Testosterone phenylpropionate

(1)H NMR determination of adulteration of anabolic steroids in seized drugs.[Pubmed:30003910]

Steroids. 2018 Oct;138:47-56.

Counterfeiting and adulteration of pharmaceuticals is a prevalent problem worldwide and represents a major health risk to the population, with anabolic steroids being one of the main classes of drugs consumed and obtained from dubious sources. In this work, we propose the use of the (1)H NMR technique to evaluate formulations containing anabolic steroids, with analysis of 40 samples of anabolic drugs that are used in injectable and capsule forms. The samples analyzed presented the following active ingredients: testosterone propionate, Testosterone phenylpropionate, testosterone isocaproate, testosterone decanoate, testosterone cypionate, testosterone undecanoate, stanozolol, drostanolone propionate, trenbolone acetate, oxymetholone, and methandrostenolone. The (1)H NMR spectroscopic measurements were performed using a 600MHz Bruker Avance III spectrometer, with deuterated chloroform (CDCl3) containing 0.1% TMS as solvent. Of the 40 samples analyzed, eight did not show the presence of the active principle stated on the label. Three types of adulteration were found in the analyzed samples: absence of the active ingredient, adulteration with other substances, and concentration values below those indicated on the label. Sildenafil citrate was found in four samples. The GC-MS technique was used to confirm the adulteration results found using (1)H NMR. Quantitative determination by NMR was performed using internal standard and ERETIC 2 methods, and the results obtained were statistically the same.

Detection and quantification of 12 anabolic steroids and analogs in human whole blood and 20 in hair using LC-HRMS/MS: application to real cases.[Pubmed:28236045]

Int J Legal Med. 2017 Jul;131(4):989-999.

We developed and validated a method to detect and quantify 12 anabolic steroids in blood (androstenedione, dihydrotestosterone, boldenone, epitestosterone, mesterolone, methandienone, nandrolone, stanozolol, norandrostenedione, tamoxifene, testosterone, trenbolone) and eight more in hair samples (nandrolone phenylpropionate, nandrolone decanoate, testosterone propionate, testosterone benzoate, testosterone cypionate, testosterone decanoate, Testosterone phenylpropionate, testosterone undecanoate) using liquid chromatography coupled to high-resolution mass spectrometry. This method used a benchtop Orbitrap mass spectrometer operating with an APCI probe under positive ionization mode. Analysis was realized in full scan experiment with a nominal resolving power of 140,000. After addition of the internal standard (testosterone-D3) and incubation in phosphate buffer pH = 5 for hair, 200 muL of blood and 30 mg of hair samples were extracted with heptane. LOQ and LOD were determined at 5 and 1 ng mL(-1) in whole blood and 10 to 100 pg mg(-1) and 2 to 20 pg mg(-1) in hair according to the compounds, respectively. The method was linear in the 5-1000 ng mL(-1) range in whole blood and between 10 or 100 pg mg(-1) and 1000 pg mg(-1) in hair with correlation coefficients >0.99, and intra- and inter-day accuracy and precision were <14.8% for all compounds except for some esters in hairs (<19.9%) probably due to an important matrix effect for these compounds. This sensitive and specific method to detect anabolic steroids has been successfully applied to two real cases, for which various anabolic steroids in whole blood, urine, and hair were identified and quantified.

Detection of testosterone esters in blood.[Pubmed:26695486]

Drug Test Anal. 2015 Nov-Dec;7(11-12):983-9.

Injections of synthetic esters of testosterone are among the most common forms of testosterone application. In doping control, the detection of an intact ester of testosterone in blood gives unequivocal proof of the administration of exogenous testosterone. The aim of the current project was to investigate the detection window for injected testosterone esters as a mixed substance preparation and as a single substance preparation in serum and plasma. Furthermore, the suitability of different types of blood collection devices was evaluated. Collection tubes with stabilizing additives, as well as non-stabilized serum separation tubes, were tested. A clinical study with six participants was carried out, comprising a single intramuscular injection of either 1000 mg testosterone undecanoate (Nebido((R))) or a mixture of 30 mg testosterone propionate, 60 mg Testosterone phenylpropionate, 60 mg testosterone isocaproate, and 100 mg testosterone decanoate (Sustanon((R))). Blood was collected throughout a testing period of 60 days. The applied analytical method for blood analysis included liquid-liquid extraction and preparation of oxime derivatives, prior to TLX-sample clean-up and liquid chromatography-tandem mass spectrometry (LC-MS/MS) detection. All investigated testosterone esters could be detected in post-administration blood samples. The detection time depended on the type of ester administered. Furthermore, results from the study show that measured blood concentrations of especially short-chained testosterone esters are influenced by the type of blood collection device applied. The testosterone ester detection window, however, was comparable.

Use of dried blood spots in doping control analysis of anabolic steroid esters.[Pubmed:24713476]

J Pharm Biomed Anal. 2014 Aug 5;96:21-30.

