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PubMed1980

7 alpha- and 7 beta-carboxymethyl-derivatives of 17-hydroxyprogesterone and 11-deoxycortisol. Synthesis and immunogenic properties.

7 alpha- and 7 beta-carboxymethyl-derivatives of 17-hydroxyprogesterone and 11-deoxycortisol have been synthesized. After coupling to bovine serum albumin, they were used to elicit antibodies in rabbits. No major difference in the steroid specificity of the antisera was observed when either 7 alpha- or 7 beta-epimers were used for immunization. In both cases, highly specific antisera were obtained which may possibly be used to assay human plasma 17-hydroxyprogesterone and 11-deoxycortisol without chromatographic purification.

17-Hydroxycorticosteroids↗
PubMed1981

17-Hydroxyprogesterone metabolism in the monkey fetal adrenal: C17-20lyase and 21-hydroxylase activities.

C17-20Lyase and 21-hydroxylase activities were measured during late gestation in the rhesus monkey (Macaca mulatta) fetal adrenal. Activities were assessed in 10,000 x g supernatants with 17-hydroxyprogesterone and NADPH as substrates. Although conversion of [14C]17-hydroxyprogesterone to [14C]androstenedione was noted, activity was often nonlinear and far less than the rate of hydroxylation which together prevented an accurate estimation of lyase rate, Km and Vmax. 21-Hydroxylase activity was characterized; the mean reaction rate was 1.6 x 10(-3) mumoles NADPH oxidized/min. x mg-1 protein with an apparent Km of 3.6 x 10(-7) M and a Vmax of 2.2 x 10(-3) mumoles/min. x mg-1 protein. These values were similar to data obtained in adrenals from adult monkeys. A relatively high level of hydroxylase activity in the fetal gland might lead to an inadequate supply of precursors for the synthesis of dehydroepiandrosterone sulfate (DHEAS) in the adrenal if it also contained 3 beta-hydroxysteroid dehydrogenase (3 beta-hsdh). However, the fact that the fetal adrenal reportedly is deficient in 3 beta-hsdh may serve to protect both DHEAS and corticoid synthesis.

Adrenal Glands↗
PubMed2003

Use of liquid chromatography-diode-array detection and mass spectrometry for rapid product identification in biotechnological synthesis of a hydroxyprogesterone.

In exploratory scale biotechnological process development, the product must be rapidly identified although a reference compound may not always be available. LC-diode-array detection and MS were used for this purpose in a process producing 9alpha-hydroxyprogesterone from progesterone as substrate. The electrospray ionization mass spectrometer was combined with an ion trap mass spectrometer for the second generation MS. The preliminary identification, which could be carried out within the course of a day, confirmed that the product was a hydroxyprogesterone. The final identification step, which was much more material intensive and hence time consuming, involved a two-step preparative separation to yield quantities necessary for definitive product identification based on 1H- and 13C NMR.

Biotechnology↗
PubMed1998

Determination of progesterone and 17-hydroxyprogesterone by high performance liquid chromatography after pre-column derivatization with 4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene-3-propionohydra zide.

Progesterone, 17-hydroxyprogesterone and four other 3-keto steroids were determined by high performance liquid chromatography with fluorescence detection. Each steroid was derivatized with 4,4-difluoro-5,7-dimethyl-4-bora-3a,4a-diaza-s-indacene++ +-3- propionohydrazide (BODIPY FL hydrazide) and separated on a Wakosil 5C4 column with acetonitrile-water (7 + 3) as mobile phase. The limits of detection of progesterone, 17-hydroxyprogesterone, dehydroepiandrosterone, androstenedione, testosterone and 17-methyltestosterone were 550-3700 fmol per 10 microliters injection (signal-to-noise ratio = 5) serum. The calibration curves were linear up to 1000 ng/ml serum. The proposed method was most sensitive among the available high performance liquid chromatographic methods after fluorescence and chemiluminescence pre-labeling with dansylhydrazine.

17-alpha-Hydroxyprogesterone↗
PubMed1998

Cortisol in dried blood screening specimens from newborns with raised 17-hydroxyprogesterone and congenital adrenal hyperplasia.

BACKGROUND AND OBJECTIVE: Screening for congenital adrenal hyperplasia (CAH) in newborns has become a routine part of many programmes by measuring levels of 17 alpha-hydroxyprogesterone (17-OHP) in the newborn filter-paper blood specimen. Unfortunately, raised levels of 17-OHP, which are largely the consequence of cross-reacting metabolites, are also found in low birth weight, premature and ill neonates. We speculated that differences in concentrations of cortisol in the newborn screening specimen would aid in distinguishing between CAH positive and CAH negative infants among those with raised levels of 17-OHP. DESIGN: Comparison of cortisol concentrations was made between newborns with CAH and those without but with raised 17-OHP levels. PATIENTS: Newborn filter-paper blood specimens from 31 infants with transient 17-OHP elevations and 16 infants with confirmed CAH were analysed for cortisol. In addition, assay performance was validated by comparing cortisol values obtained from dried whole blood on filter-paper with the corresponding plasma from 31 adults and six neonates. MEASUREMENTS: Cortisol in filter-paper blood specimens was determined by adapting a commercial radioimmunoassay kit that had been designed for the determination of cortisol in serum. RESULTS: The mean cortisol level in the CAH negative group was significantly higher than the mean value in the group with documented CAH (means 1190 +/- 795 nmol/l vs 627 +/- 210 nmol/l; P < 0.01). However, approximately half of the CAH negative infants had cortisol values that overlapped those from the CAH positive group. There was no relationship between the magnitude of the 17-OHP elevation and cortisol concentrations. CONCLUSION: The measurements of cortisol in dried blood on filter-paper using a commercial radioimmunoassay kit has been shown to be reliable and simple to carry out. The level of cortisol in newborn blood specimens can be used to exclude some infants with elevated 17 alpha-hydroxyprogesterone levels from further testing for CAH. However, overlapping cortisol values between CAH positive and negative infants precludes the assay of cortisol from being used routinely as a reliable means of decision making.

17-alpha-Hydroxyprogesterone↗
PubMed2004

A male twin infant with skull deformity and elevated neonatal 17-hydroxyprogesterone: a prismatic case of P450 oxidoreductase deficiency.

We report on a male twin infant who presented with brachy-turri-cephaly, frontal bossing, large anterior fontanelle, low set and malformed ears, and mild arachnodactyly. He had normal male genitalia. There was no evidence for maternal virilization during pregnancy. The pattern of malformations resembled Antley-Bixler-Syndrome (ABS). However, sequencing analysis of the fibroblast growth factor receptor 2 gene (FGFR2) did not reveal mutations. The boy's twin sister did not show any somatic or endocrine abnormalities. In the boy, neonatal screening for congenital adrenal hyperplasia was positive with moderately elevated 17-hydroxyprogesterone. Sequence analysis of his CYP21 gene did not reveal any mutations. The short synacthen test revealed an exaggerated 17-hydroxyprogesterone and a blunted cortisol response. Urinary steroid profiling by gas chromatography-mass spectrometry (GC-MS) revealed a unique steroid metabolome suggestive of impaired activity of both 17-hydroxylase and 21-hydroxylase. Clinical and metabolic findings therefore were compatible with the recently described variant of congenital adrenal hyperplasia, P450 oxidoreductase deficiency (ORD). Subsequently, sequencing analysis of CPR, the gene encoding P450 oxidoreductase (OR), revealed a homozygous mutation in the patient, resulting in an amino acid exchange in position 284 of the OR protein (A284P). Both the female twin sister and the parents were heterozygous for the A284P mutation. P450 oxidoreductase deficiency represents a novel autosomal recessively inherited form of congenital adrenal hyperplasia. Its characteristic steroid metabolome can readily be detected by GC-MS analysis of spot urine. Clinical features may include an ABS phenotype, ambiguous genitalia (virilization in girls, feminization in boys), and glucocorticoid deficiency. If required, hydrocortisone replacement should be provided.

17-alpha-Hydroxyprogesterone↗
PubMed1982

The effect of the antiandrogen II alpha-hydroxyprogesterone on sebum production and cholesterol concentration of sebum.

II alpha-Hydroxyprogesterone, a synthetic antiandrogen of low toxicity, was applied topically. In short-term experiments the sebum production of the forehead in normal male subjects was reduced significantly. The cholesterol concentration of sebum decreased to a greater extent. In long-term studies in patients with seborrhoea and male-pattern alopecia, the steroid caused a marked and constant reduction of greasiness of the hair. In this group also, the cholesterol concentration of the sebum obtained from scalp hair decreased more markedly than total sebum production. Possible effects of II alpha-hydroxyprogesterone on androgenic alopecia are discussed.

Adult↗
PubMed1988

14 beta-Hydroxyprogesterone binds to the digitalis receptor, inhibits the sodium pump and enhances cardiac contractility.

1. Certain derivatives of progesterone are potent inhibitors of high affinity, specific binding of 3H-cardiac glycosides. The steroids interact at the cardiac glycoside site on Na,K-ATPase and inhibit the enzyme (the sodium pump) in cardiac and other tissues. However, the active congeners identified previously have been, unlike the cardiac glycosides, predominantly cardiodepressant. 2. Because a 14 beta-hydroxy substituent is an important determinant of activity of the cardiotonic cardiac glycosides, we synthesized 14 beta-hydroxyprogesterone. This derivative has about one-tenth the potency of the aglycone, ouabagenin, in a [3H]-ouabain binding assay. 3. Like ouabagenin, but in contrast to the cardiodepressant congeners of progesterone, 14 beta-hydroxyprogesterone consistently elicited positive inotropy in isolated cardiac muscle and enhanced both the magnitude and frequency of fluctuations in scattered light (an index of oscillatory intracellular release of calcium). 4. Thus, at least one hydroxylated derivative (and putative endogenous metabolite) of progesterone, mimics the cardiac effects of cardiac glycosides including enhanced contractility.

Adult↗
PubMed1988

Digitalis-like pregnanes. Cardiac and renal effects of a glycoside of 14 beta-hydroxyprogesterone.

The synthesis of the glucoside, 3 beta-[(beta-D-glucopyranosyl)oxy]-14-hydroxy-14 beta-pregn-4-en-20-one, a 14 beta-hydroxyprogesterone glucoside (14 beta-OHP-glu), is described. This compound has an IC50 of 1 microM in a [3H]ouabain binding assay, and is about 10 times more potent than the aglycone. Like 14 beta-hydroxyprogesterone, the glucoside enhances contractility of isolated cardiac muscle. 14 beta-OHP-glu or ouabain, when infused at comparable doses into the renal artery of the anesthetized rat, markedly increases urine volume. Whereas ouabain significantly enhances urinary potassium excretion with little or no effect on sodium excretion, 14 beta-OHP-glu promotes a marked natriuresis with no significant effect on potassium excretion.

Animals↗
PubMed2000

Determination of 17-hydroxyprogesterone in plasma by stable isotope dilution/benchtop liquid chromatography-tandem mass spectrometry.

An assay based on stable isotope dilution liquid chromatography-tandem mass spectrometry (ID/LC-MS-MS) was developed for the quantification of 17-hydroxyprogesterone, the most important indicator of 21-hydroxylase deficiency in human plasma. Plasma was extracted using ethyl acetate and Extrelut columns. LC was performed on a reversed-phase C18 column using a water/methanol gradient. A benchtop triple quadrupole mass spectrometer, operating in selected reaction monitoring mode, served as mass detector. The analytical run time was 9 min per sample. The sensitivity was high: 0.06 pmol of 17-hydroxyprogesterone yielded a signal-to-noise ratio of 13. Precision (CV) and accuracy (relative error) derived from the analyses of unspiked and spiked validation samples were 7.4-12.0% and 6.4%, respectively. When analyzing the same samples - median (range), in nanomoles per liter - from neonates and adults independently by ID/LC-MS-MS as well as by ID/gas chromatography (GC)-MS, corresponding results were obtained: neonates (n = 10), ID/LC-MS-MS 3.99 (0.48-16.05), ID/GC-MS 5.39 (1.57-13.02); adults (n = 10), ID/LC-MS-MS 2.66 (1.39-6.15), ID/GC-MS 2.54 (0.51-5.12). The technique permitted reliable detection of classical and nonclassical forms of 21- hydroxylase deficiency. The much simpler sample preparation, the faster analytical run time and the operational ease possible with ID/LC-MS-MS permit a considerable increase of sample testing per day without compromising on analytical sensitivity and specificity. We expect that benchtop tandem mass spectrometry will open new avenues in clinical steroid analysis.

17-alpha-Hydroxyprogesterone↗
PubMed1986

The combination of 17 alpha-hydroxyprogesterone and 11-epicortisol prevents the delayed feedback effect of natural and synthetic glucocorticoids.

Subcutaneous injection of 400 micrograms/100 g body weight of corticosterone (B) 2 h previously in male rats prevented the stress response, as assessed by the ability of adrenal glands removed from these animals to produce endogenous B. Two injections of a combination of 17 alpha-hydroxyprogesterone and 11-epicortisol, the first given 30 min before and the second with the B, were able to block this inhibitory effect on the stress response. Neither of the steroids alone was effective in this regard. The combination was also effective against the early delayed feedback effects of 400 micrograms/100 g body weight cortisol, prednisolone or beclomethasone dipropionate in the same system. The minimum effective dose for reversal of feedback by B or beclomethasone dipropionate (2 mg/100 g body weight of each antagonist) was lower than that required for the same effect against prednisolone or cortisol (5 mg/100 g body weight). Previous injection of B also abolished the ability of anterior pituitary gland fragments to respond to corticotropin-releasing factors (CRFs) added in vitro, an effect which was not abolished by the injection of the combination of putative antagonistic steroids. From experiments designed to measure the ability of 17 alpha-hydroxyprogesterone and 11-epicortisol to compete with 3H-corticosterone in binding to macromolecular components in hypothalamic, hippocampal and pituitary cytosolic preparations, it was deduced that the competition seen in the hypothalamic and hippocampal, rather than the pituitary, preparations was in better accord with the effect seen on the stress response.(ABSTRACT TRUNCATED AT 250 WORDS)

