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(RS)-baclofen

Structure via PubChem · Public domain (PubChem)

EntityQ413717· pop 29· linked from 1,143 articles

(RS)-baclofen

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Also 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

~13 min read

Encyclopedic overview

16 sections
Contents
  • 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.

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