Dried blood spot (DBS) sampling, a technique for whole blood sampling on a piece of filter paper, has more than 50-years tradition, particularly in the diagnostic analysis of metabolic disorders in neonatal screening. Due to the minimal invasiveness, straightforwardness, robustness against manipulation and fastness DBS sampling recommends itself as an advantageous technique in doping control analysis. The present approach highlights the development of a screening assay for the analysis of eight anabolic steroid esters (nandrolone phenylpropionate, trenbolone enanthate, testosterone acetate, testosterone cypionate, testosterone isocaproate, Testosterone phenylpropionate, testosterone decanoate and testosterone undecanoate) and nandrolone in DBS. The detection of the intact esters allows an unequivocal proof of the administration of conjugates of exogenous testosterone and its derivatives. Precise, specific and linear conditions were obtained by means of liquid chromatography high resolution/high accuracy mass spectrometry. Sensitivity in the low ppb range was accomplished by the preparation of the methyloxime derivatives of the target compounds. Labeled internal standards (d3-nandrolone, d3-nandrolone caproate and d3-nandrolone undecanoate) were applied to compensate for the broad range in chain length of the esters. The assay presented here outlines the application of DBS for the analysis of anabolic steroid esters in doping controls for the first time providing great potential to simplify the proof of exogenous administration of testosterone.

Effects of sustanon on the distribution of satellite cells and the morphology of skeletal muscle fibers during maturation.[Pubmed:24199455]

Pak J Biol Sci. 2012 Mar 1;15(5):215-23.

Sustanon is one of the most commonly used anabolic androgenic drugs to increase skeletal muscle mass and strength. This drug is a blend of four esterized testosterone derivatives: Testosterone propionate, Testosterone phenylpropionate, testosterone isocaproate and testosterone decanoate. Little is known about the effects of this drug on skeletal muscle at the cellular level. This study aimed to investigate the influence of Sustanon on the morphology of skeletal muscle fibers and the distribution of myogenic stem cells known as Satellite Cells (SCs) during postnatal growth. We hypothesized that Sustanon-induced skeletal muscle hypertrophy is associated with an increase in the number of SCs. Robust immunocytochemical techniques and morphometric analyses were used to calculate the numbers of SCs and myonuclei within the pectoralis muscle of chickens. Also, DNA concentration and Pax7 protein levels were measured to confirm immunocytochemical findings. Sustanon significantly increased pectoralis mass and fiber size. All SC indices and the number of myonuclei increased significantly by Sustanon administration. In addition, greater DNA concentration and Pax7 protein expression were found in Sustanon-treated birds. This study indicates that Sustanon can induce avian skeletal muscle hypertrophy and that this is correlated with increased numbers of SCs and myonuclei.

Determination of circular dichroism and ultraviolet spectral parameters of norgestimate- and other Delta(4)-3-ketosteroid oxime isomers via normal phase HPLC method.[Pubmed:11562270]

Curr Med Chem. 2001 Sep;8(11):1341-7.

The oxime formation reaction of therapeutical progestogen (levonorgestrel, levonorgestrel acetate, norethisterone), androgen (methyltestosterone, Testosterone phenylpropionate) and anabolic (norTestosterone phenylpropionate) Delta(4)-3-ketosteroids has been investigated. The ketosteroid-hydroxylamine reaction was monitored by reversed phase HPLC system. It was established, that under the experimental conditions applied the oxime formation was complete within 2 h. The reaction leads to the formation of Z and E oxime isomers. The isomers of norgestimate (levonorgestrel 17-acetate oxime) and other Delta(4)-3-ketosteroid oximes have been separated by a new normal phase HPLC method. The identification (elution order assignation) and determination of the formation ratio of the isomers have been performed by 1H NMR spectroscopy on the basis of the chemical shift differences of 4-H signals. The on-line CD and UV spectra of the pure oxime isomers were recorded and then molar ellipticities and absorbances of the isomers were calculated in the wavelength range of 200-300 nm via parameter estimation method.

Determination of delta4-3-ketosteroids based on oxime formation by difference circular dichroism spectroscopy.[Pubmed:11227508]

Fresenius J Anal Chem. 2000 Oct;368(4):384-8.

delta4-3-Ketosteroids exhibit an intensive negative Cotton effect on the circular dichroism (CD) spectra in the wavelength range for the n-pi* electronic transition (270-350 nm). With hydroxylamine hydrochloride, delta4-3-ketosteroid compounds can be transformed into oxime derivatives. Following oxime formation, positive ellipticity with low intensity can be registered in this wavelength range. The quantitative determination of delta4-3-ketosteroids is based on the considerable difference between the ellipticities before and after oxime formation. The difference ellipticity for the six ketosteroids examined (norethisterone, levonorgestrel, levonorgestrel acetate, methyltestosterone, Testosterone phenylpropionate, norTestosterone phenylpropionate) varies linearly with the concentration in the interval 6 x 10(-6)-3 x 10(-3) mol/L. The method can be well applied to determination of delta4-3-ketosteroid contamination of norgestimate [(+)-13-ethyl-17-hydroxy-18,19-dinor-17alpha-pregn4-en-20-yn-3-one oxime acetate]; 0.02-10% impurity can be measured.

