Testosterone cypionate Chemical Properties

Melting point:

101-102°

alpha 

D25 +87° (CHCl3)

Boiling point:

492.01°C (rough estimate)

Density 

0.9795 (rough estimate)

refractive index 

1.5460 (estimate)

storage temp. 

2-8°C

solubility 

DMF: 25 mg/mL; DMSO: 5 mg/mL; Ethanol: 15 mg/mL; Ethanol:PBS (pH 7.2)(1:2): 0.3 mg/mL

form 

A crystalline solid

InChI

InChI=1/C27H40O3/c1-26-15-13-20(28)17-19(26)8-9-21-22-10-11-24(27(22,2)16-14-23(21)26)30-25(29)12-7-18-5-3-4-6-18/h17-18,21-24H,3-16H2,1-2H3/t21-,22-,23-,24-,26-,27-/s3

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 DataBase Reference

58-20-8(CAS DataBase Reference)

NIST Chemistry Reference

Testosterone cypionate(58-20-8)

Safety Information

Hazard Codes 

T

Risk Statements 

45-63

Safety Statements 

53-22-26-36

WGK Germany 

3

RTECS 

XA3066000

HS Code 

2937290000

MSDS

• Language:English Provider:SigmaAldrich

Testosterone cypionate Usage And Synthesis

Description

Testosterone cypionate is an anabolic steroid that is classified as a male hormone (androgen). Testosterone cypionate is an injectable solution whose brand name is Depo-testosterone. The generic drug is administered to enhance performance in athletics and bodybuilding, and as a prescription drug that alleviates the symptoms of hypogonadism in men. In most cases, the drug is administered to the muscle or the subcutaneous layer of the skin through an injection based on clinical indications or once every few weeks. The androgenic/anabolic structure of Testosterone cypionate has a score of 100, which makes it an appropriate steroid for strength and size associated gains. Testosterone cypionate influences changes in the size, shape, number, and appearance of muscle fibers.

Mechanism of Action

In humans, the influence of testosterone may take place based on two mechanisms: through alteration of the hormone to estradiol and trigger specific estrogen receptors, and by triggering of the androgen receptor. Free testosterone (T) is transmitted to the cytoplasm of selected cells for attachment with the androgen receptor, or diminution to 5α-dihydrotestosterone (DHT) through the cytoplasmic enzyme 5α-reductase.
DHT creates a strong bond with a similar androgen receptor, one that is stronger than free testosterone to enhance its androgenic potency. The DHT-receptor or the T-receptor undergoes structural modifications that allow its free flow into the nucleus of the cell for binding with certain nucleotide sequences particular to the chromosomal DNA. Notably, these binding spots are referred to as hormone response elements (HREs), and their effect on the transcriptional activity of specific genes results in the androgenic effects.
When Testosterone cypionate is absorbed into the body, the drug is processed in the blood and 40% of the resultant testosterone binds with plasma globulin, the remaining 2% either binds with proteins such as albumin or it remains unbound.

Information on Dosing

The dosage requirements of Testosterone cypionate are dependent on an individual’s age, the need for testosterone therapy, the intensity of the condition, additional medical conditions and one’s reaction after injection of the first dose. For primary hypogonadism and hypogonadotropic hypogonadism, 50-400mg is injected into one’s gluteal muscle every 2-4weeks.
The administration of Testosterone cypionate to enhance performance may necessitate a weekly injection of the hormone, where two smaller injections could be more effective. Noteworthy, multiple injections ensure that an individual’s blood levels are at a peak, which mitigates the effects of performance level dosage instructions. In this case, the administration of smaller doses of the hormone may range from 200mg-1000mg per week, which is solely dependent on an individual’s needs.

Interactions

Testosterone cypionate can interact with herbs, vitamins and other medications that one may be taking. Such interactions may inhibit the appropriate functionality of the drug hence to avoid this, it is advisable to consult a doctor for management of medications. Notably, some of the drug interactions may include oral blood thinners, adrenocorticotropic and corticosteroid hormones, oral diabetes drugs and insulin.

Indications

In men, Testosterone cypionate is indicated for primary or secondary hypogonadism. The testosterone cypionate injection should only be used to treat specific symptoms of testosterone deficiency. Before the initiation of Testosterone cypionate treatment, testosterone deficiency should be validated by clinical features and biochemical assays.

Contraindications

Testosterone cypionate is contradicted in persons who have known or suspected breast and testicular carcinomas. If one is allergic to testosterone they should refrain from the use of Testosterone cypionate. Females should keep off the drug especially if one is either breastfeeding or pregnant.

Side Effects

The common side effects associated with testosterone cypionate include headaches, mood swings, erections which last longer than normal, frequent erections, gynecomastia, hair growth, pain and swelling at the point of injection, acne, retention of excess water, and a reduction of the sperm count when one indulges in high dosages of the drug.
Serious side effects of testosterone cypionate use include aromatization, heart attack, stroke, prostate cancer, liver problems, deep vein thrombosis, pulmonary embolism, polycythemia, and enlargement of the prostate gland.
Testosterone cypionate is well-tolerated amongst most men hence the common side effects can be controlled easily while the serious side effects are not guaranteed.

Testosterone Cypionate Warnings

Before administering Testosterone cypionate, one should take into consideration the fact that people with liver problems may experience liver damage, people with heart and kidney problems may experience water and salt retention. For people with breast cancer, prostate cancer, sleep apnea, polycythemia, high cholesterol levels and blood clots, Testosterone cypionate may amplify their respective conditions.
It is not advisable for seniors above the age of 65 to take Testosterone cypionate as it may increase their chances of contracting prostate cancer, heart disease or an enlarged prostate. The drug should only be used by males.

Chemical Properties

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

Uses

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.

References

[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

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