Vigabatrin

Base Information

• Chemical Name: Vigabatrin
• CAS No.: 60643-86-9
• Molecular Formula: C6H11NO2
• Molecular Weight: 129.159
• Hs Code.: 2922499990
• Mol file: 60643-86-9.mol

Synonyms:Vigabatrin

Chemical Property of Vigabatrin

Chemical Property:

• Melting Point: 209°
• Boiling Point: 73?°C749?mm Hg(lit.)
• Flash Point: 9℃
• PSA: 63.32000
• Density: 1.108?g/mL?at 25?°C(lit.)
• LogP: 1.06480
• Storage Temp.: Desiccate at +4°C
• Solubility.: Freely soluble in water, slightly soluble in methanol, practically insoluble in methylene chloride.

Purity/Quality:

99.9% ^*data from raw suppliers

Vigabatrin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R36/37/38:
• Hazard Codes: Xi,T,F
• Statements: 36/37/38-39/23/24/25-23/24/25-11
• Safety Statements: 26-36-45-36/37-16-7

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Description: Vigabatrin is a second- generation anti- epileptic drug (AED), known under the proprietary brand name of Sabril? (Sanofi, Paris) in the UK and USA. Vigabatrin, the gamma-vinyl derivative of GABA, is a new anticonvulsant reportedly effective in the treatment of intractable seizures unresponsive to currently available therapy. Mechanistically vigabatrin is a potent irreversible GABA aminotransferase inhibitor which modifies the enzyme's active-site by Michael addition. Other potential indications have been suggested for vigabatrin, including depression and schizophrenia.
• Indications: Epilepsy: adjunctive therapy of focal seizures with or without secondary generalization not satisfactorily controlled with other AEDs. Recommendations summarized from NICE (2012) Seizure types: on referral to tertiary care (focal seizures), contraindicated (generalized tonic- clonic seizures, tonic/ atonic seizures, absence seizures, myoclonic seizures). Epilepsy types: on referral to tertiary care (benign epilepsy with centrotemporal spikes, panayiotopoulos syndrome, late- onset childhood occipital epilepsy), contraindicated (absence syndromes, idiopathic generalized epilepsy, juvenile myoclonic epilepsy, Dravet syndrome, Lennox– Gastaut syndrome).
• Uses: antineoplastic antibiotic Vigabatrin is a selective GABA transaminase inhibitor.
• Biological Functions: Vigabatrin (Sabril) is a relatively specific irreversible inhibitor of GABA-transaminase (GABA-T), the major enzyme responsible for the metabolism of GABA in the mammalian CNS. As a result of inhibition of GABA-T, there is an increase in the concentration of GABA in the brain and consequently an increase in inhibitory neurotransmission. Vigabatrin is well absorbed orally and is distributed to all body systems.The major route of elimination for vigabatrin is renal excretion of the parent compound; no metabolites have been identified in humans. At present, the primary indication for vigabatrin is in the treatment of patients with partial seizures, but it appears to be an effective and generally well tolerated antiepileptic medication for other seizure types as well. It should not be used in patients with absence epilepsy or with myoclonic seizures. Vigabatrin is not approved as an AED in the United States, although it is approved in many other countries.
• Drug interactions: Potentially hazardous interactions with other drugs Antidepressants: anticonvulsant effect antagonised, convulsive threshold lowered; avoid with St John’s wort. Antiepileptics: concentration of phenytoin reduced. Antimalarials: mefloquine antagonises anticonvulsant effect. Antipsychotics: anticonvulsant effect antagonised. Orlistat: increased risk of convulsions.

Technology Process of Vigabatrin

There total 16 articles about Vigabatrin 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: 100.0%

→ 4-amino-5-hexenoic acid (60643-86-9,68506-86-5)

Guidance literature:

Reference yield: 74.0%

5(S)-Vinyl-2-Pyrrolidinone (7529-16-0) → 4-amino-5-hexenoic acid (60643-86-9,68506-86-5)

Guidance literature:

5(S)-Vinyl-2-Pyrrolidinone; With potassium hydroxide; In water; for 2h; Reflux;

With acetic acid; In water; isopropyl alcohol; at 0 - 30 ℃; for 4.5h;

DOI:10.1007/s11696-019-01030-2

Reference yield: 63.0%

4-benzenesulphonamido 5-hexenoic acid (144085-15-4) → 4-amino-5-hexenoic acid (60643-86-9,68506-86-5)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran;

DOI:10.1016/S0040-4020(01)86670-9

upstream raw materials:

4-benzenesulphonamido 5-hexenoic acid

4-(carbobenzyloxy)amino-5-hexenenitrile

5-bromo-3-(carbobenzyloxy)amino-1-pentene

3-(carbobenzyloxy)amino-4-penten-1-ol

Downstream raw materials:

5(S)-Vinyl-2-Pyrrolidinone

Boc-4-amino-4-vinylbutyric acid

(+)-Vigabatrin

4-ethyl aminobutyric acid

Refernces

• 1、 -. "Preparation method of aminohexenoic acid". Paragraph 0016; 0040; 0045; 0046; 0051; 0054; 0062; 0064. . Retrieved 2020/02/14.
• 2、 -. "Process for preparing 4-amino-5-hexenoic acid from succinimide". Page/Page column 9. . Retrieved 2013/02/28.