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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 of AXELOPRAN SULFATE

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

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
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
Patents

Sample Use Guides

Capsules once daily
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 08:37:28 UTC 2023
Edited
by admin
on Sat Dec 16 08:37:28 UTC 2023
Record UNII
8OJM0A31U9
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
AXELOPRAN SULFATE
USAN   WHO-DD  
USAN  
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
Created by admin on Sat Dec 16 08:37:29 UTC 2023 , Edited by admin on Sat Dec 16 08:37:29 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL3137313
Created by admin on Sat Dec 16 08:37:29 UTC 2023 , Edited by admin on Sat Dec 16 08:37:29 UTC 2023
PRIMARY
SMS_ID
300000044464
Created by admin on Sat Dec 16 08:37:29 UTC 2023 , Edited by admin on Sat Dec 16 08:37:29 UTC 2023
PRIMARY
DRUG BANK
DBSALT002121
Created by admin on Sat Dec 16 08:37:29 UTC 2023 , Edited by admin on Sat Dec 16 08:37:29 UTC 2023
PRIMARY
USAN
BC-62
Created by admin on Sat Dec 16 08:37:29 UTC 2023 , Edited by admin on Sat Dec 16 08:37:29 UTC 2023
PRIMARY
CAS
949904-50-1
Created by admin on Sat Dec 16 08:37:29 UTC 2023 , Edited by admin on Sat Dec 16 08:37:29 UTC 2023
PRIMARY
CAS
1050202-71-5
Created by admin on Sat Dec 16 08:37:29 UTC 2023 , Edited by admin on Sat Dec 16 08:37:29 UTC 2023
NON-SPECIFIC STOICHIOMETRY
NCI_THESAURUS
C142943
Created by admin on Sat Dec 16 08:37:29 UTC 2023 , Edited by admin on Sat Dec 16 08:37:29 UTC 2023
PRIMARY
FDA UNII
8OJM0A31U9
Created by admin on Sat Dec 16 08:37:29 UTC 2023 , Edited by admin on Sat Dec 16 08:37:29 UTC 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY