Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C10H12ClNO2.ClH |
| Molecular Weight | 250.122 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.NCC(CC(O)=O)C1=CC=C(Cl)C=C1
InChI
InChIKey=WMNUVYYLMCMHLU-UHFFFAOYSA-N
InChI=1S/C10H12ClNO2.ClH/c11-9-3-1-7(2-4-9)8(6-12)5-10(13)14;/h1-4,8H,5-6,12H2,(H,13,14);1H
| 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 | ( + / - ) |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator'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
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2111463 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | GABLOFEN Approved UseGablofen (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 Date2010 |
Cmax
| 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 |
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 |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.75 h |
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 |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
70% |
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 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Effects of GABA(B) receptor agents on cocaine priming, discrete contextual cue and food induced relapses. | 2007-10-01 |
|
| Attenuation of cocaine-seeking by GABA B receptor agonists baclofen and CGP44532 but not the GABA reuptake inhibitor tiagabine in baboons. | 2007-07-10 |
|
| 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 |
|
| Experience with external pump trial prior to implantation for intrathecal baclofen in ambulatory patients with spastic cerebral palsy. | 2007-04-10 |
|
| Genomic and functional conservation of sedative-hypnotic targets in the zebrafish. | 2007-04 |
|
| Baclofen alters flash-evoked potentials in Long-Evans rats. | 2007-04 |
|
| GABA(B) receptor-positive modulation decreases selective molecular and behavioral effects of cocaine. | 2007-02 |
|
| 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 |
|
| GABAB1 receptor subunit isoforms exert a differential influence on baseline but not GABAB receptor agonist-induced changes in mice. | 2006-12 |
|
| Ethanol blocks nicotine-induced seizures in mice: comparison with midazolam and baclofen. | 2006-11 |
|
| Baclofen-induced neurotoxicity in chronic renal failure patients with intractable hiccups. | 2006-11 |
|
| Baclofen-induced psychosis. | 2006-11 |
|
| Continuous intrathecal baclofen administration by a fully implantable electronic pump for severe spasticity treatment: our experience. | 2006-10 |
|
| Point mutations in either subunit of the GABAB receptor confer constitutive activity to the heterodimer. | 2006-10 |
|
| Baclofen-induced sexual dysfunction. | 2006-09-26 |
|
| 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 |
|
| Effects of baclofen on cocaine self-administration: opioid- and nonopioid-dependent volunteers. | 2006-08 |
|
| [Coma induced by an overdose of intrathecal baclofen]. | 2006-06-30 |
|
| [Radiculopathy following intrathecal baclofen pump implantation]. | 2006-06 |
|
| GABAergic network activation of glial cells underlies hippocampal heterosynaptic depression. | 2006-05-17 |
|
| Aseptic meningitis after intrathecal baclofen injection. | 2006-05 |
|
| Antinociceptive and behavioral effects of ribavirin in mice. | 2006-02 |
|
| [Baclofen-associated encephalopathy in a hemodialysis patient with hiccups]. | 2006 |
|
| Intrathecal baclofen toxicity and deep coma in minutes. | 2006 |
|
| Intrathecal baclofen overdose followed by withdrawal: clinical and EEG features. | 2005-11 |
|
| Possible azithromycin-associated hiccups. | 2005-08 |
|
| Injections of baclofen into the ventral medial prefrontal cortex block the initiation, but not the expression, of cocaine sensitization in rats. | 2005-07 |
|
| Prolonged intrathecal baclofen withdrawal syndrome. Case report and discussion of current therapeutic management. | 2005-06 |
|
| Severe seizures during propofol induction in a patient with syringomyelia receiving baclofen. | 2005-05 |
|
| Intracerebral baclofen administration decreases amphetamine-induced behavior and neuropeptide gene expression in the striatum. | 2005-05 |
