AXELOPRAN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H39N3O4
Molecular Weight	457.6056
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC(=O)C1=CC=CC(=C1)[C@@H]2C[C@@H]3CC[C@H](C2)N3CCN(CC4CCCCC4)C(=O)[C@@H](O)CO

InChI

InChIKey=ATLYLVPZNWDJBW-KIHHCIJBSA-N

InChI=1S/C26H39N3O4/c27-25(32)20-8-4-7-19(13-20)21-14-22-9-10-23(15-21)29(22)12-11-28(26(33)24(31)17-30)16-18-5-2-1-3-6-18/h4,7-8,13,18,21-24,30-31H,1-3,5-6,9-12,14-17H2,(H2,27,32)/t21-,22+,23-,24-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C26H39N3O4
Molecular Weight	457.6056
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/30289777 | https://clinicaltrials.gov/ct2/show/NCT01401985 | https://www.ncbi.nlm.nih.gov/pubmed/30289777

Axelopran (previously known as TD-1211), a peripherally selective, multivalent µ-opioid receptor antagonist that is under development by Theravance Biopharma. This drug participated in phase II clinical trials in subjects with opioid-induced constipation. The most common adverse events were abdominal pain, nausea, and diarrhea. There were no indications of opioid withdrawal effects or reductions in opioid analgesia in patients treated with axelopran.

Originator

Approval Year

PubMed

Title	Date	PubMed
Novel Oral Therapies for Opioid-induced Bowel Dysfunction in Patients with Chronic Noncancer Pain.	2016 Mar	26945548
Discovery of N-substituted-endo-3-(8-aza-bicyclo[3.2.1]oct-3-yl)-phenol and -phenyl carboxamide series of μ-opioid receptor antagonists.	2017 Jul 1	28499731

Patents

Sample Use Guides

In Vivo Use Guide

Capsules once daily

Route of Administration: Oral

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:42:29 UTC 2023` Edited by `admin` on `Sat Dec 16 05:42:29 UTC 2023`
Record UNII	85U7ROB149
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AXELOPRAN

Official Name

English

BENZAMIDE, 3-((3-ENDO)-8-(2-((CYCLOHEXYLMETHYL)((2S)-2,3-DIHYDROXY-1-OXOPROPYL)AMINO)ETHYL)-8-AZABICYCLO(3.2.1)OCT-3-YL)-

Common Name

English

axelopran [INN]

Common Name

English

TD-1211

Code

English

AXELOPRAN [USAN]

Common Name

English

Axelopran [WHO-DD]

Common Name

English

3-((1R,3R,5S)-8-(2-(CYCLOHEXYLMETHYL((2S)-2,3-DIHYDROXYPROPANOYL)AMINO(ETHYL)-8-AZABICYCLO(3.2.1)OCTAN-3-YL(BENZAMIDE

Common Name

English

Code System Code Type Description

WIKIPEDIA

Axelopran