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Pregnanetriol

(Synonyms: 孕三醇) 目录号 : GC48724

A metabolite of 17α-hydroxyprogesterone

Pregnanetriol Chemical Structure

Cas No.:1098-45-9

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产品描述

Pregnanetriol is a metabolite of 17α-hydroxyprogesterone .1,2 It is formed from 17α-hydroxyprogesterone by reduction of the C-20 ketone.2 Urinary levels of pregnanetriol are elevated in patients with 21-hydroxylase deficiency and congenital adrenal hyperplasia.3,4

1.Kamrath, C., Hartmann, M.F., Boettcher, C., et al.Diagnosis of 21-hydroxylase deficiency by urinary metabolite ratios using gas chromatography-mass spectrometry analysis: Reference values for neonates and infantsJ. Steroid Biochem. Mol. Biol.15610-16(2016) 2.Schiffer, L., Barnard, L., Baranowski, E.S., et al.Human steroid biosynthesis, metabolism and excretion are differentially reflected by serum and urine steroid metabolomes: A comprehensive reviewJ. Steroid Biochem. Mol. Biol.194105439(2019) 3.Disorders of steroidogenesis guide to steroid profiling and biochemical diagnosis1(2019) 4.Shackleton, C.H.L.Role of a disordered steroid metabolome in the elucidation of sterol and steroid biosynthesisLipids47(1)1-12(2012)

Chemical Properties

Cas No. 1098-45-9 SDF
别名 孕三醇
Canonical SMILES C[C@@]12[C@](CC[C@]2(O)[C@H](C)O)([H])[C@@]3([H])[C@@](CC1)([H])[C@@]4([C@](C[C@@H](CC4)O)([H])CC3)C
分子式 C21H36O3 分子量 336.5
溶解度 Methanol: soluble 储存条件 -20°C
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1 mM 2.9718 mL 14.8588 mL 29.7177 mL
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Research Update

First Morning Pregnanetriol and 17-Hydroxyprogesterone Correlated Significantly in 21-Hydroxylase Deficiency

Front Endocrinol (Lausanne) 2022 Jan 24;12:808254.PMID:35140686DOI:10.3389/fendo.2021.808254.

Background: Biochemically monitoring 21-hydroxylase deficiency (21-OHD) is challenging. Serum/blood 17-hydroxyprogesterone (17OHP) measurements are normally used for this purpose. Urinary Pregnanetriol (PT), a urinary metabolite of 17OHP, may also be used. Based on auxological data, we previously reported that the optimal first morning PT value fell in the range of 2.2-3.3 mg/gCr (95% confidence interval of the mean) and 0.59-6.0 mg/gCr (10th - 90th percentile) for monitoring 21-OHD treatment. No report thus far has directly compared the first morning urinary PT value with the 17OHP value at various times during the day. Objective: To explore the correlation between the first morning urinary PT value before glucocorticoid administration and the serum/blood 17OHP value at three time points, namely, before and two and four hours after glucocorticoid administration. Design: This was a prospective study done at two children's hospitals. Methods: In total, 25 patients with 21-OHD aged 3-25 years were recruited. Their urinary PT levels and 17OHP levels were measured for three days within a total period of one week. The first morning PT value was collected on all three days. Dried blood spots and serum were used to measure 17OHP. Results: The range for the first morning PT value for all the samples (n=69) was 0.10-56.1 mg/gCr. A significant, positive correlation was found between the first morning PT and 17OHP values before medication (r=0.87, p<0.01), and weaker correlation was observed between the first morning PT and 17OHP values after medication. Conclusions: The first morning PT correlated more significantly with 17OHP before the morning medication. Measuring the first morning PT value may be more practical and useful for monitoring 21-OHD biochemically.

Non-invasive monitoring of ovarian function in Asian elephants (Elephas maximus) by measurement of urinary 5 beta-pregnanetriol

J Reprod Fertil 1993 Nov;99(2):617-25.PMID:8107047DOI:10.1530/jrf.0.0990617.

