AXELOPRAN SULFATE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H39N3O4.H2O4S
Molecular Weight	555.684
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(O)(=O)=O.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=QNFFAKFVKCGLPK-WTKDUOFSSA-N

InChI=1S/C26H39N3O4.H2O4S/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;1-5(2,3)4/h4,7-8,13,18,21-24,30-31H,1-3,5-6,9-12,14-17H2,(H2,27,32);(H2,1,2,3,4)/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

Molecular Formula	H2O4S
Molecular Weight	98.078
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
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
Clinical Overview and Considerations for the Management of Opioid-induced Constipation in Patients With Chronic Noncancer Pain.	2019 Feb	30289777

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 08:37:28 GMT 2023` Edited by `admin` on `Sat Dec 16 08:37:28 GMT 2023`
Record UNII	8OJM0A31U9
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

AXELOPRAN SULFATE

Official Name

English

3-[(1R,3R,5S)-8-(2-{(Cyclohexylmethyl)[(2S)-2,3-dihydroxypropanoyl]amino}ethyl)-8-azabicyclo[3.2.1]octan-3-yl]benzamide monosulfate

Systematic Name

English

TD-1211 SULFATE

Code

English

Axelopran sulfate [WHO-DD]

Common 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)-, SULFATE (1:1)

Systematic Name

English

AXELOPRAN SULFATE [USAN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C681