(1R,2S,11S,13R,14R,15S,17S)-1-chloro-14-(2-chloroacetyl)-14,17-dihydroxy-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one

• ChemBase编号: 644
• 分子式: C22H28Cl2O4
• 平均质量: 427.36132
• 单一同位素质量: 426.13646474
• SMILES: Cl[C@@]12C([C@H]3[C@@]([C@](O)([C@@H](C3)C)C(=O)CCl)(C[C@@H]1O)C)CCC1=CC(=O)C=C[C@]21C
• Canonical SMILES: ClCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1(C2CCC2=CC(=O)C=C[C@]12C)Cl
• InChI: InChI=1S/C22H28Cl2O4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15?,16+,17+,19+,20+,21+,22+/m1/s1
• InChIKey: QLIIKPVHVRXHRI-KPZMXUCXSA-N

名称和登记号

名称

• IUPAC标准名: (1R,2S,11S,13R,14R,15S,17S)-1-chloro-14-(2-chloroacetyl)-14,17-dihydroxy-2,13,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
• IUPAC传统名: mometasone
• 商标名: Asmanex Twisthaler; Elocom; Elocon; Mometasone furoate; Nasonex; Asmanex
• 别名: Mometasone

登记号

• CAS号: 105102-22-5
• PubChem SID: 160964107
• PubChem CID: 123620

理论计算性质

JChem

• Acid pKa: 12.480248
• 质子受体: 4
• 质子供体: 2
• LogD (pH = 5.5): 3.4996617
• LogD (pH = 7.4): 3.499658
• Log P: 3.4996617
• 摩尔折射率: 110.287 cm^3
• 极化性: 42.948353 Å^3
• 极化表面积: 74.6 Å^2
• 可自由旋转的化学键: 2
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.81
• LOG S: -4.91
• 溶解度: 5.23e-03 g/l

分子性质

理化性质

• 溶解度: Practically insoluble.
• 疏水性(logP): 2.1

详细说明

DrugBank - DB00764

• Drug Groups: approved
• Description: Mometasone is a medium-potency synthetic corticosteroid with antiinflammatory, antipruritic, and vasoconstrictive properties. Studies in asthmatic patients have demonstrated that mometasone provides a favorable ratio of topical to systemic activity due to its primary local effect along with the extensive hepatic metabolism and the lack of active metabolites. Though effective for the treatment of asthma, glucocorticoids do not affect asthma symptoms immediately. Maximum improvement in symptoms following inhaled administration of mometasone furoate may not be achieved for 1 to 2 weeks or longer after starting treatment. he antiinflammatory actions of corticosteroids are thought to involve phospholipase A2 inhibitory proteins, lipocortins, which control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes.
• Indication: The inhaler is indicated for the maintenance treatment of asthma as prophylactic therapy. The nasal spray is indicated for the treatment of the nasal symptoms of seasonal allergic and perennial allergic rhinitis.
• Pharmacology: Mometasone is a medium-potency synthetic corticosteroid with antiinflammatory, antipruritic, and vasoconstrictive properties. Studies in asthmatic patients have demonstrated that mometasone provides a favorable ratio of topical to systemic activity due to its primary local effect along with the extensive hepatic metabolism and the lack of active metabolites. Though effective for the treatment of asthma, glucocorticoids do not affect asthma symptoms immediately. Maximum improvement in symptoms following inhaled administration of mometasone furoate may not be achieved for 1 to 2 weeks or longer after starting treatment. When glucocorticoids are discontinued, asthma stability may persist for several days or longer. Mometasone has been shown in vitro to exhibit a binding affinity for the human glucocorticoid receptor which is approximately 12 times that of dexamethasone, 7 times that of triamcinolone acetonide, 5 times that of budesonide, and 1.5 times that of fluticasone. The clinical significance of these findings is unknown.
• Toxicity: The potential for acute toxic effects following overdose with the mometasone inhaler is low. However, habitual overuse of the product can cause symptoms of steroid overload, including menstrual irregularities, acne, obesity, and muscle weakness. Single oral doses up to 8000 µg have been studied on human volunteers with no adverse events reported.
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic. Extensive metabolism to multiple metabolites. There are no major metabolites detectable in plasma. Upon in vitro incubation, one of the minor metabolites formed is 6ß-hydroxy-mometasone furoate. In human liver microsomes, the formation of the metabolite is regulated by cytochrome P-450 3A4.
• Absorption: Nasal spray is virtually undetectable in plasma
• Half Life: 5.8 hours
• Protein Binding: 98% to 99% (in a concentration range of 5 to 500 ng/mL).
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com