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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 of AXELOPRAN

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
Novel Oral Therapies for Opioid-induced Bowel Dysfunction in Patients with Chronic Noncancer Pain.
2016 Mar
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
Clinical Overview and Considerations for the Management of Opioid-induced Constipation in Patients With Chronic Noncancer Pain.
2019 Feb
Patents

Sample Use Guides

Capsules once daily
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Thu Jul 06 11:25:27 UTC 2023
Edited
by admin
on Thu Jul 06 11:25:27 UTC 2023
Record UNII
85U7ROB149
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AXELOPRAN
INN   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Thu Jul 06 11:25:27 UTC 2023 , Edited by admin on Thu Jul 06 11:25:27 UTC 2023
PRIMARY
INN
9789
Created by admin on Thu Jul 06 11:25:27 UTC 2023 , Edited by admin on Thu Jul 06 11:25:27 UTC 2023
PRIMARY
NCI_THESAURUS
C171856
Created by admin on Thu Jul 06 11:25:27 UTC 2023 , Edited by admin on Thu Jul 06 11:25:27 UTC 2023
PRIMARY
SMS_ID
300000034121
Created by admin on Thu Jul 06 11:25:27 UTC 2023 , Edited by admin on Thu Jul 06 11:25:27 UTC 2023
PRIMARY
FDA UNII
85U7ROB149
Created by admin on Thu Jul 06 11:25:27 UTC 2023 , Edited by admin on Thu Jul 06 11:25:27 UTC 2023
PRIMARY
DRUG BANK
DB12013
Created by admin on Thu Jul 06 11:25:27 UTC 2023 , Edited by admin on Thu Jul 06 11:25:27 UTC 2023
PRIMARY
USAN
BC-61
Created by admin on Thu Jul 06 11:25:27 UTC 2023 , Edited by admin on Thu Jul 06 11:25:27 UTC 2023
PRIMARY
CAS
949904-48-7
Created by admin on Thu Jul 06 11:25:27 UTC 2023 , Edited by admin on Thu Jul 06 11:25:27 UTC 2023
PRIMARY
ChEMBL
CHEMBL3137313
Created by admin on Thu Jul 06 11:25:27 UTC 2023 , Edited by admin on Thu Jul 06 11:25:27 UTC 2023
PRIMARY
EPA CompTox
DTXSID301032386
Created by admin on Thu Jul 06 11:25:27 UTC 2023 , Edited by admin on Thu Jul 06 11:25:27 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TARGET -> INHIBITOR
Related Record Type Details
ACTIVE MOIETY