Animals↗
PubMed2003

Screening for congenital adrenal hyperplasia: adjustment of 17-hydroxyprogesterone cut-off values to both age and birth weight markedly improves the predictive value.

Newborn screening procedures for congenital adrenal hyperplasia (CAH) are still suboptimal because of low specificity, particularly in premature infants. This study evaluated a multitiered strategy for reporting abnormal 17-hydroxyprogesterone screening values that simultaneously takes into account not only birth weight but also age at sampling. A cautious three-tiered cut-off scheme was used during the initial 24 months of CAH screening in Bavaria. Data were then reanalyzed using five birth weight classes to reflect more precisely the markedly higher values in low-birth-weight newborns. Because 17-hydroxyprogesterone values apparently decline with increasing age, these classes were then further subdivided into a total of 21 groups according to the age at sampling. Based on this reanalysis, we defined new multitiered cut-off levels and used them for the next 18 months. A total of 538466 newborns were screened from January 1999 to June 2002; 51 CAH cases were detected. Application of the new threshold values resulted in a 35% reduction of the total recall rate (from 1.13% to 0.74%) and an increase in the positive predictive value from 0.84% to 1.29% without reducing diagnostic sensitivity. This improvement of CAH screening can be achieved by simply using request forms that ask for both age and birth weight at the time of sampling.

17-alpha-Hydroxyprogesterone↗
PubMed1982

Identification of a 17-hydroxyprogesterone-binding immunoglobulin in the serum of a woman with periodic rashes.

A 30-year-old patient with primary infertility had a history of recurrent oral and perineal rashes that appeared just prior to the midcycle rise in basal body temperature and subsided with the onset of menses. The rashes did not appear during periods of treatment with oral contraceptives or danazol, and were suppressed by administration of cortisol. Sera obtained during the follicular and luteal phases of her cycle were found to contain a progestin-binding component with high affinity for 17-hydroxyprogesterone and a somewhat lower affinity for progesterone. Analysis of these sera showed the progestin-binding component to have properties of IgG, with an apparent binding affinity for 17-hydroxyprogesterone of 2 X 10(10) M-1. This report is the first characterization of an antibody to an endogenous steroid in human serum.

Adult↗
PubMed1983

Spermatic and peripheral venous plasma concentrations of progesterone, 17 alpha-hydroxyprogesterone, and 20 alpha-dihydroprogesterone in prepubertal boys.

Testosterone, progesterone, 17 alpha-hydroxyprogesterone, and 20 alpha-dihydroprogesterone have been measured in the spermatic and peripheral venous blood of 17 prepubertal boys undergoing surgery for undescended testis or inguinal hernia repair. Mean (+/-SE) spermatic testosterone and progesterone (538 +/- 212 and 704 +/- 110 pg/ml, respectively) were significantly higher (P less than 0.005) than peripheral levels (91 +/- 11 and 419 +/- 71 pg/ml, respectively). No significant spermatic-peripheral gradient was found for 17 alpha-hydroxyprogesterone and 20 alpha-dihydroprogesterone. These in vivo studies demonstrate that the secretory pattern of the prepubertal testis is different from the adult testis.

20-alpha-Dihydroprogesterone↗
PubMed2000

Correlation of blood-spot 17-hydroxyprogesterone daily profiles and urinary steroid profiles in congenital adrenal hyperplasia.

OBJECTIVE: To compare the value of blood-spot 17-hydroxyprogesterone (17-OHP) daily profiles and urinary steroid excretion in untreated and treated patients with congenital adrenal hyperplasia (CAH). PATIENTS: Ten patients with CAH were investigated during steroid replacement therapy (Group 1), and 11 patients were investigated without treatment (Group 2). METHODS: Capillary blood samples were collected for measurement of blood-spot 17-OHP values by non-chromatographic radioimmunoassay. Steroid profiles of 24-h urine samples were analyzed by gas chromatography. RESULTS: There was a close correlation between the individual daily means of blood-spot 17-OHP measurements and the pregnanetriol/ tetrahydrocortisone ratio in both groups of patients (Group 2: r=0.839, p<0.001; Group 1: r=0.686, p<0.001). Almost the same correlation was found between the blood-spot 17-OHP value and the sum of three 17-hydroxyprogesterone metabolites/the sum of three cortisol/cortisone metabolites ratio (Group 2: r=0.918, p<0.001; Group 1: r=0.741, p<0.001). CONCLUSIONS: Blood-spot 17-OHP measurements and 24-h urinary steroid profile have the same impact in identification and monitoring therapy of children with CAH.

17-alpha-Hydroxyprogesterone↗
PubMed1981

Dehydroxylation of 16 alpha-hydroxyprogesterone by fecal flora of man and rat.

16 alpha-Hydroxyprogesterone, precursor of biliary 16 alpha-hydroxypregnanolone, was incubated with mixed fecal flora of humans and rats. The major steroid metabolite formed in both systems was 3 alpha-hydroxy-17 alpha-pregnan-20-one. These results demonstrated that the fecal flora reduced the delta 4-3 keto structure, removed the hydroxy group at C-16 and isomerized the side chain from the beta to the alpha configuration. Ring-A reduction of the substrate resulted in a 5 beta-compound with human flora and a 5 alpha-product with rat bacteria. The prevalence of 16 alpha-dehydroxylating organisms varied considerably in human fecal flora and was approximately 10(5)/g of feces in the three rats tested. Rat fecal flora dehydroxylated 16 alpha-hydroxyprogesterone after 4-5 days incubation at 37 degrees C, at pH 6.5-7.5, and with a substrate concentration of 20-80 microgram/ml (optimal condition). Preliminary evidence suggests that 16 alpha-dehydroxylase is exclusively of bacterial origin and is synthesized by an obligate anaerobe.

Adult↗
PubMed1980

A radio-immunoassay of 17-alpha-hydroxyprogesterone.

A method is described for the determination of 17 alpha-hydroxyprogesterone (17-OHP) in plasma. Antisera were raised in rabbits against 11-deoxycortisol-21-hemisuccinate-bovine serum albumin (11-DOC-21-HS-BSA) and 17 alpha-hydroxyprogesterone-3-carboxymethyloxime-bovine serum albumin (17-OHP-3-CMO-BSA). An antiserum to 11-DOC-21-HS-BSA exhibited cross-reaction with progesterone (29%), 11-deoxycortisol (100%), cortisol (17%) and testosterone (10%) and was therefore not appropriate for quantitation of 17-OHP in plasma. An antiserum to 17-OHP-3-CMO-BSA cross-reacted with progesterone (9,7%), 11-deoxycortisol (50%) and less than 1% with all other major naturally occurring steroid hormones. A radio-immunoassay (RIA) was developed using the antiserum to 17-OHP-4-CMO-BSA. The intra-assay and interassay coefficients of variation were 7,2% and 10,5% respectively. The normal ranges (nmol/l plasma) of samples extracted with hexane:benzene (1:1) and purified by Sephadex LH-20 chromatography were 0,28-4,7 for men, 0,84-3,0 for women (follicular phase), 3,0-11,0 for women (luteal phase), 4,6-22,1 for pregnant women, 18,5-123,9 for cord blood, 0,12-5,0 for children and 56,3-1 032 for persons with congenital adrenal hyperplasia (CAH) due to a 21-hydroxylation enzyme defect. Sephadex LH-20 purification of plasma extracts could be omitted when using the RIA as a screening procedure for CAH due to a 21-hydroxylation enzyme defect.

Adult↗
PubMed1976

Diurnal testosterone and 17alpha-hydroxyprogesterone in peripheral plasma of young post-pubertal bulls. A study by frequent sampling.

Testerone and 17alpha-hydroxyprogesterone were measured in the peripheral plasma of 6 young post-pubertal bulls of 1 year of age, by separate radioimmunoassays. Samples were collected every hour for 25 h at the beginning of each of four seasons. On a separate occasion blood samples were collected from one bull every 10 min for 2 h. As a result of the study, testosterone and 17alpha-hydroxyprogesterone appeared to be secreted episodically. These two steroid peaks showed good correlation. Each 24 h period showed its own characteristic pattern of pulsatile changes. Episodic secretion seems to be progressive rather than rapid and short lived. No real circadian rhythm was observed but at about 10.00 a.m. a trough in these steroid secretions occurred. This was followed by an increase in peripheral plasma concentration. These troughs occurred at all seasons after the morning feed and while semen was being collected in the performance test station.

Animals↗