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Hydrocortisone

Hydrocortisone
Hydrocortisone structure
CAS No.
50-23-7
Chemical Name:
Hydrocortisone
Synonyms
HC;hvb;Optef;Hycort;Hytone;Signef;wycort;H-Cort;Cortril;Rectoid
CBNumber:
CB9756715
Molecular Formula:
C21H30O5
Formula Weight:
362.47
MOL File:
50-23-7.mol

Hydrocortisone Properties

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.
CAS DataBase Reference
50-23-7(CAS DataBase Reference)
EWG's Food Scores
1
FDA UNII
WI4X0X7BPJ
NCI Dictionary of Cancer Terms
cortisol; hydrocortisone
NCI Drug Dictionary
Aeroseb-HC
ATC code
A01AC03,A07EA02,C05AA01,D07AA02,D07XA01,H02AB09,R01AD60,S01BA02,S01CB03,S02BA01
NIST Chemistry Reference
Hydrocortisone(50-23-7)
EPA Substance Registry System
Hydrocortisone (50-23-7)
SAFETY
  • Risk and Safety Statements
Symbol(GHS) 
GHS08
Signal word  Warning
Hazard statements  H361
Precautionary statements  P281
Hazard Codes  Xn
Risk Statements  62-63
Safety Statements  36/37
WGK Germany  3
RTECS  GM8925000
TSCA  Yes
HS Code  29372100
Toxicity LD50 subcutaneous in mouse: > 500mg/kg

Hydrocortisone price More Price(30)

Manufacturer Product number Product description CAS number Packaging Price Updated Buy
Sigma-Aldrich 3867 Hydrocortisone - CAS 50-23-7 - Calbiochem Steroid hormone of the adrenal cortex with anti-inflammatory properties. 50-23-7 1 g $64.19 2021-03-22 Buy
Sigma-Aldrich 386698 Hydrocortisone, Chromatographic Standard 50-23-7 25mg $85.65 2021-03-22 Buy
Sigma-Aldrich C-106 Cortisol solution 1.0?mg/mL in methanol, ampule of 1?mL, certified reference material, Cerilliant? 50-23-7 1 mL $83 2021-03-22 Buy
Sigma-Aldrich H1300000 Hydrocortisone European Pharmacopoeia (EP) Reference Standard 50-23-7 $190 2021-03-22 Buy
Sigma-Aldrich 1316004 Hydrocortisone United States Pharmacopeia (USP) Reference Standard 50-23-7 200mg $366 2021-03-22 Buy

Hydrocortisone Chemical Properties,Uses,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.

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.

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

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.

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.

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

Preparation Products


Hydrocortisone Suppliers

Global( 584)Suppliers
Supplier Tel Fax Email Country ProdList Advantage
Guangzhou PI PI Biotech Inc
+8618371201331
020-81716319 sales@pipitech.com;87478684@qq.com China 3245 55
Baoji Guokang Healthchem co.,ltd
09178656283
cngksw@aliyun.com CHINA 9475 58
Henan DaKen Chemical CO.,LTD.
+86-371-66670886
info@dakenchem.com China 20911 58
Beijing Cooperate Pharmaceutical Co.,Ltd
010-60279497
010-60279497 sales01@cooperate-pharm.com CHINA 1817 55
Shanghai Bojing Chemical Co.,Ltd.
+86-21-37122233
+86-21-37127788 Candy@bj-chem.com CHINA 497 55
Henan Tianfu Chemical Co.,Ltd.
0371-55170693
0371-55170693 info@tianfuchem.com CHINA 22607 55
Hangzhou FandaChem Co.,Ltd.
008615858145714
+86-571-56059825 fandachem@gmail.com CHINA 8909 55
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02783214688 bruce@xrdchem.cn CHINA 567 55
Hefei TNJ Chemical Industry Co.,Ltd.
+86-0551-65418679
86-0551-65418697 info@tnjchem.com China 3000 55
Shanxi Naipu Import and Export Co.,Ltd
+8613734021967
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View Lastest Price from Hydrocortisone manufacturers

Image Release date Product Price Min. Order Purity Supply Ability Manufacturer
2021-12-03 Hydrocortisone
50-23-7
US $0.00 / Kg/Drum 1KG 99.9% 100000kg per month Wuhan Mulei New Material Technology Co. Ltd
2021-12-03 Hydrocortisone
50-23-7
US $0.00 / KG 100g 98%+ 100kg WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
2021-12-01 Hydrocortisone
50-23-7
US $10.50 / KG 1KG 99% 10 ton Hebei Crovell Biotech Co Ltd

Hydrocortisone Spectrum


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