Hydrocortisone

ChemicalBook > CAS DataBase List > Hydrocortisone

Product Name: Hydrocortisone
CAS No.: 50-23-7
Chemical Name: Hydrocortisone
Synonyms: CORTISOL;HC;HYDROCORTISONE BASE;HYDROCORTISONEACETATE;Hytone;H-Cort;Cortril;Epicort;Penecort;texacort
CBNumber: CB9756715
Molecular Formula: C21H30O5
Formula Weight: 362.47
MOL File: 50-23-7.mol

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Hydrocortisone Property

Melting point:: 211-214 °C(lit.)
alpha: 166 º (c=1, C2H5OH 25 ºC)
Boiling point:: 414.06°C (rough estimate)
Density: 1.0812 (rough estimate)
refractive index: 1.6120 (estimate)
Flash point:: 220°C
storage temp.: -20°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.
LogP: 1.610
CAS DataBase Reference: 50-23-7(CAS DataBase Reference)
NIST Chemistry Reference: Hydrocortisone(50-23-7)
EPA Substance Registry System: Hydrocortisone (50-23-7)

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Safety

Hazard Codes: Xn
Risk Statements: 62-63
Safety Statements: 36/37
WGK Germany: 3
RTECS: GM8925000
TSCA: Yes
HS Code: 29372100
Hazardous Substances Data: 50-23-7(Hazardous Substances Data)
Toxicity: LD50 subcutaneous in mouse: > 500mg/kg

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Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H373May cause damage to organs through prolonged or repeated exposure

Precautionary statements

P202Do not handle until all safety precautions have been read and understood.

P260Do not breathe dust/fume/gas/mist/vapours/spray.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P308+P313IF exposed or concerned: Get medical advice/attention.

P405Store locked up.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: NIST921A
Product name: Cortisol (Hydrocortisone)
Purity: NIST?SRM?
Packaging: 1G
Price: $2600
Updated: 2024/03/01

Sigma-Aldrich

Product number: H0396
Product name: Hydrocortisone-Water Soluble
Purity: BioReagent, suitable for cell culture
Packaging: 100MG
Price: $125
Updated: 2024/03/01

Sigma-Aldrich

Product number: C-106
Product name: Cortisol solution
Purity: 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant?
Packaging: 1mL
Price: $106
Updated: 2024/03/01

Sigma-Aldrich

Product number: 3867
Product name: Hydrocortisone - CAS 50-23-7 - Calbiochem
Purity: Steroid hormone of the adrenal cortex with anti-inflammatory properties.
Packaging: 1g
Price: $82.8
Updated: 2024/03/01

Sigma-Aldrich

Product number: 386698
Product name: Hydrocortisone, Chromatographic Standard
Packaging: 25mg
Price: $111
Updated: 2024/03/01

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Hydrocortisone Chemical Properties,Usage,Production

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.

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.

Biological Activity

hydrocortisone is a main glucocorticoid secreted by the adrenal cortex.

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.

Safety Profile

Poison by

Synthesis

Hydrocortisone, 11|?,17|á,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¨CC5 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.

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.

