Identification

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Name
Hydrocortisone acetate
Accession Number
DB14539  (DBSALT000369)
Type
Small Molecule
Groups
Approved, Vet approved
Description
Not Available
Structure
Thumb
Synonyms
  • 21-O-acetylcortisol
  • Cortisol 21-acetate
  • Hydrocortisone 21-acetate
Active Moieties
NameKindUNIICASInChI Key
HydrocortisoneprodrugWI4X0X7BPJ50-23-7JYGXADMDTFJGBT-VWUMJDOOSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Alocort 1% - CrmCreamTopicalUcb Inc1996-12-061998-04-21Canada
Anucort-HCSuppository25 mg/1RectalGw Pharmaceuticals Ltd.1990-01-15Not applicableUs
Anucort-HCSuppository25 mg/1RectalA-S Medication Solutions1990-01-15Not applicableUs
Anucort-HCSuppository25 mg/1RectalPreferreed Pharmaceuticals Inc.2012-03-122018-06-13Us
Anusol HCSuppository25 mg/1RectalSalix Pharmaceuticals, Inc2004-06-01Not applicableUs
CortAloGel2 g/100gTopicalAletheia LLC2009-08-102011-10-05Us
Cortamed Ont 25 mg/gOintmentOphthalmicSandoz Canada Incorporated1992-12-312019-08-01Canada
Corticreme 0.1%CreamTopicalRougier Pharma Division Of Ratiopharm Inc1980-12-311999-09-27Canada
Corticreme 1%CreamTopicalRougier Pharma Division Of Ratiopharm Inc1980-12-311999-09-27Canada
CortifoamAerosol, foam1500 mg/15gRectalAlaven Pharmaceutical1982-02-12Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Ala ScalpLotion20 mg/1mLTopicalCrown Laboratories1973-02-28Not applicableUs
Carmol HCCream10 mg/1gTopicalPharma Derm, A Division Of Fougera Pharmaceuticals Inc.1973-01-122013-08-04Us
Dermasorb HC Complete KitKit20 mg/1mLTopicalCrown Laboratories2013-11-142019-09-30Us
MiCort HCCream25 mg/1gTopicalSebela Pharmaceuticals Inc.2016-09-132020-05-31Us
U-CortCream10 mg/1gTopicalTaro Pharmaceuticals U.S.A., Inc.1988-06-13Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Advanced Anti-itch TherapySoap1 g/100gTopicalCVS Health2016-06-10Not applicableUs
Aftate Hydrocortisone CreamCream1 g/100gTopicalSabel Med Llc2016-05-01Not applicableUs
Alumier MD Intensive RecoveryCream10 mg/1mLTopicalAlumier Labs2019-07-01Not applicableUs
Alumier MD Intensive RecoveryCream11.2 mg/1mLTopicalAlumier Labs2019-07-01Not applicableUs
Ancalima Hydrocortisone CreamCream10 mg/1gTopicalANCALIMA LIFESCIENCES LIMITED2019-04-08Not applicableUs
BIO-CORNEUM HC Advanced Scar Supervision Anti-ItchGel1 g/100gTopicalAdvanced Bio-Technologies, Inc2012-01-022014-03-26Us
Biocorneum Advanced Scar Treatment Anti-itchGel1 g/100gTopicalSientra, Inc.2018-05-08Not applicableUs
bioCorneum HC Advanced Scar Supervision Anti-ItchGel1 g/100gTopicalEnaltus Inc2012-05-10Not applicableUs
CAREALL Hydrocortisone Maximum StrengthCream10 mg/1gTopicalNew World Imports, Inc2010-08-302019-12-31Us
CAREALL Hydrocortisone Maximum StrengthCream1 g/1gTopicalNew World Imports, Inc2016-03-11Not applicableUs
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

