BACLOFEN

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 Search

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

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022462s000lbl.pdf
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18221197 https://www.ncbi.nlm.nih.gov/pubmed/15486423

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 Target	Pharmacology	Condition	Potency
GABA-B receptor 32 Target ID: CHEMBL2111463 Sources: https://www.ncbi.nlm.nih.gov/pubmed/8388192	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Spasticity 11 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2010/022462s000lbl.pdf	Primary		Approved 8583	GABLOFEN Approved Use Gablofen (baclofen injection) is indicated for use in the management of severe spasticity in adult and pediatric patients age 4 years and above. Patients should first respond to a screening dose of intrathecal baclofen prior to consideration for long term infusion via an implantable pump. For spasticity of spinal cord origin, chronic infusion of Gablofen via an implantable pump should be reserved for patients unresponsive to oral baclofen therapy, or those who experience intolerable CNS side effects at effective doses. Patients with spasticity due to traumatic brain injury should wait at least one year after the injury before consideration of long term intrathecal baclofen therapy. Gablofen is intended for use by the intrathecal route in single bolus test doses (via spinal catheter or lumbar puncture) and, for chronic use, only with the Medtronic SynchroMed® II Programmable Pump or other pumps labeled for intrathecal administration of Gablofen Launch Date 2010

C_max

Value	Dose	Co-administered	Analyte	Population
0.2 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2336342/	10 mg 4 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		BACLOFEN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
178 ng/mL DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21589_kemstro_lbl.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		BACLOFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
1.1 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/2336342/	10 mg 4 times / day steady-state, oral dose: 10 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		BACLOFEN plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
3.75 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21589_kemstro_lbl.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		BACLOFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
70% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2003/21589_kemstro_lbl.pdf	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:		BACLOFEN plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:2972	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:2972
ChemicalBook	CB8669450	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8669450
eMolecules	535235	https://www.emolecules.com/cgi-bin/more?vid=535235
MolPort	MolPort-002-051-370	https://www.molport.com/shop/molecule-link/MolPort-002-051-370

