Identification
- Generic Name
- Hydrocortamate
- DrugBank Accession Number
- DB00769
- Background
Hydrocortamate is a synthetic glucocorticoid 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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Hydrocortamate (DB00769)
- Weight
- Average: 475.6175
Monoisotopic: 475.293388049 - Chemical Formula
- C27H41NO6
- Synonyms
- 17-Hydroxycorticosterone, 21-(diethylamino)acetate
- Hidrocortamato
- Hydrocortamate
- Hydrocortamatum
Pharmacology
- Indication
Used topically as an antiinflammatory in the treatment of steroid-responsive dermatoses
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Hydrocortamate is a synthetic glucocorticoid 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
Hydrocortamate 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. 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.
Target Actions Organism AGlucocorticoid receptor agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Primarily hepatic via CYP3A4
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Side effects include burning, itching, irritation, dryness, folliculitis, hypertrichosis, acneiform eruptions, hypopigmentation, perioral dermatitis, allergic contact dermatitis, maceration of the skin, secondary infection, skin atrophy, striae, miliaria.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib The metabolism of Abemaciclib can be increased when combined with Hydrocortamate. Acalabrutinib The metabolism of Acalabrutinib can be increased when combined with Hydrocortamate. Acenocoumarol The metabolism of Acenocoumarol can be increased when combined with Hydrocortamate. Albendazole The metabolism of Albendazole can be increased when combined with Hydrocortamate. Alectinib The metabolism of Alectinib can be increased when combined with Hydrocortamate. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Hydrocortamate hydrochloride 9QM8U7R83W 125-03-1 AKQNAIYKSALPKV-OYHXESGYSA-N - International/Other Brands
- Etacort (Angelini) / Magnacort (Pfizer) / Ulcort / Ulcort top
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- 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 / 11-beta-hydroxysteroids / 17-hydroxysteroids / 3-oxo delta-4-steroids / Delta-4-steroids / Alpha amino acid esters / Alpha-acyloxy ketones / Cyclohexenones / Tertiary alcohols / Alpha-hydroxy ketones show 8 more
- Substituents
- 11-beta-hydroxysteroid / 11-hydroxysteroid / 17-hydroxysteroid / 20-oxosteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Alpha-acyloxy ketone / Alpha-amino acid ester show 27 more
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- 3-oxo steroid, glycinyl ester, 11beta-hydroxy steroid, 17alpha-hydroxy steroid, glucocorticoid (CHEBI:50851)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- Y3N00BK5WK
- CAS number
- 76-47-1
- InChI Key
- FWFVLWGEFDIZMJ-FOMYWIRZSA-N
- InChI
- InChI=1S/C27H41NO6/c1-5-28(6-2)15-23(32)34-16-22(31)27(33)12-10-20-19-8-7-17-13-18(29)9-11-25(17,3)24(19)21(30)14-26(20,27)4/h13,19-21,24,30,33H,5-12,14-16H2,1-4H3/t19-,20-,21-,24+,25-,26-,27-/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 2-(diethylamino)acetate
- SMILES
- [H][C@@]12CC[C@](O)(C(=O)COC(=O)CN(CC)CC)[C@@]1(C)C[C@H](O)[C@@]1([H])[C@@]2([H])CCC2=CC(=O)CC[C@]12C
References
- Synthesis Reference
British Patent 879,208; October 4, 1961.
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0014907
- PubChem Compound
- 84088
- PubChem Substance
- 46509076
- ChemSpider
- 75860
- ChEBI
- 50851
- ChEMBL
- CHEMBL1201263
- ZINC
- ZINC000004213506
- Therapeutic Targets Database
- DAP001187
- PharmGKB
- PA164745515
- Wikipedia
- Hydrocortamate
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Pfizer laboratories div pfizer inc
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 162-163 British Patent 879,208; October 4, 1961. logP 1.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.0855 mg/mL ALOGPS logP 2.82 ALOGPS logP 2.32 Chemaxon logS -3.8 ALOGPS pKa (Strongest Acidic) 12.61 Chemaxon pKa (Strongest Basic) 6.99 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 104.14 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 129.48 m3·mol-1 Chemaxon Polarizability 53.53 Å3 Chemaxon Number of Rings 4 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9681 Blood Brain Barrier + 0.9382 Caco-2 permeable - 0.6251 P-glycoprotein substrate Substrate 0.8848 P-glycoprotein inhibitor I Inhibitor 0.8649 P-glycoprotein inhibitor II Inhibitor 0.7043 Renal organic cation transporter Non-inhibitor 0.7574 CYP450 2C9 substrate Non-substrate 0.8889 CYP450 2D6 substrate Non-substrate 0.8473 CYP450 3A4 substrate Substrate 0.7533 CYP450 1A2 substrate Non-inhibitor 0.913 CYP450 2C9 inhibitor Non-inhibitor 0.8642 CYP450 2D6 inhibitor Non-inhibitor 0.7771 CYP450 2C19 inhibitor Non-inhibitor 0.8833 CYP450 3A4 inhibitor Non-inhibitor 0.6776 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8749 Ames test Non AMES toxic 0.8229 Carcinogenicity Non-carcinogens 0.9077 Biodegradation Not ready biodegradable 0.9903 Rat acute toxicity 2.9454 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8902 hERG inhibition (predictor II) Non-inhibitor 0.5096
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-000i-9433200000-71a50fe902c19f04fdb3 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-056r-1002900000-eb0cd92252484c7b9b87 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-05fr-3309500000-7cbda5faaadb37e95b64 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-01q9-8609100000-d17ada108d458402634b Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-3523900000-82ea6f03c051f68c4f6f Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0f6x-9002000000-b2fce30c6c2978fd4c05 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-08i4-3913000000-e49b7a5e42cfab1a0ce4 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 232.0836047 predictedDarkChem Lite v0.1.0 [M-H]- 232.9360047 predictedDarkChem Lite v0.1.0 [M-H]- 230.7366047 predictedDarkChem Lite v0.1.0 [M-H]- 210.9564 predictedDeepCCS 1.0 (2019) [M+H]+ 235.0288047 predictedDarkChem Lite v0.1.0 [M+H]+ 232.6950047 predictedDarkChem Lite v0.1.0 [M+H]+ 229.9077047 predictedDarkChem Lite v0.1.0 [M+H]+ 213.48038 predictedDeepCCS 1.0 (2019) [M+Na]+ 234.3853047 predictedDarkChem Lite v0.1.0 [M+Na]+ 232.1960047 predictedDarkChem Lite v0.1.0 [M+Na]+ 230.6833047 predictedDarkChem Lite v0.1.0 [M+Na]+ 220.66368 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Agonist
- 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
- CHADFIELD HW: CORTICOSTEROID THERAPY IN CURRENT DERMATOLOGICAL PRACTICE. Postgrad Med J. 1963 Sep;39:526-33. doi: 10.1136/pgmj.39.455.526. [Article]
- Therapeutic regimens for the treatment of immunoinflammatory disorders [Link]
- Composition and method for control and treatment of cutaneous inflammation [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- 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
- El-Sankary W, Bombail V, Gibson GG, Plant N: Glucocorticoid-mediated induction of CYP3A4 is decreased by disruption of a protein: DNA interaction distinct from the pregnane X receptor response element. Drug Metab Dispos. 2002 Sep;30(9):1029-34. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:55