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hydrocortisone acetate
Hydrocortisone acetate is a corticosteroid ester commonly used in pharmaceuticals, characterized by moderate lipophilicity and low water solubility.
General Material Description
Hydrocortisone acetate is a synthetic corticosteroid ester notable for its pharmacological applications. Chemically defined as 21-(acetyl oxy)-11,17-pregn-4-ene-3,20-dione, it possesses the molecular formula C23H32O6. This compound is referred to by numerous synonyms including cortisol acetate and hydrocortisone 21-acetate, reflecting its structural relation to endogenous glucocorticoids. It typically appears as a solid substance with limited water solubility, showing characteristic corticosteroid properties such as anti-inflammatory potential. Hydrocortisone acetate is derived through acetylation of hydrocortisone, enhancing its chemical stability and modifying its pharmacokinetic profile. For detailed chemical data, refer to its ChEBI entry. The compound's primary sourcing involves pharmaceutical synthesis for therapeutic formulations.
Occurrence, Applicability & Potential Uses
Hydrocortisone acetate is primarily utilized in pharmaceutical industries as a corticosteroid agent with applications in anti-inflammatory and immunosuppressive medications. Though the compound is not naturally occurring, it is structurally related to endogenous cortisol found in mammals. Its ester form modifies absorption and distribution characteristics, making it suitable for topical, injectable, or ophthalmic preparations. Regulatory guidelines such as REACH (EU) govern its manufacturing and use within the European market to ensure compliance with safety and environmental standards. Its use is limited to pharmaceutical and chemical synthesis purposes, with no approved applications in fragrances or flavors.
Physico-Chemical Properties Summary
Hydrocortisone acetate exhibits moderate lipophilicity with a logP value of approximately 2.19, reflecting a balance between aqueous and lipid solubility. Its water solubility is low, with experimental values around 14 mg/L at 25°C, which informs formulation challenges such as bioavailability and delivery method choice. The molecular weight is 404.5 g/mol. The compound's flash point is high, measured at 385°F (approximately 196°C), indicating substantial thermal stability under typical handling conditions. These physico-chemical traits influence its formulation in pharmaceutical products, requiring consideration in solvent selection and dosage form design.
FAQ
What is hydrocortisone acetate and what are its main characteristics?
Hydrocortisone acetate is a synthetic corticosteroid ester derived from hydrocortisone. It is chemically designated as 21-(acetyl oxy)-11,17-pregn-4-ene-3,20-dione with the molecular formula C23H32O6. The compound appears as a solid with low water solubility and moderate lipophilicity. It has multiple synonyms, including cortisol acetate and hydrocortisone 21-acetate. Hydrocortisone acetate is widely used in pharmaceuticals due to its modified pharmacokinetics compared to free hydrocortisone, making it suited for topical and injectable formulations.
How is hydrocortisone acetate produced and what are its typical applications?
Hydrocortisone acetate is produced by acetylating hydrocortisone, enhancing its chemical stability and altering its absorption properties. This synthetic process allows incorporation into various pharmaceutical preparations, including creams, ointments, and injectables. Its applications are predominantly pharmaceutical, serving to deliver corticosteroid effects such as anti-inflammatory activity. It is not used in perfume or flavor industries. Compliance with regulations such as REACH (EU) ensures proper handling and quality control during its production and application.
What safety and regulatory information is associated with hydrocortisone acetate?
Hydrocortisone acetate is subject to comprehensive regulatory standards including REACH in the European Union. Safety data indicate no classification for hazards under OSHA regulations (29 CFR 1910). Toxicological data include intraperitoneal LD50 of 2300 mg/kg in mice and subcutaneous LD50 exceeding 45,000 µg/kg in mice, suggesting a relatively low acute toxicity. It is not approved for use as a fragrance or flavor ingredient. Manufacturers and users follow specific safety data sheets and regulatory guidelines to ensure appropriate handling in pharmaceutical applications.
US / EU / FDA / JECFA / FEMA / Scholar / Patents
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Literature & References
| [2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate | |
| NIST Chemistry WebBook: | Search Inchi |
| Canada Domestic Sub. List: | 50-03-3 |
| Pubchem (cid): | 5744 |
| Pubchem (sid): | 134970850 |
Other Information
| (IUPAC): | Atomic Weights of the Elements 2011 (pdf) |
| Videos: | The Periodic Table of Videos |
| tgsc: | Atomic Weights use for this web site |
| (IUPAC): | Periodic Table of the Elements |
| CHEBI: | View |
| CHEMBL: | View |
| KEGG (GenomeNet): | C02821 |
| HMDB (The Human Metabolome Database): | Search |
| ChemSpider: | View |
| Wikipedia: | View |
General Material Information
| Preferred name | hydrocortisone acetate |
| Trivial Name | Hydrocortisone acetate |
| Short Description | 21-(acetyl oxy)-11,17-pregn-4-ene-3,20-dione |
| Formula | C23 H32 O6 |
| CAS Number | 50-03-3 |
| Deleted CAS Number | 42016-02-4 |
| ECHA Number | 200-004-4 |
| FDA UNII | 3X7931PO74 |
| Nikkaji Number | J4.096G |
| Beilstein Number | 2066841 |
| MDL | MFCD00037714 |
| Bio Activity Summary | External link |
| NMR Predictor | External link |
| Synonyms |
|
Suppliers
| American International Chemical, LLC. | BOC Sciences |
| Glentham Life Sciences | Penta International |
| Sigma-Aldrich: Sigma | Penta International Corporation |
PhysChem Properties
| Material listed in food chemical codex | No |
| Molecular weight | 404.50323486328 |
| Flash Point TCC Value | 196.2 °C TCC |
| logP (o/w) | 2.19 |
| Solubility | |
| water, 38.71 mg/L @ 25 °C (est) | Yes |
| water, 14.1 mg/L @ 25 °C (exp) | Yes |
Safety Information
Safety information
| Preferred SDS: View | |
| Hazards identification | |
| Classification of the substance or mixture | |
| GHS Classification in accordance with 29 CFR 1910 (OSHA HCS) | |
| None found. | |
| GHS Label elements, including precautionary statements | |
| Pictogram | |
| Hazard statement(s) | |
| None found. | |
| Precautionary statement(s) | |
| None found. | |
| Oral/Parenteral Toxicity: | |
| intraperitoneal-mouse LD50 2300 mg/kg Compilation of LD50 Values of New Drugs. | |
| Dermal Toxicity: | |
| subcutaneous-mouse LD50 45050 ug/kg National Cancer Institute Screening Program Data Summary, Developmental Therapeutics Program. Vol. JAN1986 subcutaneous-rat LDLo 250 mg/kg Arzneimittel-Forschung. Drug Research. Vol. 27, Pg. 2102, 1977. | |
| Inhalation Toxicity: | |
| Not determined | |
Safety in use information
| Category: | |||
| pharmaceuticals / chemical synthisis | |||
| Recommendation for hydrocortisone acetate usage levels up to: | |||
| not for fragrance use. | |||
| Recommendation for hydrocortisone acetate flavor usage levels up to: | |||
| not for flavor use. | |||
Safety references
| EPI System: View |
| ClinicalTrials.gov:search |
| Daily Med:search |
| AIDS Citations:Search |
| Cancer Citations:Search |
| Toxicology Citations:Search |
| EPA ACToR:Toxicology Data |
| EPA Substance Registry Services (SRS):Registry |
| Laboratory Chemical Safety Summary :5744 |
| National Institute of Allergy and Infectious Diseases:Data |
| WGK Germany:3 |
| [2-[(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,6,7,8,9,11,12,14,15,16-decahydro-1H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate |
| Chemidplus:0000050033 |
| RTECS:GM8960000 for cas# 50-03-3 |