target

TNF-α | IL Receptor | AP-1 | MMP(e.g.TIMP) | NF-kB | IkB | IKK

storage

Store at RT

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

Semicarbazide Isopropyl acetate Potassium borohydride Cortisone acetate Saponin

Preparation Products

6,9-Difluoropregn-4-ene-11,17,21-triol-3,20-dione17,21-diacetate 9-Bromo-11,17,21-trihydroxypregn-4-ene-3,20-dione17,21-diacetate 9-Bromo-11,17,21-trihydroxypregn-4-ene-3,20-dione 21-acetate 9-Fluoropregna-1,4-diene-11,17,21-triol-3,20-dione17,21-diacetate 6,9-Difluoro-11,16,17,21-tetrahydroxypregna-1,4-diene-3,20-dione 21-acetate 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 9,11-Epoxy-6-fluoro-17,21-dihydroxypregn-4-ene-3,20-dione-17,21-diacetate 6alpha,9-difluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate Prednisolone 9,11-Epoxypregn-4-ene-17,21-diol-3,20-dione 21-acetate 17,21-Diacetyloxy-9,11-epoxypregn-4-ene-3,20-dione Pregna-4,9(11)-diene-17,21-diol-3,20-dione17,21-diacetate Anecortave Acetate Deprodone propionate Prednisone 3,17,21-Trihydroxypregna-3,5,9(11)-trien-20-one 3,17,21-triacetate Hydrocortisone acetate Hydrocortisone Butyrate Propionate 6alpha,9-difluoro-11beta,17,21-trihydroxypregna-1,4-diene-3,20-dione 17,21-di(acetate) 9-fluoro-11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate Triamcinolone 21-acetate

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Australia 1 Belgium 3 Brazil 2 Canada 5 China 548 China Hong Kong 1 Czech Republic 2 Egypt 1 Europe 4 France 6 Germany 18 India 80 Italy 2 Japan 7 Jordan 1 Malaysia 2 Mexico 2 Philippines 1 Poland 2 Singapore 1 Slovakia 1 South Korea 3 Spain 2 Switzerland 4 The Netherlands 5 United Kingdom 19 United States 112 Venezuela 1 Global 836

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View Lastest Price from Hydrocortisone manufacturers

Sinoway Industrial co., ltd.

Product: Hydrocortisone 50-23-7
Price: US $0.00-0.00/Kg/Bag
Min. Order: 1Kg/Bag
Purity: 0.99
Supply Ability: 20 tons
Release date: 2024-06-27

Henan Suikang Pharmaceutical Co.,Ltd.

Product: Hydrocortisone 50-23-7
Price: US $0.00/kg
Min. Order: 5kg
Purity: 97.0%~103.0%
Supply Ability: 1tons
Release date: 2024-04-26

Hebei Zhuanglai Chemical Trading Co Ltd

Product: Hydrocortisone 50-23-7
Price: US $150.00/kg
Min. Order: 1kg
Purity: 99%
Supply Ability: 500kg
Release date: 2024-11-26

50-23-7, HydrocortisoneRelated Search:

Hydrocortisone sodium succinate Diethylstilbestrol Hydrocortisone sodium phosphate Flurandrenolide Hydrocortisone 21-hemisuccinate Hydrocortisone acetate salt Hydrocortisone-17-butyrate Prednisolone-21-acetate Benazepril Prednisolone hydrocortisone aceponate 5-Bromo-2,3-difluorophenol D1-Hydrocortisone 21-hemisuccinate Prednisone CORTISONE Meprednisone 4-PREGNENE-11BETA,17ALPHA,21-TRIOL-3,20-DIONE 21-CAPRYLATE Hydrocortisone 21-cypionate

Hydrocortisone - CAS 50-23-7 - Calbiochem

Hydrocortisone, Chromatographic Standard - CAS 50-23-7 - Calbiochem

Hydrocortisone Acetate Impurity?A

Prednisolone Impurity 1（Prednisolone EP Impurity A）

Prednisolone EP Impurity A

21-Trihydroxypregn-4-ene-3

compoundf(kendall)

Cortanal

Cort-Dome

Cortenema

Corticreme

Cortifan

Cortiment

Cortisol alcohol

cortisolalcohol

Cortispray

Cortolotion

Cortonema

Cortoxide

Cortril

Cremesone

Delacort

demacort

Dermacort

Dermolate

Dihydrocostisone

dome-cort

Domolene-HC

Ef corlin

Efcorbin

Hidro-Colisona

hvb

Hycort

Hycortol

Hycortole

Hydrasson

Hydro-Adreson

Hydro-colisona

Hydrocorticosterone

Hydrocortisone alcohol

Hydrocortisone free alcohol

hydrocortisonefreealcohol

Hydrocortisyl

Hydroxycortisone

Hytone

Hytone lotion

hytonelotion

Incortin-H

Incortin-hydrogen

Komed HC

Lacticare-HC

lubricort

Maintasone

meusicort

NSC 10483

nsc10483

Nutracort

Optef