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Hydrocortisone structure

Hydrocortisone
  • CAS：50-23-7
  • MW:362.4599
  • MF：C21H30O5
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. View more+
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1. Names and Identifiers
1.1 Name
Hydrocortisone
1.2 Synonyms
(11b)-11,17,21-trihydroxypregn-4-ene-3,20-dione; (11Β)-11,17,21-Trihydroxy-pregn-4-ene-3,20-dione; (11Β)-11,17,21-Trihydroxypregn-4-ene-3,20-dione; (8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(hydroxyacetyl)-10,13-dimethyl-1,2,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-3H-cyclopenta[a]phenanthren-3-one; 11,17,21-trihydroxy-pregn-4-ene-3,20-dione; 11b,17,21-Trihydroxyprogesterone; 11Β,17,21-Trihydroxyprogesterone; 11Β,17α,21-Trihydroxypregn-4-ene-3,20-dione; 17a-Hydroxycorticosterone; 17-hydroxycorticosterone; 17α-Hydroxycorticosterone; 21-Trihydroxypregn-4-ene-3; 4-Pregnene-11b,17a,21-triol-3,20-dione; Alacort; CCN 90306A; Cleiton; compoundf(kendall); Cortanal; Efcortelin; EINECS 200-020-1; Eye-Cort; H-Cort; hidrocortisona; HVB; Hycort; Hydrocort; Hydrocortal; Hydrocorticosterone; Hydrocortisone - CAS 50-23-7 - Calbiochem; Hydrocortisone Acetate Impurity?A; Hydrocortisone, Chromatographic Standard - CAS 50-23-7 - Calbiochem; hydrocortisonum; Hydroskin; Hydroxycorticosterone; Hydroxycortisone; Hytone; Kendall's compound F; Medicort; MFCD00011654; Optef; Prednisolone EP Impurity A; Prednisolone Impurity 1（Prednisolone EP Impurity A）; pregn-4-ene-3,20-dione, 11,17,21-trihydroxy-, (11b)-; Pregn-4-ene-3,20-dione, 11,17,21-trihydroxy-, (11Β)-; Pregn-4-ene-3,20-dione, 11Β,17,21-trihydroxy-; Signef; wycort; Zenoxone;
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1.3 CAS No.
50-23-7
1.4 CID
5754
1.5 EINECS
200-020-1
1.6 Molecular Formula
C21H30O5
1.7 Inchi
InChI=1S/C21H30O5/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/h9,14-16,18,22,24,26H,3-8,10-11H2,1-2H3/t14-,15-,16-,18+,19-,20-,21-/m0/s1
1.8 InChkey
JYGXADMDTFJGBT-VWUMJDOOSA-N
1.9 Canonical Smiles
CC12CCC(=O)C=C1CCC3C2C(CC4(C3CCC4(C(=O)CO)O)C)O
1.10 Isomers Smiles
C[C@]12CCC(=O)C=C1CC[C@@H]3[C@@H]2[C@H](C[C@]4([C@H]3CC[C@@]4(C(=O)CO)O)C)O
2. Properties
2.1 Solubility
H2O: 100?mg/mL
2.2 Appearance
crystalline white powder
2.3 Storage
Ambient temperatures.
2.4 Chemical Properties
crystalline white powder
2.5 Color/Form
Plates from alc or iso-propyl alc
Crystalline, striated blocks from absolute ethanol or isopropanol
White, crystalline powder
2.6 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 Agroup. Marker of allergy is tixocortol pivalate.
2.7 Odor
Odorless
2.8 Water Solubility
H2O: 100 mg/mL
2.9 Spectral Properties
Specific optical rotation: +167 deg at 22 deg C/D (absolute alc)
Max absorption: 242 nm (e= 445, 1%, 1 cm)
ABSORPTIVITY OF SOLN IN METHANOL (1 IN 1000,000) @ 242 NM DOES NOT DIFFER BY MORE THAN 2.5%
SADTLER REFERENCE NUMBER: 8758 (IR, PRISM)
MASS: 62042 (NIST/EPA/MSDC Mass Spectral Database, 1990 version)
IR: 5234 (Coblentz Society Spectral Collection)
UV: 20770 (Sadtler Research Laboratories Spectral Collection)
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2.10 Stability
Stable, but may be light sensitive. Incompatible with strong oxidizing agents.
2.11 StorageTemp
-20°C
3. Use and Manufacturing
3.1 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
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3.2 Description
Hydrocortisone (CAS 50-23-7) is a white crystalline powder that belongs to the class of corticosteroids. Its basic structure consists of a steroid backbone with a hydroxyl group at the C11 position and a ketone group at the C3 position. This chemical is sparingly soluble in water but soluble in ethanol and chloroform. It has a melting point of about 213-220°C.

Hydrocortisone exhibits both anti-inflammatory and immunosuppressive properties. It acts by binding to cytoplasmic glucocorticoid receptors, which then translocate to the nucleus and modulate gene expression. This mechanism of action leads to the suppression of inflammatory responses and the regulation of immune system activity.

Applicable fields
Pharmaceutical Industry: Hydrocortisone is widely used in the pharmaceutical industry for its anti-inflammatory and immunosuppressive effects. It is commonly used in the treatment of various inflammatory conditions, such as allergies, asthma, and skin disorders. The mechanism of action involves reducing inflammation and suppressing the immune response.

Dermatology: In dermatology, hydrocortisone is utilized in the form of creams, ointments, and lotions for the treatment of skin conditions such as eczema, dermatitis, and psoriasis. Its anti-inflammatory properties help alleviate itching, redness, and swelling.

Endocrinology: Hydrocortisone is also used in endocrinology for hormone replacement therapy in individuals with adrenal insufficiency. It helps to replace the deficient cortisol hormone and maintain normal physiological functions.

Storage Conditions
Store in a cool, dry place.
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3.3 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 Preparation Products
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3.4 Usage
Principle glucocorticoid hormone produced by adrenal cortex. An anti-inflammatory hormone.
4. Safety and Handling
4.1 Exposure Standards and Regulations
The Generic Animal Drug and Patent Restoration act requires that each sponsor of an approved animal drug must submit to the FDA certain information regarding patents held for the animal drug or its method of use. The Act requires that this information, as well as a list of all animal drug products approved for safety and effectiveness, be made available to the public. Hydrocortisone and hydrocortisone acetate are included on this list.
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4.2 Octanol/Water Partition Coefficient
log Kow = 1.61
4.3 Safety Profile
Poison by
4.4 Formulations/Preparations
Ointment: 0.5% Cortizone-5, (Pfizer), 1% Cortizone-10, (Pfizer), HydroSKIN, (Rugby), 2.5% Hytone, (Dermik). Pledgets (saturated with solution): 0.5% Massengill Medicated Soft Cloth Towelette (with parabens and propylene glycol), (GlaxoSmithKline). Solution: 1% Cortaid FastStick Maximum Strength (with alcohol and methylparaben), (Pfizer), Cortaid Spray Maximum Strength (with alcohol and methylparaben), (Pfizer), Cortizone-10 Scalp Itch Formula Liquid (with alcohol SD 40-2 60% v/v, benzyl alcohol, and propylene glycol), (Pfizer), Penecort (with alcohol SD 40-2 57%, benzyl alcohol, and propylene glycol), (Allergan), Texacort (with SD alcohol 33% and propylene glycol), (Sirius), 2.5% Texacort, (Sirius).
Lotion: 0.5% HydroSKIN, (Rugby). 1% Ala-Cort, (Del-Ray), Aquanil HC (with benzyl alcohol), (Person & Covey), Cetacort (with parabens), (Healthpoint), Dermacort (with benzyl alcohol), (Solvay) HydroSKIN, (Rugby) LactiCare-HC, (Stiefel) Nutracort (with parabens), (Healthpoint), Sarnol HC, (Stiefel), 2% Ala-Scalpt, (Del-Ray); 2.5% Hydrocortisone Lotion, (Glades), Hydrocortisone Lotion, (Major), Hytone (with propylene glycol), (Dermik), LactiCare-HC, (Stiefel), Nutracort (with parabens), (Healthpoint), ProctoCream-HC (with benzyl alcohol), (Physicians Total Care).
Topical: Cream: 0.5% Cortizone-5 (with aloe and parabens), (Pfizer), Cortizone for Kids ( with aloe and parabens), (Pfizer); 1% Ala-Cort, (Del-Ray), Cortaid Intensive Therapy (with parabens and propylene glycol), (Pfizer), Cortizone-10 (with aloe and parabens), (Pfizer), Cortizone-10 External Anal Itch Relief Creme ( with aloe and parabens), (Pfizer), Dermacort, (Solvay), DermiCort (Republic), HydroSKIN, (Rugby), Hytone (with propylene glycol), (Dermik), Penecort (with benzyl alcohol and propylene glycol), (Allergan), Preparation H Hydrocortisone (with parabens and propylene glycol), (Wyeth); 2.5% Anusol-HC (with benzyl alcohol and propylene glycol), (Pfizer), Hytone (with propylene glycol), (Dermik). Gel: 1% CortaGel Extra Strength, (Norstar).
Rectal: Cream: 1 Proctocort ( with benzyl alcohol and propylene glycol), (Monarch); Suspension: 100 mg/60 mL Cortenema ( with methylparaben), (Solvay), Hydrocortisone Enema, (Copley).
Powder: (available by nonproprietary name). Rectal: Aerosol, foam suspension: 10% Cortifoam (with parabens, propylene glycol, and chlorofluorohydrocarbon propellants), (Schwarz). Suppositories: 25 mg Anucort-HC, (G&W), Anu-Med HC, (Major), Anusol-HC, (Pfizer). Hemorrhoidal-HC, (Alpharma), Hemorrhoidal-HC, (CMC), Hemorrhoidal-HC, (Sandoz), Hemorrhoidal-HC, (Rugby), Hemorrhoidal-HC, (UDL), Hemril-HC Uniserts, (Upsher-Smith), Hydrocortisone Acetate Suppositories, (Paddock), Hydrocortisone Acetate Suppositories, (Teva), Hydrocortisone Acetate Suppositories, (UDL), Hydrocortisone Acetate Suppositories, (United Research), 30 mg Proctocort, (Monarch). /Hydrocortisone acetate/
Powder: Oral: Tablets: 5 mg Cortef (scored), (Pfizer); 10 mg Cortef (scored), (Pfizer), Hydrocortone (scored), (Merck); 20 mg Cortef (scored), (Pfizer).
Topical: Cream: 0.5% Corticaine (with parabens), (UCB); 0.5% (of hydrocortisone) Cortaid Sensitive Skin Formula (with aloe and parabens), (Pfizer); 1% (of hydrocortisone) Caldecort Anti-Itch (with propylene glycol), (Novartis), Cortaid Maximum Strength (with aloe and methylparaben), (Pfizer), Dermarest DriCort, Del Dermtex HC (with menthol 1%), (Pfeiffer), Nupercainal Hydrocortisone Anti-Itch Cream (with propylene glycol), (Novartis). Lotion: 0.5% (of hydrocortisone) (available by nonproprietary name)/ Ointment: 0.5% (of hydrocortisone) Cortaid Sensitive Skin Formula (with aloe and parabens), (Pfizer); 1% Anusert HC-1, (G&W). Gynecort 10, (Combe), Lanacort 10, (Combe); 1% (of hydrocortisone) Anusol-HC-1, (Pfizer), Cortaid Maximum Strength (with aloe and methylparaben), (Pfizer). Paste: 0.5% Orabase (HCA), Colgate Solution 1% Scalp-Aid, (Major), Scalpcort Maximum Strength, Clay-Park 1% (of hydrocortisone) Dermtex HC Spray, (Pfeiffer). /Hydrocortisone acetate/
Topical: Cream: 0.1% Pandel (with parabens and propylene glycol), (Savage) /Hydrocortisone buteprate/
Topical: Cream: 0.1% Locoid (with methylparaben), (Ferndale). Ointment: 0.1% Locoid, (Ferndale). Solution: 0.1% Locoid (with isopropyl alcohol 50% and povidone), (Ferndale). /Hydrocortisone butyrate/
Topical: Cream: 0.2% Westcort (with propylene glycol), (Westwood-Squibb). Ointment: 0.2% Westcort (with propylene glycol), (Westwood-Squibb).
Parenteral: For injection: 100 mg (of hydrocortisone) A-hydroCort (with benzyl alcohol 18 mg in Univial), (Hospira), Solu-Cortef (preservative-free in vials or with benzyl alcohol 18 mg in Act-O-Vial), (Pfizer); 250 mg (of hydrocortisone) A-hydroCort ( with benzyl alcohol 18 mg in Univial), (Hospira), Solu-Cortef (with benzyl alcohol 16.4 mg in Act-O-Vial), (Pfizer); 500 mg (of hydrocortisone) A-hydroCort (with benzyl alcohol 36 mg in Univial), (Hospira), Solu-Cortef (with benzyl alcohol 33.4 mg in Act-O-Vial), (Pfizer), 1 g (of hydrocortisone) A-hydroCort ( with benzyl alcohol 72 mg in Univial), (Hospira), Solu-Cortef ( with benzyl alcohol 66.9 mg in Act-O-Vial), (Pfizer). /Hydrocortisone sodium succinate/
Parenteral: Injection: 50 mg (of hydrocortisone) per mL Hydrocortone Phosphate (with parabens and sodium bisulfite), (Merck). /Hydrocortisone sodium phosphate/
Powder: Parenteral: Injectable suspension: 25 mg/mL, 50 mg/mL Hydrocortone Acetate (with benzyl alcohol), (Merck). /Hydrocortisone acetate/
Grade: USP. Also used as acetate and sodium succinate salts.
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4.5 Report

