Remacemide HCl
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MedKoo CAT#: 326897

CAS#: 111686-79-4 (HCl)

Description: Remacemide, also known as PR-934423 and FPL 12924AA, is a low-affinity NMDA antagonist with sodium channel blocking properties. It has been studied for the treatment of acute ischemic stroke, epilepsy, Huntington's disease, and Parkinson's disease. Remacemide binds weakly and noncompetitively to the ionic channel site of the NMDA receptor complex. Remacemide binds both allosterically and in the channel. However, because remacemide binds so weakly to NMDAR, much of remacemide's in vivo effect against excitotoxicity is thought to be caused by its metabolic transformation to the more potent desglycine derivative FPL 12495.

Chemical Structure

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Remacemide HCl
CAS# 111686-79-4 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326897
Name: Remacemide HCl
CAS#: 111686-79-4 (HCl)
Chemical Formula: C17H21ClN2O
Exact Mass: 0.00
Molecular Weight: 304.818
Elemental Analysis: C, 66.99; H, 6.94; Cl, 11.63; N, 9.19; O, 5.25

Price and Availability

Size Price Availability Quantity
10mg USD 280
50mg USD 800
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Related CAS #: 128298-28-2 (free base)   111686-79-4 (HCl)    

Synonym: PR-934423; PR934423 PR 934423; PR 934-423A; FPL 12924AA; Remacemide hydrochloride

IUPAC/Chemical Name: 2-Amino-N-(1-methyl-1,2-diphenylethyl)acetamide monohydrochloride

InChi Key: HYQMIUSWZXGTCC-UHFFFAOYSA-N

InChi Code: InChI=1S/C17H20N2O.ClH/c1-17(19-16(20)13-18,15-10-6-3-7-11-15)12-14-8-4-2-5-9-14;/h2-11H,12-13,18H2,1H3,(H,19,20);1H

SMILES Code: O=C(NC(C1=CC=CC=C1)(C)CC2=CC=CC=C2)CN.[H]Cl

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: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

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: Related CAS# 128298-28-2 (Remacemide) 111686-79-4 (Remacemide hydrochloride)

Product Data:
Product Data
Instruction:
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Biological target: Remacemide hydrochloride is an non-competitive NMDA receptor antagonist that blocks ion channel and allosteric modulatory site (IC50 = 8 - 68 mM). Remacemide hydrochloride is anticonvulsant in vivo and metabolizes to a more potent desglycine analog. Weakly blocks voltage-dependent Na+ channels (IC50 = 161 mM). In an animal model of Huntington's disease, it extends survival and delays disease; this effect is more pronounced when combined with Coenzyme Q10.
In vitro activity: Electrophysiological recordings and cell swelling measurements were performed from striatal neurons in control condition and during combined oxygen and glucose deprivation in a brain slice preparation. Remacemide and lamotrigine were neuroprotective against the irreversible field potential loss and cell swelling induced by in vitro ischemia, and their coadministration exerted an additive neuroprotective action. Reference: Exp Neurol. 2003 Aug;182(2):461-9. https://pubmed.ncbi.nlm.nih.gov/12895457/
In vivo activity: Chronic treatment with ketamine or remacemide had no effect on the acquisition of incremental repeated acquisition (IRA) task performance of food-reinforced operant behaviors in female Sprague-Dawley rats at any dose tested. Chronic treatment with low-dose remacemide delayed the acquisition of audio/visual discrimination (AVD) task performance briefly midway through treatment, but chronic treatment with high-dose remacemide delayed the acquisition of AVD task performance until late in treatment. Reference: F S Rep. 2022 Nov 21;4(2 Suppl):73-82. https://pubmed.ncbi.nlm.nih.gov/17291718/

Preparing Stock Solutions

The following data is based on the product molecular weight 304.82 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.

