16alpha-Hydroxyprednisolone
[CAS# 13951-70-7]

Identification

• Classification: API >> Hormone and endocrine-regulating drugs >> Adrenal corticosteroids
• Name: 16alpha-Hydroxyprednisolone
• Synonyms: 11a,16b,17,21-Tetrahydroxy-pregna-1,4-diene-3,20-dione
• Molecular Formula: C₂₁H₂₈O₆
• Molecular Weight: 376.45
• CAS Registry Number: 13951-70-7
• EC Number: 237-731-1
• SMILES: C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1C[C@H]([C@@]2(C(=O)CO)O)O)CCC4=CC(=O)C=C[C@]34C)O

Properties

• Density: 1.4±0.1 g/cm³, Calc.^*
• Index of Refraction: 1.630, Calc.^*
• Boiling Point: 591.5±50.0 °C (760 mmHg), Calc.^*
• Flash Point: 325.6±26.6 °C, Calc.^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software.

Safety Data

• Hazard Symbols: GHS08 Danger
• Risk Statements: H360-H361-H362-H373
• Safety Statements: P203-P260-P263-P264-P270-P280-P318-P319-P405-P501

Hazard Classification

Hazard	Class	Category Code	Hazard Statement
Reproductive toxicity	Repr.	2	H361
Reproductive toxicity	Repr.	1A	H360
Reproductive toxicity	Lact.	-	H362
Specific target organ toxicity - repeated exposure	STOT RE	2	H373
Skin sensitization	Skin Sens.	1	H317
Specific target organ toxicity - repeated exposure	STOT RE	1	H372

Discovery and Applications

16alpha-Hydroxyprednisolone is a steroid compound that belongs to the class of glucocorticoids, which are widely used for their anti-inflammatory and immunosuppressive properties. It is a metabolite of prednisolone, a synthetic glucocorticoid commonly prescribed to treat conditions such as arthritis, asthma, and autoimmune diseases. The discovery of 16alpha-hydroxyprednisolone emerged from the need to understand and refine the pharmacological effects of prednisolone and other corticosteroids.

The compound was first identified as part of the metabolic breakdown process of prednisolone in the human body. Prednisolone itself is a derivative of cortisol, a naturally occurring steroid hormone produced by the adrenal glands. When prednisolone is administered, it is metabolized by the liver, and one of the key metabolic products is 16alpha-hydroxyprednisolone. The hydroxylation at the 16th position of the prednisolone molecule differentiates it from other metabolites and gives it unique properties that influence its pharmacological activity.

16alpha-Hydroxyprednisolone is of particular interest because it retains many of the anti-inflammatory effects of prednisolone but with a different pharmacokinetic and pharmacodynamic profile. Studies have suggested that 16alpha-hydroxyprednisolone has a lower mineralocorticoid activity compared to prednisolone, which can reduce some of the side effects commonly associated with corticosteroid therapy, such as fluid retention and hypertension. This property makes 16alpha-hydroxyprednisolone a potential candidate for use in the treatment of inflammatory diseases where these side effects need to be minimized.

In addition to its therapeutic applications, 16alpha-hydroxyprednisolone has been studied for its role in the development of synthetic corticosteroids. Researchers have explored the compound's structure and activity to better understand how modifications to the steroid molecule can lead to drugs with improved efficacy and fewer adverse effects. This research has contributed to the development of newer corticosteroid medications that more effectively target inflammation while minimizing unwanted systemic effects.

16alpha-Hydroxyprednisolone, as a metabolite, also provides insights into the body’s natural handling of corticosteroids, offering valuable information for drug development and therapeutic optimization. Its role in steroid metabolism and its potential for use in specific therapeutic contexts make it an important substance in the field of endocrinology and pharmacology.

In conclusion, 16alpha-hydroxyprednisolone is an important metabolite of prednisolone with unique properties that contribute to its potential therapeutic applications, particularly in reducing inflammation and minimizing side effects associated with glucocorticoid therapy. Ongoing research into its pharmacological effects and its role in corticosteroid metabolism may lead to further refinements in the use of glucocorticoids for treating a variety of inflammatory and autoimmune conditions.

References

2013. Metabolic Pathways of Inhaled Glucocorticoids by the CYP3A Enzymes. Drug Metabolism and Disposition: The Biological Fate of Chemicals, 41(2).
DOI: 10.1124/dmd.112.046318

2003. Budesonide. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-02-0132

2003. Desonide. Pharmaceutical Substances.
URL: https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-04-0034