ChemicalBook > CAS DataBase List > Hydrocortisone

Hydrocortisone

Product Name
Hydrocortisone
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
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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.
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
Warning
Hazard statements

H361Suspected of damaging fertility or the unborn child

Precautionary statements

P281Use personal protective equipment as required.

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N-Bromosuccinimide Price

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
1 g
Price
$64.19
Updated
2021/03/22
Sigma-Aldrich
Product number
386698
Product name
Hydrocortisone, Chromatographic Standard
Packaging
25mg
Price
$85.65
Updated
2021/03/22
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
1 mL
Price
$83
Updated
2021/03/22
Sigma-Aldrich
Product number
H1300000
Product name
Hydrocortisone
Purity
European Pharmacopoeia (EP) Reference Standard
Price
$190
Updated
2021/03/22
Sigma-Aldrich
Product number
1316004
Product name
Hydrocortisone
Purity
United States Pharmacopeia (USP) Reference Standard
Packaging
200mg
Price
$366
Updated
2021/03/22
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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.

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.]

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Hydrocortisone Suppliers

Hubei widely chemical technology Co., Ltd.
Tel
027-83778895-
Fax
027-51119224
Email
18602735115@163.com
Country
China
ProdList
562
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64
Taizhou DongBang Fine Chemical Co. Ltd.
Tel
0523-86235448-
Fax
0523-86235448
Email
2535251509@qq.com
Country
China
ProdList
52
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55
Wuhan Zeno Biological Technology Co., Ltd.
Fax
027-87781970
Email
znobio@qq.com
Country
China
ProdList
141
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58
ricentik
Tel
;4001-020-027
Email
846667109@qq.com;198261446@qq.com
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China
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215
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58
Nanjing Shizhou Biotechnology Co., Ltd
Tel
Fax
18013869214
Email
rose.shi@synzest.com
Country
China
ProdList
218
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58
Guangzhou Belka Biological Technology Co., Ltd.
Tel
Fax
18665676617
Email
11353066@qq.com
Country
China
ProdList
9955
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58
HUBEI JINGCHENG CHEMICAL
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027-83325090-
Fax
027-83325090
Email
237920801@qq.com
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China
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30
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J & K SCIENTIFIC LTD.
Tel
010-82848833- ;010-82848833-
Fax
86-10-82849933
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jkinfo@jkchemical.com;market6@jkchemical.com
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China
ProdList
96500
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Meryer (Shanghai) Chemical Technology Co., Ltd.
Tel
21-61259100-
Fax
86-21-61259102
Email
sh@meryer.com
Country
China
ProdList
40264
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62
3B Pharmachem (Wuhan) International Co.,Ltd.
Tel
821-50328103-801
Fax
86-21-50328109
Email
3bsc@sina.com
Country
China
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15877
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View Lastest Price from Hydrocortisone manufacturers

Hebei Yirun Sega Biological Technology Co. Ltd
Product
Hydrocortisone 50-23-7
Price
US $1.50/g
Min. Order
100g
Purity
99.99%
Supply Ability
5ton/Month
Release date
2021-11-26
WUHAN CIRCLE POWDER TECHNOLOGY CO.,LTD
Product
Hydrocortisone 50-23-7
Price
US $0.00/KG
Min. Order
100g
Purity
98%+
Supply Ability
100kg
Release date
2020-09-11
Baoji Guokang Bio-Technology Co., Ltd.
Product
Hydrocortisone 50-23-7
Price
US $730.00/Kg/Bag
Min. Order
1KG
Purity
99%
Supply Ability
1T
Release date
2021-06-03

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