    Learn more
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
4129 First Aid KitHydrocortisone acetate (1 g/100g) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzocaine (20 g/100g) + Ethanol (0.5 mL/1mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Povidone-iodine (10 mg/1mL)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4149 First Aid KitHydrocortisone acetate (1 g/100g) + Ethanol (0.5 mL/1mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Povidone-iodine (10 mg/1mL) + Water (98.6 mL/100mL) + Water (98.6 mL/100mL)KitOphthalmicHoneywell Safety Products USA, Inc.2018-09-13Not applicableUs
4157 First Aid KitHydrocortisone acetate (1 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (0.5 mL/1mL) + Lidocaine hydrochloride (2 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Povidone-iodine (10 mg/1mL) + Water (98.6 mL/100mL)KitTopicalHoneywell Safety Products USA, Inc.2018-09-13Not applicableUs
4219 First Aid KitHydrocortisone acetate (1 g/100g) + Bacitracin zinc (400 [iU]/1g) + Ethanol (0.5 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4223 First Aid KitHydrocortisone acetate (1 g/100g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4246 First Aid KitHydrocortisone acetate (1 g/100g) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzocaine (5 g/100g) + Chloroxylenol (0.1 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (2 g/100g) + Lidocaine hydrochloride (24.64 mg/1mL) + Povidone-iodine (10 mg/1mL) + Water (98.6 mL/100mL)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4248 First Aid KitHydrocortisone acetate (1 g/100g) + Acetaminophen (325 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Caffeine (32.4 mg/1) + Calcium carbonate (420 mg/1) + Ethanol (0.5 mL/1mL) + Isopropyl alcohol (0.7 mL/1mL) + Levomenthol (0.33 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Polymyxin B sulfate (5000 [iU]/1g) + Salicylamide (152 mg/1) + Tetrahydrozoline hydrochloride (0.05 g/100mL) + Water (98.6 mL/100mL)KitOphthalmicHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4252 First Aid KitHydrocortisone acetate (1 g/100g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (62 mL/100mL) + Ethanol (0.5 mL/1mL) + Lidocaine hydrochloride (2 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitTopicalHoneywell Safety Products USA, Inc.2018-09-13Not applicableUs
4274 First Aid KitHydrocortisone acetate (1 g/100g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4275 First Aid KitHydrocortisone acetate (1 g/100g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
4129 First Aid KitHydrocortisone acetate (1 g/100g) + Ammonia (0.045 g/0.3mL) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzocaine (20 g/100g) + Ethanol (0.5 mL/1mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Povidone-iodine (10 mg/1mL)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4149 First Aid KitHydrocortisone acetate (1 g/100g) + Ethanol (0.5 mL/1mL) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Povidone-iodine (10 mg/1mL) + Water (98.6 mL/100mL) + Water (98.6 mL/100mL)KitOphthalmicHoneywell Safety Products USA, Inc.2018-09-13Not applicableUs
4157 First Aid KitHydrocortisone acetate (1 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (0.5 mL/1mL) + Lidocaine hydrochloride (2 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Povidone-iodine (10 mg/1mL) + Water (98.6 mL/100mL)KitTopicalHoneywell Safety Products USA, Inc.2018-09-13Not applicableUs
4219 First Aid KitHydrocortisone acetate (1 g/100g) + Bacitracin zinc (400 [iU]/1g) + Ethanol (0.5 mL/1mL) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4223 First Aid KitHydrocortisone acetate (1 g/100g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4246 First Aid KitHydrocortisone acetate (1 g/100g) + Acetaminophen (325 mg/1) + Acetylsalicylic acid (325 mg/1) + Ammonia (0.045 g/0.3mL) + Benzocaine (5 g/100g) + Chloroxylenol (0.1 g/100g) + Isopropyl alcohol (0.7 mL/1mL) + Lidocaine hydrochloride (2 g/100g) + Lidocaine hydrochloride (24.64 mg/1mL) + Povidone-iodine (10 mg/1mL) + Water (98.6 mL/100mL)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4248 First Aid KitHydrocortisone acetate (1 g/100g) + Acetaminophen (325 mg/1) + Acetaminophen (110 mg/1) + Acetylsalicylic acid (162 mg/1) + Ammonia (0.045 g/0.3mL) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Benzethonium chloride (0.2 g/100g) + Benzethonium chloride (0.2 g/100g) + Benzocaine (10 g/100g) + Benzocaine (10 g/100g) + Caffeine (32.4 mg/1) + Calcium carbonate (420 mg/1) + Ethanol (0.5 mL/1mL) + Isopropyl alcohol (0.7 mL/1mL) + Levomenthol (0.33 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Phenylephrine hydrochloride (5 mg/1) + Polymyxin B sulfate (5000 [iU]/1g) + Salicylamide (152 mg/1) + Tetrahydrozoline hydrochloride (0.05 g/100mL) + Water (98.6 mL/100mL)KitOphthalmicHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4252 First Aid KitHydrocortisone acetate (1 g/100g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (1.3 mg/1mL) + Ethanol (62 mL/100mL) + Ethanol (0.5 mL/1mL) + Lidocaine hydrochloride (2 g/100g) + Lidocaine hydrochloride (20 mg/1mL) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g) + Water (98.6 mL/100mL)KitTopicalHoneywell Safety Products USA, Inc.2018-09-13Not applicableUs
4274 First Aid KitHydrocortisone acetate (1 g/100g) + Bacitracin zinc (400 [iU]/1g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g) + Neomycin sulfate (3.5 mg/1g) + Polymyxin B sulfate (5000 [iU]/1g)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
4275 First Aid KitHydrocortisone acetate (1 g/100g) + Benzalkonium chloride (0.13 g/100g) + Benzalkonium chloride (1.3 mg/1mL) + Lidocaine hydrochloride (0.5 g/100g)KitTopicalHoneywell Safety Products USA, Inc2018-10-18Not applicableUs
International/Other Brands
Micort-HC
Categories
UNII
3X7931PO74
CAS number
50-03-3
Weight
Average: 404.4966
Monoisotopic: 404.219888756
Chemical Formula
C23H32O6
InChI Key
ALEXXDVDDISNDU-JZYPGELDSA-N
InChI
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
IUPAC Name
2-[(1R,3aS,3bS,9aR,9bS,10S,11aS)-1,10-dihydroxy-9a,11a-dimethyl-7-oxo-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-1-yl]-2-oxoethyl acetate
SMILES
[H][C@@]12CC[C@](O)(C(=O)COC(C)=O)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C

Pharmacology

Indication

For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Also used to treat endocrine (hormonal) disorders (adrenal insufficiency, Addisons disease). It is also used to treat many immune and allergic disorders, such as arthritis, lupus, severe psoriasis, severe asthma, ulcerative colitis, and Crohn's disease.

Associated Conditions
Pharmacodynamics

Hydrocortisone is the most important human glucocorticoid. It is essential for life and regulates or supports a variety of important cardiovascular, metabolic, immunologic and homeostatic functions. Topical hydrocortisone is used for its anti-inflammatory or immunosuppressive properties to treat inflammation due to corticosteroid-responsive dermatoses. Glucocorticoids are a class of steroid hormones characterised by an ability to bind with the cortisol receptor and trigger a variety of important cardiovascular, metabolic, immunologic and homeostatic effects. Glucocorticoids are distinguished from mineralocorticoids and sex steroids by having different receptors, target cells, and effects. Technically, the term corticosteroid refers to both glucocorticoids and mineralocorticoids, but is often used as a synonym for glucocorticoid. Glucocorticoids suppress cell-mediated immunity. They act by inhibiting genes that code for the cytokines IL-1, IL-2, IL-3, IL-4, IL-5, IL-6, IL-8 and TNF-alpha, the most important of which is the IL-2. Reduced cytokine production limits T cell proliferation. Glucocorticoids also suppress humoral immunity, causing B cells to express lower amounts of IL-2 and IL-2 receptors. This diminishes both B cell clonal expansion and antibody synthesis. The diminished amounts of IL-2 also leads to fewer T lymphocyte cells being activated.

Mechanism of action

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.

TargetActionsOrganism
AAnnexin A1Not AvailableHumans
AGlucocorticoid receptorNot AvailableHumans
UCorticosteroid 11-beta-dehydrogenase isozyme 2Not AvailableHumans
U3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1Not AvailableHumans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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Absorption

Topical corticosteroids can be absorbed from normal intact skin. Inflammation and/or other disease processes in the skin increase percutaneous absorption.

Volume of distribution
Not Available
Protein binding

95%

Metabolism

Primarily hepatic via CYP3A4

Route of elimination

Corticosteroids are metabolized primarily in the liver and are then excreted by the kidneys. Some of the topical corticosteroids and their metabolites are also excreted into the bile.

Half life

6-8 hours

Clearance
Not Available
Toxicity

Side effects include inhibition of bone formation, suppression of calcium absorption and delayed wound healing

Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
(R)-warfarinThe metabolism of (R)-warfarin can be increased when combined with Hydrocortisone acetate.
(S)-WarfarinThe metabolism of (S)-Warfarin can be increased when combined with Hydrocortisone acetate.
1-TestosteroneThe risk or severity of edema formation can be increased when 1-Testosterone is combined with Hydrocortisone acetate.
1,10-PhenanthrolineThe therapeutic efficacy of 1,10-Phenanthroline can be decreased when used in combination with Hydrocortisone acetate.
16-BromoepiandrosteroneThe risk or severity of edema formation can be increased when 16-Bromoepiandrosterone is combined with Hydrocortisone acetate.
19-norandrostenedioneThe risk or severity of edema formation can be increased when 19-norandrostenedione is combined with Hydrocortisone acetate.
1alpha-Hydroxyvitamin D5The therapeutic efficacy of 1alpha-Hydroxyvitamin D5 can be decreased when used in combination with Hydrocortisone acetate.
1alpha,24S-Dihydroxyvitamin D2The therapeutic efficacy of 1alpha,24S-Dihydroxyvitamin D2 can be decreased when used in combination with Hydrocortisone acetate.
2-MethoxyethanolThe risk or severity of adverse effects can be increased when 2-Methoxyethanol is combined with Hydrocortisone acetate.
2,4-thiazolidinedioneThe risk or severity of hyperglycemia can be increased when Hydrocortisone acetate is combined with 2,4-thiazolidinedione.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

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  • Action
    Action

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Food Interactions
Not Available

References

General References
  1. de Weerth C, Zijl RH, Buitelaar JK: Development of cortisol circadian rhythm in infancy. Early Hum Dev. 2003 Aug;73(1-2):39-52. [PubMed:12932892]
  2. Palacios R, Sugawara I: Hydrocortisone abrogates proliferation of T cells in autologous mixed lymphocyte reaction by rendering the interleukin-2 Producer T cells unresponsive to interleukin-1 and unable to synthesize the T-cell growth factor. Scand J Immunol. 1982 Jan;15(1):25-31. [PubMed:6461917]
  3. KNIGHT RP Jr, KORNFELD DS, GLASER GH, BONDY PK: Effects of intravenous hydrocortisone on electrolytes of serum and urine in man. J Clin Endocrinol Metab. 1955 Feb;15(2):176-81. [PubMed:13233328]
External Links
KEGG Drug
D00165
KEGG Compound
C02821
PubChem Compound
5744
ChemSpider
5542
ChEBI
17609
ChEMBL
CHEMBL1091
Wikipedia
Hydrocortisone_acetate
AHFS Codes
  • 84:06.00 — Anti-inflammatory Agents
  • 56:36.00 — Anti-inflammatory Agents
  • 52:08.08 — Corticosteroids

