114012-12-3

Hazards Identification

Pictogram(s):

Signal:

Warning

GHS Hazard Statements:

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statement Codes:

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories:

Skin Irrit. 2 (100%)
Eye Irrit. 2 (100%)
STOT SE 3 (100%)

Usage

Uses

Used in Pharmaceutical Industry:
PHACLOFEN is used as a GABAB receptor antagonist for its potential therapeutic applications in treating various conditions related to the central nervous system. Its ability to selectively target GABAB receptors makes it a valuable tool in research and drug development for conditions such as muscle spasms, spasticity, and certain neurological disorders.
Used in Research Applications:
In the field of scientific research, PHACLOFEN is used as a research tool to study the role of GABAB receptors in cellular and molecular processes. Its selective antagonism of GABAB receptors allows researchers to investigate the specific functions and signaling pathways associated with these receptors, contributing to a better understanding of their role in health and disease.
Used in Drug Development:
PHACLOFEN is also used in the development of new drugs targeting GABAB receptors. Its selective antagonistic properties make it a promising candidate for the development of novel therapeutics for conditions where modulation of GABAB receptor activity may be beneficial. This includes potential applications in the treatment of neurological disorders, pain management, and other related conditions.

Biological Activity

Selective GABA B antagonist. Phosphono analog of GABA B agonist baclofen ((RS)-4-Amino-3-(4-chlorophenyl)butanoic acid ).

Biochem/physiol Actions

Phaclofen plays a vital role in identifying the physiological importance of central and peripheral bicuculline-insensitive receptors with which GABA and (?) baclofen interact. Phaclofen acts as a GABAB receptor antagonist. Phaclofen has an ability to reversibly block the late, bicuculline resistant, K+ dependent inhibitory postsynaptic potential (IPSP) logged in projection cells of the cat and rat dorsal lateral geniculate nucleus and in rat hippocampal CA1 pyramidal neurons.

InChI:InChI=1/C9H13ClNO3P/c10-9-3-1-7(2-4-9)8(5-11)6-15(12,13)14/h1-4,8H,5-6,11H2,(H2,12,13,14)

Upstream product

• 114567-00-9 3-(4-chlorophenyl)-4-phosphonobutanoic acid 
• 21757-98-2 ethyl (E)-3-(4-chlorophenyl)-2-butenoate 
• 114566-97-1 ethyl 3-(4-chlorophenyl)-4-dimethoxyphosphinylbutanoate 
• 706-07-0 1-chloro-4-(2-nitrovinyl)benzene 
• 124831-11-4 Dimethyl 2-(4-chlorophenyl)-3-nitropropylphosphonate 
• 153805-70-0 (Z)-ethyl 4-bromo-3-(4-chlorophenyl)but-2-enoate 
• 124831-12-5 Dimethyl 3-amino-2-(4-chlorophenyl)propylphosphonate 

Related news

Actions of baelofen and PHACLOFEN (cas 114012-12-3) upon ON- and OFF-ganglion cells in the cat retina09/03/2019

The effects of the GABAB (γ-amino butyric acidB) receptor agonist, baclofen and its antagonist, phaclofen on physiologically identified retinal ganglion cells were studied in the optically intact eye of pentobarbitone-anaesthetized cats. These results were compared with the effects of the GABAA...detailed

Short communicationStimulation by PHACLOFEN (cas 114012-12-3) of inositol 1,4,5-triphosphate production in cultured neurons from chick tectum09/02/2019

The influence of γ-aminobutyric acid (GABA) receptor agonists and antagonists on the intracellular concentration of inositol 1,4,5-triphosphate (IP3) was examined in neuronal cultures of embryonic chick tectum. GABA and selective agonists of its receptors were inactive, whereas phaclofen, a GAB...detailed

Thioether analogues of baclofen, PHACLOFEN (cas 114012-12-3) and saclofen08/30/2019

Analogues of baclofen, phaclofen and saclofen, incorporating a sulfur atom within the methylene chain, have been tested against responses induced by baclofen for activity at γ-aminobutyric acid-B (GABAB) receptor sites, using a number of preparations including the guinea-pig isolated ileum and ...detailed

PHACLOFEN (cas 114012-12-3) antagonizes the depressant effect of baclofen on spinal reflex transmission in rats08/29/2019

The action of phaclofen, the phosphonic acid derivative of baclofen, on baclofen-induced suppression of spinal reflex transmission was tested in anaesthetized rats. Intrathecal (i.th.) injection of phaclofen, 100 nmol, antagonized the depressant effect of baclofen, 2 nmol, on spinal Hoffmann (H)...detailed

PHACLOFEN (cas 114012-12-3) antagonizes the antinociceptive but not the sedative effects of (−)-baclofen08/26/2019

1. Intraperitoneal (ip) injection of (−)-baclofen induced long-lasting antinociceptive and sedative effects in rats.2. Phaclofen, the phosphonic derivative of baclofen, fully antagonized the antinociceptive effect of (−)-baclofen. when injected intracerebroven-tricularly (icv), but not ip, phacl...detailed

Relevant academic research and scientific papers

The Synthesis of Phosphonobaclofen, an Antagonist of Baclofen

Phosphonobaclofen 3-amino-2-(4-chlorophenyl)propylphosphonic acid, has been synthesized in five steps from ethyl 3-(4-chlorophenyl)but-2-enoate, and is a specific antagonist of baclofen.The alternative synthetic pathways, involving conjugate addition of phosphite to 2-(4-chlorophenyl)propenenitrile and of cyanide to 2-(4-chlorophenyl)ethylphosphonate ester, failed.Cyanide ion did add efficiently to ethyl 3-(4-chlorophenyl)-2-diethoxyphosphinylprop-2-enoate and hydrogenation followed by hydrolysis of the product gave (2 S, 3 S)- and (2R, 3 R)-4-amino-3-(4-chlorophenyl)-2-phosphonobutanoic acid, which is also undergoing pharmacological evaluation.