The development of an enzymeimmunoassay for 5 beta-pregnanetriol and its use for non-invasive monitoring of reproductive cycles in Asian elephants is described. Gas chromatography-mass spectrometry (GCMS) and high performance liquid chromatography (HPLC) confirmed the presence of 5 beta-pregnane-3 alpha,17 alpha,20 alpha/beta-triols as the two most abundant urinary progesterone metabolites. The assay developed used the antiserum anti-5 beta-pregnane-17 alpha,20 alpha-diol-3 alpha-gamma l glucuronide but was designed to measure the free steroid in urine samples after hydrolysis and extraction. HPLC confirmed the presence of immunoreactive Pregnanetriol in urine, but indicated that the measurement was nonspecific. Immunoreactive Pregnanetriol concentrations were significantly correlated with the concentrations of both progesterone (r = 0.98, n = 269, P < 0.01) and 17 alpha-hydroxyprogesterone (r = 0.95, n = 205, P < 0.01), the metabolic precursor of Pregnanetriol. The mean +/- SEM deviation of cycles as determined by measurements of plasma progesterone, 17 alpha-hydroxyprogesterone and urinary Pregnanetriol, respectively, were 15.54 +/- 1.5 (n = 23, where n = number of cycles), 15.21 +/- 1.7 (n = 15) and 15.45 +/- 0.94 weeks (n = 20). These results demonstrate that it is possible to monitor ovarian function in Asian elephants by the measurement of urinary immunoreactive Pregnanetriol concentrations.

The radioimmunoassay of Pregnanetriol 3 alpha-glucuronide

J Steroid Biochem 1985 Jun;22(6):843-9.PMID:4021487DOI:10.1016/0022-4731(85)90295-x.

The hapten (5 beta-pregnane-17,20 alpha-diol-3 alpha-yl glucuronide) required to develop the radioimmunoassay was synthesized by an unambiguous chemical synthesis. An immunogenic complex was synthesized by coupling bovine serum albumin (BSA) to the glucuronide by mixed acid anhydride reaction. The immunogenic complex was used to induce the formation of specific antibodies in rabbits. In addition, the required radioligand [6,7-3H]5 beta-pregnanetriol 3 alpha-glucuronide was prepared with appropriate specific radioactivity. The characteristics of the antibody were determined with regard to specificity and sensitivity and the precision and accuracy of the assay method established. As applied to urine samples this method is superior to existing procedures in that they avoid the hydrolysis step and can be used directly on diluted urine. Examples have been given of useful application of this technique in clinical practice.

Prediction and detection of ovulation by the measurement of urinary pregnanetriol-3 alpha-glucuronide. A multicentre study

J Steroid Biochem 1986 Apr;24(4):921-7.PMID:3702465DOI:10.1016/0022-4731(86)90455-3.

The urine excretion pattern of Pregnanetriol 3 alpha-glucuronide (PT-3G) throughout the menstrual cycle in 26 normal ovulating women was evaluated in a multicentre study. The concentration of PT-3G was measured by radioimmunoassay in daily samples of early morning urine (EMU) from 20 women for three consecutive cycles and from 6 women who conceived during the period of study. PT-3G was also measured in 24-h urine samples from 5 additional women. The peak of urine LH was used as a reference point for ovulation (Day 0). The EMU concentration of PT-3G in the follicular phase of 60 normal ovulatory cycles was 5.10 mumol/l +/- 0.11 (arithmetic mean +/- SE). The first PT-3G defined rise (CUSUM analysis) occurred during the late follicular phase (Days -3 to 0) with a PT-3G maximum excretion (9.69 mumol/1 +/- 0.55) on Day 0, whereas a PT-3G excretion peak occurred during mid-luteal phase (Days +5 to +9). The overall PT-3G excretion during the luteal phase (8.06 mumol/1 +/- 0.17) was significantly higher than that of the follicular phase (P less than 0.001). A further sustained increase in PT-3G excretion was noted after day +11 in the conceptional cycles. The 24-h excretion profile of PT-3G was similar to that obtained in EMU samples. No inter-centre significant variation was noticed in terms of PT-3G concentration values. The results were interpreted as demonstrating that the PT-3G excretion profile throughout the cycle exhibits a close resemblance to that of serum 17-OH progesterone. The data also indicates that although the immunoanalytical measurement of this urine steroid metabolite does not give an early sign for the occurrence of ovulation, it can be used for both the immediate prediction and the detection of ovulation.

Urinary Pregnanetriol excretion in hirsutism

Clin Chim Acta 1977 Oct 15;80(2):373-9.PMID:199379DOI:10.1016/0009-8981(77)90046-8.

Eighteen consecutive hirsute women attending an endocrine clinic have been studied by measurement of the urinary Pregnanetriol excretion before and following the concurrent administration of corticotrophin and metyrapone. An abnormal increment in Pregnanetriol excretion was observed in 11 of these 18 patients. It is suggested that this is evidence that an adrenal abnormality, probably operative at the 21-hydroxylase level, might be a factor responsible for the hirsutism in these 11 patients. Five adrenalectomized women who were also studied showed no significant increase in urinary Pregnanetriol excretion in response to concurrent corticotrophin and metyrapone administration.