| Name | Hydrocortisone |
|---|---|
| Synonyms | 11-B,17-A,21-TRIHYDROXY-4-PREGNEN-3,20-DIONE 11BETA,17ALPHA,21-TRIHYDROXYPREGN-4-ENE-3,20-DIONE 17ALPHA-HYDROXYCORTICOSTERONE 17-HYDROXYCORTICOSTERONE 4-PREGNEN-11BETA,11A,21-TRIOL-3,20-DIONE 4-PREGNEN-11-BETA, 17,21-TRIOL-3,20-DIONE 4-PREGNEN-11BETA,17ALPHA,21-TRIOL-3,20-DIONE 4-PREGNEN-3,20-DIONE-11BETA,17ALPHA,21-TRIONE 4-PREGNENE-11B,17A,21-TRIOL-3,20-DIONE 4-PREGNENE-11BETA,17ALPHA,21-TRIOL-3,20-DIONE (8S,9S,10R,11S,13S,14S,17R)-11,17-DIHYDROXY-17-(2-HYDROXY-ACETYL)-10,13-DIMETHYL-1,2,6,7,8,9,10,11,12,13,14,15,16,17-TETRADECAHYDRO-CYCLOPENTA[A]PHENANTHREN-3-ONE CORTISOL DELTA4-PREGNEN-11BETA,17ALPHA,21-TRIOL-3,20-DIONE HYDROCORTISONE HYDROCORTISONE BASE HYDROCORTISONE, CYCLODEXTRIN-ENCAPSULATED HYDROCORTISONE-WATER SOLUBLE HYDROCORTONE KENDALL'S COMPOUND F KENDALL'S COMPOUND ''F'' |
| CAS NO | 50-23-7 |
| [EINECS(EC#)] | 200-020-1 |
| Molecular Formula | C21H30O5 |
| MDL Number | MFCD00011654 |
| Molecular Weight | 362.46 |
| Hydrocortisone Chemical Properties | |
|---|---|
| Melting point | 211-214 °C(lit.) |
| alpha | 166 º (c=1, C2H5OH 25 ºC) |
| density | 1.0812 (rough estimate) |
| Boiling poin | 414.06°C (rough estimate) |
| storage temp | −20°C |
| refractive index | 1.6120 (estimate) |
| Fp | 220°C |
| solubility | H2O: 100 mg/mL |
| form | powder |
| color | White |
| Water Solubility | 319.7mg/L(25 ºC) |
| Decomposition | 220 ºC |
| Merck | 14,4787 |
| BRN | 1354819 |
| Stability | Stable, but may be light sensitive. Incompatible with strong oxidizing agents. |
| CAS DataBase Reference | 50-23-7(CAS DataBase Reference) |
| NIST Chemistry Reference | Hydrocortisone(50-23-7) |
| EPA Substance Registry System | Hydrocortisone (50-23-7) |
| Safety Information | |
|---|---|
| Safety Statements | 36/37 |
| WGK Germany | 3 |
| RTECS | GM8925000 |
| HS Code | 29372100 |
| Hazard Codes | Xn |
| TSCA | Yes |
| Hazardous Substances Data | 50-23-7(Hazardous Substances Data) |
| Toxicity | LD50 subcutaneous in mouse: > 500mg/kg |
| Hydrocortisone Usage And Synthesis | |
|---|---|
| Chemical Properties | crystalline white powder |
| Uses | Principle glucocorticoid hormone produced by adrenal cortex. An anti-inflammatory hormone |
| Uses | glucocorticoid, antiinflammatory |
| Uses | Cortisol, or Hydrocortisone, is a steroid hormone, more specifically a glucocorticoid, produced by the zona fasciculata of the adrenal gland. Cortisol is released in response to stress and a low level of blood glucocorticoids. Its primary functions are to increase blood sugar through gluconeogenesis; suppress the immune system; and aid in fat, protein and carbohydrate metabolism. |
| Originator | Hydrocortone,MSD,US,1952 |
| Definition | ChEBI: A C21-steroid that is pregn-4-ene substituted by oxo groups at positions 3 and 20 and hydroxy groups at positions 11, 17 and 21. Cortisol is a corticosteroid hormone or glucocorticoid produced by zona fasciculata of the adrenal cortex, which is a part of the adrenal gland. It is usually referred to as the "stress hormone" as it is involved in response to stress and anxiety, controlled by corticotropin-releasing hormone (CRH). It increases blood pressure and blood sugar, and reduces immun responses |
| Indications | Hydrocortisone (Cortizone, Cortaid, Anusol-HC, Hytone, LactiCare-HC, Sarnol HC, Penecort, Texacort, and many other branded products) may be purchased as a generic drug |
| Manufacturing Process | The following example from US Patent 2,602,769 illustrates the preparation of 17-hydroxycorticosterone (compound F) from 11-desoxy-17- hydroxycorticosterone (compound S). A medium was prepared from 0.5% peptone, 2% dextrose, 0.5% soybean meal, 0.5% KH2PO4, 0.5% sodium chloride and 0.3% yeast extract in tap water. To 200 ml of this sterilized medium was added an inoculum of the vegetative mycella of Cunninghamella blakesleeana. The spores had first been transferred from a sport slant to a broth medium and the broth medium was aerobically incubated at 24°C for 24 to 72 hours in a .reciprocating shaker until the development of vegetative growth. The inoculated medium containing added vegetative mycella of Cunninghamella blakesleeana was incubated for 48 hours