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Details

Stereochemistry RACEMIC
Molecular Formula C10H12ClNO2
Molecular Weight 213.661
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BACLOFEN

SMILES

NCC(CC(O)=O)C1=CC=C(Cl)C=C1

InChI

InChIKey=KPYSYYIEGFHWSV-UHFFFAOYSA-N
InChI=1S/C10H12ClNO2/c11-9-3-1-7(2-4-9)8(6-12)5-10(13)14/h1-4,8H,5-6,12H2,(H,13,14)

HIDE SMILES / InChI

Molecular Formula C10H12ClNO2
Molecular Weight 213.661
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Baclofen (brand names Kemstro, Lioresal, and Gablofen) is a derivative of gamma-aminobutyric acid (GABA). Baclofen is a muscle relaxer and an antispastic agent and is used to treat muscle symptoms caused by multiple sclerosis, including spasm, pain, and stiffness. It is primarily used to treat spasticity and is under investigation for the treatment of alcoholism. Although baclofen is an analog of the putative inhibitory neurotransmitter gamma-aminobutyric acid (GABA), there is no conclusive evidence that actions on GABA systems are involved in the production of its clinical effects. Baclofen is rapidly and extensively absorbed and eliminated. Absorption may be dose-dependent, being reduced with increasing doses. Baclofen is excreted primarily by the kidney in unchanged form and there is relatively large intersubjective variation in absorption and/or elimination. Baclofen is a direct agonist at GABA-B receptors. The precise mechanism of action of baclofen is not fully known. It is capable of inhibiting both monosynaptic and polysynaptic reflexes at the spinal level, possibly by hyperpolarization of afferent terminals, although actions at supraspinal sites may also occur and contribute to its clinical effect.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
GABLOFEN

Cmax

ValueDoseCo-administeredAnalytePopulation
0.2 μg/mL
10 mg 4 times / day steady-state, oral
BACLOFEN plasma
Homo sapiens
178 ng/mL
10 mg single, oral
BACLOFEN plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
1.1 μg × h/mL
10 mg 4 times / day steady-state, oral
BACLOFEN plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.75 h
10 mg single, oral
BACLOFEN plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
70%
10 mg single, oral
BACLOFEN plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
Gablofen is approved only for use with the Medtronic SynchroMed® II Programmable Pump or other pumps labeled 34 for intrathecal administration of Gablofen (baclofen injection). Lowest dose with an optimal response should be used, generally 300 to 800 mcg/day for spasticity of spinal cord origin and 90 to 700 mcg/day for spasticity of cerebral origin; Titrate Gablofen to maintain some degree of muscle tone and allow occasional spasms
Route of Administration: Other
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
H789N3FKE8
Record Status Validated (UNII)
Record Version