481-29-8 Usage
Description
Epiandrosterone is a steroid hormone with weak androgenic activity, derived from 5 α-androstane. It is a dehydroepiandrosterone metabolite and an androgen. It is a precursor of testosterone and estradiol with hypolipidemic and anabolic activities.
Chemical Properties
white to off-white crystalline powder. Musky odor when heated.
Uses
Epiandrosterone is used for weight loss, to improve athletic performance, to reduce sexual problems, and for many other uses, but there is no good scientific evidence to support its use. Epiandrosterone might also be unsafe.Epiandrosterone is a steroid hormone that is present in normal human urine as a minor constituent , it is a less active 3β-isomer of the androgen Androsterone (A635535). Controlled Substance.
Definition
ChEBI: Epiandrosterone is a 3beta-hydroxy steroid that is (5alpha)-androstane substituted by a beta-hydroxy group at position 3 and an oxo group at position 17. It has a role as an androgen and a human metabolite. It is a 17-oxo steroid, a 3beta-hydroxy steroid and an androstanoid. It derives from a 5alpha-androstane.
Preparation
Epiandrosterone is naturally produced by the enzyme 5α-reductase from the adrenal hormone DHEA. Epiandrosterone can also be produced from the natural steroids androstanediol via 17β-hydroxysteroid dehydrogenase or from androstanedione via 3β-hydroxysteroid dehydrogenase.
Application
Epiandrosterone presents some neurological activity since it can bind to the ?-aminobutyric acid (GABA)/benzodiazepine-receptor complex (GABA-RC), acting as a negative non-competitive modulator of GABA-RC, and signaling through the N-methyl-D-aspartate receptor.It can also inhibit the pentose phosphate pathway, dilating blood vessels pre-contracted by partial depolarization.Epiandrosterone can inhibit the thromboxane A2 synthesis in activated platelets, decrease plasma plasminogen activator inhibitor type 1, reduce tissue plasminogen activator antigen, improve insulin-like growth factor 1 serum levels, and increase the synthesis of cyclic guanosine monophosphate and nitric oxide.In vitro assays demonstrate that this compound inhibits Junin virus replication vitro anti-adenovirus (AdV) activity.Epiandrosterone affects glucose oxidation and interleukin-1 beta in in vitro pancreatic islets.
Side effects
When taken by mouth: Epiandrosterone is POSSIBLY UNSAFE for most people when taken by mouth. Side effects include infertility, behavioral changes, hair loss, and breast development (in men). Epiandrosterone can also lead to liver damage and heart disease.
in vitro
it was reported that epi, at concentrations from 10 to 100 mm, decreased left-ventricular developed pressure (lvdp) and myocardial contraction rate dose-dependently. in addition, epi also increased cpp in isolated hearts, down-regulated levels of myocardial nadph and nitrite, as well as relaxed rat aortic rings in the dose-dependent manner. findings from whole cell clamp via electrophysiological analysis of single ventricular myocytes demonstrated that epi could reversibly block l-type channel currents carried by ba2+ in a dose-dependent manner with an ic50 of2 ± 6 m. moreover, epi, at a concentration of 30 mm, accelerated the decay of iba during depolarization, which suggested this agent as a l-type ca2+ channel antagonist with similar properties to those of 1, 4-dihydropyridine (dhp) ca2+ channel blockers. [1]
in vivo
in vivo tests were performed using g-6-pd-low c57l/j mouse erythrocytes. every other day, mice were orally administered with 450 or 900 mg/kg of tested agents including dhea, epi, pregnenolone (preg) and androstanedione (andr) for seven days (four doses). three hours after the final dose, mice were sacrificed. findings from blood samples suggested that g-6-pd activity had no significant changes, which might be caused by the lack of receptor sites for the steroids on the erythrocyte membrane. [2]
IC 50
blocking l-type calcium channels of ventricular myocytes with an ic50 of 42 ± 6 m.
Purification Methods
Purify epi-androsterone via the acetate, hydrolyse this and recrystallise it from CHCl3/hexane or aqueous EtOH. The acetate [1239-31-2] is purified by chromatography and when crystallised from pet ether has m 103-104o, []D +68.5o (c 1, CHCl3). The oxime has m 194-196o (from MeOH), []D +17.5o (c 6.2, CHCl3). The racemic ketone is sublimed at 130o/high vacuum and after two crystallisations from methylcyclohexane it gives prisms with m 161-162o (which changed crystal form at 140-145o). [Ruzicka & Wettstein Helv Chim Acta 18 1264 1935, Johnson et al. J Am Chem Soc 75 2275 1953, 78 6331 1956, Cordwell et al. J Chem. Soc 361 1953, Beilstein 8 IV 462.]
Mode of action
Epiandrosterone is a dehydroepiandrosterone metabolite and a precursor of testosterone and estradiol with hypolipidemic and anabolic property. Epiandrosterone, a potential neurosteroid, appears to bind to the gamma-aminobutyric acid (GABA)/benzodiazepine-receptor complex (GABA-RC), acting as a negative non-competitive modulator of GABA-RC as well as signal through the N-methyl-D-aspartate receptor. In addition this agent inhibits the pentose phosphate pathway (PPP) thereby dilating blood vessels pre-contracted by partial depolarization. Also, epiandrosterone inhibits the synthesis of thromboxane A2 in activated platelets, reduces plasma plasminogen activator inhibitor type 1 and tissue plasminogen activator antigen, increases serum levels of insulin-like growth factor 1 and increases cyclic guanosine monophosphate and nitric oxide synthesis. These effects may improve circulation in the microvasculature.
references
[1]gupte sa, tateyama m, okada t, oka m and ochi r. epiandrosterone, a metabolite of testosterone precursor, blocks l-type calcium channels of ventricular myocytes and inhibits myocardial contractility. j mol cell cardiol. 2002 mar; 34: 679- 88.[2]calabrese ej, horton hm and leonard da. the in vivo effects of four steroids on glucose-6-phosphate dehydrogenase activity of c57l/j mouse erythrocytes. j. environ. sci. health. 1987; a22(6): 563-74.[3]forrest ad, drewery j, fotherby k and laverty sg. a
Check Digit Verification of cas no
The CAS Registry Mumber 481-29-8 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 1 respectively; the second part has 2 digits, 2 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 481-29:
(5*4)+(4*8)+(3*1)+(2*2)+(1*9)=68
68 % 10 = 8
So 481-29-8 is a valid CAS Registry Number.
InChI:InChI=1/C19H30O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h12-16,20H,3-11H2,1-2H3/t12-,13-,14-,15-,16+,18-,19-/m0/s1
481-29-8Relevant articles and documents
Synthesis and antituberculosis activity of several steroids from 3αacetoxy-5βpregn-16-En-20-one
Sikharulidze,Nadaraia,Kakhabrishvili
, p. 423 - 425 (2012)
The semicarbazone and isonicotinoylhydrazone of 5βpregn-2-en-20-one, which was prepared from 3βacetoxy-5βpregn-16-en-20-one, were synthesized for the first time. The antituberculosis activity of these and semicarbazones and isonicotinoylhydrazones of saturated, unsaturated, and adamantane-modified ketosteroids synthesized by us earlier was studied in vitro experiments.
UNUSUAL HIGH REACTIVITIES OF Δ5 STEROIDS IN PALLADIUM CATALYZED HYDROGENATION
Nishimura, Shigeo,Takahashi, Izumi,Shiota, Michio,Ishige, Masayoshi
, p. 877 - 878 (1981)
Hydrogenation of a mixture of 3β-hydroxyandrost-5-en-17-one or cholesterol with α-pinene has revealed that the Δ5 steroids are more reactive than α-pinene over palladium while α-pinene is much more reactive than the Δ5 steroids with other platinum metals.
