U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C22H29N2O4
Molecular Weight 385.4767
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 1

SHOW SMILES / InChI
Structure of METHYLSAMIDORPHAN

SMILES

[H][C@]12CC3=C(C(O)=C(C=C3)C(N)=O)[C@@]5(CC[N@+]1(C)CC4CC4)CC(=O)CC[C@@]25O

InChI

InChIKey=ATCVVCBJNHXIEX-ZAHKBLQYSA-O
InChI=1S/C22H28N2O4/c1-24(12-13-2-3-13)9-8-21-11-15(25)6-7-22(21,28)17(24)10-14-4-5-16(20(23)27)19(26)18(14)21/h4-5,13,17,28H,2-3,6-12H2,1H3,(H2-,23,26,27)/p+1/t17-,21-,22-,24-/m1/s1

HIDE SMILES / InChI

Molecular Formula C22H28N2O4
Molecular Weight 384.4687
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 3 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Methylsamidorphan (previously known as ALKS 37), an opioid receptor antagonist that was developed to treat opioid-induced bowel dysfunction. This drug participated in phase II clinical trial to evaluate the safety, tolerability, and efficacy when administered daily for 4 weeks to adults with Opioid-induced Constipation. However, the product profile did not satisfy the pre-specified criteria for advancing into phase III clinical trials. Based on this evaluation, was made the decision of discontinuation of the further methylsamidorphan study.

Approval Year

Sample Use Guides

In Vivo Use Guide
Capsules for oral administration
Route of Administration: Oral
Substance Class Chemical
Record UNII
8347HC35J6
Record Status Validated (UNII)
Record Version