CAS 156053-89-3|alvimopan|Entereg|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...

General Information

Structure

Molecular Formula

C₂₅H₃₂N₂O₄

Molecular Mass

424.53258

Exact Mass

424.23620751

Charge

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

Calculated Properties

JChem

Acid pKa

3.7093873

H Acceptors

H Donor

LogD (pH = 5.5)

0.81727153

LogD (pH = 7.4)

0.8211437

Log P

0.82215357

Molar Refractivity

120.5593

Polarizability

46.90431

Polar Surface Area

89.87

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.25

LOG S

-4.71

Solubility (Water)

8.34e-03 g/l

Data Source

Academic Data

Commercial Catalog

Data Source

Names and Identifiers

Brand Name

Entereg

Synonyms

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

IUPAC name

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

IUPAC Traditional name

entereg alvimopan

Names and Identifiers

Registration numbers

PubChem CID

5488548

PubChem SID

16096785799443242

CAS Number

156053-89-3

Registration numbers

Properties

Physical Property

Solubility

<0.1 mg/mL [FDA]

Safety Information

MSDS Link

Download link

Product Information

Certificate of Analysis

Download link

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

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.

Molecule Details

References

PubChem Literature

From Data Sources

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

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