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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H31N5O6.C2H4O2
Molecular Weight 473.5206
Optical Activity UNSPECIFIED
Defined Stereocenters 6 / 6
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of RAPASTINEL ACETATE

SMILES

CC(O)=O.[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=MNEQLJKNUQMKNP-GDLIIDCZSA-N
InChI=1S/C18H31N5O6.C2H4O2/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;1-2(3)4/h9-14,24-25H,3-8,19H2,1-2H3,(H2,20,26)(H,21,27);1H3,(H,3,4)/t9-,10-,11+,12+,13+,14+;/m1./s1

HIDE SMILES / InChI

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
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.
Name Type Language
RAPASTINEL ACETATE
Common Name English
L-THREONINAMIDE, L-THREONYL-L-PROLYL-L-PROLYL-, MONOACETATE
Systematic Name English
THR-PRO-PRO-THR-AMIDE ACETATE
Common Name English
L-THREONINAMIDE, L-THREONYL-L-PROLYL-L-PROLYL-, ACETATE (1:1)
Systematic Name English
Code System Code Type Description
FDA UNII
90B8PDG67N
Created by admin on Fri Dec 15 16:30:57 GMT 2023 , Edited by admin on Fri Dec 15 16:30:57 GMT 2023
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PUBCHEM
126480238
Created by admin on Fri Dec 15 16:30:57 GMT 2023 , Edited by admin on Fri Dec 15 16:30:57 GMT 2023
PRIMARY
CAS
491872-39-0
Created by admin on Fri Dec 15 16:30:57 GMT 2023 , Edited by admin on Fri Dec 15 16:30:57 GMT 2023
PRIMARY