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5-Androstenetriol Sale

(Synonyms: Δ5-AT) 目录号 : GC49827

An active metabolite of DHEA

5-Androstenetriol Chemical Structure

Cas No.:4150-30-5

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1 mg
¥1,031.00
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5 mg
¥4,647.00
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10 mg
¥8,248.00
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产品描述

5-Androstenetriol is a steroid and an active metabolite of dehydroepiandrosterone .1 In vivo, 5-androstenetriol (0.75 mg/25 g body weight) reduces radiation-induced lethality and induces hematopoietic recovery from surviving stem cells in mice. It increases survival in a rat model of surgical trauma-induced sepsis when administered at a dose of 40 mg/kg.2 Urinary levels of 5-androstenetriol are increased in women with androgenic alopecia.3

1.Loria, R.M., Conrad, D.H., Huff, T., et al.Androstenetriol and androstenediol. Protection against lethal radiation and restoration of immunity after radiation injuryAnn. N. Y. Acad. Sci.917(1)860-867(2000) 2.Marcu, A.C., Kielar, N.D., Paccione, K.E., et al.Androstenetriol improves survival in a rodent model of traumatic shockResuscitation71(3)379-386(2006) 3.Juricskay, S., and Telegdy, E.Urinary steroids in women with androgenic alopeciaClin. Biochem.33(2)97-101(2000)

Chemical Properties

Cas No. 4150-30-5 SDF Download SDF
别名 Δ5-AT
Canonical SMILES C[C@@]12[C@]3([H])[C@](CC=C1C[C@H](CC2)O)([H])[C@@]4([H])[C@](CC3)([C@H]([C@@H](C4)O)O)C
分子式 C19H30O3 分子量 306.4
溶解度 DMSO: soluble,Ethanol: soluble 储存条件 -20°C
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1 mg 5 mg 10 mg
1 mM 3.2637 mL 16.3185 mL 32.6371 mL
5 mM 0.6527 mL 3.2637 mL 6.5274 mL
10 mM 0.3264 mL 1.6319 mL 3.2637 mL
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Research Update

Molecular specificity of 5-androstenediol as a systemic radioprotectant in mice

Immunopharmacol Immunotoxicol 2005;27(1):15-32.PMID:15803857DOI:10.1081/iph-51289.

We compared in vivo radioprotective efficacy of 5-androstenediol (5-AED) to that of ten other steroids: 17alpha-androstenediol, dehydroepiandrosterone, 5-Androstenetriol (AET), 4-androstenedione (AND), testosterone, estradiol, fluasterone, 16alpha-bromoepiandrosterone, 16alpha-fluoro-androst-5-en-17alpha-ol (alpha-fluorohydrin, AFH), and 16alpha-fluoro-androst-5-en-17beta-ol (beta-fluorohydrin). Steroids were administered 24 or 48 hr before, or 1 hr after, whole-body gamma-irradiation. Two days after irradiation at 3 Gy, blood elements were counted. In addition, after irradiation at 9-12.5 Gy, survival was recorded for 30 days. The results showed radioprotective efficacy was specific for 5-AED. One other steroid, AFH, demonstrated appreciable survival effects but was less efficacious than 5-AED. AND and AET produced slight enhancement of survival in some experiments. This is the first demonstration that the prophylactic window for survival enhancement by 1 subcutaneous (s.c.) injection of 5-AED is as long as 48 hr in mice. Moreover, the results indicate that 1 s.c. injection of 5-AED 1 hr after irradiation is much less effective than 1 injection 24-48 hr before irradiation. Comparing the molecular features of steroids with radioprotective efficacy leads to the following conclusions: 1) these effects are due to interaction with specific receptors, since s.c. injection of extremely similar molecules with the same physicochemical properties as 5-AED were not radioprotective; 2) the 17-hydroxyl group is essential; 3) this group must be in the beta configuration in the absence of nearby side groups; 4) a halogen atom at 16 changes the 17-hydroxyl specificity to alpha; 5) the 3beta-hydroxyl group is not essential; 6) addition of a 7beta-hydroxyl group is deleterious; and 7) the effects are not due to activation of sex steroid receptors.

Effects of whole-body gamma irradiation and 5-androstenediol administration on serum G-CSF

Immunopharmacol Immunotoxicol 2005;27(4):521-34.PMID:16435574DOI:10.1080/08923970500416707.

5-Androstenediol (5-AED) is a natural circulating adrenocortical steroid hormone that interconverts in vivo with other members of the 5-androstene family of steroids: dehydroepiandrosterone and 5-Androstenetriol. These steroids stimulate immune responses and resistance to infection. 5-AED has been identified as a systemic radiation countermeasure that enhances survival in mice exposed to gamma irradiation and ameliorates radiation-induced neutropenia in mice and nonhuman primates. 5-AED mitigates radiation-induced decreases in platelets, natural killer (NK) cells, red blood cells, and monocytes. Administration of 5-AED causes functional activation of circulating granulocytes (phagocytic ability), monocytes (oxidative burst), and NK cells (surface CD11b expression). The effects of 5-AED on survival and hematological parameters are consistent with induction of hematopoietic cytokines. To test this hypothesis, we measured serum cytokines by ELISA, Luminex, and a cytokine array. A cytokine array was used for 62 different cytokines, chemokines, growth factors, and soluble receptors. 5-AED caused significant increases in circulating granulocyte colony-stimulating factor (G-CSF) in irradiated and unirradiated animals as observed with ELISA and Luminex. The cytokine array results suggest induction of G-CSF and additional cytokines, and related molecules. Since G-CSF is an important hematopoietic cytokine, the results support our hypothesis that the previously observed increases in numbers of hematopoietic progenitors, circulating innate immune cells and platelets, and functional activation of granulocytes, monocytes, and NK cells result from a cytokine cascade induced by 5-AED.

[Biosynthesis of steroids by human fetal kidney perfused in vitro (author's transl)]

Acta Obstet Gynaecol Jpn 1981 Jun;33(6):805-12.PMID:7246068doi

In the present experiments, human fetal kidneys obtained from two fetuses aborted at mid-term (gestational age 21 weeks) were perfused in vitro with labeled precursor including 14G-dehydroepiandrosterone (DHA) and 14C-dehydroepiandrosterone-sulfate (DHA-S). Radioactive metabolites extracted after the termination of perfusion from the perfusate and the tissue were separated the free fraction by ether and conjugate fraction by n-butanol. Furthermore, recovery of the radioactivities were separated and purified by thin layer chromatography. Radiochemical purity of the metabolites were achieved by recrystallization to constant specific activity. When DHA was used as a precursor, in the perfusate, DHA-S, delta 5-Androstenediol, delta 5-Androstenetriol were identified as the metabolites derived from DHA, and they were successively recrystallized. But, when DHA-S was used as a precursor, the radioactive purity of the metabolite was not obtained. The result of this perfusion studies demonstrate a powerful activity of steroids sulfokinase and a slight activity of steroids 16 alpha-hydroxylase, 17 beta-hydroxysteroid dehydrogenase in fetal kidney.