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

Details

Stereochemistry ABSOLUTE
Molecular Formula C21H26N2O4.C4H6O5
Molecular Weight 504.5296
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SAMIDORPHAN L-MALATE

SMILES

O[C@@H](CC(O)=O)C(O)=O.NC(=O)C1=CC=C2C[C@H]3N(CC4CC4)CC[C@@]5(CC(=O)CC[C@@]35O)C2=C1O

InChI

InChIKey=RARHXUAUPNYAJF-QSYGGRRVSA-N
InChI=1S/C21H26N2O4.C4H6O5/c22-19(26)15-4-3-13-9-16-21(27)6-5-14(24)10-20(21,17(13)18(15)25)7-8-23(16)11-12-1-2-12;5-2(4(8)9)1-3(6)7/h3-4,12,16,25,27H,1-2,5-11H2,(H2,22,26);2,5H,1H2,(H,6,7)(H,8,9)/t16-,20-,21-;2-/m10/s1

HIDE SMILES / InChI

Molecular Formula C4H6O5
Molecular Weight 134.0874
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Molecular Formula C21H26N2O4
Molecular Weight 370.4421
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Samidorphan was developed as a sublingually bioavailable µ-opioid receptor antagonist. This drug participated in clinical trials for the treatment of Schizophrenia, Alcohol Dependence, and Binge Eating Disorder. The oral dose pharmacokinetics, safety, and tolerability of samidorphan were evaluated in phase II double blind, placebo-controlled, randomized studies in healthy adults. In addition, the combination of samidorphan (SAM) with buprenorphine (BUP) was studied in phase III clinical trial in patients with major depressive disorder (MDM). It was shown that the long-term treatment did not reveal any new safety findings and confirmed that the risk of abuse and dependence with BUP/SAM was low.

Approval Year

PubMed

PubMed

TitleDatePubMed
Opioid Modulation With Buprenorphine/Samidorphan as Adjunctive Treatment for Inadequate Response to Antidepressants: A Randomized Double-Blind Placebo-Controlled Trial.
2016 May 1
Evaluation of samidorphan, a μ-opioid antagonist, in a drug discrimination assay in rats.
2018 Aug
Patents

Sample Use Guides

Samidorphan (Low Dose). Tablets taken once daily
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:37:17 GMT 2023
Edited
by admin
on Sat Dec 16 01:37:17 GMT 2023
Record UNII
0AJQ5N56E0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SAMIDORPHAN L-MALATE
USAN   WHO-DD  
USAN  
Official Name English
SAMIDORPHAN MALATE
Common Name English
Samidorphan l-malate [WHO-DD]
Common Name English
LYBALVI COMPONENT SAMIDORPHAN L-MALATE
Brand Name English
SAMIDORPHAN L-MALATE [ORANGE BOOK]
Common Name English
SAMIDORPHAN L-MALATE [USAN]
Common Name English
MORPHINAN-3-CARBOXAMIDE, 17-(CYCLOPROPYLMETHYL)-4,14-DIHYDROXY-6-OXO-, (2S)-2-HYDROXYBUTANEDIOATE (1:1)
Common Name English
SAMIDORPHAN L-MALATE COMPONENT OF LYBALVI
Brand Name English
RDC-0313-02
Code English
17-(CYCLOPROPYLMETHYL)-4,14-DIHYDROXY-6-OXOMORPHINAN-3-CARBOXAMIDE HYDROGEN (2S)-2-HYDROXYBUTANEDIOATE SALT
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C681
Created by admin on Sat Dec 16 01:37:17 GMT 2023 , Edited by admin on Sat Dec 16 01:37:17 GMT 2023
Code System Code Type Description
PUBCHEM
53362094
Created by admin on Sat Dec 16 01:37:17 GMT 2023 , Edited by admin on Sat Dec 16 01:37:17 GMT 2023
PRIMARY
NCI_THESAURUS
C152294
Created by admin on Sat Dec 16 01:37:17 GMT 2023 , Edited by admin on Sat Dec 16 01:37:17 GMT 2023
PRIMARY
EVMPD
SUB177950
Created by admin on Sat Dec 16 01:37:17 GMT 2023 , Edited by admin on Sat Dec 16 01:37:17 GMT 2023
PRIMARY
RXCUI
2570387
Created by admin on Sat Dec 16 01:37:17 GMT 2023 , Edited by admin on Sat Dec 16 01:37:17 GMT 2023
PRIMARY
SMS_ID
100000163599
Created by admin on Sat Dec 16 01:37:17 GMT 2023 , Edited by admin on Sat Dec 16 01:37:17 GMT 2023
PRIMARY
CAS
1204592-75-5
Created by admin on Sat Dec 16 01:37:17 GMT 2023 , Edited by admin on Sat Dec 16 01:37:17 GMT 2023
PRIMARY
USAN
XX-133
Created by admin on Sat Dec 16 01:37:17 GMT 2023 , Edited by admin on Sat Dec 16 01:37:17 GMT 2023
PRIMARY
FDA UNII
0AJQ5N56E0
Created by admin on Sat Dec 16 01:37:17 GMT 2023 , Edited by admin on Sat Dec 16 01:37:17 GMT 2023
PRIMARY
DAILYMED
0AJQ5N56E0
Created by admin on Sat Dec 16 01:37:17 GMT 2023 , Edited by admin on Sat Dec 16 01:37:17 GMT 2023
PRIMARY
ChEMBL
CHEMBL426084
Created by admin on Sat Dec 16 01:37:17 GMT 2023 , Edited by admin on Sat Dec 16 01:37:17 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY