Structure via PubChem · Public domain (PubChem)
(RS)-baclofen
Sign in to saveAlso known as beta-(p-chlorophenyl)-gamma-aminobutyric acid, beta-(aminomethyl)-4-chlorobenzenepropanoic acid, beta-(4-chlorophenyl)gaba, DL-4-amino-3-p-chlorophenylbutanoic acid, 4-amino-3-(4-chlorophenyl)butyric acid, (+-)-baclofen, beta-(aminomethyl)-p-chlorohydrocinnamic acid, gamma-amino-beta-(p-chlorophenyl)butyric acid
Baclofen, sold under the brand name Lioresal among others, is a central nervous system (CNS) depressant and derivative of the inhibitory neurotransmitter, γ-Aminobutyric acid (GABA). It is a skeletal muscle relaxant medication used to treat muscle spasms, muscle spasticity, such as from a spinal cord injury or multiple sclerosis. Baclofen is a potent GABAB receptor agonist. It may also be used for hiccups and muscle spasms near the end of life, and off-label to treat alcohol use disorder or opioid withdrawal symptoms. It is taken orally or by intrathecal pump (delivered into the spinal canal v
Key facts
- Drug.routes_of_administration
- By mouth, intrathecal, transdermal
- Drug.ATC_prefix
- M03
- Drug.ATC_suffix
- BX01
- Drug.legal_AU
- S4
- Drug.legal_CA
- Rx-only
- Drug.legal_NZ
- Prescription only
- Drug.legal_UK
- POM
- Drug.legal_US
- Rx-only
- Drug.bioavailability
- Well-absorbed
- Drug.protein_bound
- 30%
- Drug.metabolism
- 85% excreted in urine/faeces unchanged. 15% metabolised by deamination
- Drug.elimination_half life
- 2.5–7 hours
- Drug.excretion
- Kidney (70–80%)
- Drug.CAS_number
- 1134-47-0
- Drug.PubChem
- 2284
- Drug.IUPHAR_ligand
- 1084
- Drug.DrugBank
- DB00181
- Drug.ChemSpiderID
- 2197
via Wikipedia infobox
Chemical data
- Formula
- C10H12ClNO2
- Molecular weight
- 213.66 g/mol
- IUPAC name
- 4-azaniumyl-3-(4-chlorophenyl)butanoate
- SMILES
- C1=CC(=CC=C1C(CC(=O)[O-])C[NH3+])Cl
- InChIKey
- KPYSYYIEGFHWSV-UHFFFAOYSA-N
- XLogP
- -0.3
- Polar surface area
- 67.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
16 papers- Enantioresolution of (RS)-baclofen by liquid chromatography: A review.Biomedical chromatography : BMC · 2017
- Is R(+)-Baclofen the best option for the future of Baclofen in alcohol dependence pharmacotherapy? Insights from the preclinical side.Addiction biology · 2021
- Racemic resolution of RS-baclofen using lipase from Candida cylindracea.Mededelingen (Rijksuniversiteit te Gent. Fakulteit van de Landbouwkundige en Toegepaste Biologische Wetenschappen) · 2001
- Resolution of Enantiomers of (RS)-Baclofen by Ligand-Exchange Thin-Layer Chromatography.Journal of chromatographic science · 2016
- Baclofen antagonizes intravenous self-administration of nicotine in mice and rats.Alcohol and alcoholism (Oxford, Oxfordshire) · 2002
via PubMed
~13 min read
Encyclopedic overview
16 sectionsContents
- Medical uses
- Adverse effects
- Withdrawal syndrome
- Abuse
- Overdose
- Pharmacology
- Pharmacodynamics
- Pharmacokinetics
- Chemistry
- History
- Society and culture
- Routes of administration
- Other names
- Research
- See also
- References
Baclofen, sold under the brand name Lioresal among others, is a central nervous system (CNS) depressant and derivative of the inhibitory neurotransmitter, γ-Aminobutyric acid (GABA). It is a skeletal muscle relaxant medication used to treat muscle spasms, muscle spasticity, such as from a spinal cord injury or multiple sclerosis. Baclofen is a potent GABAB receptor agonist. It may also be used for hiccups and muscle spasms near the end of life, and off-label to treat alcohol use disorder or opioid withdrawal symptoms. It is taken orally or by intrathecal pump (delivered into the spinal canal via an implantable pump device). It is believed to work by decreasing levels of certain neurotransmitters.
Baclofen should be avoided in the setting of chronic kidney disease and end stage renal disease as even small doses can cause excessive toxicity. Common side effects include sleepiness, weakness, and dizziness. Serious side effects, such as seizures and rhabdomyolysis, may occur if use of baclofen is stopped abruptly. Use during pregnancy is of unclear safety, whilst use during breastfeeding is likely safe, and even more so if oral administration is avoided.
Excerpted from Wikipedia’s “(RS)-baclofen” article, available under the CC BY-SA 4.0 licence.