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Tetrahydrocortisone Sale

(Synonyms: 四氢可的松) 目录号 : GC38859

A metabolite of cortisol

Tetrahydrocortisone Chemical Structure

Cas No.:53-05-4

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5mg
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产品描述

Tetrahydrocortisone is a metabolite of cortisol .1,2 It is formed from cortisol via cortisone as an intermediate.

1.Abel, S.M., Maggs, J.L., Back, D.J., et al.Cortisol metabolism by human liver in vitro—I. Metabolite identification and inter-individual variabilityJ. Steroid. Biochem. Mol. Biol.43(7)713-719(1992) 2.White, P.C., Mune, T., and Agarwal, A.K.11β-hydroxysteroid dehydrogenase and the syndrome of apparent mineralocorticoid excessEndocr. Rev.18(1)135-156(1997)

Chemical Properties

Cas No. 53-05-4 SDF
别名 四氢可的松
Canonical SMILES C[C@@]1([C@]([H])([C@]2([C@]([H])3[C@]4(C)[C@]([H])(CC2)C[C@@H](CC4)O)[H])CC[C@@]1(C(CO)=O)O)CC3=O
分子式 C21H32O5 分子量 364.48
溶解度 Soluble in DMSO 储存条件 Store at -20°C
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1 mg 5 mg 10 mg
1 mM 2.7436 mL 13.7182 mL 27.4363 mL
5 mM 0.5487 mL 2.7436 mL 5.4873 mL
10 mM 0.2744 mL 1.3718 mL 2.7436 mL
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Research Update

Tetrahydrocortisol/Tetrahydrocortisone ratio (H4F/H4E) as an indicator of depressive feelings

Psychosom Med 1976 Jan-Feb;38(1):13-8.PMID:1257380DOI:10.1097/00006842-197601000-00003.

Tetrahydrocortisol (H4F) and Tetrahydrocortisone (H4E) were determined for a group of 15 depressed patients and 25 normal controls following the administration of cortisol-4-C14. The ratio, H4F/H4E, was significantly greater for the depressed patients than for the normal controls (P less than 0.001), although the sum of the two metabolites, H4F + H4E, was not significantly different. Three of four objective test measures of depressive feelings likewise discriminated between the two groups. All four depression measures correlated significantly with the H4F/H4E ratio at the 0.01 level or better. It is suggested that the data of the present report and those of Zumoff et al. (J Clin Endocrinol Metab 39:1120, 1974) may be explained by the paradigm: depressive feelings leads to reduced thyroid function leads to elevated H4F/H4E ratio.

Urinary Tetrahydrocortisone and tetrahydrocortisol glucosiduronates in normal newborns, children and adults

Acta Endocrinol (Copenh) 1980 Jul;94(3):371-5.PMID:7424479DOI:10.1530/acta.0.0940371.

Utilizing a simple, highly specific radioimmunoassay (RIA), we measured the excretion of the glucosiduronate conjugates of Tetrahydrocortisone (THE-gluc) and tetrahydrocortisol (THF-gluc) in adults (n = 16), children (n = 58) and newborns (n = 5), in order to establish a normal range of values for age and surface area. Both tetrahydrometabolites showed a linear increase with age but became constant for all individuals except newborns when results were calculated per square meter. Newborns excreted disproportionately low levels of these metabolites for their size. In children of similar ages, when 24h urine collections (n = 13) were compared to spot AM specimens (AM-Sp) (n = 45) in which the daily volume was estimated by creatinine excretion, THE-gluc/m2 levels were significantly higher in AM-Sp urines but THF-gluc/m2 levels were similar. Levels of both metabolites were markedly elevated in two patients with hyperadrenal states and low in three patients with hypoadrenal states compared to normal values per m2. These results indicate that the RIA for THE-gluc and THF-gluc can be a useful indirect test of cortisol secretion in children as well as in adults. Although 24h urine collections are more accurate, creatinine corrected AM-Sp urines may be clinically useful when values of these metabolites per m2 are compared to appropriate controls.

