A group of compounds forming the nucleus of the estrogenic steroid family.

Steroid inhibition of rat neuronal nicotinic alpha4beta2 receptors expressed in HEK 293 cells. (1/17)

Steroids, in addition to regulating gene expression, directly affect a variety of ion channels. We examined the action of steroids on human embryonic kidney 293 cells stably transfected to express rat alpha4beta2 neuronal nicotinic receptors. Each steroid that was tested inhibited acetylcholine responses from these receptors, with slow kinetics requiring seconds for block to develop and recover. The action of one steroid [3alpha,5alpha, 17beta-3-hydroxyandrostane-17-carbonitrile (ACN)] was studied in detail. Block showed enantioselectivity, with an IC(50) value of 1.5 microM for ACN and 4.5 microM for the enantiomer. Inhibition curves had Hill slopes larger than 1, indicating more than one binding site per receptor. Block did not require intracellular compounds containing high-energy phosphate bonds and was not affected by analogs of GTP, suggesting that the mechanism does not require the activation of second messengers. Block did not appear to be strongly selective between open and closed channel states or to involve changes in desensitization. A comparison of different steroids showed that a beta-orientation of groups at the 17 position produced more block than alpha-orientated diastereomers. The stereochemistry at the 3 and 5 positions was less influential for block of alpha4beta2 nicotinic receptors, despite its importance for potentiation of gamma-aminobutyric acid(A) receptors. The ability of steroids to block neuronal nicotinic receptors correlated with their ability to produce anesthesia in Xenopus tadpoles, but the concentrations required for inhibition are generally greater. Similarly, the concentrations of endogenous neurosteroids required to inhibit receptors are larger than estimates of brain concentrations.  (+info)

Pregnenolone sulfate block of GABA(A) receptors: mechanism and involvement of a residue in the M2 region of the alpha subunit. (2/17)

Neurosteroids are produced in the brain, and can have rapid actions on membrane channels of neurons. Pregnenolone sulfate (PS) is a sulfated neurosteroid which reduces the responses of the [gamma]-aminobutyric acid A (GABA(A)) receptor. We analysed the actions of PS on single-channel currents from recombinant GABA(A) receptors formed from [alpha]1, [beta]2 and [gamma]2L subunits. Currents were elicited by a concentration of GABA eliciting a half-maximal response (50 microM) and a saturating concentration (1 mM). PS reduced the duration of clusters of single-channel activity at either concentration of GABA. PS had no discernable effect on rapid processes: no effects were apparent on channel opening and closing, nor on GABA affinity, and a rapidly recovering desensitised state was not affected. Instead, PS produced a slowly developing block which occurred at a similar rate for receptors with open or closed channels and with one or two bound GABA molecules. The rate of block was independent of membrane potential, implying that the charged sulfate moiety does not move through the membrane field. Change in a specific residue near the intracellular end of the channel lining portion of the [alpha]1 subunit had a major effect on the rate of block. Mutation of the residue [alpha]1 V256S reduced the rate of block by 30-fold. A mutation at the homologous position of the [beta]2 subunit ([beta]2 A252S) had no effect, nor did a complementary mutation in the [gamma]2L subunit ([gamma]2L S266A). It seems likely that this residue is involved in a conformational change underlying block by PS, instead of forming part of the binding site for PS.  (+info)

Correlation between retention and 1-octanol-water partition coefficients of some estrane derivatives in reversed-phase thin-layer chromatography. (3/17)

The retention constants (RM) of a series of estrane and secoestrane derivatives are experimentally determined on C18-modified silica gel layers with methanol-water mobile phases of various concentrations. The slopes (m) and intercepts (RMW) of the linear relationships between RM and the volume fraction of methanol are calculated. Both constants increase when the retention of compounds increases, and there is a linear dependence between them indicating their additivity; they represent the sums of particular retention contributions of skeleton and substituents. The contributions, particularly the retention fragmental constants, are calculated by combining the linear relationships RM/log P, RM/m, and RMW/log P. The log P values of the compounds and skeleton were calculated using Rekker's fragmental constants.  (+info)

[13C]Nandrolone excretion in trained athletes: interindividual variability in metabolism. (4/17)

BACKGROUND: Nandrolone is one of the most abused anabolic steroids, and its use in doping is increasing, as revealed by numerous positive cases during recent years in various sports. Different authors have reported the possible natural production of nandrolone metabolites in humans, and some of these authors argued that exhaustive exercise could increase nandrolone production in the body or induce dehydration and consequently lead to an increase of nandrolone metabolites in urine. METHODS: Volunteers (n = 22) ingested two 25-mg doses of [(13)C]nandrolone at 24-h intervals and collected urine specimens for 5 days. The labeled nandrolone metabolites 19-norandrosterone and 19-noretiocholanolone were identified and quantified by gas chromatography-mass spectrometry. RESULTS: Interindividual variability was observed in nandrolone excretion patterns and kinetics, as well as for the noretiocholanolone:norandrosterone ratio. The amounts of nandrolone metabolites measured at the excretion peak varied between 1180 and 38 661 microg/L for norandrosterone and 576 and 12 328 microg/L for noretiocholanolone. At the end of the excretion period, the noretiocholanolone:norandrosterone ratio was sometimes >1. The analysis of numerous spot-urine samples allowed the determination of an acceptable correlation between urinary creatinine and specific gravity for placebo- and steroid-treated individuals: y = 0.0052ln(x) + 1.0178 (r(2) = 0.8142) and y = 0.0068ln(x) + 1.0172 (r(2) = 0.7730), respectively. CONCLUSIONS: The excretion kinetics and patterns of labeled nandrolone show interindividual variability. More investigations are currently underway to estimate the influence of exhaustive exercises on excretion of labeled nandrolone metabolites in urine.  (+info)

Neuroactive steroids have multiple actions to potentiate GABAA receptors. (5/17)

The effects of neuroactive steroids on the function of GABAA receptors were studied using cell-attached records of single channel activity recorded from HEK293 cells transfected with alpha1 beta2 gamma2L subunits. Activity was elicited with a half-maximal (50 microM) concentration of GABA. Two steroids were studied in detail: ACN ((3alpha,5alpha,17beta)-3-hydroxyandrostane-17-carbonitrile) and B285 ((3alpha,5beta,17beta)-3-hydroxy-18-norandrostane-17-carbonitrile). Four effects on channel activity were seen, two on open time distributions and two on closed times. When clusters of openings were elicited in the absence of steroid, the open time distribution contained three components. ACN produced concentration-dependent alterations in the open time distribution. The prevalence of the longest duration class of open times was increased from about 15% to about 40% (EC50 about 180 nM ACN), while the duration of the longest class increased from 7.4 ms to 27 ms (EC50 about 35 nM ACN). B285 also increased the prevalence of the longest duration open times (EC50 about 18 nM B285) but increased the duration only at concentrations close to 10 microM. The differences in the actions of these two steroids suggest that the effects on proportion and duration of the long duration open time component are produced by independent mechanisms and that there are separate recognition sites for the steroids which are associated with the two functional actions. The closed time distributions also showed three components in the absence of steroid. The rate of occurrence of the two brief duration closed time components decreased with increasing ACN, with an EC50 of about 50 nM ACN. In contrast, B285 did not reduce the rate of occurrence of the brief closings until high concentrations were applied. However, both B285 and ACN reduced the rate of occurrence of the activation-related closed state selectively, with comparable IC50 concentrations (about 40 nM ACN, 20 nM B285). As in the case for action on open times these data suggest that there are two recognition sites and two independent mechanisms, perhaps the sites and mechanisms associated with actions on open times. The presence of 1 microM ACN had no effect on the estimated channel opening rate or on the apparent affinity of the receptor for GABA. Mutation of the carboxy terminus of the gamma2 subunit, but not the alpha1 or beta2 subunits, abolished the ability of ACN to increase the duration of OT3 but had no effect on the reduction of the rate of occurrence of the activation-related closed state. These observations are also consistent with the idea that there is more than one distinguishable steroid recognition site on the GABAA receptor.  (+info)

Quantification and profiling of 19-norandrosterone and 19-noretiocholanolone in human urine after consumption of a nutritional supplement and norsteroids. (6/17)

Nandrolone is one of the synthetic anabolic steroids banned in sports and has been a popular substance abused by athletes in recent years. One of its major metabolites, 19-norandrosterone (19-NA), has been used as a determinant for drug violations in sports. Current reports regarding nandrolone-positive cases have been related to intake of some nandrolone-free nutritional supplements. The aim of this study was to learn whether if a nutritional supplement sold by over-the-counter (OTC) nutritional stores could yield the same metabolic products as that of nandrolone. If so, what is (are) the substance(s) that contributed to the nandrolone metabolites? To determine the content of an OTC nutritional supplement, a tablet was dissolved in methanol, followed by N-methyl-N-trimethylsilyltrifluoroacetamide (MSTFA)-trimethyliodosilane (TMIS) derivatization prior to gas chromatography-mass spectrometry (GC-MS) analysis. The collected urine samples underwent extraction, enzymatic hydrolysis, and derivatization before the analyses of GC-MS. The results showed that seven anabolic steroids were found as contaminants in the nutritional supplement, in addition to six that were listed in the ingredients by the manufacturer. We confirmed previous reports that administration of the OTC supplement could produce a positive urine test for nandrolone metabolites. Furthermore, the results from excretion studies showed that 19-NA and 19-noretiocholanolone (19-NE) were present in urine after consuming the nutritional supplement, nandrolone, 19-nor-4-androsten-3,17-dione, 19-nor-4-androsten-3beta,17beta-diol, and 19-nor-5-androsten-3beta,17beta-diol. The 19-NA concentrations in urine were generally higher than that of 19-NE (19-NA/19-NE ratio > 1.0) especially during the early stage of excretion, that is, before 6 h post-administration. After this period of time, the concentrations of 19-NA and 19-NE fluctuated and might even have reversed (19-NA/19-NE ratio < 1.0) in their ratio, that is, higher yield in 19-NE than that in 19-NA. On the basis of this study, we postulate that some doping violations of nandrolone could be attributed by indiscriminate administration of the OTC nutritional supplements that contained 19-norsteroids.  (+info)

Unintentional doping through the use of contaminated nutritional supplements. (7/17)

OBJECTIVE: To determine whether the intake of contaminated nutritional supplements could cause an athlete to fail a dope test. DESIGN: A contaminated nutritional supplement was used, identified in an ongoing study screening over-the-counter nutritional supplements. One capsule of the supplement, containing small amounts of 19-nor-4-androstenedione and 4-androsten-3,17-dione, not listed on the label, was administered to 5 healthy male volunteers. Fractional urine collection was done at prescribed intervals. Outcome measures. The samples were analysed using gas chromatography/mass spectrometry (GC/MS). Samples containing 19-norandrosterone, the main metabolite of 19-nor-4-androstenedione, were quantified using GC/MS. RESULTS: All the volunteers had urinary concentrations of 19-norandrosterone above the World Anti-Doping Agency threshold of 2 ng/ml from 2 hours post administration. In 2 volunteers 19-norandrosterone above the threshold value could still be detected beyond 36 hours post administration. The highest concentration of 19-norandrosterone found in a sample was 54.6 ng/ml at 8 hours post administration. CONCLUSION: The results of this study showed that the intake of microgram amounts of a prohibited substance in a nutritional supplement could cause an athlete to fail a dope test.  (+info)

Significance of 19-norandrosterone in athletes' urine samples. (8/17)

Nandrolone and other 19-norsteroid potent anabolic steroids have been prohibited in sports for 30 years. The detection of the main urinary metabolite--19-norandrosterone--in amounts greater than 2 ng/ml constitutes an adverse analytical finding. The presence in nutritional sport supplements of steroids not listed on the label has undoubtedly resulted in positive tests, but inadvertent consumption of meat containing residues of hormonal treatment should not realistically cause apprehension. Although highly improbable, athletes should prudently avoid meals composed of pig offal in the hours preceding the test since the consumption of edible parts of a non-castrated pig, containing 19-nortestosterone, has been shown to results in the excretion of 19-norandrosterone in the following hours. Norsteroid metabolites are formed during pregnancy and excreted as minor metabolites of norethisterone, and minute amounts have been identified in some male and female samples when using more sensitive techniques of detection. Whereas exercise does not seem to be a significant factor in 19-norandrosterone excretion, some rare urine samples were found to be a suitable medium for in situ 19-demethylation of urinary metabolites.  (+info)

Estranes are a type of steroid hormone related to estrogen, which is a female sex hormone. Estranes are not normally produced in the human body but can be found in some plants and animals. They are often used in hormone replacement therapy and contraceptives. Examples of estranes include equilin and equilenin, which are found in the urine of pregnant mares.

