2-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenol

• ChemBase编号: 73214
• 分子式: C22H31NO2
• 平均质量: 341.48704
• 单一同位素质量: 341.23547924
• SMILES: c1ccccc1[C@H](c1c(ccc(c1)CO)O)CCN(C(C)C)C(C)C
• Canonical SMILES: OCc1ccc(c(c1)[C@@H](c1ccccc1)CCN(C(C)C)C(C)C)O
• InChI: InChI=1S/C22H31NO2/c1-16(2)23(17(3)4)13-12-20(19-8-6-5-7-9-19)21-14-18(15-24)10-11-22(21)25/h5-11,14,16-17,20,24-25H,12-13,15H2,1-4H3/t20-/m1/s1
• InChIKey: DUXZAXCGJSBGDW-HXUWFJFHSA-N

名称和登记号

名称

• IUPAC标准名: 2-[(1R)-3-[bis(propan-2-yl)amino]-1-phenylpropyl]-4-(hydroxymethyl)phenol
• IUPAC传统名: 2-[(1R)-3-(diisopropylamino)-1-phenylpropyl]-4-(hydroxymethyl)phenol
• 别名: PNU 200577; 5-hydroxymethyl tolterodine; 3-[(1R)-3-[Bis(1-methylethyl)amino]-1-phenylpropyl]-4-hydroxybenzenemethanol; (+)-N,N-Diisopropyl-3-(2-hydroxy-5-hydroxymethylphenyl)-3-phenylpropylamine; (R)-5-Hydroxymethyl Tolterodine

登记号

• CAS号: 207679-81-0
• PubChem SID: 162038134
• PubChem CID: 9819382

理论计算性质

• Acid pKa: 9.5834055
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 1.0560644
• LogD (pH = 7.4): 1.572271
• Log P: 3.42528
• 摩尔折射率: 105.7319 cm^3
• 极化性: 41.04398 Å^3
• 极化表面积: 43.7 Å^2
• 可自由旋转的化学键: 8
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; Methanol
• 外观: Pale Yellow Solid
• 熔点: 68-72°C

安全信息

• 保存条件: -20°C; -20°C Freezer

药理学性质

• 作用靶点: mAChRs

产品相关信息

• 成盐信息: Free Base

详细说明

Selleck Chemicals - S2659

Biological Activity:
5-hydroxymethyl tolterodine (PNU 200577) is a potent and selective muscarinic receptor antagonist with a Kb and a pA2 of 0.84 nM and 9.14, respectively. 5-hydroxymethyl tolterodine (PNU 200577) is a major pharmacologically active metabolite of tolterodine. In vitro, PNU-200577 prevented carbachol-induced contraction of guinea-pig isolated urinary bladder strips in a competitive and concentration-dependent manner. In vivo, PNU-200577 was significantly more potent at suppressing acetylcholine-induced urinary bladder contraction than electrically induced salivation in the anaesthetised cat (ID50=15 and 40 nmol/kg, respectively). In radioligand binding studies carried out in homogenates of guinea-pig tissues and Chinese hamster ovary cell lines expressing human muscarinic m1-m5 receptors, 5-hydroxymethyl tolterodine (PNU 200577) was not selective for any muscarinic receptor subtype. Thus, 5-hydroxymethyl tolterodine (PNU 200577) is similar to tolterodine in terms of antimuscarinic potency, functional selectivity for the urinary bladder in vivo and absence of selectivity for muscarinic receptor subtypes in vitro. The results of this study clearly indicate that 5-hydroxymethyl tolterodine (PNU 200577) contributes to the therapeutic action of tolterodine, in view of its high antimuscarinic potency, similar serum concentration and lower degree of protein binding. [1] References on 5-hydroxymethyl tolterodine (PNU 200577)[1] Pharmacol Toxicol, 1997 Oct, 81(4):169-72

Toronto Research Chemicals - H948363

A metabolite of Tolterodine (T535800), a muscarinic receptor antagonist used in the treatment of urinary incontinence.

参考文献

• Nilvebrant L et al. Pharmacol Toxicol. 1997 Oct;81(4):169-72.
• Palmer, L., et al.: J. Pharm. Biomed. Anal., 16, 155 (1997)
• Hills, C., et al.: Drugs, 55, 813 (1997)
• Wefer, J., et al.: World J. Urol., 19, 312 (1997)