Synthesis of deuterium-labeled tetrahydrocortisol and Tetrahydrocortisone for study of cortisol metabolism in humans

Steroids 1999 Dec;64(12):805-11.PMID:10576214DOI:10.1016/s0039-128x(99)00056-2.

A method is described for the preparation of multi-labeled tetrahydrocortisol (3alpha,11beta,17alpha,21-tetrahydroxy-5beta-[1, 2,3,4,5-2H5]pregnan-20-one, THF-d5), allo-tetrahydrocortisol (3alpha,11beta,17alpha,21-tetrahydroxy-5alpha-[1 ,2,3,4,5-2H5]pregnan-20-one, allo-THF-d5), and Tetrahydrocortisone (3alpha,17alpha,21-trihydroxy-5beta-[1,2,3,4,5-2H5]pre gnane-11,20-dione, THE-d5) containing five non-exchangeable deuterium atoms in the steroid ring A. Reductive deuteration at C-1, C-2, C-3, C-4, and C-5 of prednisolone or prednisone was performed in CH3COOD with rhodium (5%) on alumina under the deuterium atmosphere. The isotopic purities of the labeled compounds as [2H5]-form were estimated to be 86.17 atom%D for THF-d5, 74.46 atom%D for allo-THF-d5 and 81.90 atom%D for THE-d5, based on the ion intensities in the region of the molecular ion of methoxime-trimethylsilyl (MO-TMS) derivatives measured by GC-MS.

Effect of apolipoprotein a-I complex with Tetrahydrocortisone on protein biosynthesis and glucose absorption by rat hepatocytes

Bull Exp Biol Med 2009 Aug;148(2):207-9.PMID:20027330DOI:10.1007/s10517-009-0667-z.

We studied the effect of apolipoprotein A-I-tetrahydrocortisone complex on (14)C glucose absorption and lactate accumulation and on the rate of protein biosynthesis in isolated rat hepatocytes. The presence of apolipoprotein A-I-tetrahydrocortisone complex in the incubation medium increased absorption of labeled glucose by hepatocytes by 52%, while lactate content in the conditioning medium increased 4-fold. The rate of protein biosynthesis increased by 80% in comparison with control cells. It is hypothesized that the increase in protein biosynthesis rate in hepatocytes under the effect of apolipoprotein A-I-tetrahydrocortisone complex is due to stimulation of energy metabolism, specifically, of its glycolytic component.

Direct determination of the ratio of tetrahydrocortisol+allo-tetrahydrocortisol to Tetrahydrocortisone in urine by LC-MS-MS

J Chromatogr B Analyt Technol Biomed Life Sci 2006 Jan 18;830(2):278-85.PMID:16310418DOI:10.1016/j.jchromb.2005.11.011.

The 11beta-hydroxysteroid dehydrogenase (11beta-HSD) is responsible for the interconversion of both the hormonally inactive cortisone and the active cortisol. This enzyme activity, which has implications in the pathogenesis of numerous diseases, is reflected in the ratio of tetrahydrometabolites of cortisol (allo-tetrahydrocortisol and tetrahydrocortisol) to those of cortisone (Tetrahydrocortisone). Several methods have been proposed in the literature to determine such a ratio in urine. Most of them require tedious and extensive extraction and derivatization steps and make use of gas-chromatographic techniques, including gas chromatography coupled to mass spectrometry (GC-MS). We present here an alternative approach for the direct determination of such a ratio in urine by using liquid chromatography-electrospray ionization-tandem mass spectrometry (LC-ESI-MS-MS), based on a minimal sample treatment. Actually, the limit of detections (LODs) for pure standards in water permitted a simple dilution of the urine samples prior to the analysis, hence, an accurate optimization of the high performance liquid chromatography (HPLC) separation was needed in order to get rid of the severe influence of the urine matrix on the ionization efficiency. Besides, the nature of some interfering species was deeply investigated, as well as the suitability of some commercial deuterated steroids as internal standards. All these led to the final method, which was based on a HPLC separation on a C8 column and a ternary gradient water/methanol/acetonitrile. In parallel, an appropriate sample preparation was set up, which consisted of an enzymatic hydrolysis of the conjugated species and a followed 1:20 dilution. Preliminary measurements on real urine samples were performed as well.