PubMed

Title	Date	PubMed
Effects of GABA(B) receptor agents on cocaine priming, discrete contextual cue and food induced relapses.	2007-10-01	17610868
Attenuation of cocaine-seeking by GABA B receptor agonists baclofen and CGP44532 but not the GABA reuptake inhibitor tiagabine in baboons.	2007-07-10	17234367
Interactions of the basolateral amygdala with the dorsal hippocampus and dorsomedial prefrontal cortex regulate drug context-induced reinstatement of cocaine-seeking in rats.	2007-07	17650119
Experience with external pump trial prior to implantation for intrathecal baclofen in ambulatory patients with spastic cerebral palsy.	2007-04-10	17418354
Genomic and functional conservation of sedative-hypnotic targets in the zebrafish.	2007-04	17496723
Baclofen alters flash-evoked potentials in Long-Evans rats.	2007-04	17407791
GABA(B) receptor-positive modulation decreases selective molecular and behavioral effects of cocaine.	2007-02	16710312
Differential effects of chronic amphetamine and baclofen administration on cAMP levels and phosphorylation of CREB in distinct brain regions of wild type and monoamine oxidase B-deficient mice.	2006-12-15	16983645
GABAB1 receptor subunit isoforms exert a differential influence on baseline but not GABAB receptor agonist-induced changes in mice.	2006-12	16990508
Ethanol blocks nicotine-induced seizures in mice: comparison with midazolam and baclofen.	2006-11	17418694
Baclofen-induced neurotoxicity in chronic renal failure patients with intractable hiccups.	2006-11	17195438
Baclofen-induced psychosis.	2006-11	17047139
Continuous intrathecal baclofen administration by a fully implantable electronic pump for severe spasticity treatment: our experience.	2006-10	17006418
Point mutations in either subunit of the GABAB receptor confer constitutive activity to the heterodimer.	2006-10	16847143
Baclofen-induced sexual dysfunction.	2006-09-26	17000991
Cocaine-induced locomotor activity and Fos expression in nucleus accumbens are sensitized for 6 months after repeated cocaine administration outside the home cage.	2006-08	16930414
Effects of baclofen on cocaine self-administration: opioid- and nonopioid-dependent volunteers.	2006-08	16407903
[Coma induced by an overdose of intrathecal baclofen].	2006-06-30	16807874
[Radiculopathy following intrathecal baclofen pump implantation].	2006-06	16675056
GABAergic network activation of glial cells underlies hippocampal heterosynaptic depression.	2006-05-17	16707789
Aseptic meningitis after intrathecal baclofen injection.	2006-05	16172626
Antinociceptive and behavioral effects of ribavirin in mice.	2006-02	16563475
[Baclofen-associated encephalopathy in a hemodialysis patient with hiccups].	2006	17058862
Intrathecal baclofen toxicity and deep coma in minutes.	2006	16859228
Intrathecal baclofen overdose followed by withdrawal: clinical and EEG features.	2005-11	16243227
Possible azithromycin-associated hiccups.	2005-08	15985056
Injections of baclofen into the ventral medial prefrontal cortex block the initiation, but not the expression, of cocaine sensitization in rats.	2005-07	15696327
Prolonged intrathecal baclofen withdrawal syndrome. Case report and discussion of current therapeutic management.	2005-06	16028775
Severe seizures during propofol induction in a patient with syringomyelia receiving baclofen.	2005-05	15845707
Intracerebral baclofen administration decreases amphetamine-induced behavior and neuropeptide gene expression in the striatum.	2005-05	15592348
GABA(B) receptor modulators potentiate baclofen-induced depression of dopamine neuron activity in the rat ventral tegmental area.	2005-04	15711597
Incidence of seizures in patients with multiple sclerosis treated with intrathecal baclofen.	2005-03-22	15781838
Pruritus after intrathecal baclofen withdrawal: A retrospective study.	2005-03	15759234
An unusual cause of overdose after baclofen pump implantation: case report.	2005-03	15730591
Different sensitivity to the motor incoordinating effects of gamma-hydroxybutyric acid (GHB) and baclofen in GHB-sensitive and GHB-resistant rats.	2005-02-01	15680346
Attenuation of d-amphetamine self-administration by baclofen in the rat: behavioral and neurochemical correlates.	2005-02	15630589
Pharmacological complications of the chronic baclofen infusion in the severe spinal spasticity. Personal experience and review of the literature.	2004-12	15876986
Baclofen as adjunctive treatment for a patient with cocaine dependence and schizoaffective disorder.	2004-10	15349029
Involvement of G protein betagamma-subunits in diverse signaling induced by G(i/o)-coupled receptors: study using the Xenopus oocyte expression system.	2004-10	15151902
Altered GABAB receptor immunoreactivity in the gerbil hippocampus induced by baclofen and phaclofen, not seizure activity.	2004-08	15236866
GABAB receptor stimulation decreases amphetamine-induced behavior and neuropeptide gene expression in the striatum.	2004-04-09	15033416
Charles Bonnet syndrome and GABAergic drugs--a case report.	2004-04	15066092
A case of mania associated with high-dose baclofen therapy.	1992-06	1629392
A case of baclofen-induced psychotic depression.	1992-06	1607352
Flumazenil counteracts intrathecal baclofen-induced central nervous system depression in tetanus.	1992-06	1599091
[Baclofen intoxication in chronic hemodialysis and kidney transplantation].	1992-05-08	1576939
Involvement of GABAergic mechanisms in chloroquine-induced seizures in mice.	1992-03	1639237
Prolonged seizure activity after baclofen withdrawal.	1992-03	1549245
Effects of nitrendipine, chlordiazepoxide, flumazenil and baclofen on the increased anxiety resulting from alcohol withdrawal.	1992-01	1557510
GABA/BZ-and NMDA-receptor interaction in digoxin-induced convulsions in rats.	1991-07	1665475

Patents

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 Created by `admin` on `Mon Mar 31 17:51:07 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:07 GMT 2025`
Record UNII	H789N3FKE8
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BACLOFEN

Official Name

English

FLEQSUVY

Preferred Name

English

KEMSTRO

Brand Name

English

BACLOFEN [JAN]

Common Name

English

BACLOFEN [USP MONOGRAPH]

Common Name

English

OZOBAX

Brand Name

English

Baclofen [WHO-DD]

Common Name

English

BACLOFEN [MI]

Common Name

English

BA-34647

Code

English

BACLOFEN [USAN]

Common Name

English

BACLOFEN [ORANGE BOOK]

Common Name

English

BACLOFEN [USP-RS]

Common Name

English

4-AMINO-3-(4-CHLOROPHENYL)BUTANOIC ACID

Systematic Name

English

baclofen [INN]

Common Name

English

BACLOFEN [MART.]

Common Name

English

GABLOFEN

Brand Name

English

LYVISPAH

Brand Name

English

BUTANOIC ACID, 4-AMINO-3-(4-CHLOROPHENYL)-

Common Name

English

BA-34,647

Code

English

BACLOFEN [EP MONOGRAPH]

Common Name

English

NSC-755906

Code

English

BACLOFEN [VANDF]

Common Name

English

(RS)-BACLOFEN

Common Name

English

LIORESAL

Brand Name

English

.BETA.-(AMINOMETHYL)-P-CHLOROHYDROCINNAMIC ACID

Common Name

English

Classification Tree Code System Code

WHO-ATC

M03BX01