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| 17α-Hydroxyprogesterone (17α-OHP), also known as 17-OH progesterone (17-OHP), or hydroxyprogesterone (OHP), is an endogenous progestogen steroid hormone related to progesterone. It is also a chemical intermediate in the biosynthesis of many other endogenous steroids, including androgens, estrogens, glucocorticoids, and mineralocorticoids, as well as neurosteroids. |
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Read full article at Wikipedia
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InChI=1S/C21H30O3/c1- 13(22)21(24)11-8-18-16-5-4-14-12-15(23)6-9-19(14,2)17(16)7-10-20(18,21)3/h12,16-18,24H,4-11H2,1-3H3/t16-,17+,18+,19+,20+,21+/m1/s1 |
| DBPWSSGDRRHUNT-CEGNMAFCSA-N |
| [H][C@@]12CC[C@](O)(C(C)=O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C |
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Mus musculus
(NCBI:txid10090)
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Source: BioModels - MODEL1507180067
See:
PubMed
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Homo sapiens
(NCBI:txid9606)
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See:
DOI
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metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
progestin
A synthetic progestogen.
human metabolite
Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).
mouse metabolite
Any mammalian metabolite produced during a metabolic reaction in a mouse (Mus musculus).
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View more via ChEBI Ontology
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17-hydroxypregn-4-ene-3,20-dione
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hidroxiprogesterona
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ChemIDplus
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hydroxyprogesterone
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KEGG DRUG
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hydroxyprogesteronum
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ChemIDplus
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17-Hydroxypregn-4-en-3,20-dione
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NIST Chemistry WebBook
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17-hydroxyprogesterone
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ChemIDplus
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17alpha-Hydroxy-4-pregnene-3,20-dione
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KEGG COMPOUND
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17alpha-Hydroxy-progesterone
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KEGG COMPOUND
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17alpha-Hydroxyprogesterone
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KEGG COMPOUND
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17α-hydroxyprogesterone
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UniProt
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delta(4)-Pregnene-17alpha-ol-3,20-dione
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ChemIDplus
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hydroxyprogesterone
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ChemIDplus
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Pregn-4-ene-3,20-dione-17-ol
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KEGG COMPOUND
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2062088
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Reaxys Registry Number
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Reaxys
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68-96-2
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CAS Registry Number
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ChemIDplus
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68-96-2
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CAS Registry Number
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NIST Chemistry WebBook
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Dou J, Doyle L, Jr Greisen P, Schena A, Park H, Johnsson K, Stoddard BL, Baker D (2017)
Sampling and energy evaluation challenges in ligand binding protein design.
Protein science : a publication of the Protein Society 26, 2426-2437 [PubMed:28980354]
[show Abstract]
The steroid hormone 17α-hydroxylprogesterone (17-OHP) is a biomarker for congenital adrenal hyperplasia and hence there is considerable interest in development of sensors for this compound. We used computational protein design to generate protein models with binding sites for 17-OHP containing an extended, nonpolar, shape-complementary binding pocket for the four-ring core of the compound, and hydrogen bonding residues at the base of the pocket to interact with carbonyl and hydroxyl groups at the more polar end of the ligand. Eight of 16 designed proteins experimentally tested bind 17-OHP with micromolar affinity. A co-crystal structure of one of the designs revealed that 17-OHP is rotated 180° around a pseudo-two-fold axis in the compound and displays multiple binding modes within the pocket, while still interacting with all of the designed residues in the engineered site. Subsequent rounds of mutagenesis and binding selection improved the ligand affinity to nanomolar range, while appearing to constrain the ligand to a single bound conformation that maintains the same "flipped" orientation relative to the original design. We trace the discrepancy in the design calculations to two sources: first, a failure to model subtle backbone changes which alter the distribution of sidechain rotameric states and second, an underestimation of the energetic cost of desolvating the carbonyl and hydroxyl groups of the ligand. The difference between design model and crystal structure thus arises from both sampling limitations and energy function inaccuracies that are exacerbated by the near two-fold symmetry of the molecule. | Wang C, Pallan PS, Zhang W, Lei L, Yoshimoto FK, Waterman MR, Egli M, Guengerich FP (2017)
Functional analysis of human cytochrome P450 21A2 variants involved in congenital adrenal hyperplasia.
The Journal of biological chemistry 292, 10767-10778 [PubMed:28539365]
[show Abstract]
Cytochrome P450 (P450, CYP) 21A2 is the major steroid 21-hydroxylase, converting progesterone to 11-deoxycorticosterone and 17α-hydroxyprogesterone (17α-OH-progesterone) to 11-deoxycortisol. More than 100 CYP21A2 variants give rise to congenital adrenal hyperplasia (CAH). We previously reported a structure of WT human P450 21A2 with bound progesterone and now present a structure bound to the other substrate (17α-OH-progesterone). We found that the 17α-OH-progesterone- and progesterone-bound complex structures are highly similar, with only some minor differences in surface loop regions. Twelve P450 21A2 variants associated with either salt-wasting or nonclassical forms of CAH were expressed, purified, and analyzed. The catalytic activities of these 12 variants ranged from 0.00009% to 30% of WT P450 21A2 and the extent of heme incorporation from 10% to 95% of the WT. Substrate dissociation constants (Ks) for four variants were 37-13,000-fold higher than for WT P450 21A2. Cytochrome b5, which augments several P450 activities, inhibited P450 21A2 activity. Similar to the WT enzyme, high noncompetitive intermolecular kinetic deuterium isotope effects (≥ 5.5) were observed for all six P450 21A2 variants examined for 21-hydroxylation of 21-d3-progesterone, indicating that C-H bond breaking is a rate-limiting step over a 104-fold range of catalytic efficiency. Using UV-visible and CD spectroscopy, we found that P450 21A2 thermal stability assessed in bacterial cells and with purified enzymes differed among salt-wasting- and nonclassical-associated variants, but these differences did not correlate with catalytic activity. Our in-depth investigation of CAH-associated P450 21A2 variants reveals critical insight into the effects of disease-causing mutations on this important enzyme. | Petrunak EM, DeVore NM, Porubsky PR, Scott EE (2014)
Structures of human steroidogenic cytochrome P450 17A1 with substrates.
The Journal of biological chemistry 289, 32952-32964 [PubMed:25301938]
[show Abstract]
The human cytochrome P450 17A1 (CYP17A1) enzyme operates at a key juncture of human steroidogenesis, controlling the levels of mineralocorticoids influencing blood pressure, glucocorticoids involved in immune and stress responses, and androgens and estrogens involved in development and homeostasis of reproductive tissues. Understanding CYP17A1 multifunctional biochemistry is thus integral to treating prostate and breast cancer, subfertility, blood pressure, and other diseases. CYP17A1 structures with all four physiologically relevant steroid substrates suggest answers to four fundamental aspects of CYP17A1 function. First, all substrates bind in a similar overall orientation, rising ∼60° with respect to the heme. Second, both hydroxylase substrates pregnenolone and progesterone hydrogen bond to Asn(202) in orientations consistent with production of 17α-hydroxy major metabolites, but functional and structural evidence for an A105L mutation suggests that a minor conformation may yield the minor 16α-hydroxyprogesterone metabolite. Third, substrate specificity of the subsequent 17,20-lyase reaction may be explained by variation in substrate height above the heme. Although 17α-hydroxyprogesterone is only observed farther from the catalytic iron, 17α-hydroxypregnenolone is also observed closer to the heme. In conjunction with spectroscopic evidence, this suggests that only 17α-hydroxypregnenolone approaches and interacts with the proximal oxygen of the catalytic iron-peroxy intermediate, yielding efficient production of dehydroepiandrosterone as the key intermediate in human testosterone and estrogen synthesis. Fourth, differential positioning of 17α-hydroxypregnenolone offers a mechanism whereby allosteric binding of cytochrome b5 might selectively enhance the lyase reaction. In aggregate, these structures provide a structural basis for understanding multiple key reactions at the heart of human steroidogenesis. | Schwarz E, Liu A, Randall H, Haslip C, Keune F, Murray M, Longo N, Pasquali M (2009)
Use of steroid profiling by UPLC-MS/MS as a second tier test in newborn screening for congenital adrenal hyperplasia: the Utah experience.