Treatment of constitutional delayed puberty with a combination of testosterone esters.[Pubmed:8719438]

Horm Res. 1995;44 Suppl 3:32-4.

Thirteen boys who had constitutional delayed puberty (CDP) were treated with a combination of short- and long-acting testosterone esters (testosterone propionate, Testosterone phenylpropionate, testosterone isocaproate). Mean age at the onset of treatment was 14.9 +/- 0.6 years and bone age delay was -2.7 +/- 0.9 years. An intramuscular dose of 200 mg testosterone was administered 4 times at 3-week intervals and the treated CDP boys were followed for 2 years. All boys with CDP entered puberty after the last dose (testicular volume > or = 4 ml) and growth rate increased from 4.5 +/- 0.5 cm/year pretreatment to 8.4 +/- 1.6 cm/year posttreatment after the 2-year follow-up period. Height for bone age SD score did not alter significantly from a mean of -1.1 pretreatment to -1.3 posttreatment as well as predicted height pretreatment (173.5 +/- 6.6 cm) and posttreatment (173.3 +/- 4.9 cm). A combination of testosterone esters in a given dose and schedule is a safe and effective treatment for prepubertal boys with CDP.

Effects of testosterone on the rat renal medullary vasopressin receptor concentration and the antidiuretic response.[Pubmed:7475899]

Life Sci. 1995;56(14):1215-22.

The renal concentrating ability declines with age in humans and animals. Studies suggest that the concentrating defect is due to a decrease in renal vasopressin sensitivity. With ageing, expression of the renal vasopressin V2 receptor in rat is impaired; the normal receptor expression is restored by testosterone treatment. The effect of testosterone on the renal sensitivity to vasopressin was investigated in young rats. Male rats after orchidectomy and chronic antiandrogen cyproterone acetate treatment, and female rats after chronic Testosterone phenylpropionate treatment, were used. The plasma arginine-vasopressin (AVP) and testosterone concentrations, and the antidiuretic responses to AVP and the V2 agonist deamino-[8-D-arginine]-vasopressin (dDAVP) after volume loading were measured, and the renal [3H]AVP binding density was determined. The plasma AVP level decreased slightly, but not significantly, in male rats after orchidectomy and cyproterone acetate treatment, but did not alter in female rats after testosterone treatment. The AVP and dDAVP sensitivities decreased in male rats after orchidectomy and cyproterone acetate administration, and increased in female rats treated with testosterone, as compared with the animals with a normal gonadal function. [3H]AVP binding to the renal inner medullary membranes was decreased following orchidectomy or antiandrogen treatment in male rats, and increased in testosterone-treated female rats. The results suggest that testosterone may play a physiological role in maintenance of the V2 vasopressin receptor expression and hence in the normal urinary concentrating ability in rat.

Treatment of constitutional delayed puberty with a combination of testosterone esters.[Pubmed:8160278]

Turk J Pediatr. 1993 Oct-Dec;35(4):271-5.

Thirteen boys with constitutional delayed puberty (CDP) were treated with a combination of short and long-acting testosterone esters (testosterone propionate, Testosterone phenylpropionate, testosterone isocaproate). Mean age at the onset of treatment was 14.9 +/- 0.6 years and bone age delay was -2.7 +/- 0.9 years. The dose of testosterone used was 200 mg intramuscularly four times at three week intervals, and the treated CDP boys were followed for two years. All the boys with CDP entered puberty after the last dose (testicular volume > or = 4 ml), and growth rate increased from 4.5 +/- 0.5 cm/year, pretreatment, to 8.4 +/- 1.6 cm/year, posttreatment, at the two year follow-up. Height for bone age SD score did not change significantly from a mean of -1.1 before treatment to -1.3 after treatment, nor did predicted height before treatment (173.5 +/- 6.6 cm) and after treatment (173.3 +/- 4.9 cm). Combination of testosterone esters in a given dose and schedule is a safe and effective treatment for prepubertal boys with constitutional delayed puberty.

The action of trenbolone acetate, a synthetic anabolic steroid, on ovarian function in the guinea pig.[Pubmed:1857092]

Lab Anim. 1991 Apr;25(2):117-21.

The action of trenbolone acetate, a synthetic anabolic steroid, on ovarian function was investigated in the guinea pig. Certain comparisons were made with testosterone, the naturally occurring androgen, administered as the phenylpropionate ester. Two milligrams trenbolone acetate per kg given subcutaneously on alternate days for 20 days blocked oestrous cyclicity and ovulation in 9 of 10 animals. A similar effect was shown by 2.2 mg of Testosterone phenylpropionate. Treatment of trenbolone acetate-treated animals with exogenous gonadotrophins suggested that the production of follicle-stimulating hormone had been suppressed. Signs of abnormality were seen in the livers of animals receiving 2 mg trenbolone acetate and 2.2 mg Testosterone phenylpropionate.