at 24°C following which was added 66 mg of compound S, 11-desoxy-17-hydroxycorticosterone in solution in a minimum of ethanol, and incubation was maintained for 7 hours at 24°C. The beer containing steroid was diluted with 800 ml of acetone, shaken 1 hour on a reciprocating shaker and filtered. The cake was suspended in 500 ml of acetone, shaken another hour and again filtered. The filtrates were combined and the acetone was volatilized under reduced pressure at 50°C. Acetone was then added, if necessary, to bring the concentration to 20% acetone and this resulting aqueous acetone solution was extracted five times each with one-third volume of Skellysolve B petroleum ether to remove fatty materials. These extracts were back washed two times with one-tenth volume of 20% aqueous acetone and the washings were added to the main acetone extract. The combined acetone extracts were extracted six times with one-fourth volume of ethylene dichloride and the ethylene dichloride extract was evaporated under vacuum to leave the steroid residue. This steroid residue was taken up in a minimum of methylene chloride and applied to the top of a column packed with 30 grams of silica which had been previously triturated with 21 ml of ethylene glycol. Then various developing mixtures, saturated with ethylene glycol, were passed over the column. Cuts were made as each steroid was eluted as determined by the lowering of the absorption of light at 240 nm on the automatic chromatographic fraction cutter. Band Solvent Tube No. (60ml) Crude Solids (mg) 1 Cyclohexane 1-4 11 2 Cyclohexane-methylene chloride 3:1 5-13 6.4 compound S 3 Cyclohexane-methylene chloride 1:1 14-16 3.0 4 Cyclohexane-methylene chloride 2:3 17-23 6.0 compound E 5 Cyclohexane-methylene chloride 1:4 24-38 12.2 compound F 6 Methylene chloride 39-59 4.8 A 7.7 mg portion of band 5 was taken up in a minimum of acetone and refrigerated until crystals separated. This cold acetone mixture was centrifuged and the supernatant liquid removed by pipette. To the remaining crystals, a few drops of ice-cold ether-acetone, three to one mixture, were added, shaken, recentrifuged and the supernatant wash liquid removed by pipette. The ether-acetone wash was repeated. The resulting crystals were dried under vacuum yielding 3.3 mg of pure compound F, 17- hydroxycorticosterone. . |
| Brand name | Acticort (Baker Norton); Ala-Cort (Del Ray); Cetacort (Healthpoint); Colocort (Paddock); Cort- Dome (Bayer); Cortef (Pharmacia & Upjohn); Cortenema (Solvay Pharmaceuticals); Cortril (Pfizer); Dermacort (Monarch); Dermacort (Solvay Pharmaceuticals); Eldecort (Valeant); Epicort (Bluline); Flexicort (Westwood- Squibb); Glycort (Heran); Hi-Cor (C & M); Hydro-Rx (X Gen); Hydrocortone (Merck); Hytone (Dermik); Hytone (Sanofi Aventis); Nutracort (Healthpoint); Penecort (Allergan); Proctocort (Monarch); Stie-Cort (Stiefel); Synacort (Medicis); Texacort (Sirius). |
| Therapeutic Function | Glucocorticoid |
| General Description | Hydrocortisone, 11β,17,21-trihydroxypregn-4-ene-3,20-dione, is the primary natural GCin humans. Despite the large number of synthetic GCs, hydrocortisone,its esters, and its salts remain a mainstay ofmodern adrenocortical steroid therapy and the standard forcomparison of all other GCs and MCs . It isused for all the indications mentioned previously. |
| Health Hazard | Cortisol Increases (1) protein catabolism (excepting liver) gluconeogenesis; (2) carbohydrate anabolism (liver); (3) blood sugar; (4) glucose absorption; (5) brain excitation; (6) spread of infections; (7)urinary glucose and nitrogen; (8) stress tolerance; (9) lactation; (10) water diuresis. Regulates general adaptation syndrome, water balance, blood pressure, and hormone release. Decreases (1) fat anabolism; (2) growth rate; (3) inflammation; (4) eosinophils; (5) lymphocytes; (6) antigen sensitivity; (7) respiratory quotient; (8) ketosis; (9) wound healing; (10) skin pigmentation; (11)RBC hemolysis. |
| Contact allergens | Hydrocortisone is the principal glucocorticoid hor- mone produced by the adrenal cortex and is used topi- cally or systemically. It belongs to the allergenic A group. Marker of allergy is tixocortol pivalate. |
| Clinical Use | Hydrocortisone is endogenous, and it has both glucocorticoid and mineralocorticoid activity. It is the fundamental structure by which the glucocorticoid and mineralocorticoid activities of all other corticosteroids are judged. Functional groups that are essential for both mineralocorticoid and glucocorticoid activity include the pregnane skeleton with an all-trans backbone, the ring A-en-one system (?4 -3-one ring A) and the 17β-ketol side chain (C-20-keto-C-21-hydroxy). The glucocorticoid activity is enhanced by the C-11 and C-17 hydroxyl groups. Hydrocortisone can be used to treat severe asthmatic attacks that do not respond to conventional treatment. It is available as various ester forms. |
| Safety Profile | Poison by |
| Veterinary Drugs and Treatments | Because of its rapid effect and relatively high mineralocorticoid effect, hydrocortisone sodium succinate (Solu-Cortef?) is the most commonly used form of this medication when an acute glucocorticoid/ mineralocorticoid effect is desired (e.g., acute adrenal insufficiency). Corticosteroids have not been shown beneficial in treating hypovolemic shock, but low dose glucocorticoids probably reduce mortality associated with septic shock. Glucocorticoids have been used in an attempt to treat practically every malady that afflicts man or animal, but there are three broad uses and dosage ranges for use of these agents. 1) Replacement of glucocorticoid activity in patients with adrenal insufficiency, 2) as an antiinflammatory agent, and 3) as an immunosuppressive. Among some of the uses for glucocorticoids include treatment of: endocrine conditions (e.g., adrenal insufficiency), rheumatic diseases (e.g., rheumatoid arthritis), collagen diseases (e.g., systemic lupus), allergic states, respiratory diseases (e.g., asthma), dermatologic diseases (e.g., pemphigus, allergic dermatoses), hematologic disorders (e.g., thrombocytopenias, autoimmune hemolytic anemias), neoplasias, nervous system disorders (increased CSF pressure), GI diseases (e.g., ulcerative colitis exacerbations), and renal diseases (e.g., nephrotic syndrome). 2) Some glucocorticoids are used topically in the eye and skin for various conditions or are injected intra-articularly or intra-lesionally. The above listing is certainly not complete. |
| Purification Methods | Recrystallise hydrocortisone from EtOH or isoPrOH. It is bitter tasting and has UV with max at 242 nm (log 4.20). Its solubility at 25o is: H2O (0.28%), EtOH (1.5%), MeOH (0.62%), Me2CO (0.93%), CHCl3 (0.16%), propylene glycol (1.3%) and Et2O (0.35%). It gives an intense green colour with conc H2SO4. [Wendler et al. J Am Chem Soc 72 5793 1950, Beilstein 8 IV 3422.] |
Hydrocortisone Preparation Products And Raw materials | |
|---|---|
| Raw materials | Potassium borohydride-->Isopropyl acetate-->Semicarbazide-->Cortisone acetate-->Saponin-->CORTEXOLONE |
| Preparation Products | Deprodone propionate-->6,9-Difluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione 21-acetate-->6alpha,9-difluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate-->9-Fluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione 21-acetate-->Prednisone-->9-fluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate-->9-Fluoropregna-1,4-diene-11,17,21-triol-3,20-dione17,21-diacetate-->3,17,21-Trihydroxypregna-3,5,9(11)-trien-20-one 3,17,21-triacetate-->Prednisolone-->6alpha,9-difluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 17,21-di(acetate)-->Anecortave Acetate-->6,9-Difluoropregn-4-ene-11,17,21-triol-3,20-dione17,21-diacetate-->Hydrocortisone acetate-->9,11-Epoxypregn-4-ene-17,21-diol-3,20-dione 21-acetate-->Pregna-4,9(11)-diene-17,21-diol-3,20-dione17,21-diacetate-->9,11-Epoxy-6-fluoro-17,21-dihydroxypregn-4-ene-3,20-dione-17,21-diacetate-->17,21-Diacetyloxy-9,11-epoxypregn-4-ene-3,20-dione-->Hydrocortisone Butyrate Propionate-->9-Bromo-11,17,21-trihydroxypregn-4-ene-3,20-dione 21-acetate-->9-Bromo-11,17,21-trihydroxypregn-4-ene-3,20-dione17,21-diacetate-->6-Fluoro-17,21-dihydroxypregna-4,9(11)-diene-3,20-dione 17,21-diacetate-->11alpha,17,21-trihydroxypregn-4-ene-3,20-dione 21-acetate |
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