(1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase编号: 835
• 分子式: C22H30O5
• 平均质量: 374.4706
• 单一同位素质量: 374.20932406
• SMILES: O[C@]1([C@@]2([C@H]([C@H]3[C@H]([C@@H](O)C2)[C@@]2(C(=CC(=O)C=C2)[C@H](C3)C)C)CC1)C)C(=O)CO
• Canonical SMILES: OCC(=O)[C@@]1(O)CC[C@@H]2[C@]1(C)C[C@H](O)[C@H]1[C@H]2C[C@@H](C2=CC(=O)C=C[C@]12C)C
• InChI: InChI=1S/C22H30O5/c1-12-8-14-15-5-7-22(27,18(26)11-23)21(15,3)10-17(25)19(14)20(2)6-4-13(24)9-16(12)20/h4,6,9,12,14-15,17,19,23,25,27H,5,7-8,10-11H2,1-3H3/t12-,14-,15-,17-,19+,20-,21-,22-/m0/s1
• InChIKey: VHRSUDSXCMQTMA-PJHHCJLFSA-N

名称和登记号

名称

• IUPAC标准名: (1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one; (1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-5-one
• IUPAC传统名: methylprednisolone; (1S,2R,8S,10S,11S,14R,15S,17S)-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,8,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• 商标名: Artisone-Wyeth; Besonia; Dopomedrol; Esametone; Firmacort; Lemod; Medesone; Medixon; Medlone 21; Medrate; Medrol Adt Pak; Medrol Dosepak; Medrone; Mesopren; Metastab; Metilbetasone; Metrisone; Metrocort; Metysolon; Moderin; Nirypan; Noretona; Predni N Tablinen; Promacortine; Reactenol; Sieropresol; Solomet; Summicort; Suprametil; Urbason; Urbasone; Wyacort
• 别名: 11β,17α,21-三羟基-6α-甲基-1,4-孕甾二烯-3,20-二酮; 6α-甲基-11β,17α,21-三羟基-1,4-孕甾二烯-3,20-二酮; 甲基强的松龙; 甲基泼尼松龙; 6α-甲基泼尼松龙; (6α,11β)-11,17,21-Trihydroxy-6-methylpregna-1,4-diene-3,20-dione; Medrate; 6α-Methyl Prednisolone; Medrol; Solu-Medrol; Medrone; 6α-Methylprednisolone; 11β,17α,21-Trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione; 6α-Methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione; 11β,17α,21-Trihydroxy-6α-methyl-1,4-pregnadiene-3,20-dione; 6α-Methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione; 6-α-METHYLPREDNISOLONE; Methyleneprednisolone; Methylprednisolon; Methylprednisolonum [INN-Latin]; Metilprednisolona [INN-Spanish]; Metilprednisolone [Dcit]; 6alpha-Methylprednisolone; Methylprednisolone; Methylprednisolone-gellan ester

登记号

• CAS号: 83-43-2
• EC号: 201-476-4
• MDL号: MFCD00010591
• Beilstein号: 2340300
• PubChem SID: 160964298; 24896564; 46504885; 24870169
• PubChem CID: 6741

理论计算性质

JChem

• Acid pKa: 12.584675
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): 1.560009
• LogD (pH = 7.4): 1.5600061
• Log P: 1.560009
• 摩尔折射率: 103.0419 cm^3
• 极化性: 39.87477 Å^3
• 极化表面积: 94.83 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: 2.06
• LOG S: -3.54
• 溶解度: 1.09e-01 g/l

分子性质

理化性质

• 溶解度: 120 mg/L; Acetone; Chloroform; chloroform/methanol (9:1): soluble50 mg/mL, clear, faintly yellow; DMSO
• 外观: White to Off-White Solid
• 熔点: 213-215°C (dec.); 228-237 °C
• 疏水性(logP): 1.5

安全信息

• 保存条件: -20°C; -20°C Freezer; Room Temperature (15-30°C)
• RTECS编号: TU4146000
• 德国WGK号: 2
• 个人保护装置: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

药理学性质

• 相关基因信息: rat ... Nr3c1(24413)
• 生物活性机理: ACTH antagonist; ACTH secretion inhibitor; Calcium mobilizer; Causes protein catabolism; Glucocorticoid; Gluconeogenesis promoter; Glycogen deposition inhibitor; Phosphorus mobilizer

产品相关信息

• 纯度: ≥98%; ≥98.0% (HPLC)
• 级别: VETRANAL™, analytical standard
• 成盐信息: Free Base
• 应用领域: Immunomodulator; Potent antiinflammatory agent
• Empirical Formula (Hill Notation): C22H30O5

详细说明

MP Biomedicals - 02151671

Crystalline
m.p. 228-237°C

DrugBank - DB00959

• Drug Groups: approved
• Description: A prednisolone derivative with similar anti-inflammatory action. [PubChem]
• Indication: Adjunctive therapy for short-term administration in rheumatoid arthritis.
• Pharmacology: Methylprednisolone and its derivatives, methylprednisolone sodium succinate and methylprednisolone acetate, are synthetic glucocorticoids used as antiinflammatory or immunosuppressive agents.
• Toxicity: LD₅₀=2000 mg/kg (orally in rat)
• Affected Organisms: Humans and other mammals
• Biotransformation: Hepatic
• Absorption: Oral bioavailability 80-99%
• Half Life: 1-3 hours
• Protein Binding: 78%
• References: Sloka JS, Stefanelli M: The mechanism of action of methylprednisolone in the treatment of multiple sclerosis. Mult Scler. 2005 Aug;11(4):425-32. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Selleck Chemicals - S1733

Research Area: Immunology , Inflammation
Biological Activity:
Methylprednisolone is a synthetic corticosteroid with anti-inflammatory and immunomodulating properties. Methylprednisolone binds to and activates specific nuclear receptors, resulting in altered gene expression and inhibition of proinflammatory cytokine production. This agent also decreases the number of circulating lymphocytes, induces cell differentiation, and stimulates apoptosis in sensitive tumor cell populations. [1, 2]

Sigma Aldrich - 46436

法律信息
VETRANAL 商标 Sigma-Aldrich Co. LLC

Toronto Research Chemicals - M325934

A glucocorticoid.

参考文献

• Sloka JS, Stefanelli M: The mechanism of action of methylprednisolone in the treatment of multiple sclerosis. Mult Scler. 2005 Aug;11(4):425-32. Pubmed
• http://en.wikipedia.org/wiki/Methylprednisolone
• Hall, E.D., et al.: J. Neurosurg., 76, 13 (1992)
• Hommes, O.R., et al.: Mult. Scler., 1, 327 (1992)
• Bracken, M.B., et al.: J. Neurosurg., 89, 699 (1992)
• Dammers, J.W.H.H., et al.: Brit. Med. J., 319, 884 (1999)