Pediatric research 66, 230-235 [PubMed:19390483]
[show Abstract]
Newborn screening allows the diagnosis of congenital adrenal hyperplasia (CAH) before symptoms appear, preventing the severe and potentially life-threatening crisis associated with this disease in infancy. Traditional screening by enzyme immunoassay results in a large number of false positives. To reduce the number of unnecessary tests, anxiety to families and physicians, and the burden to the newborn screening follow-up program, we implemented a second-tier test for CAH using steroid profiling by an ultra-performance liquid chromatography-tandem mass spectrometry. We measured three steroids: 17-hydroxyprogesterone, androstenedione, and cortisol and correlated them with the age of infant at the time of sample collection and birth weight. Both age at collection and birth weight affected the levels of adrenal steroids, but the use of appropriate cut offs and analyte ratios allowed the identification of infants with CAH. This approach was effective in identifying infants with CAH, with both salt-wasting and simple virilizing forms, while reducing the false-positive rate from 2.6 to 0.09%. | Sharma S, Ou J, Strom S, Mattison D, Caritis S, Venkataramanan R (2008)
Identification of enzymes involved in the metabolism of 17alpha-hydroxyprogesterone caproate: an effective agent for prevention of preterm birth.
Drug metabolism and disposition: the biological fate of chemicals 36, 1896-1902 [PubMed:18573861]
[show Abstract]
Preterm delivery, that is delivery before 37 completed weeks of gestation, is the major determinant of neonatal morbidity and mortality. Until recently, no effective therapies for prevention of preterm birth existed. In a recent multicentered trial, 17alpha-hydroxyprogesterone caproate (17-OHPC) reduced the rate of preterm birth by 33% in a group of high-risk women. Limited pharmacologic data exist for this drug. The recommended dose is empiric; the metabolic pathways are not well defined especially in pregnant women; and the fetal exposure has not been quantified. To define the metabolic pathways of 17-OHPC we used human liver microsomes (HLMs), fresh human hepatocytes (FHHs), and expressed enzymes. HLMs in the presence of NADPH generated three metabolites, whereas two major metabolites were observed with FHHs. Metabolism of 17-OHPC was significantly inhibited by the CYP3A4 inhibitors ketoconazole and troleandomycin in HLM and FHH. Metabolism of 17-OHPC was significantly greater in FHH treated with the CYP3A inducers, rifampin and phenobarbital. Furthermore, studies with expressed enzymes showed that 17-OHPC is metabolized exclusively by CYP3A4 and CYP3A5. The caproic acid ester was intact in the major metabolites generated, indicating that 17-OHPC is not converted to the primary progesterone metabolite, 17alpha-hydroxyprogesterone. In summary, this study shows that 17-OHPC is metabolized by CYP3A. Because CYP3A is involved in the oxidative metabolism of numerous commonly used drugs, 17-OHPC may be involved in clinically relevant metabolic drug interactions with coadministered CYP3A inhibitors or inducers. | Dudás I, Gidai J, Czeizel AE (2006)
Population-based case-control teratogenic study of hydroxyprogesterone treatment during pregnancy.
