17β-Hydroxyandrost-4-en-3-oncyclopentylpropionat

Bezeichnung:17β-Hydroxyandrost-4-en-3-oncyclopentylpropionat

CAS-Nr58-20-8

Englisch Name:Testosterone cypionate

CBNumberCB0727220

SummenformelC27H40O3

Molgewicht412.6

MOL-Datei58-20-8.mol

Synonyma

17β-Hydroxyandrost-4-en-3-oncyclopentylpropionat

17β-Hydroxyandrost-4-en-3-oncyclopentylpropionat physikalisch-chemischer Eigenschaften

Schmelzpunkt	101-102°
alpha	D25 +87° (CHCl3)
Siedepunkt	492.01°C (rough estimate)
Dichte	0.9795 (rough estimate)
Brechungsindex	1.5460 (estimate)
storage temp.	2-8°C
Löslichkeit	DMF: 25 mg/mL; DMSO: 5 mg/mL; Ethanol: 15 mg/mL; Ethanol:PBS (pH 7.2)(1:2): 0.3 mg/mL
Aggregatzustand	A crystalline solid
InChIKey	HPFVBGJFAYZEBE-ZLQWOROUSA-N
SMILES	[C@@]12([H])CCC3=CC(=O)CC[C@]3(C)[C@@]1([H])CC[C@]1(C)[C@H](CC[C@@]21[H])OC(=O)CCC1CCCC1 \|&1:0,10,12,16,18,21,r\|
CAS Datenbank	58-20-8(CAS DataBase Reference)
NIST chemische Informationen	Testosterone cypionate(58-20-8)

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	45-63
S-Sätze:	53-22-26-36
WGK Germany	3
RTECS-Nr.	XA3066000
HS Code	2937290000

Gefahreninformationscode (GHS)

Testosterone cypionate Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R45:Kann Krebs erzeugen.
R63:Kann das Kind im Mutterleib möglicherweise schädigen.
S-Sätze Betriebsanweisung:
S53:Exposition vermeiden - vor Gebrauch besondere Anweisungen einholen.
S22:Staub nicht einatmen.
S26:Bei Berührung mit den Augen sofort gründlich mit Wasser abspülen und Arzt konsultieren.
S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.
Chemische Eigenschaften
Testosterone cypionate is a white or creamy white crystalline powder, odorless or nearly so and stable in air. It is insoluble in water, freely soluble in alcohol, chloroform, dioxane, ether, and soluble in vegetable oils.
Originator
Depo-Testosterone,Upjohn,US,1951
Verwenden
Testosterone Cypionate is an anabolic steroid with androgenic properties. Testosterone Cypionate is used for testosterone therapy in males with hypogonadism. Controlled Substance.
Definition
ChEBI: Testosterone cypionate is a sterol ester. It is functionally related to a 3-cyclopentylpropionic acid and a testosterone.
Manufacturing Process
1 g of crude 3-enol-ethyl ether of testosterone dissolved in 3 cc of pyridine is treated with 2 cc of β-cyclopentylpropionic anhydride (obtained from the β- cyclopentylpropionic acid and acetic anhydride: boiling point 180°C/2 mm Hg). After standing at room temperature overnight the mixture is diluted with water and extracted with ether, the ethereal layer, washed with water to neutrality and dried, is evaporated by vacuum. The oily residue is taken up in petroleum ether and filtered through a layer of aluminum oxide, which is afterwards washed with a further amount of petroleum ether. The solution so filtered and purified is evaporated to dryness; the crystalline residue is recrystallized from a small amount of methanol containing a trace of pyridine: about 1 g of 3-enol-ethyl-ether of the β-cyclopentyl propionate of testosterone, melting point 86°C to 88°C, is so obtained (by further recrystallization melting point 90°C to 91°C). This product (that may be employed either in the crystalline state, or in the oily one, that is, before the purification by filtration through aluminum oxide) by treatment with a small amount of hydrochloric acid in acetone solution yields the β-cyclopentyl propionate of testosterone, melting point 99°C to 101°C (recrystallized from methanol).
Therapeutic Function
Androgen
Veterinary Drugs and Treatments
The use of injectable esters of testosterone in veterinary medicine is limited primarily to its use in dogs (and perhaps cats) for the treatment of testosterone-responsive urinary incontinence in neutered males. Testosterone has been used to treat a rare form of dermatitis (exhibited by bilateral alopecia) in neutered male dogs. These drugs are also used in bovine medicine to produce an estrus-detector (teaser) animal in cull cows, heifers, and steers.
The effectiveness of testosterone to increase libido, treat hypogonadism, aspermia, and infertility in domestic animals has been disappointing.
Einzelnachweise
[1] BEHRE H, NIESCHLAG E. Testosterone: Testosterone preparations for clinical use in males[C]. 2012: 0. DOI:10.1017/CBO9781139003353.016.
[2] H M BEHRE. Intramuscular injection of testosterone undecanoate for the treatment of male hypogonadism: phase I studies.[J]. European Journal of Endocrinology, 1999, 140 5: 414-419. DOI:10.1530/eje.0.1400414.
[3] V. DUMESTRE-TOULET. Hair analysis of seven bodybuilders for anabolic steroids, ephedrine, and clenbuterol.[J]. Journal of forensic sciences, 1900, 47 1 1: 211-214. DOI:10.1520/JFS15228J.
[4] YOUWEN YOU. Simultaneous separation and determination of 16 testosterone and nandrolone esters in equine plasma using ultra high performance liquid chromatography-tandem mass spectrometry for doping control.[J]. Journal of Chromatography A, 2011, 1218 26: 3982-3993. DOI:10.1016/j.chroma.2011.04.087.
[5] J. SHOSKES M. S M Wilson. Pharmacology of testosterone replacement therapy preparations[J]. Translational andrology and urology, 2016, 5 1: 834-843. DOI:10.21037/tau.2016.07.10.
[6] https://www.pfizermedicalinformation.com/depo-testosterone/description

Testosterone cypionate Upstream-Materialien And Downstream Produkte

17β-Hydroxyandrost-4-en-3-oncyclopentylpropionat Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

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