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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H31N5O6
Molecular Weight 413.4686
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RAPASTINEL

SMILES

[H][C@]1(CCCN1C(=O)[C@]2([H])CCCN2C(=O)[C@@H](N)[C@@H](C)O)C(=O)N[C@@H]([C@@H](C)O)C(N)=O

InChI

InChIKey=GIBQQARAXHVEGD-BSOLPCOYSA-N
InChI=1S/C18H31N5O6/c1-9(24)13(19)18(29)23-8-4-6-12(23)17(28)22-7-3-5-11(22)16(27)21-14(10(2)25)15(20)26/h9-14,24-25H,3-8,19H2,1-2H3,(H2,20,26)(H,21,27)/t9-,10-,11+,12+,13+,14+/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H31N5O6
Molecular Weight 413.4686
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 6 / 6
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: description was created based on several sources, including: http://mentalhealthdaily.com/2014/12/17/new-antidepressant-glyx-13-clinical-trials-partial-nmda-receptor-agonist/ | http://www.allergan.com/news/news/thomson-reuters/allergan-s-rapastinel-receives-fda-breakthrough-th | http://www.2shoesapp.com/event_files/280220120233Sussman%20--%20Novel%20Antidepressants%20in%20Development.pdf

Rapastinel (formerly known as GLYX-13) is an investigational intravenous formulation of a novel NMDA receptor partial agonist, which is being evaluated for adjunctive treatment of Major depressive disorder, and has shown a rapid onset of antidepressant efficacy 1 day after a single dose in a Phase 2 clinical trial of patients with Major depressive disorder who had an inadequate response to one or more antidepressants. No psychotomimetic or hallucinogenic side effects were observed with rapastinel. Few adverse events were reported by 5% or more of subjects and these were rated as mild or moderate. These included headache, somnolence, dizziness, dysgeusia, and fatigue. On January 29, 2016, Allergan (who acquired Naurex in July 2015) announced that rapastinel had received Breakthrough Therapy designation from the U.S. FDA for adjunctive treatment of major depressive disorder.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
100 μg/mL
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPASTINEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
26 μg/mL
5 mg/kg single, intravenous
dose: 5 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPASTINEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
5.2 μg/mL
1 mg/kg single, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPASTINEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
182 μg/mL
20 mg/kg single, intravenous
dose: 20 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPASTINEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1162 μg × min/mL
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPASTINEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
288 μg × min/mL
5 mg/kg single, intravenous
dose: 5 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPASTINEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
32 μg × min/mL
1 mg/kg single, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPASTINEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4030 μg × min/mL
20 mg/kg single, intravenous
dose: 20 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPASTINEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
9 min
10 mg/kg single, intravenous
dose: 10 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPASTINEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
7.4 min
5 mg/kg single, intravenous
dose: 5 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPASTINEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
4.7 min
1 mg/kg single, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPASTINEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
14 min
20 mg/kg single, intravenous
dose: 20 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
RAPASTINEL plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Antinociceptive action of GLYX-13: an N-methyl-D-aspartate receptor glycine site partial agonist.
2008 Jul 2
Rapastinel (GLYX-13) has therapeutic potential for the treatment of post-traumatic stress disorder: Characterization of a NMDA receptor-mediated metaplasticity process in the medial prefrontal cortex of rats.
2015 Nov 1
Patents

Patents

Sample Use Guides

450 mg weekly injections
Route of Administration: Intravenous
The enhancement of burst-evoked NMDAR EPSCs produced by 100 nM–1 uM GLYX-13 and, was converted by ifenprodil into a reduction in NMDAR currents, supporting the hypothesis that GLYX-13 produces enhancement of NMDAR-mediated conductance by a selective action on the glycine site of extrasynaptically enriched NMDARs that contain NR2B subunits.
Substance Class Chemical
Created
by admin
on Sat Dec 16 01:58:59 UTC 2023
Edited
by admin
on Sat Dec 16 01:58:59 UTC 2023
Record UNII
6A1X56B95E
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
RAPASTINEL
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
RAPASTINELUM
Common Name English
L-THREONINAMIDE, L-THREONYL-L-PROLYL-L-PROLYL-
Systematic Name English
TPPT-AMIDE
Common Name English
L-THREONYL-L-PROLYL-L-PROLYL-L-THREONINAMIDE
Systematic Name English
GLYX-13
Code English
rapastinel [INN]
Common Name English
Rapastinel [WHO-DD]
Common Name English
RAPASTINEL [USAN]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 199404
Created by admin on Sat Dec 16 01:58:59 UTC 2023 , Edited by admin on Sat Dec 16 01:58:59 UTC 2023
NCI_THESAURUS C265
Created by admin on Sat Dec 16 01:58:59 UTC 2023 , Edited by admin on Sat Dec 16 01:58:59 UTC 2023
Code System Code Type Description
SMS_ID
100000177061
Created by admin on Sat Dec 16 01:58:59 UTC 2023 , Edited by admin on Sat Dec 16 01:58:59 UTC 2023
PRIMARY
ChEMBL
CHEMBL3544917
Created by admin on Sat Dec 16 01:58:59 UTC 2023 , Edited by admin on Sat Dec 16 01:58:59 UTC 2023
PRIMARY
WIKIPEDIA
Rapastinel
Created by admin on Sat Dec 16 01:58:59 UTC 2023 , Edited by admin on Sat Dec 16 01:58:59 UTC 2023
PRIMARY
EPA CompTox
DTXSID501030481
Created by admin on Sat Dec 16 01:58:59 UTC 2023 , Edited by admin on Sat Dec 16 01:58:59 UTC 2023
PRIMARY
CAS
117928-94-6
Created by admin on Sat Dec 16 01:58:59 UTC 2023 , Edited by admin on Sat Dec 16 01:58:59 UTC 2023
PRIMARY
DRUG BANK
DB11801
Created by admin on Sat Dec 16 01:58:59 UTC 2023 , Edited by admin on Sat Dec 16 01:58:59 UTC 2023
PRIMARY
NCI_THESAURUS
C152156
Created by admin on Sat Dec 16 01:58:59 UTC 2023 , Edited by admin on Sat Dec 16 01:58:59 UTC 2023
PRIMARY
INN
9981
Created by admin on Sat Dec 16 01:58:59 UTC 2023 , Edited by admin on Sat Dec 16 01:58:59 UTC 2023
PRIMARY
FDA UNII
6A1X56B95E
Created by admin on Sat Dec 16 01:58:59 UTC 2023 , Edited by admin on Sat Dec 16 01:58:59 UTC 2023
PRIMARY
USAN
CD-27
Created by admin on Sat Dec 16 01:58:59 UTC 2023 , Edited by admin on Sat Dec 16 01:58:59 UTC 2023
PRIMARY
PUBCHEM
14539800
Created by admin on Sat Dec 16 01:58:59 UTC 2023 , Edited by admin on Sat Dec 16 01:58:59 UTC 2023
PRIMARY
MESH
C507283
Created by admin on Sat Dec 16 01:58:59 UTC 2023 , Edited by admin on Sat Dec 16 01:58:59 UTC 2023
PRIMARY
Related Record Type Details
TARGET->PARTIAL AGONIST
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY