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Details

Stereochemistry ABSOLUTE
Molecular Formula C29H42O6
Molecular Weight 486.6402
Optical Activity UNSPECIFIED
Defined Stereocenters 7 / 7
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of HYDROCORTISONE CYPIONATE

SMILES

[H][C@@]12CC[C@](O)(C(=O)COC(=O)CCC3CCCC3)[C@@]1(C)C[C@H](O)[C@@]4([H])[C@@]2([H])CCC5=CC(=O)CC[C@]45C

InChI

InChIKey=DLVOSEUFIRPIRM-KAQKJVHQSA-N
InChI=1S/C29H42O6/c1-27-13-11-20(30)15-19(27)8-9-21-22-12-14-29(34,28(22,2)16-23(31)26(21)27)24(32)17-35-25(33)10-7-18-5-3-4-6-18/h15,18,21-23,26,31,34H,3-14,16-17H2,1-2H3/t21-,22-,23-,26+,27-,28-,29-/m0/s1

HIDE SMILES / InChI

Molecular Formula C29H42O6
Molecular Weight 486.6402
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 7 / 7
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Hydrocortisone is the main glucocorticoid secreted by the adrenal cortex. Its synthetic counterpart is used, either as an injection or topically, in the treatment of inflammation, allergy, collagen diseases, asthma, adrenocortical deficiency, shock, and some neoplastic conditions. Topical hydrocortisone is used for its anti-inflammatory or immunosuppressive properties to treat inflammation due to corticosteroid-responsive dermatoses. Hydrocortisone binds to the cytosolic glucocorticoid receptor. After binding the receptor the newly formed receptor-ligand complex translocates itself into the cell nucleus, where it binds to many glucocorticoid response elements (GRE) in the promoter region of the target genes. The DNA bound receptor then interacts with basic transcription factors, causing the increase in expression of specific target genes. The anti-inflammatory actions of corticosteroids are thought to involve lipocortins, phospholipase A2 inhibitory proteins which, through inhibition arachidonic acid, control the biosynthesis of prostaglandins and leukotrienes. Specifically glucocorticoids induce lipocortin-1 (annexin-1) synthesis, which then binds to cell membranes preventing the phospholipase A2 from coming into contact with its substrate arachidonic acid. This leads to diminished eicosanoid production. The cyclooxygenase (both COX-1 and COX-2) expression is also suppressed, potentiating the effect. In other words, the two main products in inflammation Prostaglandins and Leukotrienes are inhibited by the action of Glucocorticoids. Glucocorticoids also stimulate the lipocortin-1 escaping to the extracellular space, where it binds to the leukocyte membrane receptors and inhibits various inflammatory events: epithelial adhesion, emigration, chemotaxis, phagocytosis, respiratory burst and the release of various inflammatory mediators (lysosomal enzymes, cytokines, tissue plasminogen activator, chemokines etc.) from neutrophils, macrophages and mastocytes. Additionally the immune system is suppressed by corticosteroids due to a decrease in the function of the lymphatic system, a reduction in immunoglobulin and complement concentrations, the precipitation of lymphocytopenia, and interference with antigen-antibody binding. For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Also used to treat endocrine (hormonal) disorders (adrenal insufficiency, Addisons disease). Hydrocortisone is also used to treat many immune and allergic disorders, such as arthritis, lupus, severe psoriasis, severe asthma, ulcerative colitis, and Crohn's disease.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
50.0 nM [IC50]
0.1 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Cortef
Primary
Cortef
Palliative
Cortef
Primary
Cortef

Cmax

ValueDoseCo-administeredAnalytePopulation
258 ng/mL
20 mg single, oral
HYDROCORTISONE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1162 ng × h/mL
20 mg single, oral
HYDROCORTISONE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
1.82 h
20 mg single, oral
HYDROCORTISONE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
9.9%
HYDROCORTISONE plasma
Homo sapiens

Doses

AEs

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer



Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
The initial dosage of CORTEF (Hydrocortisone) Tablets may vary from 20 mg to 240 mg of hydrocortisone per day depending on the specific disease entity being treated.
Route of Administration: Oral
In Vitro Use Guide
Hydrocortisone concentration-dependently inhibited the current induced by 3 x 10(-5) M ACh with a half maximum inhibitory concentration (IC50) of 2.1 x 10(-4) M (in rats).
Substance Class Chemical
Record UNII
4XDY25L70B
Record Status Validated (UNII)
Record Version