Transfer of the 1-pro-R and the 1-pro-S hydrogen atoms of ethanol in metabolic reductions in vivo. (1/122)
The transfer of deuterium from [1 R-2H]ethanol and [1 S-2H]-ethanol to reduced metabolites of administered compounds was measured in female rats provided with bile fistulas. Administered cyclohexanone was reduced to cyclohexanol, and in this reduction hydrogen was transferred only from the 1-pro-R position of the ethanol. The deuterium content in the cyclohexanol was about 67% of that in the ethanol. In the reduction of the 17-oxo group in 3beta-hydroxy-5alpha-androstan-17-one, hydrogen was transferred both from the 1-pro-R position and the 1-pro-S position, resulting in degrees of labelling that were about 25% and 2%, respectively, of those in the specific positions of the ethanols. The 1-pro-R and 1-pro-S positions of ethanol contributed about 9% and 5%, respectively, of the 3beta hydrogen in lithocholic acid formed from 3-oxo-5beta-cholanoic acid. The results indicate that alcohol dehydrogenase and aldehyde dehydrogenase do not share a common pool of NAD, and that NADH formed during acetaldehyde oxidation is utilized for reductions in the cytosol to a smaller extent than the NADH formed in the alcohol dehydrogenase reaction. This result supports the concept that aldehyde oxidation is mainly an intramitochondrial process. The relatively extensive utilization of the 1-pro-S hydrogen of ethanol in the reduction of 3-oxo-5beta-cholanoic acid, that is probably NADPH-dependent, indicates that cytosolic NADPH may be produced from malate or isocitrate formed intramitochondrially. (+info)Induction of delta-aminolevulinic acid synthetase in isolated rat liver cells by steroids. (2/122)
The role of steroids in regulation of delta-aminolevulinic acid synthetase has been studied in isolated rat liver cell suspensions under conditions previously shown to support inducation of the enzyme by drugs. Addition of a variety of C-19 and C-21 steroids to cell suspensions resulted, after 4 to 6 hours of incubation, in 2- to 5-fold increase in the activity of delta-aminolevulinic acid synthetase as measured in liver cell homogenates. The increase was prevented by cycloheximide. The most active steroid inducers tested were pregnene or pregnane derivatives with keto or hydroxyl groups at C-3 and C-20; in particular a beta-hydroxyl group at C-20 enhanced activity. These C-21 steroids at optimal initial concentrations caused 3- to 5-fold induction over 4 hours. A number of C-19 androstene and androstane compounds caused 2- to 3-fold inducation over the same period. Hydrocortisone had no effect. For a variety of androstane and pregnane derivatives, inducation by 5alphaH steroids was as great as or greater than that by 5betaH compounds, in contrast to previous findings in chick embryo liver. Induction of delta-aminolevulinic acid synthetase by steroids in isolated liver cells was shown to be subject to feedback repression by hemin. (+info)Regulation and substrate specificity of a steroid sulfate-specific hydroxylase system in female rat liver microsomes. (3/122)
The sulfate-specific hydroxylase system in liver microsomes from rats has been investigated with respect to its substrate specificity. Eighteen different C18, C19, C21, and C27 steroid sulfates and the coresponding free steroids have been incubated with microsomal preparations from male and female rats. The sulfate-specific system was only present in preparations from female rats and primarily catalyzed hydroxylation in position 15beta but also in position 7beta. In contrast to this, male liver microsomes were more efficient than female liver microsomes in hydroxylating free steroids; these were hydroxylated in positions 2alpha,2beta,6alpha,6beta,7alpha,7beta,16alpha, and 18. The sulfate-specific hydroxylase system in female liver microsomes was found to have rigid requirements c concerning the structure of ring D in the substrate molecule; only 17beta-sulfates (C18 and C19 steroids) and 21-sulfates (C21 steroids) were hydroxylated. Less rigid criteria, however, exist concerning the structure of ring A. The following K-m values were determined for microsomal 15beta-hydroxylation: 5alpha-androstane-3alpha,17beta-diol disulfate, 17.2 muM; 5beta-androstane-3alpha,17beta-diol disulfate, 16muM;5alpha-androstane-3alpha,17beta-diol 17-sulfate, 26 muM; and estradiol 17-sulfate, 181 muM. Some of the regulatory mechanism controlling the activity of the sex-specific 15beta-hydroxylase system also have been studied and compared to the mechanism controlling the activities of the less specific 2alpha-, 7alpha-, and 18-hydroxylase systems active on 5alpha-[4-14C]androstane-3alpha,17beta-diol. Biliary drainage did not affect the 15beta-hydroxylase activity, whereas the 2alpha- and 7alpha-hydroxylase activities decreased.. (+info)Antiarrhythmic, haemodynamic and metabolic effects of 3alpha-amino-5alpha-androstan-2beta-ol-17-one hydrochloride in greyhounds following acute coronary artery ligation. (4/122)
