Detail of "13951-70-7"

CAS Number:
13951-70-7
Name:
16alpha-Hydroxyprednisolone
Molecular Structure:
Formula:
C₂₁H₂₈O₆
Molecular Weight:
376.45
Synonyms:
Pregna-1,4-diene-3,20-dione,11b,16a,17,21-tetrahydroxy- (6CI,7CI,8CI);16a-Hydroxyprednisolone;16α-hydroxy-prednisonlone;Pregna-1,4-diene-3,20-dione,11,16,17,21-tetrahydroxy-, (11b,16a)-;
EINECS:
237-731-1
Density:
1.381 g/cm³
Melting Point:
235-238 °C
Boiling Point:
591.5 °C at 760 mmHg
Flash Point:
325.6 °C
Appearance:
white crystalline solid

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Reference

Effect of structural alterations on the biotransformation rate of glucocorticosteroids in rat and human liver: Effect of structural alterations on the biotransformation rate of glucocorticosteroids in rat and human liver. Andersson, P.; Lihne, M.; Thalen, A.In this study， 51372-28-2 and 51547-52-5 are also used.; Ryrfeldt, A. (Pharmacokinet. Lab., AB Draco, Lund S-221 00, Swed.). Xenobiotica, 17(1), 35-44 (English) 1987. CODEN: XENOBH. ISSN: 0049-8254. DOCUMENT TYPE: Journal CA Section: 2 (Mammalian Hormones) The effect of structural alterations on the biotransformation rate of glucocorticosteroids (GCS) by rat- and human-liver 9000-g supernatant fraction was studied. Insertion of a 16a-hydroxy group in the prednisolone (I) [50-24-8] mol. (16a-hydroxyprednisolone [13951-70-7]) decreased the rate of biotransformation. Substitution of the 16a,17a-hydroxy groups with a sym. acetal (in, for example, desonide [638-94-8]) or esp. a non-sym. acetal (in, for example, budesonide), enhanced the biotransformation rate several-fold, particularly in human liver. Differences in the rates of metab. in rat and human liver were obsd. Hydrogenation of the 1,2-double bond in prednisolone and budesonide (hydrocortisone [50-23-7] and 1,2-dihydrobudesonide [83649-24-5]) enhanced the biotransformation rate 9-fold in rat liver but only 2-fold in human liver. Fluorination of the steroid nucleus in 6a- and 9a-positions enhanced the biotransformation rate several-fold in human liver, but in rat liver fluorination marginally decreased the rate of biotransformation. These in vitro results correlate well with available data on the 1st-pass liver metab. of the studied GCS. This indicates that in vitro data can be useful in predicting oral bioavailability of GCS. .

Correlation between chemical structure, receptor binding, and biological activity of some novel, highly active, 16a,17a-acetal-substituted glucocorticoids: Correlation between chemical structure, receptor binding, and biological activity of some novel, highly active, 16a,17a-acetal-substituted glucocorticoids. Dahlberg, Erik; Thalen, Arne; Brattsand, Ralph; Gustafsson, Jan Aake; Johansson, Ulf; Roempke, Karin; Saartok, Tonu (Dep. Med. Nutr., Karolinska Inst., Huddinge S-141 86, Swed.). Mol. Pharmacol., 25(1), 70-8 (English) 1984. CODEN: MOPMA3. ISSN: 0026-895X. DOCUMENT TYPE: Journal CA Section: 2 (Mammalian Hormones) The affinity for the glucocorticoid receptor in rat skeletal muscle of some glucocorticoids with a new type of 16a,17a-acetal substituent was estd. and correlated to the glucocorticoid activities in 3 in vivo systems in rats. Budesonide [51333-22-3] (an approx. 1:1 mixt. of the C(22) epimers of 11b,21-dihydroxy-16a,17a-[(22R,S)-propylmethylenedioxyl]-pregna-1, 4-diene-3,20-dione) and the isolated (22R) [51372-29-3]- and (22S)-epimers [51372-28-2] bound to the same binding site as the potent glucocorticoids dexamethasone (DEX) [50-02-2] or triamcinolone 16a,17a-acetonide (TA) [76-25-5], but with even higher affinity than DEX or TA. The (22R)-epimer was twice as active as the (22S)-epimer, 4 times more active than TA, and 14 times more active than DEX. The introduction of a 9a-fluoro atom slightly decreased the binding affinity of the (22R)-epimer of budesonide, in contrast to the pos. effect of 9a-fluorination of, e.g., 16a,17a-acetonides. The neg. influence of 9a-fluorination of the (22R)-epimer was partially reversed in the 6a,9a-difluorinated (22R)-epimer [51547-52-5]. Nevertheless, the fluorinated compds. were more active than DEX and TA. Budesonide is metabolized mainly to 16a-hydroxyprednisolone [13951-70-7] and 6b-hydroxy-budesonide [88411-77-2]. Both metabolites were very weak competitors for the ligand-binding sites on the receptor. The affinity for the receptor in vitro was closely correlated to the topical glucocorticoid activity in vivo for the 12 steroids compared, which supports the contention that in vitro tests for receptor affinity are useful when screening for agonists among steroids with the present type of structures. The results on receptor-ligand interaction are in accordance with x-ray cyrstallog. data available for some steroids.

Detail of "13951-70-7"

16alpha-Hydroxyprednisolone

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Reference