It's important to note that while estranes have estrogen-like effects on the body, they may also have unique properties and potential side effects compared to traditional estrogens. Therefore, their use should be carefully monitored and managed by a healthcare professional.

... is a C18 steroid derivative, with a gonane core. Estrenes are estrane derivatives that contain a double bond, with an ... Estratrienes (estrins) are estrane derivatives that contain three double bonds, for instance estrin (estra-1,3,5(10)-triene). ...
This family is subdivided into two groups: the estranes and the gonanes. The estranes include norethisterone (norethindrone), ... 489-. ISBN 978-1-59259-375-0. Estranes. Estrane and gonane progestogens are derived from 19-nortestosterone, the progestogenic ... Estranes are characterized by the presence of an ethinyl group at position 17 and by the absence of a methyl group between the ... The gonanes share the structural modifications found in the estranes and also possess an ethinyl group at position 13 and a ...
Morais GR, Yoshioka N, Watanabe M, Mataka S, Oliveira CD, Thiemann T (2006). "C7-Substituted Estranes and Related Steroids". ... Estranes, Estrogens, Ketones, All stub articles, Steroid stubs, Genito-urinary system drug stubs). ...
Highly selective for estrogens; 100-fold higher affinity for estranes over androstanes. However, also catalyzes the conversion ...
... is a synthetic estrane steroid and the C17β valerate (pentanoate) fatty acid ester of estradiol. It is also ... "Esters of unsaturated polyhydroxy estrane". Shoham Z, Kopernik G (June 2004). "Tools for making correct decisions regarding ...
Catechol-O-methyltransferase inhibitors, Estranes, Estrogens, Human metabolites, Steroid hormones). ...
Estrane and pregnane C19H32 Wilson JD (1996). "Role of dihydrotestosterone in androgen action". Prostate Suppl. 6 (S6): 88-92. ...
Estradiol is a naturally occurring estrane steroid. It is also known as 17β-estradiol (to distinguish it from 17α-estradiol) or ... Estranes, Estrogens, Galactagogues, GPER agonists, Hepatotoxins, Hormonal antineoplastic drugs, Phenols, Prolactin releasers). ...
The estrogen steroid hormones are estrane steroids. In 1929, Adolf Butenandt and Edward Adelbert Doisy independently isolated ... an estrane, is the most potent and prevalent. Another estrogen called estetrol (E4) is produced only during pregnancy. ... Estranes, Estrogens, Fertility, Hepatotoxins, Hormones of the hypothalamus-pituitary-gonad axis, Hormones of the hypothalamic- ...
5α-Gonane 5β-Gonane 5α-Gonane, side-perspective view 5β-Gonane, side-perspective view Estrane (C18) is the 13β-methyl variant ... The term is used to distinguish them from the estranes (19-nortestosterone derivatives). Yang, Yanqing; Krin, Anna; Cai, Xiaoli ...
Articles with short description, Short description matches Wikidata, Estranes, Estrogens, Human metabolites, Steroid hormones) ...
Gonane Androstane Estrane Howard J.A. Carp, ed. (9 April 2015). Progestogens in Obstetrics and Gynecology. Springer. pp. 35-. ...
Sources were Jacobi & Altwein (1979) and Derra (1981). Estradiol undecylate is a synthetic estrane steroid and an estradiol ...
Alternatively, estranes such as noretynodrel and norethisterone are classified as first-generation while gonanes such as ... Testosterone derivatives can be classified into subgroups including androstanes, estranes (19-norandrostanes), and gonanes (18- ... and the estranes norethisterone acetate, norethisterone enanthate, levonorgestrel, levonorgestrel butanoate, desogestrel, and ...
... is a synthetic estrane steroid and the C3 acetate ester of estradiol. It is also known as estradiol 3-acetate ...
... and androstenone and the estrane estratetraenol. Certain other endogenous steroids, such as pregnenolone, progesterone, ...
... is a synthetic estrane steroid and the C3 benzoate (benzenecarboxylate) ester of estradiol. It is also known ...
