dimethyl({2-[(2-methylphenyl)(phenyl)methoxy]ethyl})amine

• ChemBase编号: 1044
• 分子式: C18H23NO
• 平均质量: 269.38132
• 单一同位素质量: 269.17796436
• SMILES: O(C(c1c(cccc1)C)c1ccccc1)CCN(C)C
• Canonical SMILES: CN(CCOC(c1ccccc1C)c1ccccc1)C
• InChI: InChI=1S/C18H23NO/c1-15-9-7-8-12-17(15)18(20-14-13-19(2)3)16-10-5-4-6-11-16/h4-12,18H,13-14H2,1-3H3
• InChIKey: QVYRGXJJSLMXQH-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: dimethyl({2-[(2-methylphenyl)(phenyl)methoxy]ethyl})amine
• IUPAC传统名: orphenadrine
• 商标名: Antiflex; Banflex; Biorphen; Brocadisipal; Brocasipal; Disipal; Flexoject; Mio-Rel; Myolin; Myotrol; Norflex; Orfro; Invagesic
• 别名: O-Methyldiphenhydramine; Orphenadrine Citrate; Orphenadine; Orphenadrin; Orphenate; Orphenedrine; Mephenamine; Orphenadrine

登记号

• CAS号: 83-98-7
• PubChem SID: 46506085; 160964507
• PubChem CID: 4601
• CHEBI ID: 7789
• ATC码: N04AB02; M03BC01
• CHEMBL: 900
• Chemspider ID: 4440
• DrugBank ID: DB01173
• KEGG ID: D08305
• 美国药典/FDA物质标识码: AL805O9OG9
• 维基百科标题: Orphenadrine
• Medline Plus: a682162

理论计算性质

JChem

• 质子受体: 2
• 质子供体: 0
• LogD (pH = 5.5): 1.0371032
• LogD (pH = 7.4): 2.6876686
• Log P: 4.1653285
• 摩尔折射率: 84.9682 cm^3
• 极化性: 33.17157 Å^3
• 极化表面积: 12.47 Å^2
• 可自由旋转的化学键: 6
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 3.5
• LOG S: -3.95
• 溶解度: 3.00e-02 g/l

分子性质

理化性质

• 溶解度: Sparingly soluble in water
• 疏水性(logP): 3.6

药理学性质

• 给药途径: Oral, intravenous, intramuscular
• 生物利用度: 90%
• 排泄: Renal and biliary
• 半衰期: 13-20 hours
• 代谢: Hepatic demethylation
• 蛋白结合率: 95%
• 法定药品分级: OTC (Canada); POM (UK); Rx-only (US)
• 妊娠期药物分类: B2 (Australia); C (US)

详细说明

DrugBank - DB01173

• Drug Groups: approved
• Description: A muscarinic antagonist used to treat drug-induced parkinsonism and to relieve pain from muscle spasm. [PubChem]
• Indication: Indicated for the treatment of Parkinson's disease.
• Pharmacology: Orphenadrine is indicated as an adjunct to rest, physical therapy, and other measures for the relief of discomfort associated with acute painful musculoskeletal conditions. Orphenadrine is an anticholinergic with a predominantly central effect and only a weak peripheral effect. In addition, it has mild antihistaminic and local anaesthetic properties. Parkinson's syndrome is the consequence of a disturbed balance between cholinergic and dopaminergic neurotransmission in the basal ganglia caused by a decrease in dopamine. Orphenadrine restores the physiological equilibrium and has a favourable effect on the rigidity and tremor of Parkinson's disease and Parkinsonian syndromes. The effect is somewhat less on bradykinesia.
• Toxicity: Oral, mouse LD₅₀ = 100 mg/kg; oral, rat LD₅₀ = 255 mg/kg
• Affected Organisms: Humans and other mammals
• Biotransformation: Biotransformation occurs mainly in the liver. Pharmacologically active metabolites are N-demethyl orphenadrine and N,N-didemethyl orphenadrine.
• Absorption: Orphenadrine is almost completely absorbed in the gastrointestinal tract.
• Half Life: 13-20 hours
• Protein Binding: 95%
• References: Ji D, Sui ZY, Ma YY, Luo F, Cui CL, Han JS: NMDA receptor in nucleus accumbens is implicated in morphine withdrawal in rats. Neurochem Res. 2004 Nov;29(11):2113-20. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

参考文献

• Ji D, Sui ZY, Ma YY, Luo F, Cui CL, Han JS: NMDA receptor in nucleus accumbens is implicated in morphine withdrawal in rats. Neurochem Res. 2004 Nov;29(11):2113-20. Pubmed