|
| GABA(B) receptor modulators potentiate baclofen-induced depression of dopamine neuron activity in the rat ventral tegmental area. | 2005-04 |
|
| Incidence of seizures in patients with multiple sclerosis treated with intrathecal baclofen. | 2005-03-22 |
|
| Pruritus after intrathecal baclofen withdrawal: A retrospective study. | 2005-03 |
|
| An unusual cause of overdose after baclofen pump implantation: case report. | 2005-03 |
|
| Different sensitivity to the motor incoordinating effects of gamma-hydroxybutyric acid (GHB) and baclofen in GHB-sensitive and GHB-resistant rats. | 2005-02-01 |
|
| Attenuation of d-amphetamine self-administration by baclofen in the rat: behavioral and neurochemical correlates. | 2005-02 |
|
| Pharmacological complications of the chronic baclofen infusion in the severe spinal spasticity. Personal experience and review of the literature. | 2004-12 |
|
| Baclofen as adjunctive treatment for a patient with cocaine dependence and schizoaffective disorder. | 2004-10 |
|
| 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 |
|
| Altered GABAB receptor immunoreactivity in the gerbil hippocampus induced by baclofen and phaclofen, not seizure activity. | 2004-08 |
|
| GABAB receptor stimulation decreases amphetamine-induced behavior and neuropeptide gene expression in the striatum. | 2004-04-09 |
|
| Charles Bonnet syndrome and GABAergic drugs--a case report. | 2004-04 |
|
| A case of mania associated with high-dose baclofen therapy. | 1992-06 |
|
| A case of baclofen-induced psychotic depression. | 1992-06 |
|
| Flumazenil counteracts intrathecal baclofen-induced central nervous system depression in tetanus. | 1992-06 |
|
| [Baclofen intoxication in chronic hemodialysis and kidney transplantation]. | 1992-05-08 |
|
| Involvement of GABAergic mechanisms in chloroquine-induced seizures in mice. | 1992-03 |
|
| Prolonged seizure activity after baclofen withdrawal. | 1992-03 |
|
| Effects of nitrendipine, chlordiazepoxide, flumazenil and baclofen on the increased anxiety resulting from alcohol withdrawal. | 1992-01 |
|
| GABA/BZ-and NMDA-receptor interaction in digoxin-induced convulsions in rats. | 1991-07 |
Patents
Sample Use Guides
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
Curator's Comment: In vitro, baclofen reduces chemotaxis of human peripheral blood mononuclear cells towards CCL2, CCL5, CXCL10, CXCL2 and CX3CL1 in a dose-dependant manner. Protein kinase C inhibitors calphostin C and G0 6976 could reverse this effect, pointing towards the involvement of both calcium-dependent and -independent protein kinase C in baclofen-induced inhibition of chemokine receptors.
Unknown
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:48:31 GMT 2025
by
admin
on
Mon Mar 31 18:48:31 GMT 2025
|
| Record UNII |
64OSE3996V
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Preferred Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English |
| Classification Tree | Code System | Code | ||
|---|---|---|---|---|
|
NCI_THESAURUS |
C29696
Created by
admin on Mon Mar 31 18:48:31 GMT 2025 , Edited by admin on Mon Mar 31 18:48:31 GMT 2025
|
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
6602720
Created by
admin on Mon Mar 31 18:48:31 GMT 2025 , Edited by admin on Mon Mar 31 18:48:31 GMT 2025
|
PRIMARY | |||
|
70206-22-3
Created by
admin on Mon Mar 31 18:48:31 GMT 2025 , Edited by admin on Mon Mar 31 18:48:31 GMT 2025
|
SUPERSEDED | |||
|
28311-31-1
Created by
admin on Mon Mar 31 18:48:31 GMT 2025 , Edited by admin on Mon Mar 31 18:48:31 GMT 2025
|
PRIMARY | |||
|
C90887
Created by
admin on Mon Mar 31 18:48:31 GMT 2025 , Edited by admin on Mon Mar 31 18:48:31 GMT 2025
|
PRIMARY | |||
|
64OSE3996V
Created by
admin on Mon Mar 31 18:48:31 GMT 2025 , Edited by admin on Mon Mar 31 18:48:31 GMT 2025
|
PRIMARY | |||
|
m2200
Created by
admin on Mon Mar 31 18:48:31 GMT 2025 , Edited by admin on Mon Mar 31 18:48:31 GMT 2025
|
PRIMARY | Merck Index | ||
|
DBSALT002256
Created by
admin on Mon Mar 31 18:48:31 GMT 2025 , Edited by admin on Mon Mar 31 18:48:31 GMT 2025
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |