Cortisone - Cortical Steroid

Cortisone

Name	Cortisone
Synonyms	11-DEHYDRO-17-HYDROXYCORTICOSTERONE 17A 21-DIHYDROXY-4-PREGNEN-3 17 20-TRIONE 17ALPHA,21-DIHYDROXY-4-PREGNENE-3,11,20-TRIONE 17ALPHA,21-DIHYDROXYPREGN-4-ENE-3,11,20-TRIONE 17ALPHA-HYDROXY-11-DEHYDROCORTICOSTERONE 17-HYDROXY-11-DEHYDROCORTICOSTERONE 4-PREGEN-17A,21-DIOL-3,11,20-TRIONE 4-PREGNEN-17,21-DIOL-3,11,20-TRIONE 4-PREGNEN-17ALPHA,21-DIOL-3,11,20-TRIONE 4-PREGNENE-17ALPHA,21-DIOL-3,11,20-TRIONE CORTISONE CORTONE DELTA4-PREGNENE-17, 21-DIOL-3, 11, 20-TRIONE DELTA4-PREGNENE-17ALPHA,21-DIOL-3,11,20-TRIONE DELTA-PREGNENE-17ALPHA,21-DIOL-3,11,20-TRIONE KENDALL'S CMPD ''E'' KENDALL'S COMPOUND E KENDALL'S COMPOUND 'E' KENDALL'S ''E'' REICHSTEIN'S COMPOUND ''FA''
CAS NO	53-06-5
EINECS(EC#)	200-162-4
Molecular Formula	C21H28O5
MDL Number	MFCD00003610
Molecular Weight	360.44
MOL File	53-06-5.mol

CORTISONE Chemical Properties
Melting point	223-228 °C (dec.)(lit.)
alpha	D25 +209° (c = 1.2 in 95% alcohol); 25546 +269° (c = 0.125 in benzene); 25546 +248° (c = 0.1 to 0.2 in alcohol)
Boiling point	412.46°C (rough estimate)
density	1.28±0.1 g/cm3 (20 ºC 760 Torr)
refractive index	210 ° (C=1, EtOH)
storage temp	-20°C Freezer
Fp	9℃
pka	12.37±0.60(Predicted)
Water Solubility	229.9mg/L(25 ºC)
Merck	2539
CAS DataBase Reference	53-06-5(CAS DataBase Reference)

Safety Information
Hazard Codes	F,T,Xn
Risk Statements	11-23/24/25-39/23/24/25-63
Safety Statements	22-24/25-45-36/37-16-7
WGK Germany	3
RTECS	GM9020000
HS Code	2937210000
F	18
RIDADR	UN1230 - class 3 - PG 2 - Methanol, solution

CORTISONE Usage And Synthesis
Chemical Properties	Off-White Crystalline Powder
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
Uses	Glucocorticoid, anti-inflammatory agent
Uses	antiinflammatory, glucocorticoid
Uses	Anticoagulant
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.
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.]

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