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50-03-3

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50-03-3 Usage

Adrenocorticotropic hormone drugs

Hydrocortisone acetate is an adrenal hormone drugs, white crystalline powder, odorless, bitter taste. The melting point is 216~222 ℃, right optical. Slightly soluble in ethanol, ether, chloroform, acetone, insoluble in water. It was synthesized by In 17α-hydroxy progesterone. Hydrocortisone acetate has important physiological activities such as anti-inflammatory, anti-viral, anti-allergic, anti-shock, reducing inflammatory exudation effect, commonly used in clinical adrenal insufficiency and autoimmune diseases. Preparations are injection, tablets, ointments and eye drops. Adding a small amount of hydrocortisone acetate in some cosmetics cortisol can increase the efficacy of anti-allergy and improve the degree of whitening of the skin, but long-term using of such substances can cause the skin produce hormone-dependent disease. Our cosmetics cosmetics specifications prescribedthathormone substances can not be added.

Indications

For allergic, non-infectious skin diseases and a number of proliferative skin disorders. Such as dermatitis, eczema, neurodermatitis, seborrheic dermatitis and itching psychosis. Figure 1 the chemical structure formula of tetra-fluoroethane.

Contraindications

1. This medicine and matrix components allergy and allergic to other glucocorticoids are prohibited. 2. The primary bacterial, fungal and viral infectious skin diseases such as disabledare prohibited. The above information is edited by the lookchem of KuiMing.

Adverse Reactions

Long-term using can cause local skin atrophy, telangiectasia, pigmentation, folliculitis, perioral dermatitis and secondary infection.

Precautions

1. Not long-term, large-scale use. 2. The coated parts such as a burning sensation, itching, swelling, etc., should stop the medication.

Chemical Property

White or almost white crystalline powder, odorless. Mp218-221.5 ℃; 25D + 166 ° (dioxane) Specific rotation [α]; ethanol maximum absorption at 240nm wavelength. Insoluble in water, slightly soluble in ethanol (1: 230) and chloroform (1: 150), insoluble in ether.

Uses

Different sources of media describe the Uses of 50-03-3 differently. You can refer to the following data:
1. Corticosteroid drugs, have anti-inflammatory, anti-allergic, anti-toxins, anti-shock effect.
2. Hydrocortisone acetate is used to treat hemorrhoids and itching/swelling in the rectum and anus. It is used to treat certain intestinal problems (such as ulcerative colitis of the rectum and other rectal/anal inflammatory conditions).

Production methods

Hydrocortisone and acetic anhydride in pyridine esterification.

Chemical Properties

white powder

Brand name

Cortef Acetate (Pharmacia & Upjohn); Cortifoam (Schwarz Pharma); Cortril (Pfizer); Dricort (Ingram); Hydrocortone (Merck).

Clinical Use

Corticosteroid: Local inflammation of joints and soft tissue

Drug interactions

Potentially hazardous interactions with other drugs Aldesleukin: avoid concomitant use. Antibacterials: metabolism accelerated by rifampicin; metabolism possibly inhibited by erythromycin; concentration of isoniazid possibly reduced. Anticoagulants: efficacy of coumarins and phenindione may be altered. Antiepileptics: metabolism accelerated by carbamazepine, phenobarbital, fosphenytoin, phenytoin and primidone. Antifungals: increased risk of hypokalaemia with amphotericin - avoid; metabolism possibly inhibited by itraconazole and ketoconazole. Antivirals: concentration possibly increased by ritonavir. Ciclosporin: rare reports of convulsions in patients on ciclosporin and high-dose corticosteroids. Cobicistat: concentration of hydrocortisone possibly increased - increased risk of adrenal suppression. Diuretics: enhanced hypokalaemic effects of acetazolamide, loop diuretics and thiazide diuretics. Vaccines: high dose corticosteroids can impair immune response to vaccines - avoid concomitant use with live vaccines.

Purification Methods

The acetate recrystallises from Me2CO/Et2O or aqueous Me2CO as hygroscopic monoclinic crystals. UV has max at 242 nm (A1cm 1% 390) in MeOH. Its solubility at 25o is: H2O (0.001%), EtOH (0.45%), MeOH (0.04%), Me2CO (1.1%), CHCl3 (0.5%), Et2O (0.15%), and it is very soluble in Me2NCHO. [Wendler et al. J Am Chem Soc 74 3630 1952; Antonucci et al. J Org Chem 18 7081 1953, Beilstein 8 IV 3424.]

Check Digit Verification of cas no

The CAS Registry Mumber 50-03-3 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 0 respectively; the second part has 2 digits, 0 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 50-03:
(4*5)+(3*0)+(2*0)+(1*3)=23
23 % 10 = 3
So 50-03-3 is a valid CAS Registry Number.
InChI:InChI=1/C23H32O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h10,16-18,20,26,28H,4-9,11-12H2,1-3H3/t16?,17?,18-,20?,21-,22-,23-/m0/s1

50-03-3 Well-known Company Product Price

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  • Detail
  • TCI America

  • (H0184)  Hydrocortisone Acetate  >98.0%(HPLC)

  • 50-03-3

  • 1g

  • 190.00CNY

  • Detail
  • TCI America

  • (H0184)  Hydrocortisone Acetate  >98.0%(HPLC)

  • 50-03-3

  • 5g

  • 690.00CNY

  • Detail
  • Alfa Aesar

  • (A18089)  Hydrocortisone acetate, 97+%   

  • 50-03-3

  • 1g

  • 210.0CNY

  • Detail
  • Alfa Aesar

  • (A18089)  Hydrocortisone acetate, 97+%   

  • 50-03-3

  • 5g

  • 814.0CNY

  • Detail

50-03-3SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name cortisol 21-acetate

1.2 Other means of identification

Product number -
Other names Hydrocortisone acetate

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:50-03-3 SDS

50-03-3Synthetic route

HYDROCORTISONE
50-23-7

HYDROCORTISONE

acetic anhydride
108-24-7

acetic anhydride

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
With pyridine at 20℃;100%
With pyridine at 0 - 25℃; for 24h;99%
With pyridine at 0 - 20℃;91%
HYDROCORTISONE
50-23-7

HYDROCORTISONE

acetic acid methyl ester
79-20-9

acetic acid methyl ester

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
With Candida antarctica lipase B In ethyl acetate at 55℃; regioselective reaction;92%
Δ6-hydrocortisone-21-acetate
21940-45-4

Δ6-hydrocortisone-21-acetate

A

hydrocortisone acetate
50-03-3

hydrocortisone acetate

B

11β,17α-dihydroxy-21-acetoxy-5α/5β-pregnan-3-one

11β,17α-dihydroxy-21-acetoxy-5α/5β-pregnan-3-one

Conditions
ConditionsYield
With hydrogen; Pd/SrCO3 In ethyl acetate for 0.333333h; atmospheric pressure;A 42%
B 19%
Ketene
463-51-4

Ketene

HYDROCORTISONE
50-23-7

HYDROCORTISONE

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
With acetone
21-acetoxy-11β-hydroxy-pregna-4,17(20)c-dien-3-one
31085-34-4

21-acetoxy-11β-hydroxy-pregna-4,17(20)c-dien-3-one

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
With osmium(VIII) oxide; [bis(acetoxy)iodo]benzene
With osmium(VIII) oxide; triethylamine N-oxide; dihydrogen peroxide
4β-chloro-17-hydroxy-5β-pregnane-3,11,20-trione
114160-28-0

4β-chloro-17-hydroxy-5β-pregnane-3,11,20-trione

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
ueber mehrere Stufen;
21-acetoxy-11β-hydroxy-pregna-4,17(20)t-dien-3-one
119180-68-6

21-acetoxy-11β-hydroxy-pregna-4,17(20)t-dien-3-one

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
With osmium(VIII) oxide; [bis(acetoxy)iodo]benzene
With osmium(VIII) oxide; triethylamine N-oxide; dihydrogen peroxide
RU 18760
64313-94-6

RU 18760

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
With bromine dann mit Semicarbazid und anschliessend mit Brenztraubensaeure;
vinyl acetate
108-05-4

vinyl acetate

HYDROCORTISONE
50-23-7

HYDROCORTISONE

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
With Candida antarctica lipase B In tetrahydrofuran at 45℃; for 4h; Yield given;
22-acetoxy-11β-hydroxy-3-oxo-23,24-dinor-5β-chol-17(20)ξ-ene-21-nitrile
102213-14-9

22-acetoxy-11β-hydroxy-3-oxo-23,24-dinor-5β-chol-17(20)ξ-ene-21-nitrile

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: OsO4
2: bromine / dann mit Semicarbazid und anschliessend mit Brenztraubensaeure
View Scheme
3α,11α,17-trihydroxy-5β-pregnan-20-one
603-96-3

3α,11α,17-trihydroxy-5β-pregnan-20-one

A

hydrocortisone acetate
50-03-3

hydrocortisone acetate

B

CrO3

CrO3

Conditions
ConditionsYield
Multi-step reaction with 3 steps
2: CrO3; pyridine
3: ueber mehrere Stufen
View Scheme
3α,17-dihydroxy-5β-pregnane-11,20-dione
641-78-1

