2-{14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl}-2-oxoethyl propanoate

• ChemBase编号: 1001
• 分子式: C27H36O8
• 平均质量: 488.56994
• 单一同位素质量: 488.24101811
• SMILES: O(C1(C2(C(C3C(C(O)C2)C2(C(=CC(=O)C=C2)CC3)C)CC1)C)C(=O)COC(=O)CC)C(=O)OCC
• Canonical SMILES: CCOC(=O)OC1(CCC2C1(C)CC(O)C1C2CCC2=CC(=O)C=CC12C)C(=O)COC(=O)CC
• InChI: InChI=1S/C27H36O8/c1-5-22(31)34-15-21(30)27(35-24(32)33-6-2)12-10-19-18-8-7-16-13-17(28)9-11-25(16,3)23(18)20(29)14-26(19,27)4/h9,11,13,18-20,23,29H,5-8,10,12,14-15H2,1-4H3
• InChIKey: FNPXMHRZILFCKX-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 2-{14-[(ethoxycarbonyl)oxy]-17-hydroxy-2,15-dimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl}-2-oxoethyl propanoate
• IUPAC传统名: prednicarbate
• 商标名: Dermatop; Dermatop E Emollient
• 别名: Prednicarbate

登记号

• CAS号: 73771-04-7
• PubChem SID: 160964464; 46506799
• PubChem CID: 52421

理论计算性质

JChem

• Acid pKa: 14.829222
• 质子受体: 6
• 质子供体: 1
• LogD (pH = 5.5): 3.8318758
• LogD (pH = 7.4): 3.8318756
• Log P: 3.8318758
• 摩尔折射率: 127.7954 cm^3
• 极化性: 50.123066 Å^3
• 极化表面积: 116.2 Å^2
• 可自由旋转的化学键: 9
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.08
• LOG S: -4.94
• 溶解度: 5.62e-03 g/l

分子性质

理化性质

• 疏水性(logP): 2.9

详细说明

DrugBank - DB01130

• Drug Groups: approved
• Description: Prednicarbate is a relatively new topical corticosteroid drug. It is similar in potency to hydrocortisone. It is used in the treatment of inflammatory skin diseases, such as atopic dermatitis. It has a favorable benefit-risk ratio, with an inflammatory action similar to that of a medium potency corticosteroid, but with a low potential to cause skin atrophy. The anti-inflammation action of corticosteroids is associated with the inhibition of the interleukin 1-alpha cytokine within keratinocytes. IL-1a is also found in fibroblasts, where it is responsible for proliferation, collagenase induction and IL-6 synthesis, which are related to skin thickness.
• Indication: For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
• Pharmacology: Corticosteroids diffuse across cell membranes and complex with specific cytoplasmic receptors. These complexes then enter the cell nucleus, bind to DNA (chromatin), and stimulate transcription of messenger RNA (mRNA) and subsequent protein synthesis of various inhibitory enzymes responsible for the anti-inflammatory effects of topical corticosteroids. These anti-inflammatory effects include inhibition of early processes such as edema, fibrin deposition, capillary dilatation, movement of phagocytes into the area, and phagocytic activities. Later processes, such as capillary production, collagen deposition, and keloid formation also are inhibited by corticosteroids.
• Affected Organisms: Humans and other mammals
• Biotransformation: Primarily in skin
• Absorption: Absorbed systemically across the stratum corneum.
• References: Gupta AK, Chow M: A review of prednicarbate (Dermatop). Skin Therapy Lett. 2004 Dec-2005 Jan;9(10):5-6, 9. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Gupta AK, Chow M: A review of prednicarbate (Dermatop). Skin Therapy Lett. 2004 Dec-2005 Jan;9(10):5-6, 9. Pubmed