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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

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

Molecular Formula C2H4O2
Molecular Weight 60.052
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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
GLYX-13: a monoclonal antibody-derived peptide that acts as an N-methyl-D-aspartate receptor modulator.
2005 Dec
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 Fri Dec 15 16:30:57 GMT 2023
Edited
by admin
on Fri Dec 15 16:30:57 GMT 2023
Record UNII
90B8PDG67N
Record Status Validated (UNII)
Record Version
  • Download
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
PRIMARY
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
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ACTIVE MOIETY