERONE unknown
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
7 h
8.2 mg single, topical
TESTOSTERONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
13%
8.2 mg single, topical
TESTOSTERONE plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

PubMed

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
Record UNII
WI93Z9138A
Record Status Validated (UNII)
Record Version