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(-)-Baclofen

(-)-Baclofen structure

CAS No:
69308-37-8
Formula:
C10H12ClNO2
Chemical Name:
(-)-Baclofen
Synonyms:
Benzenepropanoic acid,β-(aminomethyl)-4-chloro-,(βR)-;Benzenepropanoic acid,β-(aminomethyl)-4-chloro-,(R)-;(βR)-β-(Aminomethyl)-4-chlorobenzenepropanoic acid;l-Baclofen;(-)-Baclofen;(R)-Baclofen;(R)-(-)-Baclofen;(R)-4-Amino-3-(4-chlorophenyl)butanoic acid;D-Baclofen;R-(-)-Baclofen;(R)-4-Amino-3-(4-chlorophenyl)butyric acid;Arbaclofen;STX 209;AGI 006;(R)-4-Amino-3-(4-chlorophenyl)butanoic acid;(3R)-4-Amino-3-(4-chlorophenyl)butanoic acid;2375745-79-0
Categories:
Biochemical Engineering > Inhibitors

Description

(R)-Baclofen(STX209) is a selective GABAB receptor agonist. IC50 value:Target: GABAB receptorGABAB receptors are metabotropic receptors which produce slow inhibitory signals. By manipulating GABAB receptor activity using Baclofen, a variety of functions are studied including synaptic transmissions and antinociception events.

Arbaclofen, or STX209, is the R-enantiomer of baclofen. It is believed to be a selective gamma-amino butyric acid type B receptor agonist, and has been investigated as a treatment for autism spectrum disorder and fragile X syndrome in randomized, double blind, placebo controlled trials. It has also been investigated as a treatment for spasticity due to multiple sclerosis and spinal cord injury. Arbaclofen was investigated as a treatment for gastroesophageal reflux disease (GERD); however, with disappointing results.

(-)-Baclofen Basic Attributes

Molecular Weight：

213.66

Exact Mass：

213.66

UNII：

NYU6UTW25B

DSSTox ID：

DTXSID90219366

Characteristics

PSA：

63.3

XLogP3：

-1

Density：

1.3±0.1 g/cm3

Melting Point：

188-189 °C @ Solvent: Hexane, Isopropanol

Boiling Point：

364.3°C at 760 mmHg

Flash Point：

174.1±25.1 °C

Refractive Index：

1.577

Water Solubility：

2090

Storage Conditions：

Store at RT

Safety Information

Hazard category：

6.1

Transport codes：

2811

RTECS Number：

DA8339450

Precautionary statement(s)：

P261, P264, P270, P271, P272, P280, P285, P301+P310, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, P501

Hazard Statements：

H300

GHS Classification：

|Danger|H300 (33.33%): Fatal if swallowed [Danger Acute toxicity, oral]|P261, P264, P270, P271, P272, P280, P285, P301+P310, P302+P352, P304+P340, P304+P341, P305+P351+P338, P312, P321, P330, P332+P313, P333+P313, P337+P313, P342+P311, P362, P363, P403+P233, P405, and P501|Aggregated GHS information provided by 3 companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Drug Information

Drug Indication：

Investigated in clinical trials as a potential treatment for spasticity in multiple sclerosis, autism spectrum disorder, and social withdrawal in fragile X syndrome.

Absorption：

Unlike baclofen, absorption of arbaclofen is not limited to the upper small intestine. Arbaclofen can also be absorbed in the lower small intestine and the colon, allowing for the development of sustained release formulations.|>80% of R-baclofen is renally eliminated unchanged.|Blood clearance of an IV bolus of R-baclofen in rats, monkeys, and dogs, resulted in a half life of 1.6-3.4hours, in one study. Total blood clearance was reported to be 0.51±0.13L/h/kg in rats, 0.31±0.11L/h/kg in monkeys, and 0.24±0.01L/h/kg in dogs. (2)

Mechanism of Action：

Arbaclofen, or R-baclofen, acts upstream of the mGluR5 receptor to increase inhibitory neurotransmission. It is the isomer of baclofen which harbors antispastic activity.

(-)-Baclofen Use and Manufacturing

Uses

R-Enantiomer of Baclofen. Specific GABA-B receptor agonist. Muscle relaxant (skeletal).

Use Classification：

Human drugs -> Rare disease (orphan)

Computed Properties

Molecular Weight:213.66
XLogP3:-1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:4
Exact Mass:213.0556563
Monoisotopic Mass:213.0556563
Topological Polar Surface Area:63.3
Heavy Atom Count:14
Complexity:191
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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