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0Not Yet RecruitingBasic ScienceDepression1
0RecruitingBasic ScienceDepression1
1CompletedTreatmentHealthy Volunteers1
1RecruitingTreatmentAcute Myeloid Leukemia Arising From Previous Myelodysplastic Syndrome / Acute, recurrent Myeloid Leukemia / Blasts 0.1 Percent or More of Bone Marrow Nucleated Cells / Blasts 5 Percent or More of Bone Marrow Nucleated Cells / Recurrent High Risk Myelodysplastic Syndrome / Refractory Acute Myeloid Leukemia1
1, 2RecruitingTreatmentAdult Burkitt Lymphoma / B-Cell Lymphoma, Unclassifiable, With Features Intermediate Between Diffuse Large B-Cell Lymphoma and Burkitt Lymphoma / Lymphoma, Large B-Cell, Diffuse (DLBCL) / MYC Gene Mutation / Plasmablastic Lymphoma1
1, 2RecruitingTreatmentTacrolimus / Vitiligo1
1, 2TerminatedTreatmentAdenocarcinoma, Prostate / Recurrent Prostate Carcinoma / Stage III Prostate Cancer / Stage IV Prostate Cancer1
2CompletedSupportive CareAdvanced Malignant Neoplasm / Dermatologic Complication / Dermatologic Complications / Neoplasms, Malignant1
2CompletedTreatmentAtopic Dermatitis (AD)1
2CompletedTreatmentHemorrhoids1
2CompletedTreatmentHemorrhoids, Internal1
2RecruitingTreatmentHemorrhoids, Internal1
3Active Not RecruitingTreatmentB Acute Lymphoblastic Leukemia / Recurrent Adult Acute Lymphoblastic Leukemia / Recurrent Childhood Acute Lymphoblastic Leukemia1
3CompletedTreatmentAcute Lymphoblastic Leukaemias (ALL) / Acute Undifferentiated Leukemia (AUL) / Childhood T Acute Lymphoblastic Leukemia / T-cell Childhood Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
3CompletedTreatmentProstate Cancer1
3RecruitingTreatmentAcute Lymphoblastic Leukaemias (ALL) / B Acute Lymphoblastic Leukemia / B Acute Lymphoblastic Leukemia With t(9;22)(q34.1;q11.2); BCR-ABL1 / BCR-ABL1 Fusion Protein Expression / Minimal Residual Disease / Philadelphia Chromosome Positive / T Acute Lymphoblastic Leukemia / Untreated Adult Acute Lymphoblastic Leukemia / Untreated Childhood Acute Lymphoblastic Leukemia1
3TerminatedTreatmentInfluenza in Humans / Viral Pneumonia1
4CompletedNot AvailableHemorrhoids / Pregnancy1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
KitOphthalmic
KitRespiratory (inhalation)
KitIrrigation
PowderTopical
Powder, for solutionTopical
SoapTopical1 g/100g
LotionTopical20 mg/1mL
GelTopical
OintmentTopical
CreamTopical10 mg/1mL
CreamTopical11.2 mg/1mL
KitTopical
OintmentRectal; Topical
OintmentRectal
SuppositoryRectal
GelTopical1 g/100g
CreamTopical1 g/1g
CreamTopical
GelTopical2 g/100g
OintmentOphthalmic
Aerosol, foamRectal10 %
Aerosol, foamRectal1500 mg/15g
Aerosol, foamRectal90 mg/900mg
Aerosol, foamTopical1500 mg/15g
SuppositoryRectal
SuspensionAuricular (otic)
KitTopical20 mg/1mL
Aerosol, foamTopical
CreamTopical0.5 g/100g
SuppositoryRectal0.025 g/2g
SuppositoryRectal25 mg/2g
Lotion / shampooTopical5 mg/1mL
ShampooTopical5 mg/1mL
CreamTopical
CreamTopical1 g/100g
CreamTopical10 mg/1g
OintmentTopical1.12 g/100g
OintmentTopical1 g/100g
SuppositoryRectal25 mg/1
SuppositoryRectal25 mg/100mg
SuppositoryRectal30 mg/1
KitRectal
LotionTopical0.088 mL/88mL
LotionTopical1 g/88mL
CreamRectal; Topical
LotionTopical
CreamRectal
GelRectal
CreamTopical0.01 g/1g
CreamTopical20 mg/1g
SolutionTopical
SuspensionAuricular (otic); Ophthalmic
OintmentOphthalmic
LotionTopical20 mg/1g
LotionTopical2 g/102.04mL
CreamTopical25 mg/1g
AerosolRectal
Aerosol, foamRectal
OintmentAuricular (otic); Ophthalmic
Solution / dropsOphthalmic
SuspensionOphthalmic
Solution / dropsAuricular (otic)
CreamTopical280 mg/28g
CreamTopical1.12 g/100g
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0582 mg/mLALOGPS
logP2.31ALOGPS
logP1.72ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)12.61ChemAxon
pKa (Strongest Basic)-2.8ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area100.9 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity106.55 m3·mol-1ChemAxon
Polarizability43.82 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as gluco/mineralocorticoids, progestogins and derivatives. These are steroids with a structure based on a hydroxylated prostane moiety.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Pregnane steroids
Direct Parent
Gluco/mineralocorticoids, progestogins and derivatives
Alternative Parents
20-oxosteroids / 3-oxo delta-4-steroids / 17-hydroxysteroids / 11-beta-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Alpha-acyloxy ketones / Tertiary alcohols / Alpha-hydroxy ketones / Secondary alcohols
show 5 more
Substituents
Progestogin-skeleton / 20-oxosteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / 17-hydroxysteroid / 11-hydroxysteroid / 11-beta-hydroxysteroid / Oxosteroid / Hydroxysteroid / Delta-4-steroid
show 18 more
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
cortisol ester (CHEBI:17609) / C21 steroids (gluco/mineralocorticoids, progestogens) and derivatives (C02821) / C21 steroids (gluco/mineralocorticoids, progestogins) and derivatives (LMST02030093)

