53-06-5 Usage
Chemical Properties
Off-White Crystalline Powder
Uses
Different sources of media describe the Uses of 53-06-5 differently. You can refer to the following data:
1. Cortisone is used for inflammatory processes, allergies, and adrenal insufficiency.
2. Glucocorticoid, anti-inflammatory agent
3. antiinflammatory, glucocorticoid
4. Anticoagulant
Definition
ChEBI: A C21-steroid that is pregn-4-ene substituted by hydroxy groups at positions 17 and 21 and oxo group at positions 3, 11 and 20.
Therapeutic Function
Glucocorticoid
General Description
Cortisone is a corticosteroid produced in the adrenal glands. Cortisone is administered for short term pain relief and to reduce swelling from inflammation. This Certified Spiking Solution? is applicable in LC-MS/MS applications for endocrinology, clinical chemistry and neonatal screening.
Hazard
Damaging side effects, e.g., sodium retention from ingestion.
Pharmacokinetics
Following oral administration, cortisone acetate and hydrocortisone acetate are completely and
rapidly deacetylated by first-pass metabolism. Much of the oral cortisone, however, is inactivated by
oxidative metabolism before it can be converted to hydrocortisone in the liver. The pharmacokinetics
for hydrocortisone acetate is indistinguishable from that of orally administered hydrocortisone. Oral
hydrocortisone is completely absorbed, with a bioavailability of greater than 95% and a half-life of 1 to 2 hours
(23).
Clinical Use
Cortisone is administered orally or by intramuscular (IM) injection as its 21-acetate (cortisone acetate).Cortisone acetate or hydrocortisone usually is the corticosteroid of choice for replacement therapy in patients
with adrenocortical insufficiency, because these drugs have both glucocorticoid and mineralocorticoid
properties.
Synthesis
Cortisone, 17α,21-dihydroxypregn-4-en-3,11,20-trione (27.1.26), is also
synthesized in various ways from compounds already having the steroid skeleton. One of
them is very similar to a method of making hydrocortisone described above, in which it
is synthesized from progesterone, which undergoes microbiological oxidation, forming
11α-hydroxyprogesterone (27.1.9). The hydroxyl group of the last is oxidized by
chromium(VI) oxide in acetic acid, giving 11-ketoprogesterone (27.1.10). This is reacted
with diethyloxalate in the presence of sodium ethoxide, forming the corresponding
α-ketoester in the form of a sodium enolate 27.1.11, which undergoes bromination with
two equivalents of bromine, giving a dibromoketone 27.1.12. The resulting dibromoketone
undergoes a Favorskii rearrangement, but the product is not hydrolyzed, and the
unsaturated acid is isolated in the form of a methyl ester 27.1.20. Reacting this with
pyrrolidine gives a dienamine 27.1.21, which undergoes reduction by lithium aluminum
hydride, which results in that, the keto-group on C11 transforms into a hydroxyl group,
and the carbmethoxy group to a primary alcohol, forming the compound 27.1.22. Acidic
hydrolysis of the product and subsequent acetylation gives an acetate 27.1.23, and the
hydroxyl group at C11 in which it is oxidized with chromium(VI) oxide to a ketone, forming
the compound 27.1.24. This undergoes a reaction with osmium tetroxide, and the
resulting osmate is oxidized by magnesium dioxide in N-methylmorpholine, giving cortisone
acetate 27.1.25. Hydrolysis of the acetyl group using sodium bicarbonate leads to
the formation of cortisone (27.1.26).
Metabolism
The metabolism of hydrocortisone has been previously described. Cortisone acetate is slowly
absorbed from IM injection sites over a period of 24 to 48 hours and is reserved for patients who are unable to
take the drug orally. The acetate ester derivative demonstrates increased stability and has a longer duration of
action when administered by IM injection. Thus, smaller doses can be used. Similarly, hydrocortisone may be
dispensed as its 21-acetate (hydrocortisone acetate), which is superior to cortisone acetate when injected
intra-articularly.
Purification Methods
Crystallise cortisone from 95% EtOH or acetone. The UV has 14,000 M-1cm -1 at 237nm (EtOH). [Beilstein 8 IV 3480, Hems J Pharm Pharmacol 5 409 1953, Beilstein 8 IV 3480.]
Check Digit Verification of cas no
The CAS Registry Mumber 53-06-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 3 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 53-06:
(4*5)+(3*3)+(2*0)+(1*6)=35
35 % 10 = 5
So 53-06-5 is a valid CAS Registry Number.
InChI:InChI=1/C21H28O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h9,14-15,18,22,26H,3-8,10-11H2,1-2H3/t14?,15?,18?,19-,20-,21-/m0/s1
53-06-5Relevant articles and documents
Fukushima et al.
, p. 487 (1952)
-
Reichstein,v. Euw
, p. 1181,1183, 1184 (1938)
-
Nitrate esters of corticoid compounds and pharmaceutical applications thereof
-
, (2008/06/13)
Compounds of the formula and use of the compounds as medicaments.
Photochemical Studies, 64. - Photostability of Glucocorticoids in the Solid State
Reisch, Johannes,Iranshahi, Lotfollah,Ekiz-Guecer, Nurten
, p. 1199 - 1200 (2007/10/02)
Most of the pharmacopoeia require that the glucocorticoids hydrocortisone (1), cortisone (2), hydrocortisone 21-acetate (3) and cortisone 21-acetate (4) must be protected from light during storage.The present study shows that irradiation of these compounds in the solid state leads to the loss of the side chain at C-17.Two-17-ketosteroids, 11β-hydroxy-4-androstene-3,17-dione (6) and 4-androstene-3,11,17-trione (7), were obtained as photoproducts (yields 3percent and 4percent, respectively).Key Words: Hydrocortisone / Cortisone / Steroids / Photochemistry