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Merck

86541

Testosterone propionate

tested according to Ph. Eur.

Synonym(s):

Testosteroni propionas, 17β-Hydroxy-4-androsten-3-one 17-propionate, 17β-Propionyloxy-4-androsten-3-one, 4-Androsten-17β-ol-3-one 17-propionate

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About This Item

Empirical Formula (Hill Notation):
C22H32O3
CAS Number:
57-85-2
Molecular Weight:
344.49
UNSPSC Code:
12352211
NACRES:
NA.21
PubChem Substance ID:
329769470
EC Number:
200-351-1
Beilstein/REAXYS Number:
3221760
MDL number:
MFCD00003653

Product Name

Testosterone propionate, tested according to Ph. Eur.

InChI key

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

SMILES string

[H][C@@]12CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]4(C)[C@H](CC[C@@]24[H])OC(=O)CC

Gene Information

human ... AR(367), CYP17A1(1586)
rat ... Ar(24208)

agency

tested according to Ph. Eur.

form

solid

drug control

USDEA Schedule IIIN; regulated under CDSA - not available from Sigma-Aldrich Canada

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Application

Testosterone propionate has been used:
  • to determine the effect of testosterone on the uptake of certain amino acids, such as isoleucine and α-(methylamino)isobutyric acid
  • in a study to understand the effects of testosterone on brain aromatase activity in neonatal quail brain
  • for testosterone treatment of Celf1 knockout mice in a study to investigate the upregulation of aromatase activity in association with hypogonadism
  • to investigate the ontogeny of aromatase-expressing neurons in Japanese quail brain
  • to study the effects of in vivo administration of testosterone propionate on fluid reabsorption in the efferent ducts of rat.

Biochem/physiol Actions

Testosterone is the major circulating androgen in men and is mainly produced by the testis. A small amount is secreted by the adrenal gland. It is produced from cholesterol in the Leydig cells. Testosterone is metabolized to dihydrotestosterone, a potent androgen that associates with a cytoplasmic receptor protein, to form a complex. This complex is activated and transported into the nucleus, where it triggers several biological responses. It mainly participates in the development of the male phenotype during embryogenesis and at puberty.

General description

Testosterone propionate is the esterified form of testosterone that is most commonly used in clinical applications for the treatment of hypogonadism, oligospermia, and impotence. 17β-hydroxyl group of propionate is esterified to get this form. It is a fast and short-acting form when compared to enanthate and cypionate forms, which are long-acting esters more commonly used in androgen replacement therapies.

Other Notes

Sales restrictions may apply

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Danger

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Carc. 2 - Repr. 1A

Storage Class

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk

WGK 3

ppe

Eyeshields, Gloves, type P3 (EN 143) respirator cartridges

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Certificates of Analysis (COA)

Lot/Batch Number
BCCN6480
BCCL7068
BCCK7443
BCCJ3672
BCCG4695

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Clinical Use and Abuse of Androgens and Antiandrogens
Becker KL., (eds.)
Principles and Practice of Endocrinology and Metabolism, 957-957 null
M Fujioka et al.
The Journal of clinical endocrinology and metabolism, 63(6), 1361-1364 (1986-12-01)
The pharmacokinetic characteristics of testosterone propionate were studied in normal men after a single im dose of 25 mg testosterone propionate-19,19,19-d3. Plasma levels of testosterone propionate-19,19,19-d3, its active metabolite testosterone-19,19,19-d3, and endogenous testosterone were measured by gas chromatography-mass spectrometry. Testosterone
Sylvia M Bardet et al.
Neuroreport, 21(5), 376-380 (2010-02-12)
It was shown earlier that, in Japanese quail the mechanism controlling the induction by testosterone of aromatase activity develops between embryonic days 10 and 14. The cellular processes underlying this activation have, however, not been investigated in detail. Here, we
Testosterone: An overview of biosynthesis, transport, metabolism and nongenomic actions
Rommerts, Focko FG
Testosterone, 1-31 (1998)
Francois Mougeot et al.
Proceedings. Biological sciences, 276(1659), 1093-1100 (2009-01-09)
Extravagant ornaments evolved to advertise their bearers' quality, the honesty of the signal being ensured by the cost paid to produce or maintain it. The oxidation handicap hypothesis (OHH) proposes that a main cost of testosterone-dependent ornamentation is oxidative stress
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