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
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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24251380Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24251380
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.
Originator
Approval Year
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
PubMed
Title | Date | PubMed |
---|---|---|
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
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02943577
450 mg weekly injections
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16051282
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
Edited
Fri Dec 15 16:30:57 GMT 2023
by
admin
on
Fri Dec 15 16:30:57 GMT 2023
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Record UNII |
90B8PDG67N
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Record Status |
Validated (UNII)
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Record Version |
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ACTIVE MOIETY |