3α,17-dihydroxy-5β-pregnane-11,20-dione

A

hydrocortisone acetate
50-03-3

hydrocortisone acetate

B

CrO3

CrO3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tert-butyl hypochlorite; water; tert-butyl alcohol; HCl
2: ueber mehrere Stufen
View Scheme
4β-chloro-11α,17-dihydroxy-5β-pregnane-3,20-dione

4β-chloro-11α,17-dihydroxy-5β-pregnane-3,20-dione

A

hydrocortisone acetate
50-03-3

hydrocortisone acetate

B

CrO3

CrO3

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: CrO3; pyridine
2: ueber mehrere Stufen
View Scheme
20,20-ethanediyldioxy-3α,17-dihydroxy-5β-pregnan-11-one
116105-53-4

20,20-ethanediyldioxy-3α,17-dihydroxy-5β-pregnan-11-one

A

hydrocortisone acetate
50-03-3

hydrocortisone acetate

B

CrO3

CrO3

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: LiAlH4 / folgenden mit wss.HCl
3: CrO3; pyridine
4: ueber mehrere Stufen
View Scheme
21-acetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione
50733-54-5

21-acetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione

chromium(III) chloride
10025-73-7

chromium(III) chloride

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
With acetic acid In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone
chromium chloride hexahydrate

chromium chloride hexahydrate

21-acetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione
50733-54-5

21-acetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
With zinc In methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone
21-acetoxy-9-chloro-11β,17-dihydroxy-pregn-4-ene-3,20-dione
29042-01-1

21-acetoxy-9-chloro-11β,17-dihydroxy-pregn-4-ene-3,20-dione

hydrocortisone acetate
50-03-3

hydrocortisone acetate

9α-bromohydrocortisone acetate

9α-bromohydrocortisone acetate

mercaptoacetic acid
68-11-1

mercaptoacetic acid

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
In N,N-dimethyl-formamide
In N,N-dimethyl-formamide
C25H38N6O6

C25H38N6O6

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
Stage #1: C25H38N6O6 With hydrogenchloride In chloroform; water at 25 - 30℃; for 0.5h;
Stage #2: With sodium nitrite In chloroform; water at 5 - 10℃; for 2h;
18.1 g
C23H36N6O5

C23H36N6O5

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: sodium acetate; acetic acid / acetone / 5 h / Reflux
2.1: hydrogenchloride / water; chloroform / 0.5 h / 25 - 30 °C
2.2: 2 h / 5 - 10 °C
View Scheme
C25H38N6O6

C25H38N6O6

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
Stage #1: C25H38N6O6 With hydrogenchloride In chloroform; water at 25 - 30℃; for 0.5h;
Stage #2: With sodium nitrite In chloroform; water at 5 - 10℃; for 2h;
anecortave
7753-60-8

anecortave

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
With rhodium chloride; water In methanol at 20 - 65℃; for 4h; Autoclave;85 g
Multi-step reaction with 2 steps
1: water; tetrafluoroboric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / acetone / -5 °C
2: mercaptoacetic acid; zinc; chromium(III) chloride hexahydrate / dimethyl sulfoxide; 2-methyltetrahydrofuran / -5 °C / Inert atmosphere
View Scheme
androst-4,9(11)-dien-3,17-dione
1035-69-4

androst-4,9(11)-dien-3,17-dione

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: potassium tert-butylate / tetrahydrofuran / 8 h / 20 - 40 °C
2: dihydrogen peroxide / dichloromethane / 1.5 h / 20 - 40 °C
3: water; rhodium chloride / methanol / 4 h / 20 - 65 °C / Autoclave
View Scheme
21-acetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione
50733-54-5

21-acetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
With hydrogenchloride; chromium chloride; mercaptoacetic acid In tetrahydrofuran; water; N,N-dimethyl-formamide at 10 - 60℃; for 2.5h; Inert atmosphere;
With chromium(III) chloride hexahydrate; mercaptoacetic acid; zinc In 2-methyltetrahydrofuran; dimethyl sulfoxide at -5℃; Solvent; Temperature; Inert atmosphere;45.5 g
21-chloro-11,17-dihydroxy-pregn-4-ene-3,20-dione
65208-85-7

21-chloro-11,17-dihydroxy-pregn-4-ene-3,20-dione

potassium acetate
127-08-2

potassium acetate

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
In N,N-dimethyl-formamide at 80℃;0.94 g
9-bromo-21-chloro-11β,17-dihydroxy-pregn-4-ene-3,20-dione
110529-68-5

9-bromo-21-chloro-11β,17-dihydroxy-pregn-4-ene-3,20-dione

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: hydrogenchloride; chromium chloride; zinc / N,N-dimethyl-formamide; water / 0 - 15 °C / Inert atmosphere
2: N,N-dimethyl-formamide / 80 °C
View Scheme
21-chloro-17-hydroxy-pregna-4,9(11)-diene-3,20-dione
75868-48-3

21-chloro-17-hydroxy-pregna-4,9(11)-diene-3,20-dione

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: perchloric acid; N-Bromosuccinimide / acetone / 5 - 20 °C
2: hydrogenchloride; chromium chloride; zinc / N,N-dimethyl-formamide; water / 0 - 15 °C / Inert atmosphere
3: N,N-dimethyl-formamide / 80 °C
View Scheme
Cortisone acetate
50-04-4

Cortisone acetate

hydrocortisone acetate
50-03-3

hydrocortisone acetate

Conditions
ConditionsYield
With 9-bora-bicyclo[3.3.1]nonane In tetrahydrofuran at 20℃; for 6h; Time;14.6 g
hydrocortisone acetate
50-03-3

hydrocortisone acetate

anecortave
7753-60-8

anecortave

Conditions
ConditionsYield
With pyridine; methanesulfonyl chloride In N,N-dimethyl-formamide at 50 - 82℃; for 2h;95.85%
With N,N'-Thionyldiimidazole In tetrahydrofuran for 0.5h; Ambient temperature;40%
With pyridine; methanesulfonyl chloride In N,N-dimethyl-formamide
hydrocortisone acetate
50-03-3

hydrocortisone acetate

HYDROCORTISONE
50-23-7

HYDROCORTISONE

Conditions
ConditionsYield
With potassium carbonate In methanol for 1h;95%
With sodium methylate In methanol at 20℃; for 0.5h;94.82%
With water; sodium hydroxide In tetrahydrofuran at 20℃; for 3h;91.3%
hydrocortisone acetate
50-03-3

hydrocortisone acetate

2-((4aS,4bR,10aR,10bS,11S,12aS)-11-hydroxy-10a,12a-dimethyl-8-oxo-4a,4b,5,6,8,9,10,10a,10b,11,12,12a-dodecahydro-4H-naphtho[2,1-f]chromen-2-yl)-2-oxoethyl acetate

2-((4aS,4bR,10aR,10bS,11S,12aS)-11-hydroxy-10a,12a-dimethyl-8-oxo-4a,4b,5,6,8,9,10,10a,10b,11,12,12a-dodecahydro-4H-naphtho[2,1-f]chromen-2-yl)-2-oxoethyl acetate

Conditions
ConditionsYield
With 1,1,1,3',3',3'-hexafluoro-propanol; 1,1'-(phenyl-λ3-iodanediyl)bis(2-methoxypyridin-1-ium)trifluoromethanesulfonate In 1,2-dichloro-ethane at 60℃; Molecular sieve; Inert atmosphere;82%

50-03-3Relevant articles and documents

Dehalogenation methodof 9-halogenated steroid compound and application

-

Paragraph 0164-0166, (2021/01/11)

The invention provides a dehalogenation method of a 9-halogenated steroid compound and application, and relates to the technical field of chemical synthesis. The dehalogenation method of the 9-halogenated steroid compound comprises the following steps: reacting a compound I with a hydrogen donor and an azo radical initiator to obtain a 9-dehalogenated product compound II of the 9-halogenated steroid compound. According to the dehalogenation method of the 9-halogenated steroid compound, a hydrogen donor adopts one or a combination of more of hypophosphorous acid and hypophosphite, formic acid and formate, organic silicon hydride, hydrazine compounds or cyclohexene, and an initiator adopts an azo free radical initiator. Reagents such as chromium, divalent chromium salt, trivalent chromium salt or tributyltin hydride which are high in toxicity and cause serious pollution to the environment are not used in the reaction, the method is green and environmentally friendly, the synthesis process is simple, convenient and easy to implement, and the production applicability is improved.

9α-dehalogenation process

-

, (2008/06/13)

The present invention involves improved processes for the dehalogenation of 9α-halosteroids (I) STR1 to produce the corresponding 11β-hydroxy steroids (II) STR2 which are known to be useful as pharmaceutical, where the improvements comprise (1) adding the 9α-halo steroid (I) to the chromium and (2) using catalytic amounts of chromium in the presence of a means of converting chromium (II) to chromium (III).

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