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
General Function
Structural molecule activity
Specific Function
Plays important roles in the innate immune response as effector of glucocorticoid-mediated responses and regulator of the inflammatory process. Has anti-inflammatory activity (PubMed:8425544). Play...
Gene Name
ANXA1
Uniprot ID
P04083
Uniprot Name
Annexin A1
Molecular Weight
38713.855 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423]
  3. Sato-Matsumura KC, Matsumura T, Nakamura H, Sawa H, Nagashima K, Koizumi H: Membrane expression of annexin I is enhanced by calcium and TPA in cultured human keratinocytes. Arch Dermatol Res. 2000 Oct;292(10):496-9. [PubMed:11142771]
  4. White MV, Igarashi Y, Lundgren JD, Shelhamer J, Kaliner M: Hydrocortisone inhibits rat basophilic leukemia cell mediator release induced by neutrophil-derived histamine releasing activity as well as by anti-IgE. J Immunol. 1991 Jul 15;147(2):667-73. [PubMed:1712816]
  5. Serres M, Viac J, Comera C, Schmitt D: Expression of annexin I in freshly isolated human epidermal cells and in cultured keratinocytes. Arch Dermatol Res. 1994;286(5):268-72. [PubMed:8060156]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
General Function
Zinc ion binding
Specific Function
Receptor for glucocorticoids (GC). Has a dual mode of action: as a transcription factor that binds to glucocorticoid response elements (GRE), both for nuclear and mitochondrial DNA, and as a modula...
Gene Name
NR3C1
Uniprot ID
P04150
Uniprot Name
Glucocorticoid receptor
Molecular Weight
85658.57 Da
References
  1. Grossman R, Yehuda R, Golier J, McEwen B, Harvey P, Maria NS: Cognitive effects of intravenous hydrocortisone in subjects with PTSD and healthy control subjects. Ann N Y Acad Sci. 2006 Jul;1071:410-21. [PubMed:16891588]
  2. Rautanen A, Eriksson JG, Kere J, Andersson S, Osmond C, Tienari P, Sairanen H, Barker DJ, Phillips DI, Forsen T, Kajantie E: Associations of body size at birth with late-life cortisol concentrations and glucose tolerance are modified by haplotypes of the glucocorticoid receptor gene. J Clin Endocrinol Metab. 2006 Nov;91(11):4544-51. Epub 2006 Aug 8. [PubMed:16895953]
  3. Hammer F, Stewart PM: Cortisol metabolism in hypertension. Best Pract Res Clin Endocrinol Metab. 2006 Sep;20(3):337-53. [PubMed:16980198]
  4. Shaw JR, Gabor K, Hand E, Lankowski A, Durant L, Thibodeau R, Stanton CR, Barnaby R, Coutermarsh B, Karlson KH, Sato JD, Hamilton JW, Stanton BA: Role of glucocorticoid receptor in acclimation of killifish (Fundulus heteroclitus) to seawater and effects of arsenic. Am J Physiol Regul Integr Comp Physiol. 2007 Feb;292(2):R1052-60. Epub 2006 Oct 12. [PubMed:17038445]
  5. Sher L: Combined dexamethasone suppression-corticotropin-releasing hormone stimulation test in studies of depression, alcoholism, and suicidal behavior. ScientificWorldJournal. 2006 Oct 31;6:1398-404. [PubMed:17086345]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Steroid binding
Specific Function
Catalyzes the conversion of cortisol to the inactive metabolite cortisone. Modulates intracellular glucocorticoid levels, thus protecting the nonselective mineralocorticoid receptor from occupation...
Gene Name
HSD11B2
Uniprot ID
P80365
Uniprot Name
Corticosteroid 11-beta-dehydrogenase isozyme 2
Molecular Weight
44126.06 Da
References
  1. Furstenberger C, Vuorinen A, Da Cunha T, Kratschmar DV, Saugy M, Schuster D, Odermatt A: The anabolic androgenic steroid fluoxymesterone inhibits 11beta-hydroxysteroid dehydrogenase 2-dependent glucocorticoid inactivation. Toxicol Sci. 2012 Apr;126(2):353-61. doi: 10.1093/toxsci/kfs022. Epub 2012 Jan 23. [PubMed:22273746]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Steroid delta-isomerase activity
Specific Function
3-beta-HSD is a bifunctional enzyme, that catalyzes the oxidative conversion of Delta(5)-ene-3-beta-hydroxy steroid, and the oxidative conversion of ketosteroids. The 3-beta-HSD enzymatic system pl...
Gene Name
HSD3B1
Uniprot ID
P14060
Uniprot Name
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 1
Molecular Weight
42251.25 Da
References
  1. Bhatia C, Oerum S, Bray J, Kavanagh KL, Shafqat N, Yue W, Oppermann U: Towards a systematic analysis of human short-chain dehydrogenases/reductases (SDR): Ligand identification and structure-activity relationships. Chem Biol Interact. 2015 Jun 5;234:114-25. doi: 10.1016/j.cbi.2014.12.013. Epub 2014 Dec 16. [PubMed:25526675]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
Inducer
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Joellenbeck L, Qian Z, Zarba A, Groopman JD: Urinary 6 beta-hydroxycortisol/cortisol ratios measured by high-performance liquid chromatography for use as a biomarker for the human cytochrome P-450 3A4. Cancer Epidemiol Biomarkers Prev. 1992 Nov-Dec;1(7):567-72. [PubMed:1302569]
  2. Litt J. (2016). Litt's Drug eruption & reaction manual (22nd ed.). CRC Press LLc.
  3. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A5
Uniprot ID
P20815
Uniprot Name
Cytochrome P450 3A5
Molecular Weight
57108.065 Da
References
  1. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxygen binding
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP3A7
Uniprot ID
P24462
Uniprot Name
Cytochrome P450 3A7
Molecular Weight
57525.03 Da
References
  1. Flockhart Table of Drug Interactions [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid 11-beta-monooxygenase activity
Specific Function
Has steroid 11-beta-hydroxylase activity. In addition to this activity, the 18 or 19-hydroxylation of steroids and the aromatization of androstendione to estrone have also been ascribed to cytochro...
Gene Name
CYP11B1
Uniprot ID
P15538
Uniprot Name
Cytochrome P450 11B1, mitochondrial
Molecular Weight
57572.44 Da
References
  1. Freel EM, Shakerdi LA, Friel EC, Wallace AM, Davies E, Fraser R, Connell JM: Studies on the origin of circulating 18-hydroxycortisol and 18-oxocortisol in normal human subjects. J Clin Endocrinol Metab. 2004 Sep;89(9):4628-33. doi: 10.1210/jc.2004-0379. [PubMed:15356073]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid 11-beta-monooxygenase activity
Specific Function
Preferentially catalyzes the conversion of 11-deoxycorticosterone to aldosterone via corticosterone and 18-hydroxycorticosterone.
Gene Name
CYP11B2
Uniprot ID
P19099
Uniprot Name
Cytochrome P450 11B2, mitochondrial
Molecular Weight
57559.62 Da
References
  1. Freel EM, Shakerdi LA, Friel EC, Wallace AM, Davies E, Fraser R, Connell JM: Studies on the origin of circulating 18-hydroxycortisol and 18-oxocortisol in normal human subjects. J Clin Endocrinol Metab. 2004 Sep;89(9):4628-33. doi: 10.1210/jc.2004-0379. [PubMed:15356073]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inducer
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2C8
Uniprot ID
P10632
Uniprot Name
Cytochrome P450 2C8
Molecular Weight
55824.275 Da
References
  1. Bauersachs J, Christ M, Ertl G, Michaelis UR, Fisslthaler B, Busse R, Fleming I: Cytochrome P450 2C expression and EDHF-mediated relaxation in porcine coronary arteries is increased by cortisol. Cardiovasc Res. 2002 Jun;54(3):669-75. [PubMed:12031713]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Androgen binding
Specific Function
Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name
SHBG
Uniprot ID
P04278
Uniprot Name
Sex hormone-binding globulin
Molecular Weight
43778.755 Da
References
  1. Khoromi S, Muniyappa R, Nackers L, Gray N, Baldwin H, Wong KA, Matheny LA, Moquin B, Rainer A, Hill S, Remaley A, Johnson LL, Max MB, Blackman MR: Effects of chronic osteoarthritis pain on neuroendocrine function in men. J Clin Endocrinol Metab. 2006 Nov;91(11):4313-8. Epub 2006 Aug 15. [PubMed:16912126]
  2. Stroud LR, Solomon C, Shenassa E, Papandonatos G, Niaura R, Lipsitt LP, Lewinn K, Buka SL: Long-term stability of maternal prenatal steroid hormones from the National Collaborative Perinatal Project: still valid after all these years. Psychoneuroendocrinology. 2007 Feb;32(2):140-50. Epub 2007 Jan 31. [PubMed:17270355]
  3. Lombardi G, Mondaini N, Macchiarella A, Del Popolo G: Female sexual dysfunction and hormonal status in spinal cord injured (SCI) patients. J Androl. 2007 Sep-Oct;28(5):722-6. Epub 2007 May 9. [PubMed:17494102]
  4. Shifren JL, Desindes S, McIlwain M, Doros G, Mazer NA: A randomized, open-label, crossover study comparing the effects of oral versus transdermal estrogen therapy on serum androgens, thyroid hormones, and adrenal hormones in naturally menopausal women. Menopause. 2007 Nov-Dec;14(6):985-94. [PubMed:17507833]
  5. Rizzo L, Dobrovsky V, Danilowicz K, Kral M, Cross G, Serra HA, Bruno OD: Low-dose glucocorticoids in hyperandrogenism. Medicina (B Aires). 2007;67(3):247-52. [PubMed:17628912]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Steroid binding
Specific Function
Major transport protein for glucocorticoids and progestins in the blood of almost all vertebrate species.
Gene Name
SERPINA6
Uniprot ID
P08185
Uniprot Name
Corticosteroid-binding globulin
Molecular Weight
45140.49 Da
References
  1. Henley DE, Lightman SL: New insights into corticosteroid-binding globulin and glucocorticoid delivery. Neuroscience. 2011 Apr 28;180:1-8. doi: 10.1016/j.neuroscience.2011.02.053. Epub 2011 Mar 1. [PubMed:21371536]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Schwab D, Fischer H, Tabatabaei A, Poli S, Huwyler J: Comparison of in vitro P-glycoprotein screening assays: recommendations for their use in drug discovery. J Med Chem. 2003 Apr 24;46(9):1716-25. [PubMed:12699389]
  2. Kim RB, Wandel C, Leake B, Cvetkovic M, Fromm MF, Dempsey PJ, Roden MM, Belas F, Chaudhary AK, Roden DM, Wood AJ, Wilkinson GR: Interrelationship between substrates and inhibitors of human CYP3A and P-glycoprotein. Pharm Res. 1999 Mar;16(3):408-14. [PubMed:10213372]
  3. Yates CR, Chang C, Kearbey JD, Yasuda K, Schuetz EG, Miller DD, Dalton JT, Swaan PW: Structural determinants of P-glycoprotein-mediated transport of glucocorticoids. Pharm Res. 2003 Nov;20(11):1794-803. [PubMed:14661924]
  4. Ueda K, Okamura N, Hirai M, Tanigawara Y, Saeki T, Kioka N, Komano T, Hori R: Human P-glycoprotein transports cortisol, aldosterone, and dexamethasone, but not progesterone. J Biol Chem. 1992 Dec 5;267(34):24248-52. [PubMed:1360010]
  5. Orlowski S, Mir LM, Belehradek J Jr, Garrigos M: Effects of steroids and verapamil on P-glycoprotein ATPase activity: progesterone, desoxycorticosterone, corticosterone and verapamil are mutually non-exclusive modulators. Biochem J. 1996 Jul 15;317 ( Pt 2):515-22. [PubMed:8713080]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Mediates the Na(+)-independent transport of organic anions such as sulfobromophthalein (BSP) and conjugated (taurocholate) and unconjugated (cholate) bile acids (By similarity). Selectively inhibit...
Gene Name
SLCO1A2
Uniprot ID
P46721
Uniprot Name
Solute carrier organic anion transporter family member 1A2
Molecular Weight
74144.105 Da
References
  1. Kanai N, Lu R, Bao Y, Wolkoff AW, Schuster VL: Transient expression of oatp organic anion transporter in mammalian cells: identification of candidate substrates. Am J Physiol. 1996 Feb;270(2 Pt 2):F319-25. [PubMed:8779893]
  2. Bossuyt X, Muller M, Hagenbuch B, Meier PJ: Polyspecific drug and steroid clearance by an organic anion transporter of mammalian liver. J Pharmacol Exp Ther. 1996 Mar;276(3):891-6. [PubMed:8786566]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Imai Y, Asada S, Tsukahara S, Ishikawa E, Tsuruo T, Sugimoto Y: Breast cancer resistance protein exports sulfated estrogens but not free estrogens. Mol Pharmacol. 2003 Sep;64(3):610-8. [PubMed:12920197]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Curator comments
Cortisol demonstrated substrate activity in vitro using human OAT3 expressed on Xenopus Laevis.
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [PubMed:19953504]

Drug created on July 12, 2018 14:55 / Updated on November 11, 2019 07:10