Congenital anomalies 46, 194-198 [PubMed:17096820]
[show Abstract]
Hydroxyprogesterone, a synthetic progestin, was used for the treatment of pregnant women with threatened abortion and preterm delivery. Previous studies showed some association between hydroxyprogesterone use during early pregnancy and some specific congenital abnormalities. The population-based large Hungarian data set seemed to be appropriate to check this possible association. The Hungarian Case-Control Surveillance of Congenital Abnormalities between 1980 and 1996 includes 22 843 cases with congenital abnormalities and 38 151 controls without any defect. 318 (1.4%) cases, while 433 (1.1%) controls had mothers with hydroxyprogesterone treatment during pregnancy (adjusted POR with 95% CI: 1.3, 1.1-1.5). However, there was no association between risk for any congenital abnormality group and a higher use of maternal hydroxyprogesterone treatment during the second and third month of gestation. On the other hand hydroxyprogesterone is not effective in the prevention of preterm delivery. In conclusion, there was no detectable risk for congenital abnormalities in the offspring of mothers with hydroxyprogesterone treatment during early pregnancy, however, there is no reasonable indication of this treatment during pregnancy. | Pau DA, Mackley A, Bartoshesky L (2006)
Newborn screening levels of 17-hydroxyprogesterone in very low birth weight infants and the relationship to chronic lung disease.
Journal of pediatric endocrinology & metabolism : JPEM 19, 1119-1124 [PubMed:17128559]
[show Abstract]
Objectives17-Hydroxyprogesterone (17-OHP), an intermediary hormone in cortisol synthesis, has been shown to be elevated in premature infants. However, the relationship between levels of 17-OHP with chronic lung disease (CLD) have not been extensively explored. The objective of this study was to determine whether there is an association between CLD and levels of 17-OHP in a population of very low birth weight infants.Study designCohort study of very low birth weight infants cared for at a single level 3 NICU during a 3-year period from July 2001-July 2004, n=435. Infants had a minimum of one screen for 17-OHP. 17-OHP was measured on the 5th day of life and at 2-4 weeks of life as part of the State of Delaware Newborn Screening Program. Statistical analysis included chi-squared, Pearson correlation, and logistic regression.ResultsLevels of 17-OHP were higher at the time of the 1st screen compared to the 2nd screen (42.2 +/- 36.7 vs 23.5 +/- 32.3 ng/ml, respectively, p = 0.01). After controlling for potential confounding variables, gestational age and prenatal steroids were independently associated with 17-OHP. However, logistic regression analysis showed no association between a 1 log increase in levels of 17-OHP with the outcomes of CLD (odds ratio 1.7, 95% CI 0.7-3.8), or death and/or CLD (odds ratio 2.1, 95% CI 0.9-4.8).ConclusionsIn our population of very low birth weight infants elevated levels of 17-OHP were not associated with the development of CLD. | Shkumatov VM, Frolova Ns, Rudaia EV, Faletrov IaV, Mauerberger S, Barth G (2006)
[Range of substrates and steroid bioconversion reactions performed by recombinant microorganisms Saccharomyces cerevisiae and Yarrowia lipolytica expressing cytochrome P450c17].
Prikladnaia biokhimiia i mikrobiologiia 42, 539-546 [PubMed:17066953]
[show Abstract]
The relationship between 17alpha-hydroxylation and 20-oxidation-reduction of progesterone and some of its derivatives was studied in yeast strains Saccharomyces cerevisiae YEp51alpha, Yarrowia lipolytica E129A15, and expressing cytochrome P450c17. The key metabolites were found to be 17alpha-hydroxyprogesterone and 17alpha,20(alpha,beta)-dihydroxypregn-4-ene-3-ones. The bioconversion pathways of pregn-4-ene-20(alpha,beta)-ol-3-ones were determined. They included cycles of 20-oxidation, 17alpha-hydroxylation, and stereospecific 20-reduction. The efficiency and kinetic parameters of steroid bioconversion by the recombinant strains were determined. The role of yeast analogs of mammalian steroid dehydrogenases is discussed. It was found that any of the desired derivatives, 17alpha-hydroxyprogesterone or progesterone 17alpha,20(alpha,beta)-diols, could be obtained from progesterone. | Sencan M, Dokmetas HS (2005)
A case of postpartum hypopituitarism accompanied by Cushing's syndrome as a result of an adrenocortical carcinoma.
Endocrine journal 52, 219-222 [PubMed:15863951]
[show Abstract]
Sheehan's syndrome frequently causes hypopituitarism either immediately or after a delay of several years, depending on the degrees of postpartum ischemic pituitary necrosis. A 55 year-old woman whose last child was born 27 yr ago with massive hemorrhage was diagnosed as postpartum hypopituitarism. She had deficiency of growth hormone, prolactin, gonadotropins and thyrotropin. However, she interestingly had apparent hypercortisolism without suppression response to the dexamethasone tests. We found an adrenal mass with distant metastases to the liver and lung while investigating the origin of the hypercortisolism. Hyperandrogenism and very high levels of 17alpha hydroxyprogesterone were present. Accordingly, the patient was diagnosed as hypopituitarism due to Sheehan's syndrome accompanied by Cushing's syndrome as a result of an adrenocortical carcinoma. | Paul DA, Leef KH, Stefano JL, Bartoshesky L (2004)
Factors influencing levels of 17-hydroxyprogesterone in very low birth weight infants and the relationship to death and IVH.
Journal of perinatology : official journal of the California Perinatal Association 24, 252-256 [PubMed:14999215]
[show Abstract]
Objectives17-Hydroxyprogesterone, an intermediary hormone in cortisol synthesis, has been shown to be elevated in premature infants. However, the relationship between levels of 17-hydroxyprogesterone with death and intraventricular hemorrhage has not been extensively explored. The objective of this study was to determine the factors influencing 17-hydroxyprogesterone and determine if there is an association between intraventricular hemorrhage, mortality, and levels of 17-hydroxyprogesterone in a population of very low birth weight infants.Study designCohort study of very low birth weight infants cared for at a single level 3 NICU during a 1-year period from July 2001 to July 2002. Infants had a minimum of one screen for 17-hydroxyprogesterone and one cranial sonogram. 17-Hydroxyprogesterone was measured on the fifth day of life and at 2 to 4 weeks of life as part of the State of Delaware Newborn Screening Program. Statistical analysis included chi(2), Pearson correlation, multiple-linear regression, and logistic regression.ResultsLevels of 17-hydroxyprogesterone were higher at the time of the first screen compared to the second screen (28.3+/-25.6 vs 17.0+/-18.0 ng/ml, p=0.01), respectively. After controlling for potential confounding variables, gestational age, T(4), and prenatal steroids were all independently associated with 17-hydroxyprogesterone. However, logistic regression analysis showed no association between a 1 log increase in levels of 17-hydroxyprogesterone with the outcomes of death (odds ratio 1.8, 95% CI 0.6 to 5.6), severe IVH (0.7, 0.3 to 1.7), and death and/or severe intraventricular hemorrhage (0.9, 0.4 to 2.1).ConclusionsIn our population of very low birth weight infants, low gestational age, low T(4), and prenatal steroids were all associated with an elevation in levels of 17-hydroxyprogesterone. High levels of 17-hydroxyprogesterone were not associated with death and/or severe IVH. Our data indicate that factors such as gestational age and antenatal steroids must be considered when interpreting 17-hydroxyprogesterone results from newborn screening. | Quinkler M, Meyer B, Oelkers W, Diederich S (2003)
Renal inactivation, mineralocorticoid generation, and 11beta-hydroxysteroid dehydrogenase inhibition ameliorate the antimineralocorticoid effect of progesterone in vivo.