It is dehydrogenated estrane with double bonds specifically at the C1, C3, and C5(10) positions. Estrin is a parent structure ... Estrin (American English), or oestrin (British English), also known as estra-1,3,5(10)-triene, is an estrane steroid. ...
... the estrogens possess an estrane skeleton (C18), and androgens, an androstane skeleton (C19). The terms progesterone, ...
The steroidal estrogens are estranes and include estradiol and its analogues, such as ethinylestradiol and conjugated estrogens ...
... , or nandrolone 17β-phenylpropionate, is a synthetic estrane steroid and a derivative of ...
EDE is a synthetic estrane steroid and the C3 and C17β heptanoate (enanthate) diester of estradiol. It is also known as ...
... , or nandrolone 17β-decanoate, is a synthetic estrane steroid and a derivative of testosterone. It is an ...
... , also known as 17α-ethynyl-19-nortestosterone or as 17α-ethynylestra-4-en-17β-ol-3-one, is a synthetic estrane ... This group is divided by chemical structure into the estranes (derivatives of norethisterone) and the gonanes (18-methylgonanes ... Estranes, Hormonal contraception, Human drug metabolites, Progestogens, Syntex, Synthetic estrogens). ...
EBB is a synthetic estrane steroid and the C3 benzoate (benzenecarboxylate) and C17β butyrate (butanoate) diester of estradiol ...
... , or trenbolone 17β-acetate, is a synthetic estrane steroid and a derivative of nandrolone (19- ... Estranes, Glucocorticoids, Ketones, Prodrugs, Progestogens, Veterinary drugs). ...
... , also known as ethinylestradiol 3-cyclopentyl ether (EE2CPE), is a synthetic estrane steroid and a derivative of ... Estranes, Estrogen ethers, Synthetic estrogens, Tertiary alcohols). ...
... is a synthetic estrane steroid and a derivative of estradiol. It is an estrogen ester; specifically, it is the C3,17β ...
Estrane is a C18 steroid derivative, with a gonane core. Estrenes are estrane derivatives that contain a double bond, with an ... Estratrienes (estrins) are estrane derivatives that contain three double bonds, for instance estrin (estra-1,3,5(10)-triene). ...
Estranes. Norethindrone. Second generation. Levonorgestrel. Gonanes. Norgestrel. Norgestimate* (active metabolite ...
Estrane derivatives. C00951 Estradiol-17beta. Hormones and transmitters. Steroid hormones. Estrogens. C00951 Estradiol-17beta ( ...
These are steroids with a structure containing a 3-hydroxylated estrane. Thus, 2-Hydroxyestrone is considered to be a steroid ...
Estrane. 105-1074. Androstane. 1075-1182. Etianic acid. 1183-2099. Pregnane. 2100-2125. Cardane, Cardenolide. ...
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Synthesis and cytotoxic evaluation of novel hybrid estrane heterocycles as chemotherapeutic anti-cancer agents.. Nada DS; ...
Estranes,N0000008196, Iodobenzoates,N0000008195, Vinyl Compounds,N0000008194, Erythropoietin,N0000008193, Granulocyte Colony- ...
The synthetic progestins used for contraception are structurally related either to testosterone (estranes and gonanes) or to ...
D4.210.500.365.415.248.320 Estranes D4.808.365 D4.210.500.365 Estrenes D4.808.365.415 D4.210.500.365.415 Estriol D4.808.365.415 ...
Estranes Preferred Term Term UI T015144. Date01/01/1999. LexicalTag NON. ThesaurusID NLM (1968). ... Estranes Preferred Concept UI. M0007786. Registry Number. 0. Scope Note. A group of compounds forming the nucleus of the ... Estranes. Tree Number(s). D04.210.500.365. Unique ID. D004962. RDF Unique Identifier. http://id.nlm.nih.gov/mesh/D004962 ...
Estranes Preferred Term Term UI T015144. Date01/01/1999. LexicalTag NON. ThesaurusID NLM (1968). ... Estranes Preferred Concept UI. M0007786. Registry Number. 0. Scope Note. A group of compounds forming the nucleus of the ... Estranes. Tree Number(s). D04.210.500.365. Unique ID. D004962. RDF Unique Identifier. http://id.nlm.nih.gov/mesh/D004962 ...
Estranes (1972-1974). Hydroxysteroids (1972-1974). Methyl Ethers (1972-1974). Public MeSH Note:. 91; was see under ESTRENES ...
Riley: Would Ensign Whale, Ensign Eren and Ensign Estrane ((OOC: Ensign Estranes promotion is in effect a promotion for ... Eren/Estrane: RESPONSES Riley: The three of you are invaluable to the crew. Ensign Whale, your devotion to the security ... Riley: And last but not least Ensign Estrane. Doctor, your bedside manner is excellent, your devotion to treat anyone ...
17α-Ethyl-5α-estrane-3α,17β-diol. $990.00 - $2,750.00 ... 17α-Ethyl-5α-estrane-3α,17β-diol. 10/11/2009 ...
Estranes [D04.808.365]. *Estrenes [D04.808.365.415]. *Trenbolone Acetate [D04.808.365.415.930]. Below are MeSH descriptors ...
Estranes [D04.808.365]. *Estrenes [D04.808.365.415]. *Estradiol [D04.808.365.415.248]. *Hormones, Hormone Substitutes, and ...
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Estrane (substance) {126088007 , SNOMED-CT } Parent/Child (Relationship Type) 16 alpha-hydroxyestrone (substance) {708724009 , ...
These are steroids with a structure containing a 3-hydroxylated estrane.. Kingdom. Organic compounds ...
A lipid is generally considered to be any molecule that is insoluble in water and soluble in an organic solvent
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37] M. Watanabe, T. Matsumoto, S. Mataka and T. Thiemann: "Heteroarenoannelated estranes by triene cyclization", Centr. Eur. J ...
Estrane derivative 4_2Cl was most active in the ovarian cancer cell line COV362 compared to the control cell line HIO80 with an ... Estrane derivatives that have low or minimal estrogenic activity can affect both pathways. In this study, we investigated the ... Estrane derivatives 3 and 4_2Cl showed a stronger effect on the endometrial cancer cell lines KLE and Ishikawa, respectively, ... In addition, estrane derivative 2_4I showed a strong antiproliferative effect on endometrial and ovarian cancer cell lines, ...
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Estrane-skeleton / Estrogen-skeleton / Hydrocarbon derivative. Molecular Framework. Aromatic homopolycyclic compounds. External ...
At that time, there was a significant variety of life and evidence of estrane is also seen. This chemical compound is a ...
Nandrolone decanoate, or nandrolone 17β-decanoate, is a synthetic estrane steroid and a derivative of testosterone. [8] [9] It ... Nandrolone decanoate, or nandrolone 17β-decanoate, is a synthetic estrane steroid and a derivative of testosterone. [8] [9] It ...
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  • Estrenes are estrane derivatives that contain a double bond, with an example being nandrolone. (wikipedia.org)
  • Estratrienes (estrins) are estrane derivatives that contain three double bonds, for instance estrin (estra-1,3,5(10)-triene). (wikipedia.org)
  • Unsaturated derivatives of the ESTRANES with methyl groups at carbon - 13 , with no carbon at carbon - 10 , and with no more than one carbon at carbon - 17 . (dictionary.net)
  • In addition to the synthesis of small molecules by classical chemistry, he succeeded by developing solid-phase syntheses of C18-steroid (estrane) derivatives as well as C19-steroid (androstane) derivatives that enabled the generation of model libraries of targeted therapeutic compounds. (ulaval.ca)
  • Estrane is a C18 steroid derivative, with a gonane core. (wikipedia.org)
  • Nandrolone phenylpropionate, or nandrolone 17β-phenylpropionate, is a synthetic estrane steroid and a derivative of testosterone. (allstarcollectable.com)
  • Trenbolone, also known as 19-nor-δ9,11-testosterone or as estra-4,9,11-trien-17β-ol-3-one, is a synthetic estrane steroid and a derivative of. (leedonss.com)
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  • Eren''': RESPONSE '''Riley''': And last but not least Ensign Estrane. (starbase118.net)
  • These are steroids with a structure containing a 3-hydroxylated estrane. (hmdb.ca)
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  • Estrane is a C18 steroid derivative, with a gonane core. (wikipedia.org)