(7-nitro-2-{[(propan-2-yl)amino]methyl}-1,2,3,4-tetrahydroquinolin-6-yl)methanol

• ChemBase编号: 967
• 分子式: C14H21N3O3
• 平均质量: 279.33484
• 单一同位素质量: 279.15829155
• SMILES: OCc1cc2CCC(Nc2cc1[N+](=O)[O-])CNC(C)C
• Canonical SMILES: OCc1cc2CCC(Nc2cc1[N+](=O)[O-])CNC(C)C
• InChI: InChI=1S/C14H21N3O3/c1-9(2)15-7-12-4-3-10-5-11(8-18)14(17(19)20)6-13(10)16-12/h5-6,9,12,15-16,18H,3-4,7-8H2,1-2H3
• InChIKey: XCGYUJZMCCFSRP-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: (7-nitro-2-{[(propan-2-yl)amino]methyl}-1,2,3,4-tetrahydroquinolin-6-yl)methanol
• IUPAC传统名: oxamniquine
• 商标名: Mansil; Vansil
• 别名: Oxamniquine

登记号

• CAS号: 21738-42-1
• PubChem SID: 160964430; 46508789
• PubChem CID: 4612

理论计算性质

JChem

• Acid pKa: 14.55208
• 质子受体: 5
• 质子供体: 3
• LogD (pH = 5.5): -1.6410065
• LogD (pH = 7.4): -0.8572615
• Log P: 1.5718622
• 摩尔折射率: 79.865 cm^3
• 极化性: 29.408848 Å^3
• 极化表面积: 90.11 Å^2
• 可自由旋转的化学键: 5
• 里宾斯基五规则: true

ALOGPS 2.1

• Log P: 1.54
• LOG S: -3.35
• 溶解度: 1.24e-01 g/l

分子性质

理化性质

• 溶解度: 820 mg/L
• 疏水性(logP): 1.5

详细说明

DrugBank - DB01096

• Drug Groups: approved
• Description: An anthelmintic with schistosomicidal activity against Schistosoma mansoni, but not against other Schistosoma spp. Oxamniquine causes worms to shift from the mesenteric veins to the liver where the male worms are retained; the female worms return to the mesentery, but can no longer release eggs. (From Martidale, The Extra Pharmacopoeia, 31st ed, p121)
• Indication: For treatment of Schistosomiasis caused by Schistosoma mansoni
• Pharmacology: Oxamniquine is an anthelmintic with schistosomicidal activity against Schistosoma mansoni, but not against other Schistosoma spp. Oxamniquine causes worms to shift from the mesenteric veins to the liver where the male worms are retained; the female worms return to the mesentery, but can no longer release egg.
• Affected Organisms: Schistosoma mansoni
• Biotransformation: Probably hepatic
• Absorption: Well absorbed orally
• Half Life: 1-2.5 hours
• References: Filho RP, de Souza Menezes CM, Pinto PL, Paula GA, Brandt CA, da Silveira MA: Design, synthesis, and in vivo evaluation of oxamniquine methacrylate and acrylamide prodrugs. Bioorg Med Chem. 2007 Feb 1;15(3):1229-36. Epub 2006 Nov 16. [Pubmed] ; See General references, Filho et. al. for synthesis of oxamniquine methacylate.
• External Links: Wikipedia; Drugs.com

参考文献

• Filho RP, de Souza Menezes CM, Pinto PL, Paula GA, Brandt CA, da Silveira MA: Design, synthesis, and in vivo evaluation of oxamniquine methacrylate and acrylamide prodrugs. Bioorg Med Chem. 2007 Feb 1;15(3):1229-36. Epub 2006 Nov 16. PubmedSee General references, Filho et. al. for synthesis of oxamniquine methacylate.