The Journal of clinical endocrinology and metabolism 88, 3767-3772 [PubMed:12915667]
[show Abstract]
Progesterone (P) is a strong mineralocorticoid receptor (MR) antagonist in vitro. The high P concentrations seen in normal pregnancy only moderately increase renin and aldosterone concentrations. In previous in vitro studies we hypothesized that this may be explained by intrarenal conversion of P to less potent metabolites. To investigate the in vivo anti-MR potency of P, we performed an infusion study in patients with adrenal insufficiency (n = 8). They omitted 9alpha-fluorocortisol for 4 d and hydrocortisone for 0.5 d before a continuous iv infusion of aldosterone for 8.5 h, with an additional iv P infusion commenced at 4 h. During aldosterone infusions the initially elevated urinary sodium to potassium ratio decreased significantly. Despite the 1000-fold excess of P over aldosterone, the urinary sodium to potassium ratio and urinary sodium excretion increased only slightly after 3 h of P infusion. We detected inhibition of renal 11beta-hydroxysteroid dehydrogenase type 2 by P, thus giving cortisol/prednisolone access to the MR. Urinary and plasma concentrations of 17alpha-hydroxyprogesterone, a major metabolite of renal P metabolism, and those of serum androstenedione and deoxycorticosterone, a mineralocorticoid itself, increased significantly during P infusion. This supports the hypothesis of an effective protection of the MR from P by efficient extraadrenal downstream conversion of P. | Schwartz RP (1999)
Home monitoring of 17 hydroxyprogesterone levels: "throw away the urine jug, mom, the filter paper just arrived".
The Journal of pediatrics 134, 140-142 [PubMed:9931518] | Arevalo JH, Stura EA, Taussig MJ, Wilson IA (1993)
Three-dimensional structure of an anti-steroid Fab' and progesterone-Fab' complex.
Journal of molecular biology 231, 103-118 [PubMed:8496956]
[show Abstract]
The monoclonal anti-progesterone antibody DB3 binds progesterone with nanomolar affinity (Ka approximately 10(9) M-1), suggesting high specificity. However, DB3 also cross-reacts with similar affinity with a subgroup of structurally distinct, progesterone-like steroids. Crystals of the unliganded Fab' and various steroid-Fab' complexes are isomorphous and belong to the hexagonal space group, P6(4)22, with unit cell dimensions of a = b = 135 A, c = 124 A. Structures of free and progesterone-bound Fab' have been determined by X-ray crystallography at 2.7 A resolution using molecular replacement techniques. Progesterone is bound in a hydrophobic pocket formed mainly by the interaction of three complementarity determining regions L1, H2 and H3. The orientation of the ligand in the binding site was aided by both crystallographic and biochemical analyses of substituted steroids. The indole side-chain of TrpH100 of the DB3 has two different conformations, inter-converting "open" and "closed" forms of the antibody combining site. The TrpH100 indole thus appears to be acting as an antibody-derived surrogate ligand for its own hydrophobic binding pocket. These structures provide the first atomic view of how a steroid interacts with a protein and offer a structural explanation for the restriction of the anti-progesterone response to the VGAM3.8 family of VH genes. | Lee BW, Goh HH, Tan SH, Yap HK, Wong HB, Ratnam SS (1983)
17 hydroxyprogesterone - normal values in Singapore children.
The Journal of the Singapore Paediatric Society 25, 60-62 [PubMed:6632812] | Morra C, Wierdis T, Lanza A, Rolfo A, Fedele M, Surico N (1979)
[Hormonal regulation of uterine contraction].
Archivio per le scienze mediche 136, 197-230 [PubMed:518278]
[show Abstract]
A personal method has been used to study spontaneous kinetic activity of the uterus in 50 women during puerperium following miscarriage between the VIIIth and XIIth weeks. Modifications induced were evaluated in several sessions (510 recordings) and at various periods of time, following administration of: 50 mg of 17B oestradiol, 200 mg natural progesterone, 500 mg of natural progesterone, 250 mg of 17 hydroxyprogesterone caproate and 500 mg of 17 hydroxyprogesterone caproate. In the case of some of the patients, hysterotonometry was evaluated following intravenous oxytocin loading. The results pointed to an activation of the uterine pacemaker after oestrogenic loading, and a clear-cut progestinic block of contractile activity. | Madjerek ZS, Smit-Vis JH (1977)
Further studies on a new bioassay of progestational activity (traumatic deciduoma formation in immature rats).