1 The antiarrhythmic, haemodynamic and metabolic effects of a new amino steroid, ORG6001, have been investigated in experimental acute myocardial infarction in anaesthetized greyhounds. 2 ORG6001 administered either intravenously (2-10 mg/kg) or orally (50 mg/kg) significantly reduced the incidence of ventricular ectopic beats in the first 30 min after ligation of the left anterior descending coronary artery. 3 In dogs pretreated with ORG6001, metabolic changes indicative of myocardial ischaemia (lactate production and potassium efflux) were less marked than those occurring in control animals. 4 Antiarrhythmic doses of ORG6001 caused only minimal transient haemodynamic effects. 5 These results suggest that ORG6001 may possess distinct advantages over presently-used antiarrhythmic drugs in the prevention and treatment of the early arrhythmias which occur after myocardial infarction. (+info)Mechanism of induction of cytochrome p450 enzymes by the proestrogenic endocrine disruptor pesticide-methoxychlor: interactions of methoxychlor metabolites with the constitutive androstane receptor system. (5/122)
Methoxychlor, a structural analog of the DDT pesticide, was previously shown to induce rat hepatic CYP2B and -3A mRNAs and the corresponding proteins [J Biochem Mol Toxicol 1998;12:315-323], Additionally, methoxychlor was found to activate the constitutive androstane receptor (CAR) system and induce CYP2B6 (J Biol Chem 1999;274:6043-6046), suggesting a mechanism for methoxychlor-mediated cytochrome P450 (P450) 2B induction. However, it has not been established whether CAR activation and P450 induction was due to methoxychlor per se and/or due to its metabolites. Also, a possible link between the estrogenic potency of methoxychlor metabolites and CAR activation or P450 induction was not investigated. The current study explores the ability of methoxychlor and its metabolites to activate CAR and whether their potency of CAR activation correlates with their respective estrogenicity. Methoxychlor and its metabolites [mono-OH-M [1,1,1-trichloro-2 (4-hydroxyphenyl)-2'-(4-methoxyphenyl)ethane]; bis-OH-M [1,1,1-trichloro-2,2'-bis(4-hydroxyphenyl)ethane]; ring-OH-M [1,1,1-trichloro-2(4-methoxyphenyl)-2'-(3-hydroxy-4-methoxyphenyl)ethane]; and tris-OH-M [1,1,1-trichloro-2(4-hydroxyphenyl)-2'-(3,4-dihydroxyphenyl)ethane]] were found to be potent activators of CAR. Dose response curves indicated that tris-OH-M is a more potent CAR activator than methoxychlor, mono-OH-M, and bis-OH-M. Since tris-OH-M is a much weaker estrogen receptor-alpha agonist than mono-OH-M and bis-OH-M, it seems that estrogenicity is not a significant factor in CAR activation. These findings indicate that alteration of methoxychlor-benzene rings, i.e., generation of phenolic constituents, does not appreciably alter CAR activation and suggest that a common structural motif in the methoxychlor class of compounds controls CAR activation. Studies are needed to identify the structural motif necessary for CAR activation and CYP2B induction. (+info)Local anaesthetic and antiarrhythmic properties of an aminosteroid: 3alpha-dimethyl-amino-5alpha-androstan-2beta-ol-17-one (Org. NA 13). (6/122)
1. The aminosteroid Org. NA13 (3alpha-dimethylamino-5alpha-androstan-2beta-ol-17-one) was shown to be a more potent local anaesthetic than lignocaine in rats and guinea-pigs. 2. Experimental arrhythmias induced in mice by chloroform, in rats by aconitine and in dogs by coronary artery ligation were corrected by Org. NA13 at doses from 10 to 50 mg/kg intravenously. 3. In contrast to lignocaine, other local anaesthetics and beta-adrenoceptor blocking drugs, Org. NA 13 did not show any activity against the arrhythmias induced by ouabian in dogs. 4. The acute toxicity in whole animals and myocardial toxicity in the rabbit isolated atrium appeared to be less than that observed with lignocaine. (+info)Steroid induction of delta-aminolevulinic acid synthase and porphyrins in liver. Structure-activity studies and the permissive effects of hormones on the induction process. (7/122)
Quantitative aspects and structure-activity relationships of the inducing effects of natural steroids on delta-aminolevulinic acid (ALA) synthase and porphyrins have been investigated in monolayer cultures of chick embryo liver cells maintained in a serum-free medium as well as in the chick embryo liver in ovo. Many 5 alpha and 5 beta metabolites of neutral C-19 and C-21 hormones and hormone precursors stimulated porphyrin formation and ALA-synthase induction in the cultured liver cells as we have previously described. In these inducing actions a number of 5 beta epimers (A:B cis) were found to be more potent than their corresponding 5 alpha epimers (A:B trans). The structure-activity relationship between 5 beta and 5 alpha steroid epimers with respect to ALA-synthase induction in culture was also found to prevail with respect to induction of this enzyme in chick embryo liver in ovo. Hemin in concentrations of 2 x 10(-7) M inhibited steroid induction of porphyrin formation, and CaMgEDTA enhanced the responsiveness of the cultured liver cells to steroids by approximately 10 times. The addition of insulin, or insulin plus hydrocortisone or insulin plus hydrocortisone plus triiodothyronine, was important for the maintenance of protein synthesis and essential for maximal expression of the ability of steroids to induce porphyrins and ALA-synthase in the "permissive" effect which insulin, hydrocortisone, and triiodothyronine exert on allylisopropylacetamide induction of porphyrins and ALA-synthase also extends to the induction process which is elicited by natural steroids. These findings also strongly suggest that the regulation of hepatic porphyrin-heme biosynthesis by endogenous as well as exogenous chemicals is significantly influenced by the internal hormonal milieu. (+info)Stereochemical aspects of the interaction between steroidal diamines and DNA. (8/122)
A complete series of stereoisomeric quaternised diaminoandrostanes, differing in their stereochemistry at the 3,5 and 17 positions, has been examined for effects on the thermal denaturation of calf thymus DNA and for the ability to remove and reverse the supercoiling of closed circular duplex PM2 DNA. In both types of test the eight isomers rank in the same order of effectiveness. The preferred stereochemistry for the quaternary substituents at positions 3 and 17 is beta; of these the orientation of the 17- substituent is more critical. Folding of the steroid skeleton between the A and B rings, as in 5beta-androstanes, diminishes effectiveness but does not necessarily abolish the effect on supercoiling. The over-riding importance of the C-D ring end of the steroid nucleus bearing a 17beta-amino substituent is confirmed by a comparison of the effects of five mon-amino androstanes. Relative helix=unwinding angles per bound steroidal diamine molecule have been determined for four of the isomers; for three 17beta compounds the estimated values are similar to that previously reported for irehdiamine A. For a fourth isomer the angle is 0.22 times that of ethidium, the lowest yet determined for any DNA-binding drug. The results lend further support to the argument that intercalation can be reled out, and alternative models for the binding mechanism are discussed. (+info)
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List of androstanes
This is a list of androstanes, or androstane derivatives. Androstanol 3α,5α-Androstanol (5α-androstan-3α-ol) - an endogenous ...
16-Androstene
Androstanes, Neurosteroids, Pheromones). ...
Androgen ester
... s, Androgens and anabolic steroids, Androstanes, Prodrugs). ...
17β-Hydroxysteroid dehydrogenase
Highly selective for estrogens; 100-fold higher affinity for estranes over androstanes. However, also catalyzes the conversion ...
Androstane
Estrane and pregnane List of androstanes C19H32 Wilson JD (1996). "Role of dihydrotestosterone in androgen action". Prostate ...
Neurosteroid
They include the androstanes androstadienol, androstadienone, androstenol, and androstenone and the estrane estratetraenol. ... the androstanes dehydroepiandrosterone (DHEA; prasterone), and dehydroepiandrosterone sulfate (DHEA-S; prasterone sulfate), and ...