ANDROSTENEDIONE METABOLISM IN EPITHELIAL CELLS DERIVED FROM EARLY-LACTATION HUMAN MILK
Perel, E.,Stolee, K. J.,Kharlip, L.,Blackstein, M. E.,Killinger, D. W.
, p. 389 - 400 (1983)
Epithelial cells derived from duct epithelium were cultured from early lactation human milk in medium supplemented with 15percent fetal calf serum, insulin (0.3 u/ml), cortisol 21-sodium succinate (6 μg/ml) and amikacin (50 μg/ml).The capacity of these cells to metabolize androstenedione to estrone, estradiol and C19 metabolites was studied during continuous culture.After extraction of the medium, the products were subjected to phenolic partition and separated by thin-layer and paper chromatography, followed by recrystallization to constant specific activity.The study demonstrated a progressive increase in the formation of estrone and testosterone over the first 24 h in culture, while estradiol formation showed an initial 2-4 h lag, then increased slowly.The C19 compounds identified were androsterone, 5α-androstanedione, epiandrosterone, dihydrotestosterone and etiocholanolone. 5α-Androstanedione and androsterone were the major 5α-reduced metabolites.Since these cells are derived from normal duct epithelium, their metabolic characteristics may be more representative of normal breast tissue than those of tissue removed from patients with pathological breast disorders.
Synthesis of guggulsterone derivatives as potential anti-austerity agents against PANC-1 human pancreatic cancer cells
Kohyama, Aki,Yokoyama, Rei,Dibwe, Dya Fita,El-Mekkawy, Sahar,Meselhy, Meselhy R.,Awale, Suresh,Matsuya, Yuji
, (2020)
E- and Z-guggulsterones and nine guggulsterone derivatives (GSDs) were synthesized and evaluated for their preferential cytotoxicity against human PANC-1 cell in nutrient deprived medium utilizing antiausterity strategy. Among the synthesized compounds, GSD-1 and GSD-7 showed potent cytotoxicity against PANC-1 cells under nutrient-deprived conditions in a concentration dependent manner, with a PC50 value of 1.6 μM and 3.2 μM, respectively. The effect of GSD-1 and GSD-7 was further evaluated in a real time using live cell imaging. Both of these compounds altered PANC-1 cell morphology, leading to cell death at sub micromolar concentration range. GSD-1 and GSD-7 also inhibited PANC-1 cell colony formation in a concentration-dependent manner. GSD-1 and GSD-7 are lead structure for the anti-austerity drug development.
Catalytic removal of tert-butyldimethylsilyl (TBS) ether by PVP-I
Ke, Yanxiong,Lu, Guangying,Ren, Jiangmeng,Wang, Di,Zeng, Bu-Bing
, (2019/09/06)
A mild, efficient and rapid protocol the deprotection of alcoholic TBDMS ethers using PVP-1 as catalyst in methanol, the procedure of deprotection of various TBDMS ethers were found to be very convenient, easy work-up, high yielding.
Abiraterone acetate reducing impurity and preparation method thereof
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Paragraph 0017, (2017/10/22)
The invention discloses an abiraterone acetate reducing impurity and a preparation method thereof. The impurity is 17-(3-pyridyl) androstane-3 beta-acetoxyl. The preparation method of the impurity includes the steps: taking dehydroepiandrosterone as a starting material; performing catalytic hydrogenation by palladium carbon to obtain (3 beta)-3-hydroxy-17-sterone; performing reaction by hydrazine hydrate to obtain 17-hydrazono-androstane-3 beta-alcohol; performing iodine substitution to obtain 17-iodine-androstane-3 beta-alcohol; reacting the 17-iodine-androstane-3 beta-alcohol with borane reagents under palladium catalysis to obtain 17-(3-pyridyl) androstane-3 beta-alcohol; performing acetic anhydride acetylation to obtain the abiraterone acetate reducing impurity 17-(3-pyridyl) androstane-3 beta-acetoxyl.
