2-{14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl}-2-oxoethyl 2-(diethylamino)acetate

• ChemBase ID: 649
• Molecular Formular: C27H41NO6
• Molecular Mass: 475.61754
• Monoisotopic Mass: 475.29338804
• SMILES: OC1(C2(C(C3C(C4(C(=CC(=O)CC4)CC3)C)C(O)C2)CC1)C)C(=O)COC(=O)CN(CC)CC
• Canonical SMILES: CCN(CC(=O)OCC(=O)C1(O)CCC2C1(C)CC(O)C1C2CCC2=CC(=O)CCC12C)CC
• 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
• InChIKey: FWFVLWGEFDIZMJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-{14,17-dihydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-14-yl}-2-oxoethyl 2-(diethylamino)acetate
• IUPAC Traditional name: hydrocortamate
• Brand Name: Hydrocortamate Hydrochloride; Magnacort; Ulcort
• Synonyms: Hydrocortamate

Database IDs

• CAS Number: 76-47-1
• PubChem SID: 160964112
• PubChem CID: 408334

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.607479
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 1.3416194
• LogD (pH = 7.4): 2.2769167
• Log P: 2.3214061
• Molar Refractivity: 129.4777 cm^3
• Polarizability: 51.001488 Å^3
• Polar Surface Area: 104.14 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.82
• LOG S: -3.75
• Solubility (Water): 8.55e-02 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 1.2

DETAILS

DrugBank - DB00769

• Drug Groups: approved
• Description: 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.
• Indication: Used topically as an antiinflammatory in the treatment of steroid-responsive dermatoses
• Pharmacology: 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.
• Toxicity: 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.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily hepatic via CYP3A4