Rapastinel | GLYX-13 | BV-102 | CAS#117928-94-6

MedKoo Cat#: 326679 | Name: Rapastinel

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Rapastinel, also known as GLYX 13 and BV 102, is a monoclonal antibody-derived tetrapeptide that acts as a partial agonist at the glycine site of the N-methyl-D-aspartate (NMDA) receptor.

Chemical Structure

Rapastinel

CAS#117928-94-6 (free base)

Theoretical Analysis

MedKoo Cat#: 326679

Name: Rapastinel

CAS#: 117928-94-6 (free base)

Chemical Formula: C18H31N5O6

Exact Mass: 413.2274

Molecular Weight: 413.48

Elemental Analysis: C, 52.29; H, 7.56; N, 16.94; O, 23.22

Price and Availability

Size	Price	Availability
10mg	USD 150.00	Ready to ship
25mg	USD 250.00	Ready to ship
50mg	USD 450.00	Ready to ship
100mg	USD 750.00	Ready to ship
200mg	USD 1,250.00	Ready to ship
500mg	USD 2,250.00	Ready to ship
1g	USD 3,650.00	Ready to ship
2g	USD 6,250.00	Ready to ship

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Related CAS #

491872-39-0 (acetate) 117928-94-6 (free base)

Synonym

GLYX-13; GLYX 13; GLYX13; BV-102; BV102; BV 102; TPPT-amide; Rapastinel

IUPAC/Chemical Name

(S)-1-(L-threonyl-L-prolyl)-N-((2S,3R)-1-amino-3-hydroxy-1-oxobutan-2-yl)pyrrolidine-2-carboxamide

InChi Key

GIBQQARAXHVEGD-BSOLPCOYSA-N

InChi Code

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

SMILES Code

C[C@@H](O)[C@@H](C(N)=O)NC([C@H]1N(C([C@H]2N(C([C@H]([C@H](O)C)N)=O)CCC2)=O)CCC1)=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO, DMF, and ethanol

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO, DMF, and ethanol

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#A24T10K22

QC Data

View QC data: current batch, Lot#A24T10K22

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Rapastinel is active in vivo when administered intravenously and passes through the blood-brain barrier. In animals, Rapastinel blocks neuropathic pain, enhances learning and memory, and significantly reduces anxiety. Rapastinel induces rapid antidepressant-like effects in animal models and rescued normal behavior in a rat model of autism.

In vitro activity:

Extracellular binding of rapastinel to the N-methyl-D-aspartate receptor (NMDAR) produces a long-range reduction in affinity of the Ca2+ inactivation site on the NMDAR C-terminus accessible to the intracellular space. This study shows that this action underlies the enhancement in NMDAR-gated conductance elicited by rapastinel. Reference: Neuroreport. 2022 May 4;33(7):312-319. https://pubmed.ncbi.nlm.nih.gov/35594441/

In vivo activity:

This study suggests that the accelerated loss of withdrawal signs and blunted relapse to morphine conditioned place preference in rapastinel treated rats could provide an adjunctive therapy for opioid dependence with rapastinel. Reference: Pharmacol Biochem Behav. 2022 Nov;221:173485. https://pubmed.ncbi.nlm.nih.gov/36302442/

	Solvent	mg/mL	mM
Solubility
	DMF	25.0	60.46
	DMSO	15.0	36.27
	Ethanol	10.0	24.18

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 413.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

1. Zhang XL, Berglund NA, Burgdorf JS, Donello JE, Moskal JR, Stanton PK. Extracellular application of the N-methyl-D-aspartate receptor allosteric modulator rapastinel acts remotely to regulate Ca2+ inactivation at an intracellular locus. Neuroreport. 2022 May 4;33(7):312-319. doi: 10.1097/WNR.0000000000001787. Epub 2022 Apr 8. PMID: 35594441. 2. Moskal JR, Burgdorf JS, Stanton PK, Kroes RA, Disterhoft JF, Burch RM, Khan MA. The Development of Rapastinel (Formerly GLYX-13); A Rapid Acting and Long Lasting Antidepressant. Curr Neuropharmacol. 2017;15(1):47-56. doi: 10.2174/1570159x14666160321122703. PMID: 26997507; PMCID: PMC5327451. 3. Shen M, Lv D, Liu X, Wang C. ERK/mTOR signaling may underlying the antidepressant actions of rapastinel in mice. Transl Psychiatry. 2022 Dec 22;12(1):522. doi: 10.1038/s41398-022-02290-5. PMID: 36550125; PMCID: PMC9780240. 4. Armstrong C, Ferrante J, Lamichhane N, Reavis Z, Walker D, Patkar A, Kuhn C. Rapastinel accelerates loss of withdrawal signs after repeated morphine and blunts relapse to conditioned place preference. Pharmacol Biochem Behav. 2022 Nov;221:173485. doi: 10.1016/j.pbb.2022.173485. Epub 2022 Oct 24. PMID: 36302442.

In vitro protocol:

In vivo protocol:

1. Shen M, Lv D, Liu X, Wang C. ERK/mTOR signaling may underlying the antidepressant actions of rapastinel in mice. Transl Psychiatry. 2022 Dec 22;12(1):522. doi: 10.1038/s41398-022-02290-5. PMID: 36550125; PMCID: PMC9780240. 2. Armstrong C, Ferrante J, Lamichhane N, Reavis Z, Walker D, Patkar A, Kuhn C. Rapastinel accelerates loss of withdrawal signs after repeated morphine and blunts relapse to conditioned place preference. Pharmacol Biochem Behav. 2022 Nov;221:173485. doi: 10.1016/j.pbb.2022.173485. Epub 2022 Oct 24. PMID: 36302442.

1: Kargbo RB. Psychoplastogens: A Novel Therapeutic Approach for Neurological Diseases and Disorders. ACS Med Chem Lett. 2023 Aug 8;14(9):1144-1145. doi: 10.1021/acsmedchemlett.3c00309. PMID: 37736170; PMCID: PMC10510528. 2: Shen M, Lv D, Liu X, Wang C. ERK/mTOR signaling may underlying the antidepressant actions of rapastinel in mice. Transl Psychiatry. 2022 Dec 22;12(1):522. doi: 10.1038/s41398-022-02290-5. PMID: 36550125; PMCID: PMC9780240. 3: Armstrong C, Ferrante J, Lamichhane N, Reavis Z, Walker D, Patkar A, Kuhn C. Rapastinel accelerates loss of withdrawal signs after repeated morphine and blunts relapse to conditioned place preference. Pharmacol Biochem Behav. 2022 Nov;221:173485. doi: 10.1016/j.pbb.2022.173485. Epub 2022 Oct 24. PMID: 36302442. 4: Vasilescu AN, Pfeiffer N, Terraneo F, Riva MA, Lang UE, Inta D, Gass P. Region-Specific Enhancement of c-fos Expression by Combined Treatment With NMDA Receptor Agonists and Antagonists With Antidepressant Potential. Int J Neuropsychopharmacol. 2022 Nov 17;25(11):946-950. doi: 10.1093/ijnp/pyac051. PMID: 35974297; PMCID: PMC9670745. 5: Rajagopal L, Huang M, He W, Ryan C, Elzokaky A, Banerjee P, Meltzer HY. Repeated administration of rapastinel produces exceptionally prolonged rescue of memory deficits in phencyclidine-treated mice. Behav Brain Res. 2022 Aug 26;432:113964. doi: 10.1016/j.bbr.2022.113964. Epub 2022 Jun 17. PMID: 35718230. 6: Zhang XL, Berglund NA, Burgdorf JS, Donello JE, Moskal JR, Stanton PK. Extracellular application of the N-methyl-D-aspartate receptor allosteric modulator rapastinel acts remotely to regulate Ca2+ inactivation at an intracellular locus. Neuroreport. 2022 May 4;33(7):312-319. doi: 10.1097/WNR.0000000000001787. Epub 2022 Apr 8. PMID: 35594441. 7: Wang YT, Zhang NN, Liu LJ, Jiang H, Hu D, Wang ZZ, Chen NH, Zhang Y. Glutamatergic receptor and neuroplasticity in depression: Implications for ketamine and rapastinel as the rapid-acting antidepressants. Biochem Biophys Res Commun. 2022 Feb 26;594:46-56. doi: 10.1016/j.bbrc.2022.01.024. Epub 2022 Jan 17. PMID: 35074585. 8: Bisht B, Madhavan N. Quick Access to High-Purity Peptide Drugs Bradykinin, Leuprolide Analogue, 2(PZ-128), and Rapastinel with Minimal Reagents. J Org Chem. 2021 Dec 17;86(24):17667-17672. doi: 10.1021/acs.joc.1c01906. Epub 2021 Nov 25. PMID: 34823358. 9: Dean RL, Hurducas C, Hawton K, Spyridi S, Cowen PJ, Hollingsworth S, Marquardt T, Barnes A, Smith R, McShane R, Turner EH, Cipriani A. Ketamine and other glutamate receptor modulators for depression in adults with unipolar major depressive disorder. Cochrane Database Syst Rev. 2021 Sep 12;9(9):CD011612. doi: 10.1002/14651858.CD011612.pub3. PMID: 34510411; PMCID: PMC8434915. 10: Su S, Kay G, Hochadel T, Rojo J, Christopher Stein J, Boinpally R, Periclou A. A randomized, multicenter trial assessing the effects of rapastinel compared to ketamine, alprazolam, and placebo on simulated driving performance. Clin Transl Sci. 2022 Jan;15(1):255-266. doi: 10.1111/cts.13145. Epub 2021 Nov 7. PMID: 34423904; PMCID: PMC8742651. 11: Hecking J, Davoudian PA, Wilkinson ST. Emerging Therapeutics Based on the Amino Acid Neurotransmitter System: An Update on the Pharmaceutical Pipeline for Mood Disorders. Chronic Stress (Thousand Oaks). 2021 Jun 2;5:24705470211020446. doi: 10.1177/24705470211020446. PMID: 34124495; PMCID: PMC8175843. 12: Henter ID, Park LT, Zarate CA Jr. Novel Glutamatergic Modulators for the Treatment of Mood Disorders: Current Status. CNS Drugs. 2021 May;35(5):527-543. doi: 10.1007/s40263-021-00816-x. Epub 2021 Apr 26. PMID: 33904154; PMCID: PMC8201267. 13: Crosta CM, Hernandez K, Bhattiprolu AK, Fu AY, Moore JC, Clarke SG, Dudzinski NR, Brzustowicz LM, Paradiso KG, Firestein BL. Characterization hiPSC- derived neural progenitor cells and neurons to investigate the role of NOS1AP isoforms in human neuron dendritogenesis. Mol Cell Neurosci. 2020 Dec;109:103562. doi: 10.1016/j.mcn.2020.103562. Epub 2020 Sep 26. PMID: 32987141; PMCID: PMC7736313. 14: Yang PS, Peng HY, Lin TB, Hsieh MC, Lai CY, Lee AS, Wang HH, Ho YC. NMDA receptor partial agonist GLYX-13 alleviates chronic stress-induced depression- like behavior through enhancement of AMPA receptor function in the periaqueductal gray. Neuropharmacology. 2020 Nov 1;178:108269. doi: 10.1016/j.neuropharm.2020.108269. Epub 2020 Aug 10. PMID: 32791085. 15: Vasilescu AN, Mallien A, Pfeiffer N, Lang UE, Gass P, Inta D. Rapastinel alleviates the neurotoxic effect induced by NMDA receptor blockade in the early postnatal mouse brain. Eur Arch Psychiatry Clin Neurosci. 2021 Dec;271(8):1587-1591. doi: 10.1007/s00406-020-01180-5. Epub 2020 Aug 13. PMID: 32789675. 16: K V A, Mohan AS, Chakravarty S. Rapid acting antidepressants in the mTOR pathway: Current evidence. Brain Res Bull. 2020 Oct;163:170-177. doi: 10.1016/j.brainresbull.2020.07.022. Epub 2020 Jul 31. PMID: 32739296. 17: Pothula S, Kato T, Liu RJ, Wu M, Gerhard D, Shinohara R, Sliby AN, Chowdhury GMI, Behar KL, Sanacora G, Banerjee P, Duman RS. Cell-type specific modulation of NMDA receptors triggers antidepressant actions. Mol Psychiatry. 2021 Sep;26(9):5097-5111. doi: 10.1038/s41380-020-0796-3. Epub 2020 Jun 2. PMID: 32488125. 18: Lee B, Pothula S, Duman RS. NMDAR modulators as rapid antidepressants: Converging and distinct signaling mechanisms. Integr Clin Med. 2020 Jun;4(2):10.15761/icm.1000173. doi: 10.15761/icm.1000173. Epub 2020 Feb 4. PMID: 34381955; PMCID: PMC8353843. 19: Banerjee P, Donello JE, Hare B, Duman RS. Rapastinel, an NMDAR positive modulator, produces distinct behavioral, sleep, and EEG profiles compared with ketamine. Behav Brain Res. 2020 Aug 5;391:112706. doi: 10.1016/j.bbr.2020.112706. Epub 2020 May 24. PMID: 32461133. 20: Hu J, Duan W, Liu Y. Ketamine inhibits aerobic glycolysis in colorectal cancer cells by blocking the NMDA receptor-CaMK II-c-Myc pathway. Clin Exp Pharmacol Physiol. 2020 May;47(5):848-856. doi: 10.1111/1440-1681.13248. Epub 2020 Jan 22. PMID: 31889340.