Urinary Metabolic Products of Prednisone and Prednisolone

Gray, C. H.; Green, Margaret A. S.; Holness, N. J.; Lunnon, J. Barbara

doi:10.1677/joe.0.0140146

Cited by 50 publications

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“…Prednisone and predni¬ solone gave a characteristic 17-oxosteroid chromatogram but generally the doses were not large enough to raise the index above the upper limit of normal. The synthetic 1-unsaturated steroids are metabolized only by reduction of the side chain (Gray, Green, Holness & Lunnon, 1964). The excreted 3-oxo-l,4,dienes are subject to attack by borohydride resulting in multiple products, the nature of which is under investiga¬ tion (H. L. J. Makin, unpublished observations).…”

Section: Discussionmentioning

confidence: 99%

Congenital Adrenal Hyperplasia and Other Conditions Associated With a Raised Urinary Steroid 11-Oxygenation Index

Clayton¹,

Edwards²,

Makin³

1971

Journal of Endocrinology

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Raised values of the 11-oxygenation index (11-OI) were found in 164 children, although it was only possible to record 97 fully. Seventy-four were fully diagnosed as having congenital adrenal hyperplasia (CAH) and among the others five had high 11-OI values which fell to normal by the 8th day of life and two gave high values due to methodological interference by 1-oxygenated steroids. Severe diarrhoea was associated with a raised 11-OI in ten boys and this presented difficulty in diagnosis; CAH was considered a possible diagnosis by the referring physician but was finally excluded.

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Section: Discussionmentioning

confidence: 99%

Congenital Adrenal Hyperplasia and Other Conditions Associated With a Raised Urinary Steroid 11-Oxygenation Index

Clayton¹,

Edwards²,

Makin³

1971

Journal of Endocrinology

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“…This is unlikely, since substitution in or near the A-ring largely prevents reduction of the 4-en-3-one system as shown by 1,2-unsaturation (Gray, Green, Holness & Lunnon, 1956;Bush & Mahesh, 1964), 20c-methyl substitution (Bush & Mahesh, 1959) and 9oc-fluoro substitution (Bush & Mahesh, 1964).…”

Section: Discussionmentioning

confidence: 99%

The partial characterization of 1-oxygenated steroids from urine of a hypertensive newborn child

Edwards

Trafford

1968

Biochemical Journal

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1. Four substances from the urine of a hypertensive newborn girl were partially characterized and shown to be 17oc-hydroxy-5, B-pregnane-1,3,20-trione, 3oc,17a-dihydroxy-5,B-pregnane-1,20-dione, 3a,17oc,20ac-trihydroxy-5p-pregnan-1-one and 5/3-pregnane-lB,3oc,17a,20c-tetrol. 2. The characterization rested mainly on RM analysis of the substances and their derivatives by glycol fission, providing evidence for position and degree of substitution and for steroidal character. Supporting evidence was provided by chemically specific location reactions. 3. Certain problems in the manipulation of these ,B-disubstituted steroids are discussed.The high 17-hydroxy corticosteroid excretion of patient S.C. when 1-3 weeks old and grossly hypertensive has been described elsewhere (Edwards, Harvey & Knight-Jones, 1968 MATERIALS AND METHODSFull details of the procedures used for the isolation of urinary steroids are described elsewhere (Edwards, 1968a) and in the present instance consisted of the following steps. Urine samples (6 days' collection, age between 8 and 20 days) from S.C. during her period of high 11-oxygenation index (ratio of metabolites of 17-hydroxylated precursors of cortisol to metabolites of cortisol; Edwards, Makin & Barratt, 1964) (Stevens, 1964). Each substance was homogeneous on the criterion that portions from the forward and rear portions ofa chromatographed zone on rechromatography gave zones side by side of identical RF values.The chemical transformations used were (i) borohydride reduction and (ii) periodate oxidation, both carried out as described by Edwards et al. (1964), and (iii) oxidation with Jones reagent carried out as described by Djerassi, Engle & Bowers (1956), but with trebled proportion of acetone. RM analysis procedure. RM values were calculated from RF values and referred to the root system of the family (light petroleum-methanol-water, 5:4:1, by vol.) as RMO values by correcting for the effects of benzene replacing light petroleum (Kabasakalian & Basch, 1960;Edwards, 1968a). Observed ARM values were compared with reference values (Table 1) and the latter used to indicate likely structural changes. For clarity the ARM value observed in changing from substance of structure A to structure B was signified ARM [A--B]. It was presumed that substances with RMO values differing by less than 0-07 (S.D. ofrepetition of a value on different occasions) were in fact one substance.Referencel-hydroxysteroid. loc-Hydroxy-5oc-androstane-3,17-dione samples from Dr Fukushima and Dr Foell were found to be identical with the exception of a small proportion of contaminant in the latter. This was assumed to be the lfl-isomer, since other isomerization was unlikely from the method of preparation. A similar contaminant was present in the lac-hydroxyandrost-4-ene-3,17-dione sample. The lc,3,B-dihydroxy-50c-androstan-17-one sample was uncontaminated.Other reference steroids were prepared by unambiguous chemical transformations and were purified by chromatography, but there was insufficient material available...

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“…Androsta-l:4-diene-3:ll:17-trione and ll^-hydroxyandrosta-l:4-diene-3:17-dione were prepared as described by Gray et al [1956].…”

Section: -14c Prednisolonementioning

confidence: 99%

The Metabolism of 4-14c Prednisolone

Vermeulen¹

1959

Journal of Endocrinology

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The urinary excretion of radioactivity after oral administration of 4-14c prednisolone was studied in a patient already receiving large daily doses of non-radioactive prednisolone. The radioactive metabolites in the urine were fractionated by various chromatographic procedures and the following radioactive compounds were identified: prednisolone; prednisone; 11\g=b\:17\g=a\:20\g=b\:21-tetrahydroxypregna-1:4-dien-3-one; 17\g=a\: 20\g=b\:21 -trihydroxypregna-1:4-diene\x=req-\ 3:11-dione; 3\g=a\: 11\g=b\:17\g=a\:21-tetrahydroxy-5\g=b\-pregnan-20-one;3\g=a\:17\g=a\:21-trihydroxy-5\g=b\-pregnane-11:20-dione. The significance of these findings is discussed.Although about 90% of the radioactivity administered as 4-14C prednisolone (lly8:17oc:21-trihydroxypregna-l:4-diene-3:20-dione) is excreted in the urine within 48 hr [Sandberg & Slaunwhite, 1957], only about 10% of the administered dose can be accounted for as known metabolites [Caspi & Pechet, 1957]. Moreover, while Gray, Green, Holness & Lunnon [1956] and Vermeulen [1956a-c] found no evidence for the presence of tetrahydrocortisone (3oc:17a:21-trihydroxy-5/3-pregnane-ll:20-dione) and tetrahydrocortisol (3a:llJ8:17a:21-tetrahydroxy-5jß-pregnan-20-one) in the urine of patients treated with non-radioactive prednisone or prednisolone, Caspi & Pechet [1957] have recently reported the isolation of the partially reduced product 17a:21-dihydroxypregn-l-ene-3:ll:20-trione as well as 20 mg tetrahydrocortisol and 3-4 mg allotetrahydrocortisol from the urine of a patient who had received a total of 940 mg prednisone (17a:21-dihydroxypregna-l:4-diene-3:ll:20-trione) during 16 days.This paper describes further investigations of the nature of the metabolites of 4-14C prednisolone. MATERIALS AND METHODS MaterialsA male patient aged 54 years, suffering from scleroderma and who had received 80 mg prednisolone/day orally in four divided doses for 4 days, was given 0-6 ixc (4 mg) 4-14C prednisolone orally in dilute ethanol. Urine specimens were collected for the periods 8, 16, 24 and 48 hr after administration of radioactive prednisolone. The specimens were stored without preservative at about 10°C and worked up immediately on completion of collection.

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Urinary Metabolic Products of Prednisone and Prednisolone

Cited by 50 publications

References 0 publications

Congenital Adrenal Hyperplasia and Other Conditions Associated With a Raised Urinary Steroid 11-Oxygenation Index

Congenital Adrenal Hyperplasia and Other Conditions Associated With a Raised Urinary Steroid 11-Oxygenation Index

The partial characterization of 1-oxygenated steroids from urine of a hypertensive newborn child

The Metabolism of 4-14c Prednisolone

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