Brivaracetam

Base Information

• Chemical Name: Brivaracetam
• CAS No.: 357336-20-0
• Molecular Formula: C11H20 N2 O2
• Molecular Weight: 212.292
• Hs Code.: 2933990090
• European Community (EC) Number: 801-184-2
• UNII: U863JGG2IA
• DSSTox Substance ID: DTXSID00905081
• Nikkaji Number: J2.411.659J
• Wikipedia: Brivaracetam
• Wikidata: Q408099
• NCI Thesaurus Code: C65270
• RXCUI: 1739745
• Pharos Ligand ID: BRWYT3F6AUL5
• Metabolomics Workbench ID: 149511
• ChEMBL ID: CHEMBL607400
• Mol file: 357336-20-0.mol

Synonyms:(2S)-2-((4R)-2-oxo-4-propylpyrrolidin-1-yl)butanamide;1-pyrrolidineacetamide, alpha-ethyl-2-oxo-4-propyl-, (alphaS,4R)-;2-(2-oxo-4-propylpyrrolidin-1-yl)butanamide;brivaracetam;Briviact;UCB 34714;UCB-34714;UCB34714

Chemical Property of Brivaracetam

Chemical Property:

• Melting Point: 76.38°
• Boiling Point: 409.3±28.0 °C(Predicted)
• PKA: 15.74±0.50(Predicted)
• PSA: 63.40000
• Density: 1.062
• LogP: 1.53710
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly), Methanol (Slightly)
• XLogP3: 1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 212.152477885
• Heavy Atom Count: 15
• Complexity: 253

Purity/Quality:

99% ,99.9%, ^*data from raw suppliers

Brivaracetam ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Anticonvulsants
• Canonical SMILES: CCCC1CC(=O)N(C1)C(CC)C(=O)N
• Isomeric SMILES: CCC[C@@H]1CC(=O)N(C1)[C@@H](CC)C(=O)N
• Recent ClinicalTrials: A Study to Test the Long-term Safety, Tolerability and Efficacy of Brivaracetam in Study Participants 2 to 26 Years of Age With Childhood Absence Epilepsy or Juvenile Absence Epilepsy
• Recent EU Clinical Trials: “FAST ACUTE SEDATION AT INTENSIVE CARE VS. HIGH-DOSE I.V. ANTI-SEIZURE MEDICATION FOR TREATMENT OF NON-CONVULSIVE STATUS EPILEPTICUS - A RANDOMIZED, MULTICENTER TRIAL (FAST TRIAL)”
• Recent NIPH Clinical Trials: A study to test the safety and tolerability of brivaracetam in pediatric study participants with seizures
• Description: Brivaracetam, a chemical analog of Levetiracetam, is a racetam derivative with anticonvulsant effect. It is used for the treatment of partial-onset seizures with or without secondary generalisation, in combination with other antiepileptic drugs. The exact mechanism of brivaracetam's anti-epileptogenic activity is unknown. What is known is thatbrivaracetam binds SV2A with high affinity. SV2A is known to play a role in epileptogenesis through modulation of synaptic GABA release. It is thought that brivaracetam exerts its anti-epileptogenic effects through its binding to SV2A. Brivaracetam can also inhibit Na+ channels which may also contribute to its anti-epileptogenic action. Brivaracetam, a novel oral antiepileptic drug with a high affinity for synaptic vesicle protein 2A (SV2A), was approved in Europe and the US as an adjunctive therapy for the treatment of partial onset seizures with or without secondary generalization in patients aged 16 or older.42 Brivaracetam is very closely related to levetiracetam, an antiepileptic treatment whose immediate release formulation has been available in the United States as a generic drug since 2008, but whose extended release formulation is under patent protection until 2028. The two drugs, which were both developed by UCB Pharma, are structurally similar with brivaracetam having an n-propyl group at the C-4 position of the pyrrolidinone ring and levetiracetam having a hydrogen at this same position. A systematic investigation of the various substitutions of levetiracetam resulted in the identification of more potent and selective SV2A ligands and ultimately culminated in the discovery of brivaracetam, which has greater affinity for SV2A, improved selectivity, more rapid brain penetration, and faster onset of action against seizures than levetiracetam.
• Uses: Treatment ofTreatment of epilepsy, neuropathic pain and essential tremor. Brivaracetam, is a 4-n-propyl analog of levetiracetam (L331500), and a racetam derivative with anticonvulsant properties.
• Clinical Use: Antiepileptic agent
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: concentration reduced by rifampicin. Antidepressants: antagonism of anticonvulsant effect (convulsive threshold lowered). Antimalarials: mefloquine antagonises anticonvulsant effect. Antipsychotics: antagonism of anticonvulsant effect (convulsive threshold lowered). Orlistat: possibly increased risk of convulsions.

Technology Process of Brivaracetam

There total 164 articles about Brivaracetam which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.3%

(2S)-4,5-dehydro-(2-oxo-4-n-propyl-1-pyrrolidinyl)-2-butanamide (357338-13-7) → brivaracetam (357336-20-0,357336-99-3,943986-70-7)

Guidance literature:

With (R)-((4,4’-bi-1,3-benzodioxole)-5,5’-diyl)bis(bis(3,5-di-t-butyl-4-methoxyphenyl))phosphine; copper(l) chloride; sodium t-butanolate; In toluene; at -40 ℃; for 24h; Inert atmosphere;

Reference yield: 93.0%

(R)-N-((S)-1-amino-1-oxobutan-2-yl)-3-(chloromethyl)hexanamide → brivaracetam (357336-20-0,357336-99-3,943986-70-7)

Guidance literature:

With potassium tert-butylate; In tetrahydrofuran;

Reference yield: 92.0%

(S)-2-amino-butanamide (7324-11-0,53726-14-0,104652-77-9,143164-46-9) + C7H13IO2 → brivaracetam (357336-20-0,357336-99-3,943986-70-7)

Guidance literature:

C₇H₁₃IO₂; With 1,1'-carbonyldiimidazole; In toluene; at 10 - 20 ℃; for 0.166667h; Inert atmosphere;

(S)-2-amino-butanamide; In toluene; at 10 - 20 ℃;

upstream raw materials:

(S)-2-amino-butanamide

5-hydroxy-4-n-propyl-2,5-dihydrofuran-2-one

3-(iodomethyl)hexanoic acid

(2S)-2-(4-propylpyrrolidin-2-one)butanamide

Refernces

• 1、 -. "Novel preparation method of iracetam". Paragraph 0021-0027. . Retrieved 2021/10/13.
• 2、 -. "Intermediate for synthesizing brivaracetam and preparation method thereof". . . Retrieved 2021/02/10.