Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C23H32O6 |
Molecular Weight | 404.4966 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(=O)OCC(=O)[C@@]1(O)CC[C@H]2[C@@H]3CCC4=CC(=O)CC[C@]4(C)[C@H]3[C@@H](O)C[C@]12C
InChI
InChIKey=ALEXXDVDDISNDU-JZYPGELDSA-N
InChI=1S/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
Molecular Formula | C23H32O6 |
Molecular Weight | 404.4966 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 7 / 7 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionSources: http://www.drugbank.ca/drugs/DB00741Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/008697s032_33lbl.pdf
Sources: http://www.drugbank.ca/drugs/DB00741
Curator's Comment: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/008697s032_33lbl.pdf
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/580108
Curator's Comment: shown in dogs
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2034 Sources: http://www.drugbank.ca/drugs/DB00741 |
|||
Target ID: CHEMBL2034 |
|||
Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10455320 |
50.0 nM [IC50] | ||
Target ID: P04083 Gene ID: 301.0 Gene Symbol: ANXA1 Target Organism: Homo sapiens (Human) Sources: http://www.drugbank.ca/drugs/DB00741 |
|||
Target ID: CHEMBL3070 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10669853 |
0.1 nM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Cortef Approved UseCORTEF Tablets are indicated in the following conditions.
1. Endocrine Disorders
Primary or secondary adrenocortical insufficiency (hydrocortisone or cortisone is the first choice; synthetic analogs may be used in conjunction with mineralocorticoids where applicable; in infancy mineralocorticoid supplementation is of particular importance)
Congenital adrenal hyperplasia
Non suppurative thyroiditis
Hypercalcemia associated with cancer
2. Rheumatic Disorders
As adjunctive therapy for short-term administration (to tide the patient over an acute episode or exacerbation) in:
Psoriatic arthritis
Rheumatoid arthritis, including juvenile rheumatoid arthritis (selected cases may require low-dose maintenance therapy)
Ankylosing spondylitis
Acute and subacute bursitis
Acute nonspecific tenosynovitis
Acute gouty arthritis
Post-traumatic osteoarthritis
Synovitis of osteoarthritis
Epicondylitis
3. Collagen Diseases
During an exacerbation or as maintenance therapy in selected cases of:
Systemic lupus erythematosus
Systemic dermatomyositis (polymyositis)
Acute rheumatic carditis
4. Dermatologic Diseases
Pemphigus
Bullous dermatitis herpetiformis
Severe erythema multiforme (Stevens-Johnson syndrome)
Exfoliative dermatitis
Mycosis fungoides
Severe psoriasis
Severe seborrheic dermatitis
5. Allergic States
Control of severe or incapacitating allergic conditions intractable to adequate trials of
conventional treatment:
Seasonal or perennial allergic rhinitis
Serum sickness
Bronchial asthma
Contact dermatitis
Atopic dermatitis
Drug hypersensitivity reactions
6. Ophthalmic Diseases
Severe acute and chronic allergic and inflammatory processes involving the eye and its
adnexa such as:
Allergic conjunctivitis
Keratitis
Allergic corneal marginal ulcers
Herpes zoster ophthalmicus
Iritis and iridocyclitis
Chorioretinitis
Anterior segment inflammation
Diffuse posterior uveitis and choroiditis
Optic neuritis
Sympathetic ophthalmia
7. Respiratory Diseases
Symptomatic sarcoidosis
Loeffler’s syndrome not manageable by other means
Berylliosis
Fulminating or disseminated pulmonary tuberculosis when used concurrently with appropriate antituberculous chemotherapy
Aspiration pneumonitis
8. Hematologic Disorders
Idiopathic thrombocytopenic purpura in adults
Secondary thrombocytopenia in adults
Acquired (autoimmune) hemolytic anemia
Erythroblastopenia (RBC anemia)
Congenital (erythroid) hypoplastic anemia
9. Neoplastic Diseases
For palliative management of:
Leukemias and lymphomas in adults
Acute leukemia of childhood
10. Edematous States
To induce a diuresis or remission of proteinuria in the nephrotic syndrome, without uremia, of the idiopathic type or that due to lupus erythematosus.
11. Gastrointestinal Diseases
To tide the patient over a critical period of the disease in:
Ulcerative colitis
Regional enteritis
12. Nervous System
Acute exacerbations of multiple sclerosis
13. Miscellaneous
Tuberculous meningitis with subarachnoid block or impending block when used concurrently with appropriate antituberculous chemotherapy
Trichinosis with neurologic or myocardial involvement Launch Date1952 |
|||
Primary | Cortef Approved UseCORTEF Tablets are indicated in the following conditions.
1. Endocrine Disorders
Primary or secondary adrenocortical insufficiency (hydrocortisone or cortisone is the first choice; synthetic analogs may be used in conjunction with mineralocorticoids where applicable; in infancy mineralocorticoid supplementation is of particular importance)
Congenital adrenal hyperplasia
Non suppurative thyroiditis
Hypercalcemia associated with cancer
2. Rheumatic Disorders
As adjunctive therapy for short-term administration (to tide the patient over an acute episode or exacerbation) in:
Psoriatic arthritis
Rheumatoid arthritis, including juvenile rheumatoid arthritis (selected cases may require low-dose maintenance therapy)
Ankylosing spondylitis
Acute and subacute bursitis
Acute nonspecific tenosynovitis
Acute gouty arthritis
Post-traumatic osteoarthritis
Synovitis of osteoarthritis
Epicondylitis
3. Collagen Diseases
During an exacerbation or as maintenance therapy in selected cases of:
Systemic lupus erythematosus
Systemic dermatomyositis (polymyositis)
Acute rheumatic carditis
4. Dermatologic Diseases
Pemphigus
Bullous dermatitis herpetiformis
Severe erythema multiforme (Stevens-Johnson syndrome)
Exfoliative dermatitis
Mycosis fungoides
Severe psoriasis
Severe seborrheic dermatitis
5. Allergic States
Control of severe or incapacitating allergic conditions intractable to adequate trials of
conventional treatment:
Seasonal or perennial allergic rhinitis
Serum sickness
Bronchial asthma
Contact dermatitis
Atopic dermatitis
Drug hypersensitivity reactions
6. Ophthalmic Diseases
Severe acute and chronic allergic and inflammatory processes involving the eye and its
adnexa such as:
Allergic conjunctivitis
Keratitis
Allergic corneal marginal ulcers
Herpes zoster ophthalmicus
Iritis and iridocyclitis
Chorioretinitis
Anterior segment inflammation
Diffuse posterior uveitis and choroiditis
Optic neuritis
Sympathetic ophthalmia
7. Respiratory Diseases
Symptomatic sarcoidosis
Loeffler’s syndrome not manageable by other means
Berylliosis
Fulminating or disseminated pulmonary tuberculosis when used concurrently with appropriate antituberculous chemotherapy
Aspiration pneumonitis
8. Hematologic Disorders
Idiopathic thrombocytopenic purpura in adults
Secondary thrombocytopenia in adults
Acquired (autoimmune) hemolytic anemia
Erythroblastopenia (RBC anemia)
Congenital (erythroid) hypoplastic anemia
9. Neoplastic Diseases
For palliative management of:
Leukemias and lymphomas in adults
Acute leukemia of childhood
10. Edematous States
To induce a diuresis or remission of proteinuria in the nephrotic syndrome, without uremia, of the idiopathic type or that due to lupus erythematosus.
11. Gastrointestinal Diseases
To tide the patient over a critical period of the disease in:
Ulcerative colitis
Regional enteritis
12. Nervous System
Acute exacerbations of multiple sclerosis
13. Miscellaneous
Tuberculous meningitis with subarachnoid block or impending block when used concurrently with appropriate antituberculous chemotherapy
Trichinosis with neurologic or myocardial involvement Launch Date1952 |
|||
Palliative | Cortef Approved UseCORTEF Tablets are indicated in the following conditions.
1. Endocrine Disorders
Primary or secondary adrenocortical insufficiency (hydrocortisone or cortisone is the first choice; synthetic analogs may be used in conjunction with mineralocorticoids where applicable; in infancy mineralocorticoid supplementation is of particular importance)
Congenital adrenal hyperplasia
Non suppurative thyroiditis
Hypercalcemia associated with cancer
2. Rheumatic Disorders
As adjunctive therapy for short-term administration (to tide the patient over an acute episode or exacerbation) in:
Psoriatic arthritis
Rheumatoid arthritis, including juvenile rheumatoid arthritis (selected cases may require low-dose maintenance therapy)
Ankylosing spondylitis
Acute and subacute bursitis
Acute nonspecific tenosynovitis
Acute gouty arthritis
Post-traumatic osteoarthritis
Synovitis of osteoarthritis
Epicondylitis
3. Collagen Diseases
During an exacerbation or as maintenance therapy in selected cases of:
Systemic lupus erythematosus
Systemic dermatomyositis (polymyositis)
Acute rheumatic carditis
4. Dermatologic Diseases
Pemphigus
Bullous dermatitis herpetiformis
Severe erythema multiforme (Stevens-Johnson syndrome)
Exfoliative dermatitis
Mycosis fungoides
Severe psoriasis
Severe seborrheic dermatitis
5. Allergic States
Control of severe or incapacitating allergic conditions intractable to adequate trials of
conventional treatment:
Seasonal or perennial allergic rhinitis
Serum sickness
Bronchial asthma
Contact dermatitis
Atopic dermatitis
Drug hypersensitivity reactions
6. Ophthalmic Diseases
Severe acute and chronic allergic and inflammatory processes involving the eye and its
adnexa such as:
Allergic conjunctivitis
Keratitis
Allergic corneal marginal ulcers
Herpes zoster ophthalmicus
Iritis and iridocyclitis
Chorioretinitis
Anterior segment inflammation
Diffuse posterior uveitis and choroiditis
Optic neuritis
Sympathetic ophthalmia
7. Respiratory Diseases
Symptomatic sarcoidosis
Loeffler’s syndrome not manageable by other means
Berylliosis
Fulminating or disseminated pulmonary tuberculosis when used concurrently with appropriate antituberculous chemotherapy
Aspiration pneumonitis
8. Hematologic Disorders
Idiopathic thrombocytopenic purpura in adults
Secondary thrombocytopenia in adults
Acquired (autoimmune) hemolytic anemia
Erythroblastopenia (RBC anemia)
Congenital (erythroid) hypoplastic anemia
9. Neoplastic Diseases
For palliative management of:
Leukemias and lymphomas in adults
Acute leukemia of childhood
10. Edematous States
To induce a diuresis or remission of proteinuria in the nephrotic syndrome, without uremia, of the idiopathic type or that due to lupus erythematosus.
11. Gastrointestinal Diseases
To tide the patient over a critical period of the disease in:
Ulcerative colitis
Regional enteritis
12. Nervous System
Acute exacerbations of multiple sclerosis
13. Miscellaneous
Tuberculous meningitis with subarachnoid block or impending block when used concurrently with appropriate antituberculous chemotherapy
Trichinosis with neurologic or myocardial involvement Launch Date1952 |
|||
Primary | Cortef Approved UseCORTEF Tablets are indicated in the following conditions.
1. Endocrine Disorders
Primary or secondary adrenocortical insufficiency (hydrocortisone or cortisone is the first choice; synthetic analogs may be used in conjunction with mineralocorticoids where applicable; in infancy mineralocorticoid supplementation is of particular importance)
Congenital adrenal hyperplasia
Non suppurative thyroiditis
Hypercalcemia associated with cancer
2. Rheumatic Disorders
As adjunctive therapy for short-term administration (to tide the patient over an acute episode or exacerbation) in:
Psoriatic arthritis
Rheumatoid arthritis, including juvenile rheumatoid arthritis (selected cases may require low-dose maintenance therapy)
Ankylosing spondylitis
Acute and subacute bursitis
Acute nonspecific tenosynovitis
Acute gouty arthritis
Post-traumatic osteoarthritis
Synovitis of osteoarthritis
Epicondylitis
3. Collagen Diseases
During an exacerbation or as maintenance therapy in selected cases of:
Systemic lupus erythematosus
Systemic dermatomyositis (polymyositis)
Acute rheumatic carditis
4. Dermatologic Diseases
Pemphigus
Bullous dermatitis herpetiformis
Severe erythema multiforme (Stevens-Johnson syndrome)
Exfoliative dermatitis
Mycosis fungoides
Severe psoriasis
Severe seborrheic dermatitis
5. Allergic States
Control of severe or incapacitating allergic conditions intractable to adequate trials of
conventional treatment:
Seasonal or perennial allergic rhinitis
Serum sickness
Bronchial asthma
Contact dermatitis
Atopic dermatitis
Drug hypersensitivity reactions
6. Ophthalmic Diseases
Severe acute and chronic allergic and inflammatory processes involving the eye and its
adnexa such as:
Allergic conjunctivitis
Keratitis
Allergic corneal marginal ulcers
Herpes zoster ophthalmicus
Iritis and iridocyclitis
Chorioretinitis
Anterior segment inflammation
Diffuse posterior uveitis and choroiditis
Optic neuritis
Sympathetic ophthalmia
7. Respiratory Diseases
Symptomatic sarcoidosis
Loeffler’s syndrome not manageable by other means
Berylliosis
Fulminating or disseminated pulmonary tuberculosis when used concurrently with appropriate antituberculous chemotherapy
Aspiration pneumonitis
8. Hematologic Disorders
Idiopathic thrombocytopenic purpura in adults
Secondary thrombocytopenia in adults
Acquired (autoimmune) hemolytic anemia
Erythroblastopenia (RBC anemia)
Congenital (erythroid) hypoplastic anemia
9. Neoplastic Diseases
For palliative management of:
Leukemias and lymphomas in adults
Acute leukemia of childhood
10. Edematous States
To induce a diuresis or remission of proteinuria in the nephrotic syndrome, without uremia, of the idiopathic type or that due to lupus erythematosus.
11. Gastrointestinal Diseases
To tide the patient over a critical period of the disease in:
Ulcerative colitis
Regional enteritis
12. Nervous System
Acute exacerbations of multiple sclerosis
13. Miscellaneous
Tuberculous meningitis with subarachnoid block or impending block when used concurrently with appropriate antituberculous chemotherapy
Trichinosis with neurologic or myocardial involvement Launch Date1952 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
305 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2050835 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCORTISONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1162 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2050835 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCORTISONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.82 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/2050835 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
HYDROCORTISONE plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/15979871/ Page: - |
no | |||
Sources: https://dmd.aspetjournals.org/content/30/9/1029.long Page: - |
yes [EC50 0.6 uM] | |||
Page: - |
yes [IC50 33.4 uM] | |||
Page: - |
yes [IC50 33.4 uM] | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/26387653/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15979871/ Page: - |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
major |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: - |
PubMed
Title | Date | PubMed |
---|---|---|
The stress hormone, cortisol, synergizes with HIV-1 gp-120 to induce apoptosis of normal human peripheral blood mononuclear cells. | 2000 Nov |
|
Modulation of P450 CYP3A4-dependent metabolism by P-glycoprotein: implications for P450 phenotyping. | 2001 Feb |
|
Glucocorticoids protect against apoptosis induced by serum deprivation, cyclic adenosine 3',5'-monophosphate and p53 activation in immortalized human granulosa cells: involvement of Bcl-2. | 2001 Feb |
|
Regulation of phosphate uptake in primary cultured rabbit renal proximal tubule cells by glucocorticoids: evidence for nongenomic as well as genomic mechanisms. | 2001 Feb |
|
Plasma adrenocorticotropin and cortisol concentrations during acute hypoxemia after a reversible period of adverse intrauterine conditions in the ovine fetus during late gestation. | 2001 Feb |
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PTH and PTH-related peptide enhance steroid secretion from human adrenocortical cells. | 2001 Feb |
|
Time course of 21-hydroxylase antibodies and long-term remission of subclinical autoimmune adrenalitis after corticosteroid therapy: case report. | 2001 Feb |
|
Aromatase p450 expression in a feminizing adrenal adenoma presenting as isosexual precocious puberty. | 2001 Feb |
|
Relationship functioning and home and work demands predict individual differences in diurnal cortisol patterns in women. | 2001 Feb |
|
Use of salivary biomarkers in biobehavioral research: cotton-based sample collection methods can interfere with salivary immunoassay results. | 2001 Feb |
|
Green fluorescent protein mutant as label in homogeneous assays for biomolecules. | 2001 Feb 1 |
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Net amino acid flux across the fetal liver and placenta during spontaneous ovine parturition. | 2001 Jan |
|
Effects of cortisol on chloride cells in the gill epithelium of Japanese eel, Anguilla japonica. | 2001 Jan |
|
Monohydroxylation and esterification as determinants of the effects of cis- and trans-9-octadecenoic acids on the permeation of hydrocortisone and 5-fluorouracil across hairless mouse skin in vitro. | 2001 Jan 16 |
|
Enzyme-mediated protection of the mineralocorticoid receptor against progesterone in the human kidney. | 2001 Jan 22 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Many Hydrocortisone products are used topically https://www.drugs.com/pro/hydrocortisone.html
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11968738
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
Created
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admin
on
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Wed Apr 02 17:59:18 GMT 2025
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Record UNII |
3X7931PO74
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C521
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FDA ORPHAN DRUG |
568616
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Code System | Code | Type | Description | ||
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4213
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PRIMARY | |||
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3X7931PO74
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741
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27197
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50-03-3
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1317007
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C021650
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Hydrocortisone acetate
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SUB02562MIG
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HYDROCORTISONE ACETATE
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PRIMARY | Description: A white or almost white, crystalline powder; odourless. Solubility: Practically insoluble in water; slightly soluble in ethanol (~750 g/l) TS; very slightly soluble in ether R. Category: Adrenocortical steroid. Storage: Hydrocortisone acetate should be kept in a well-closed container, protected from light.Additional information: Hydrocortisone acetate melts at about 220?C with decomposition. Definition: Hydrocortisone acetate contains not less than 97.0% and not more than 102.0% of C23H32O6, calculated with reference to the dried substance. | ||
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200-004-4
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DB14539
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C61785
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m6094
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3X7931PO74
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100000092260
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CHEMBL1091
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DTXSID0048686
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17609
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5744
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|
IMPURITY -> PARENT |
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
|
||
|
PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
Related Record | Type | Details | ||
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ACTIVE MOIETY |
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