Recalculate based on batch purity %
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. Calabresi P, Marti M, Picconi B, Saulle E, Costa C, Centonze D, Pisani F, Bernardi G. Lamotrigine and remacemide protect striatal neurons against in vitro ischemia: an electrophysiological study. Exp Neurol. 2003 Aug;182(2):461-9. doi: 10.1016/s0014-4886(03)00117-1. PMID: 12895457. 2. Norris SK, King AE. Electrophysiological effects of the anticonvulsant remacemide hydrochloride and its metabolite ARL 12495AA on rat CA1 hippocampal neurons in vitro. Neuropharmacology. 1997 Jul;36(7):951-9. doi: 10.1016/s0028-3908(97)00069-5. PMID: 9257939. 3. Borowicz KK, Malek R, Luszczki JJ, Ratnaraj N, Patsalos PN, Czuczwar SJ. Isobolographic analysis of interactions between remacemide and conventional antiepileptic drugs in the mouse model of maximal electroshock. Epilepsy Behav. 2007 Aug;11(1):6-12. doi: 10.1016/j.yebeh.2007.04.018. Epub 2007 Jun 29. PMID: 17602881. 4. Wright LK, Pearson EC, Hammond TG, Paule MG. Behavioral effects associated with chronic ketamine or remacemide exposure in rats. Neurotoxicol Teratol. 2007 May-Jun;29(3):348-59. doi: 10.1016/j.ntt.2006.12.004. Epub 2007 Jan 16. PMID: 17291718. Arjona Ferreira JC, Migoya E. Development of relugolix combination therapy as a medical treatment option for women with uterine fibroids or endometriosis. F S Rep. 2022 Nov 21;4(2 Suppl):73-82. doi: 10.1016/j.xfre.2022.11.010. PMID: 37223761; PMCID: PMC10201285.
In vitro protocol: 1. Calabresi P, Marti M, Picconi B, Saulle E, Costa C, Centonze D, Pisani F, Bernardi G. Lamotrigine and remacemide protect striatal neurons against in vitro ischemia: an electrophysiological study. Exp Neurol. 2003 Aug;182(2):461-9. doi: 10.1016/s0014-4886(03)00117-1. PMID: 12895457. 2. Norris SK, King AE. Electrophysiological effects of the anticonvulsant remacemide hydrochloride and its metabolite ARL 12495AA on rat CA1 hippocampal neurons in vitro. Neuropharmacology. 1997 Jul;36(7):951-9. doi: 10.1016/s0028-3908(97)00069-5. PMID: 9257939.
In vivo protocol: 1. Borowicz KK, Malek R, Luszczki JJ, Ratnaraj N, Patsalos PN, Czuczwar SJ. Isobolographic analysis of interactions between remacemide and conventional antiepileptic drugs in the mouse model of maximal electroshock. Epilepsy Behav. 2007 Aug;11(1):6-12. doi: 10.1016/j.yebeh.2007.04.018. Epub 2007 Jun 29. PMID: 17602881. 2. Wright LK, Pearson EC, Hammond TG, Paule MG. Behavioral effects associated with chronic ketamine or remacemide exposure in rats. Neurotoxicol Teratol. 2007 May-Jun;29(3):348-59. doi: 10.1016/j.ntt.2006.12.004. Epub 2007 Jan 16. PMID: 17291718. Arjona Ferreira JC, Migoya E. Development of relugolix combination therapy as a medical treatment option for women with uterine fibroids or endometriosis. F S Rep. 2022 Nov 21;4(2 Suppl):73-82. doi: 10.1016/j.xfre.2022.11.010. PMID: 37223761; PMCID: PMC10201285.

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1: Wesnes KA, Edgar C, Dean AD, Wroe SJ. The cognitive and psychomotor effects of remacemide and carbamazepine in newly diagnosed epilepsy. Epilepsy Behav. 2009 Mar;14(3):522-8. doi: 10.1016/j.yebeh.2008.11.012. Epub 2008 Dec 25. PubMed PMID: 19111629.

2: Borowicz KK, Malek R, Luszczki JJ, Ratnaraj N, Patsalos PN, Czuczwar SJ. Isobolographic analysis of interactions between remacemide and conventional antiepileptic drugs in the mouse model of maximal electroshock. Epilepsy Behav. 2007 Aug;11(1):6-12. Epub 2007 Jun 29. PubMed PMID: 17602881.

3: Wright LK, Pearson EC, Hammond TG, Paule MG. Behavioral effects associated with chronic ketamine or remacemide exposure in rats. Neurotoxicol Teratol. 2007 May-Jun;29(3):348-59. Epub 2007 Jan 16. PubMed PMID: 17291718.

4: Małek R, Borowicz KK, Kimber-Trojnar Z, Sobieszek G, Piskorska B, Czuczwar SJ. Remacemide--a novel potential antiepileptic drug. Pol J Pharmacol. 2003 Sep-Oct;55(5):691-8. Review. PubMed PMID: 14704464.

5: Calabresi P, Marti M, Picconi B, Saulle E, Costa C, Centonze D, Pisani F, Bernardi G. Lamotrigine and remacemide protect striatal neurons against in vitro ischemia: an electrophysiological study. Exp Neurol. 2003 Aug;182(2):461-9. PubMed PMID: 12895457.

6: Brodie MJ, Wroe SJ, Dean AD, Holdich TA, Whitehead J, Stevens JW. Efficacy and Safety of Remacemide versus Carbamazepine in Newly Diagnosed Epilepsy: Comparison by Sequential Analysis. Epilepsy Behav. 2002 Apr;3(2):140-146. PubMed PMID: 12609415.

7: Whitehead J, Stevens J, Brodie M, Wroe S, Dean A, Holdich T. Remacemide versus carbamazepine in newly diagnosed epilepsy. Epilepsy Behav. 2002 Aug;3(4):405-406. PubMed PMID: 12609343.

8: Nehlig A, Boehrer A. Effects of remacemide in two models of genetically determined generalized epilepsy, the GAERS and the audiogenic Wistar AS. Epilepsy Res. 2003 Jan;52(3):253-61. PubMed PMID: 12536058.

9: Leach JP, Marson AG, Hutton JL. Remacemide for drug-resistant localization related epilepsy. Cochrane Database Syst Rev. 2002;(4):CD001900. Review. PubMed PMID: 12519561.

10: Devinsky O, Vazquez B, Faught E, Leppik IE, Pellock JM, Schachter S, Alderfer V, Holdich TA. A double-blind, placebo-controlled study of remacemide hydrochloride in patients with refractory epilepsy following pre-surgical assessment. Seizure. 2002 Sep;11(6):371-6. PubMed PMID: 12160664.

11: Sills GJ, Santangeli S, Forrest G, Brodie MJ. Influence of cytochrome P450 induction on the pharmacokinetics and pharmacodynamics of remacemide hydrochloride. Epilepsy Res. 2002 May;49(3):247-54. PubMed PMID: 12076846.

12: Chadwick DW, Betts TA, Boddie HG, Crawford PM, Lindstrom P, Newman PK, Soryal I, Wroe S, Holdich TA. Remacemide hydrochloride as an add-on therapy in epilepsy: a randomized, placebo-controlled trial of three dose levels (300, 600 and 1200 mg/day) in a Q.I.D. regimen. Seizure. 2002 Mar;11(2):114-23. PubMed PMID: 11945098.

13: Jones MW, Blume WT, Guberman A, Lee MA, Pillay N, Weaver DF, Veloso F, Holdich TA. Remacemide hydrochloride as an add-on therapy in epilepsy: a randomized, placebo-controlled trial of three dose levels (300, 600 and 800 mg/day) in a B.I.D. regimen. Seizure. 2002 Mar;11(2):104-13. PubMed PMID: 11945097.

14: Popke EJ, Patton R, Newport GD, Rushing LG, Fogle CM, Allen RR, Pearson EC, Hammond TG, Paule MG. Assessing the potential toxicity of MK-801 and remacemide: chronic exposure in juvenile rhesus monkeys. Neurotoxicol Teratol. 2002 Mar-Apr;24(2):193-207. PubMed PMID: 11943507.

15: Santangeli S, Sills GJ, Thompson GG, Brodie MJ. Na(+) channel effects of remacemide and desglycinyl-remacemide in rat cortical synaptosomes. Eur J Pharmacol. 2002 Mar 1;438(1-2):63-8. PubMed PMID: 11906711.

16: Ferrante RJ, Andreassen OA, Dedeoglu A, Ferrante KL, Jenkins BG, Hersch SM, Beal MF. Therapeutic effects of coenzyme Q10 and remacemide in transgenic mouse models of Huntington's disease. J Neurosci. 2002 Mar 1;22(5):1592-9. PubMed PMID: 11880489.

17: Santangeli S, Sills GJ, Stone TW, Brodie MJ. Differential effects of remacemide and desglycinyl-remacemide on epileptiform burst firing in the rat hippocampal slice. Neurosci Lett. 2002 Mar 15;321(1-2):33-6. PubMed PMID: 11872250.

18: Ramaekers G, Lamers J, Verhey F, Muntjewerff D, Mobbs E, Sanders N, Lewis M, Lockton A. A comparative study of the effects of carbamazepine and the NMDA receptor antagonist remacemide on road tracking and car-following performance in actual traffic. Psychopharmacology (Berl). 2002 Jan;159(2):203-10. Epub 2001 Sep 22. PubMed PMID: 11862350.

19: Schilling G, Coonfield ML, Ross CA, Borchelt DR. Coenzyme Q10 and remacemide hydrochloride ameliorate motor deficits in a Huntington's disease transgenic mouse model. Neurosci Lett. 2001 Nov 27;315(3):149-53. PubMed PMID: 11716985.

20: Parkinson Study Group. Evaluation of dyskinesias in a pilot, randomized, placebo-controlled trial of remacemide in advanced Parkinson disease. Arch Neurol. 2001 Oct;58(10):1660-8. PubMed PMID: 11594926.