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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H12ClNO2
Molecular Weight 213.661
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BACLOFEN, (S)-

SMILES

NC[C@@H](CC(O)=O)C1=CC=C(Cl)C=C1

InChI

InChIKey=KPYSYYIEGFHWSV-MRVPVSSYSA-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)/t8-/m1/s1

HIDE SMILES / InChI
(S)-baclofen (or L-baclofen) is an enantiomer of baclofen, a direct GABA-B receptor mimetic. L-baclofen represents a significant improvement over racemic baclofen in the treatment of trigeminal neuralgia.

CNS Activity

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
12 mg 1 times / day multiple, oral (unknown)
Highest studied dose
Dose: 12 mg, 1 times / day
Route: oral
Route: multiple
Dose: 12 mg, 1 times / day
Sources:
unhealthy, ADULT
n = 11
Health Status: unhealthy
Condition: Trigeminal neuralgia
Age Group: ADULT
Sex: unknown
Food Status: UNKNOWN
Population Size: 11
Sources:
Other AEs: headedness, headache...
Other AEs:
headedness (1 pt)
headache (mild, 1 pt)
Sources:
AEs

AEs

AESignificanceDosePopulation
headedness 1 pt
12 mg 1 times / day multiple, oral (unknown)
Highest studied dose
Dose: 12 mg, 1 times / day
Route: oral
Route: multiple
Dose: 12 mg, 1 times / day
Sources:
unhealthy, ADULT
n = 11
Health Status: unhealthy
Condition: Trigeminal neuralgia
Age Group: ADULT
Sex: unknown
Food Status: UNKNOWN
Population Size: 11
Sources:
headache mild, 1 pt
12 mg 1 times / day multiple, oral (unknown)
Highest studied dose
Dose: 12 mg, 1 times / day
Route: oral
Route: multiple
Dose: 12 mg, 1 times / day
Sources:
unhealthy, ADULT
n = 11
Health Status: unhealthy
Condition: Trigeminal neuralgia
Age Group: ADULT
Sex: unknown
Food Status: UNKNOWN
Population Size: 11
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Potential involvement of a baclofen-sensitive autoreceptor in the modulation of the release of endogenous GABA from rat brain slices in vitro.
1988 Mar
Stereospecific actions of baclofen on sociosexual behavior, locomotor activity and motor execution.
1989
Effects of phaclofen and the enantiomers of baclofen on cardiovascular responses to intrathecal administration of L- and D-baclofen in the rat.
1991 Apr 24
Modeling of the effect site equilibration kinetics and pharmacodynamics of racemic baclofen and its enantiomers using quantitative EEG effect measures.
1992 Apr
NMDA receptor antagonists block cardiovascular responses to intrathecal administration of D-baclofen in the rat.
1992 Jun 5
Permeation and systemic absorption of R- and S-baclofen across the nasal mucosa.
2011 Jul
Intra-nucleus accumbens shell injections of R(+)- and S(-)-baclofen bidirectionally alter binge-like ethanol, but not saccharin, intake in C57Bl/6J mice.
2014 Oct 1
Bidirectional enantioselective effects of the GABAB receptor agonist baclofen in two mouse models of excessive ethanol consumption.
2015 Feb

Sample Use Guides

Patients with trigeminal neuralgia: 6-12 mg/day
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
BACLOFEN, (S)-
Common Name English
BENZENEPROPANOIC ACID, .BETA.-(AMINOMETHYL)-4-CHLORO-, (.BETA.S)-
Common Name English
(S)-4-AMINO-3-(4-CHLOROPHENYL)BUTANOIC ACID
Systematic Name English
S(+)-BACLOFEN
Common Name English
BACLOFEN, S-
Common Name English
BACLOFEN, S(+)-
Common Name English
L-BACLOFEN
Common Name English
(S)-BACLOFEN
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29696
Created by admin on Fri Dec 15 15:31:04 UTC 2023 , Edited by admin on Fri Dec 15 15:31:04 UTC 2023
FDA ORPHAN DRUG 45690
Created by admin on Fri Dec 15 15:31:04 UTC 2023 , Edited by admin on Fri Dec 15 15:31:04 UTC 2023
FDA ORPHAN DRUG 65592
Created by admin on Fri Dec 15 15:31:04 UTC 2023 , Edited by admin on Fri Dec 15 15:31:04 UTC 2023
FDA ORPHAN DRUG 57391
Created by admin on Fri Dec 15 15:31:04 UTC 2023 , Edited by admin on Fri Dec 15 15:31:04 UTC 2023
FDA ORPHAN DRUG 109397
Created by admin on Fri Dec 15 15:31:04 UTC 2023 , Edited by admin on Fri Dec 15 15:31:04 UTC 2023
Code System Code Type Description
CAS
66514-99-6
Created by admin on Fri Dec 15 15:31:04 UTC 2023 , Edited by admin on Fri Dec 15 15:31:04 UTC 2023
PRIMARY
FDA UNII
3OHN4989XM
Created by admin on Fri Dec 15 15:31:04 UTC 2023 , Edited by admin on Fri Dec 15 15:31:04 UTC 2023
PRIMARY
PUBCHEM
44600
Created by admin on Fri Dec 15 15:31:04 UTC 2023 , Edited by admin on Fri Dec 15 15:31:04 UTC 2023
PRIMARY
DRUG BANK
DB12098
Created by admin on Fri Dec 15 15:31:04 UTC 2023 , Edited by admin on Fri Dec 15 15:31:04 UTC 2023
PRIMARY
NCI_THESAURUS
C90891
Created by admin on Fri Dec 15 15:31:04 UTC 2023 , Edited by admin on Fri Dec 15 15:31:04 UTC 2023
PRIMARY