Hydrocortisone acetate

Hydrocortisone acetate Basic information
Adrenocorticotropic hormone drugs Indications Contraindications Adverse Reactions Precautions Chemical Property Uses Production methods
Product Name:Hydrocortisone acetate
Synonyms:(11beta)-21-(Acetoxy)-11,17,21-trihydroxypregna-1,4-diene-3,20-dione;11,17-Dihydroxy-3,20-dioxopregn-4-en-21-yl acetate;11-beta,17-alpha-dihydroxy-21-acetoxypregesterone;11beta17alpha-Dihydroxy-21-acetoxypregesterone;17-alpha-hydrocorticosterone21-acetate;17alpha-Hydrocorticosterone-21-acetate;17-dihydroxy-20-dion(11-beta)-pregn-4-ene-21-(acetoxy)-11;17-dihydroxy-20-dion(11beta)-pregn-4-ene-21-(acetyloxy)-11
CAS:50-03-3
MF:C23H32O6
MW:404.5
EINECS:200-004-4
Product Categories:Adrenal cortical hormone drugs;API;Intermediates & Fine Chemicals;Pharmaceuticals;Biochemistry;Hydroxyketosteroids;Steroids;Hormone Drugs;Steroid and Hormone;Veterinaries;50-03-3
Mol File:50-03-3.mol
Hydrocortisone acetate Structure
Hydrocortisone acetate Chemical Properties
Melting point 223 °C (dec.)(lit.)
Boiling point 446.1°C (rough estimate)
alpha D25 +166° (c = 0.4 in dioxane); D25 +150.7° (c = 0.5 in acetone)
density d420 1.289
refractive index 1.4593 (estimate)
Fp 223°C
storage temp. 0-6°C
solubility Practically insoluble in water, slightly soluble in anhydrous ethanol and in methylene chloride
pka12.42±0.70(Predicted)
form Solid
color White to Off-White
Water Solubility Insoluble in water.
Decomposition 223 ºC
Merck 14,4787
BRN 2066841
Stability:Stable, but may be light or moisture sensitive. Incompatible with strong oxidizing agents.
LogP2.190
CAS DataBase Reference50-03-3(CAS DataBase Reference)
NIST Chemistry ReferenceHydrocortisone acetate(50-03-3)
Safety Information
Hazard Codes Xn,T
Risk Statements 63-10-45
Safety Statements 36/37-45-53
WGK Germany 3
RTECS GM8960000
HS Code 29372100
ToxicityLD50 intraperitoneal in mouse: 2300mg/kg
MSDS Information
ProviderLanguage
SigmaAldrich English
ALFA English
Hydrocortisone acetate Usage And Synthesis
Adrenocorticotropic hormone drugsHydrocortisone 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.
IndicationsFor 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.

Contraindications1. 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 chemicalbook 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 PropertyWhite 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.
UsesCorticosteroid drugs, have anti-inflammatory, anti-allergic, anti-toxins, anti-shock effect.
Production methodsHydrocortisone and acetic anhydride in pyridine esterification.
Chemical Propertieswhite powder
UsesHydrocortisone 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).
UsesGlucocorticoid
DefinitionChEBI: Cortisol 21-acetate is a tertiary alpha-hydroxy ketone and a cortisol ester.
Brand nameCortef Acetate (Pharmacia & Upjohn); Cortifoam (Schwarz Pharma); Cortril (Pfizer); Dricort (Ingram); Hydrocortone (Merck).
Clinical UseCorticosteroid:

Local inflammation of joints and soft tissue

Drug interactionsPotentially 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.
MetabolismHydrocortisone is metabolised in the liver and most body tissues to hydrogenated and degraded forms such as tetrahydrocortisone and tetrahydrocortisol. These are excreted in the urine, mainly conjugated as glucuronides, with a very small proportion of unchanged hydrocortisone.
Purification MethodsThe 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.]
Hydrocortisone acetate Preparation Products And Raw materials
Raw materialsPyridine-->Hydrocortisone-->Saponin
Preparation ProductsPregn-4-ene-3,20-dione, 2,11,17,21-tetrahydroxy-, (2α,11β)- (9CI)-->6-Dehydrocortisol Acetate
Hydrocortisone sodium succinate Hydrocortisone-17-butyrate 4-PREGNENE-11BETA,17ALPHA,21-TRIOL-3,20-DIONE 21-CAPRYLATE Hydrocortisone hemisuccinate hydrate Hydrocortisone 21-hemisuccinate 4-PREGNEN-6-BETA, 11-BETA, 17,21-TETROL-3,20-DIONE 21-ACETATE 4-PREGNEN-6-BETA, 11-BETA, 17,21-TETROL-3,20-DIONE 21-HEMISUCCINATE 4-PREGNEN-6-BETA, 11-BETA, 17,21-TETROL-3,20-DIONE 6,21-DIACETATE Acetoxy 11BETA,17,21-TRIHYDROXY-PREGN-4-ENE-3,20-DIONE METHYL ESTER 3-[(NITROOXY) METHYL]-BENZOIC ACID HYDROCORTISONE CYPIONATE (200 MG) ACETATE Glatiramer acetate Hydrocortisone Butyrate Propionate Hydrocortisone 4-PREGNEN-11-BETA, 17,21-TRIOL-3,20-DIONE 21-HEMISUCCINATE : BSA 4-PREGNEN-6-ALPHA, 11-BETA, 17,21-TETROL-3,20-DIONE ACETATE 11-BETA,17,21-TRIHYDROXYPREGN-4-ENE-3,20-DIONE 21-VALERATE

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