Reported in EPA TSCA Inventory.

4.6 Safety

Poison by intraperitoneal route. Moderately toxic by subcutaneous route. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. A steroid. When heated to decomposition it emits very toxic fumes of SOx and NOx.
Hazard Codes: Xn
WGK Germany: 3
Risk Statements: 63-62-40?
R62: Risk of impaired fertility.?
R63: Possible risk of harm to the unborn child.?
R40: Limited evidence of a carcinogenic effect.
Safety Statements of Hydrocortisone (CAS NO.50-23-7): 36/37-45-36-22?
S36/37: Wear suitable protective clothing and gloves.?
S45: In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.)?
S36: Wear suitable protective clothing.?
S22: Do not breathe dust.

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4.7 Specification

?Hydrocortisone , its CAS NO. is 50-23-7, the synonyms are Cortisol ; 11-beta,17-alpha,21-trihydroxypregn-4-ene-3,20-dione ; Hydrocortisone Base ; Cor-Tar-Quin ; Cort-Quin ; Cortisporin ; Drotic ; Neo-Cort-Dome?; Cortisol? .

4.8 Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man TDLo oral 400mg/kg/10D- (400mg/kg) BEHAVIORAL: CHANGES IN PSYCHOPHYSIOLOGICAL TESTS Psychopharmacology Vol. 145, Pg. 260, 1999.
mouse LD50 subcutaneous > 500mg/kg (500mg/kg) ? Khimiko-Farmatsevticheskii Zhurnal. Chemical Pharmaceutical Journal. For English translation, see PCJOAU. Vol. 24(3), Pg. 26, 1990.
rat LD50 intraperitoneal 150mg/kg (150mg/kg) ? Japanese Journal of Pharmacology. Vol. 21, Pg. 377, 1971.
rat LD50 subcutaneous 449mg/kg (449mg/kg) ? Toxicology and Applied Pharmacology. Vol. 8, Pg. 250, 1966.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Reproductive toxicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word

Warning

Hazard statement(s)

H361 Suspected of damaging fertility or the unborn child
Precautionary statement(s)
Prevention

P201 Obtain special instructions before use.

P202 Do not handle until all safety precautions have been read and understood.

P280 Wear protective gloves/protective clothing/eye protection/face protection.

Response

P308+P313 IF exposed or concerned: Get medical advice/ attention.

Storage

P405 Store locked up.

Disposal

P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum
13C NMR : Predict  
1H NMR : Predict  
Predict 1H proton NMR  
IR : KBr disc  
Raman : 4880 A,200 M,powder  
Mass  
Mass spectrum (electron ionization)  
UV/Visible spectrum  
7. Synthesis Route
50-23-7Total: 22 Synthesis Route
 
50-03-3
50-03-3 324 Suppliers
 
50-23-7
50-23-7 178 Suppliers
 
68-96-2
68-96-2 216 Suppliers
 
50-23-7
50-23-7 178 Suppliers
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8. Precursor and Product
precursor:
57-83-0
57-83-0
566-35-8
566-35-8
152-58-9
152-58-9
50-03-3
50-03-3
68-96-2
68-96-2
50-04-4
50-04-4
53-06-5
53-06-5
product:
116-58-5
116-58-5
382-44-5
382-44-5
382-45-6
382-45-6
641-77-0
641-77-0
50-24-8
50-24-8
302-91-0
302-91-0
516-41-6
516-41-6
50-04-4
50-04-4
53-06-5
53-06-5
50-22-6
50-22-6
9. Computed Properties
10.Other Information
Usage
Cortisol, steroid hormone is released in response to stress and a low level of blood glucocorticoids. Its primary functions is to increase blood sugar through gluconeogenesis, suppress the immune system, and aid in fat, protein and carbohydrate metabolism.
Merck
14,4787
BRN
1354819
Chemical Properties
crystalline white powder
Originator
Hydrocortone,MSD,US,1952
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.
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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
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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.
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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).
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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.
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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.
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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.
Biochem/physiol Actions
Product does not compete with ATP.
Mechanism of action
Hydrocortisone exhibits anti-shock, anti-allergy, and anti-inflammatory action. It raises sugar content in the blood, increases potassium secretion, and lowers sodium excretion from the body. It exhibits anti-metabolic action and reduces histamine synthesis in the body.
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.
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Safety Profile
Poison by
Chemical Synthesis
Hydrocortisone, 11β,17α,21-trihydroxypregn-4-en-3,20-dione (27.1.8), is synthesized in various ways and from various compounds containing a steroid skeleton. According to one of them, hydrocortisone is synthesized from dextropregnenolone. The double bond between C16 and C17 of dextropregnenolone is oxidized using hydrogen peroxide in a base, forming an epoxide 27.1.1. Interacting this with hydrobromic acid opens the epoxide ring, forming 16-bromo-17-hydroxydextropregnenolone (27.1.2). The resulting bromo derivative undergoes debromination by hydrogen using a palladium on carbon catalyst, and then the secondary hydroxyl group undergoes esterification using formic acid in the presence of p-toluenesulfonic acid, giving 3-formyloxy-17-hydroxydextropregnenolone (27.1.3). The resulting 3-formyloxy- 17-hydroxydextropregnenolone undergoes bromination by bromine, which results in bromination of the C4–C5 double bond and the methyl group of acetyl moiety, which forms a tribromo derivative 27.1.4. Reacting the product with sodium iodide results in dehalogenation of the resulting vicinal dibromide, during which the double bond is simultaneously shifted into the position between carbon atoms C5 and C6 that gives the bromoketone 27.1.5. This is reacted with potassium acetate and then with acetic anhydride in the presence of p-toluenesulfonic acid, forming a diacetate 27.1.6. Taking into account that unlike acetates, formates are easily oxidized and give exactly the same products as do the corresponding alcohols, the resulting diacetate is oxidized in an Oppenauer oxidation reaction, using aluminum isopropoxide and cyclohexanone as a hydrogen acceptor. During this, isomerization of the double bond into the primary position between C4 and C5 simultaneously takes place, forming a stable, conjugated vinylketone, after which the acetyl protection of both hydroxyl groups is hydrolyzed using potassium hydroxide, giving 17-hydroxy-11-deoxycorticosterone (27.1.7). This undergoes microbiological oxidation at position C1, forming the desired hydrocortisone (27.1.8). Side reactions of microbiological oxidation using the very same microorganisms can cause hydroxylation of steroids in different positions, using easily accessible progesterone as an initial substance.

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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). 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.
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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.]
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12. Related Questions
What are the benefits and risks of using Hydrocortisone cream?Hydrocortisone topical is a medication used to alleviate redness, swelling, itching, and discomfort associated with various skin conditions. Belonging to the class of corticosteroids, hydrocortisone w..
What are the Clinical Applications of Hydrocortisone?Hydrocortisone Overview Hydrocortisone, a corticosteroid medication, is used to reduce pain, itching, and inflammation by suppressing the body's immune response. It is also utilized as a hormone repla..
What is the role of Hydrocortisone in the body and its applications? Hydrocortisone, also known as Cortisol, is a crucial adrenal glucocorticoid that forms a steroid-receptor complex by diffusing on target cells and combining with its receptor. This complex acts as an..
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