(1S,2S,4R,6S,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one

• ChemBase编号: 1092
• 分子式: C25H34O6
• 平均质量: 430.53386
• 单一同位素质量: 430.23553881
• SMILES: O1[C@]2([C@@]3([C@H]([C@H]4[C@H]([C@@H](O)C3)[C@@]3(C(=CC(=O)C=C3)CC4)C)C[C@H]2O[C@@H]1CCC)C)C(=O)CO
• Canonical SMILES: CCC[C@H]1O[C@H]2[C@](O1)(C(=O)CO)[C@@]1([C@@H](C2)[C@@H]2CCC3=CC(=O)C=C[C@@]3([C@H]2[C@H](C1)O)C)C
• InChI: InChI=1S/C25H34O6/c1-4-5-21-30-20-11-17-16-7-6-14-10-15(27)8-9-23(14,2)22(16)18(28)12-24(17,3)25(20,31-21)19(29)13-26/h8-10,16-18,20-22,26,28H,4-7,11-13H2,1-3H3/t16-,17-,18-,20+,21-,22+,23-,24-,25+/m0/s1
• InChIKey: VOVIALXJUBGFJZ-AMTWPJRWSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2S,4R,6S,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0^{2,9}.0^{4,8}.0^{13,18}]icosa-14,17-dien-16-one; (1S,2S,4R,6S,8S,9S,11S,12S,13R)-11-hydroxy-8-(2-hydroxyacetyl)-9,13-dimethyl-6-propyl-5,7-dioxapentacyclo[10.8.0.0^2,^9.0^4,^8.0^1^3,^1^8]icosa-14,17-dien-16-one
• IUPAC传统名: budesonide; pulmicort
• 商标名: Bidien; Budeson; Cortivent; Desowen; Entocort; Entocort EC; Micronyl; Preferid; Pulmicort; Pulmicort Nebuamp; Pulmicort Respules; Pulmicort Turbuhaler; Rhinocort; Rhinocort Aqua; Rhinocort Turbuhaler; Spirocort; Tridesilon
• 别名: budesonide; Budesonide; (11β,16α)-16,17-[(1S)-Butylidenebis(oxy)]-11,21-dihydroxypregna-1,4-diene-3,20-dione; (22S)-Budesonide (85:15 = S:R)

登记号

• CAS号: 51372-28-2; 51333-22-3
• PubChem SID: 160964555
• PubChem CID: 63006

理论计算性质

JChem

• Acid pKa: 13.743137
• 质子受体: 6
• 质子供体: 2
• LogD (pH = 5.5): 2.73389
• LogD (pH = 7.4): 2.7338898
• Log P: 2.73389
• 摩尔折射率: 116.1098 cm^3
• 极化性: 45.44829 Å^3
• 极化表面积: 93.06 Å^2
• 可自由旋转的化学键: 4
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 2.42
• LOG S: -3.97
• 溶解度: 4.57e-02 g/l

分子性质

理化性质

• 溶解度: Chloroform; insoluble; Methanol
• 外观: Off-White Solid
• 熔点: 196-198°C
• 疏水性(logP): 1.9

安全信息

• 保存条件: -20°C Freezer

详细说明

DrugBank - DB01222

• Drug Groups: approved; investigational
• Description: A glucocorticoid used in the management of asthma, the treatment of various skin disorders, and allergic rhinitis. [PubChem]
• Indication: For the treatment of mild to moderate active Crohn's disease. Also for the treatment of asthma, non-infectious rhinitis (including hay fever and other allergies), and for treatment and prevention of nasal polyposis.
• Pharmacology: Budesonide is a synthetic corticosteroid used in Crohn's disease to decrease the symptoms and inflammation associated with the disease, especially at times of flare up. Budesonide has a high topical glucocorticosteroid (GCS) activity and a substantial first pass elimination. The formulation contains granules which are coated to protect dissolution in gastric juice, but which dissolve at pH >5.5, ie, normally when the granules reach the duodenum. Thereafter, a matrix of ethylcellulose with budesonide controls the release of the drug into the intestinal lumen in a time-dependent manner.
• Toxicity: Single oral doses of 200 and 400 mg/kg were lethal in female and male mice, respectively. The signs of acute toxicity were decreased motor activity, piloerection and generalized edema.
• Affected Organisms: Humans and other mammals
• Biotransformation: Following absorption, budesonide is subject to high first pass metabolism (80-90%). In vitro experiments in human liver microsomes demonstrate that budesonide is rapidly and extensively biotransformed, mainly by CYP3A4, to its 2 major metabolites, 6b-hydroxy budesonide and 16a- hydroxy prednisolone. The glucocorticoid activity of these metabolites is negligible (<1/100) in relation to that of the parent compound.
• Absorption: Absorption is complete following oral administration.
• Half Life: 2.0 and 3.6 hours
• Protein Binding: 85-90%
• Elimination: Budesonide is excreted in urine and feces in the form of metabolites.
• Distribution: * 3 L/kg [asthmatic children 4 to 6 years of age]
• Clearance: * 0.5 L/min [Athmatic children 4 to 6 years of age]
• External Links: Wikipedia; RxList; PDRhealth; Drugs.com

Toronto Research Chemicals - B689505

Budesonide (B689490) epimer S. Budesonide 22R epimer is more active than 22S epimer. Used as an antiinflammatory agent.

参考文献

• Ryrfeldt., A., et a.: J. Steroid Biochem., 10, 317 (1979)
• Roth, G., et al.: J. Pharm. Sci., 69, 766 (1979)
• Clissold, S.P., et al.: Drugs, 28, 485 (1979)