Malouetine
5α-androstanes". Journal of Pharmacy and Pharmacology. 17 (1): 55-59. doi:10.1111/j.2042-7158.1965.tb07569.x. Buckett, W.R.; ...
Progestogen (medication)
Testosterone derivatives can be classified into subgroups including androstanes, estranes (19-norandrostanes), and gonanes (18- ...
1-Androsterone
... and other 1-dehydrogenated androstanes. The drug has been sold on the Internet as a designer steroid and "dietary supplement". ... Androstanes, Ketones, Prodrugs, All stub articles, Steroid stubs, Genito-urinary system drug stubs). ...
Androgen conjugate
v t e v t e (Androstanes, Human metabolites, Steroid hormones, Testosterone, All stub articles, Steroid stubs, Biochemistry ...
Androstenolone
Androstanes). ...
Androstanolone (disambiguation)
Androstanes, Articles with short description, Short description is different from Wikidata, All set index articles, Chemistry ...
Dehydroepiandrosterone (disambiguation)
Androstanes). ...
Androstanediol
Androstanes, Articles with short description, Short description is different from Wikidata, All set index articles, Chemistry ...
Hydroxyandrostenedione
Androstanes). ...
Androsterone
Androgen backdoor pathway List of androgens/anabolic steroids List of neurosteroids § Androstanes List of neurosteroids § ... Androstanes, Hormones of the liver, Human metabolites, Human pheromones, Mammalian pheromones, Neurosteroids, Steroid hormones ...
Androstenediol (disambiguation)
Androstanes, World Anti-Doping Agency prohibited substances). ...
Constitutive androstane receptor
Androstenol and several isomers of androstanol, androstanes, are endogenous antagonists of the CAR, and despite acting as ...
Androstenedione (disambiguation)
Androstanes, Human female endocrine system, World Anti-Doping Agency prohibited substances). ...
RU-28362
Androstanes, Glucocorticoids, All stub articles, Steroid stubs). ...
Testosterone hexahydrobenzylcarbonate
Androstanes, Carbonate esters, Testosterone esters, All stub articles, Genito-urinary system drug stubs, Steroid stubs). ...
Testosterone acetate propionate
Androstanes, Prodrugs, Testosterone esters, Propionate esters, Abandoned drugs, All stub articles, Steroid stubs, Genito- ...
11β-Hydroxyandrostenedione
Androstanes, Biomarkers, Hormones of the suprarenal cortex, Ketones, Secondary alcohols, Sex hormones, Steroid hormones, All ...
Testosterone undecanoate
Androstanes, Bayer brands, Contraception for males, Ketones, Testosterone esters, Undecanoate esters). ...
Androstanediol glucuronide
Androstanes, Human metabolites, Glucuronide esters). ...
Testosterone isocaproate
Androstanes, Isocaproate esters, Testosterone esters, All stub articles, Genito-urinary system drug stubs, Steroid stubs). ...
Testosterone acetate
Androstanes, Ketones, Testosterone esters, All stub articles, Genito-urinary system drug stubs, Steroid stubs). ...
Methyltestosterone 3-hexyl ether
Androstanes, Hepatotoxins, Prodrugs, Tertiary alcohols, All stub articles, Steroid stubs, Genito-urinary system drug stubs). ...
Δ4-Abiraterone
Androstanes, CYP17A1 inhibitors, Hormonal antineoplastic drugs, Human drug metabolites, Enones, Prostate cancer, 3-Pyridyl ...
3β-Androstenol
Androstanes, Human pheromones, Mammalian pheromones, Neurosteroids). ...
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exemestane side effects Archives - Obstipatie
Steroids1
- Androstanes have 19 carbons (c19 steroids) and include androgens. (guaterhinos.com)
Androgens1
- Pregnenolone ( P5 ), or pregn-5-en-3β-ol-20-one , is an endogenous steroid and precursor / metabolic intermediate in the biosynthesis of most of the steroid hormones , including the progestogens , androgens , estrogens , glucocorticoids , and mineralocorticoids . (wikipedia.org)
Types1
- For some types, including androstanes, women also had longer than men, anabolic steroid price in pakistan. (quark0ne.org)