Acta morphologica Neerlando-Scandinavica 15, 65-74 [PubMed:72488]
[show Abstract]
Six synthetic steroids were tested subcutaneously in a new bio-assay for short- and long-lasting progestational activity, using traumatic deciduoma production in immature female rats. As reference standard, a daily subcutaneous dose of 0.25 mg progesterone regularly induced a distinct deciduomagenic effect. A single dose of 12.5 mg of progesterone showed a prolonged activity. Medroxyprogesterone acetate showed a distinct deciduomagenic effect at the 0.05 mg daily s.c. dose level; a distinct prolonged effect was induced with a single s.c. injection of 0.5 mg. 16alpha-Aethylprogesterone induced regularly decidual reaction at the 0.1 mg s.c. dose level, it showed prolonged activity at the 0.25 mg dose level. The daily threshold dose for chlormadinone acetate was 0.25 mg; prolonged activity was shown with 2.5 mg. The daily threshold dose for duphaston is between 0.5 mg and 1.0 mg. A single s.c. dose of as much as 20.0 mg of 17alpha- hydroxyprogesterone caproate did not have a deciduomagenic effect. | Tan SY, Murphy BE (1975)
Plasma 17alpha hydroxyprogesterone: an improved radioassay method.
Steroids 25, 283-284 [PubMed:1167988] | Teoh ES, Das NP, Dawood MY, Ratnam SS (1972)
The source of circulating progesterone and 17 -hydroxyprogesterone in hydatidiform mole.
Acta endocrinologica 71, 773-780 [PubMed:4343782] | Bosu WT, Holmdahl TH, Johansson ED, Gemzell C (1972)
Peripheral plasma levels of oestrogens, progesterone and 17 -hydroxyprogesterone during the menstrual cycle of the rhesus monkey.
Acta endocrinologica 71, 755-764 [PubMed:4628727] | Holmdahl TH, Johansson ED (1972)
Peripheral plasma levels of 17 -hydroxyprogesterone during human pregnancy.
Acta endocrinologica 71, 765-772 [PubMed:4678212] | Holmdahl TH, Johansson ED (1972)
Peripheral plasma levels of 17 -hydroxyprogesterone, progesterone and oestradiol during normal menstrual cycles in women.
Acta endocrinologica 71, 743-754 [PubMed:4678211] | Shaikh AA (1972)
Estrone, estradiol, progesterone and 17 -hydroxyprogesterone in the ovarian venous plasma during the estrous cycle of the hamster.
Endocrinology 91, 1136-1140 [PubMed:5065810] | Jacobs HS, Abraham GE, Glasser EJ, Hopper K, Kondon JJ (1972)
17 -Hydroxyprogesterone and testosterone levels in congenital adrenal hyperplasia: effect of treatment with cortisone acetate, dexamethasone and corticotrophin.
The Journal of endocrinology 53, xxxvi-xxxv [PubMed:4339047] | Dodson K, Coutts JR (1972)
17 -hydroxyprogesterone levels as a measure of corpus luteum function.
The Journal of endocrinology 52, x-xi [PubMed:5061166] | Holmdahl TH, Sjövall J (1971)
Liquid-gel chromatography on hydrophobic Sephadex and competitive protein binding of 17 -hydroxyprogesterone in plasma.
Steroids 18, 69-76 [PubMed:5098538] | Stewart-Bentley M, Horton R (1971)
17- -hydroxyprogesterone in human plasma.
The Journal of clinical endocrinology and metabolism 33, 542-544 [PubMed:5571099] |
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