CAS 156053-89-3|Entereg|alvimopan|2-[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanamido]acetic acid|entereg|Alvimopan|ADL 8-2698|N-[(2S)-2-[[(3R,4R)-4-(3-Hydroxyphen...

基本信息

化学结构

分子式

C₂₅H₃₂N₂O₄

分子量

424.53258

精确质量

424.23620751

电荷

InChI

InChI=1S/C25H32N2O4/c1-18-16-27(12-11-25(18,2)21-9-6-10-22(28)14-21)17-20(24(31)26-15-23(29)30)13-19-7-4-3-5-8-19/h3-10,14,18,20,28H,11-13,15-17H2,1-2H3,(H,26,31)(H,29,30)/t18-,20-,25+/m0/s1

InChIKey

UPNUIXSCZBYVBB-JVFUWBCBSA-N

Canonic Smiles

OC(=O)CNC(=O)[C@@H](Cc1ccccc1)CN1CC[C@@]([C@H](C1)C)(C)c1cccc(c1)O

Isomeric Smiles

Oc1cc([C@]2([C@H](CN(CC2)C[C@H](Cc2ccccc2)C(=O)NCC(=O)O)C)C)ccc1

计算属性

JChem

Acid pKa

3.7093873

质子受体

质子供体

LogD (pH = 5.5)

0.81727153

LogD (pH = 7.4)

0.8211437

Log P

0.82215357

摩尔折射率

120.5593

极化性

46.90431

极化表面积

89.87

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

3.25

LOG S

-4.71

溶解度

8.34e-03 g/l

数据来源

学术数据

产品目录

数据来源

名称和标识

别名

alvimopanAlvimopanADL 8-2698N-[(2S)-2-[[(3R,4R)-4-(3-Hydroxyphenyl)-3,4-dimethyl-1-piperidinyl]methyl]-1-oxo-3-phenylpropyl]glycineLY 246736Entereg

商标名

Entereg

IUPAC标准名

2-[(2S)-2-benzyl-3-[(3R,4R)-4-(3-hydroxyphenyl)-3,4-dimethylpiperidin-1-yl]propanamido]acetic acid

IUPAC传统名

entereg alvimopan

名称和标识

数据登录号

PubChem CID

5488548

PubChem SID

16096785799443242

CAS号

156053-89-3

数据登录号

化合物性质

理化性质

溶解度

<0.1 mg/mL [FDA]

安全信息

MSDS下载

下载链接

产品相关信息

质检报告

下载链接

化合物性质

分子相关蛋白质

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分子图谱

描述信息

DrugBank

DB06274

Drug Groups

approved; investigational

Description

Alvimopan is a peripherally selective opioid antagonist being investigated for the treatment of various gastrointestinal diseases and disorders.

Indication

Used to accelerate the time to upper and lower gastrointestinal recovery following partial large or small bowel resection surgery with primary anastomosis. Also investigated for use in the treatment of pain (acute or chronic).

Affected Organisms

Humans and other mammals

Biotransformation

Alvimopan undergoes no significant hepatic metabolism, but is metabolized by intestinal flora. Gut metabolism produces an active metabolite with no clinically significant contribution to drug effect.

Absorption

Alvimopan's high affinity for the peripheral mu-receptor results in an absolute oral bioavailability of less than 7%.

Half Life

10 to 17 hours (gut metabolite: 10 to 18 hours)

Protein Binding

80% to 90% of systemically available alvimopan is bound to plasma protein.

Elimination

Biliary secretion was considered the primary pathway for alvimopan elimination. Unabsorbed drug and unchanged alvimopan resulting from biliary excretion were then hydrolyzed to its ‘metabolite’ by gut microflora.

Distribution

* 30±10 L

Clearance

* 402 +/- 89 mL/min

References

• Buchler MW, Seiler CM, Monson JR, Flamant Y, Thompson-Fawcett MW, Byrne MM, Mortensen ER, Altman JF, Williamson R: Clinical trial: alvimopan for the management of postoperative ileus after abdominal surgery: results of an international randomised, double-blind, multicentre, placebo-controlled clinical study. Aliment Pharmacol Ther. 2008 Mar 28. [Pubmed]

External Links

• [Wikipedia]

• [Drugs.com]

TRC

A575800

A peripheral μ-opioid receptor antagonist. Gastroprokinetic.

描述信息

参考文献

PubChem文献

数据源提供

• Zimmerman, D.M., et al.: J. Med. Chem., 37, 2262 (1994)

• Liu, S.S., et al.: Clin. Pharmacol. Ther., 68, 66 (1994)