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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2017-10-23 19:06:15 UTC
HMDB IDHMDB0014327
Secondary Accession Numbers
  • HMDB14327
Metabolite Identification
Common NameBaclofen
DescriptionBaclofen is a gamma-amino-butyric acid (GABA) derivative used as a skeletal muscle relaxant. Baclofen stimulates GABA-B receptors leading to decreased frequency and amplitude of muscle spasms. It is especially useful in treating muscle spasticity associated with spinal cord injury. It appears to act primarily at the spinal cord level by inhibiting spinal polysynaptic afferent pathways and, to a lesser extent, monosynaptic afferent pathways.
Structure
Thumb
Synonyms
ValueSource
(+-)-BaclofenChEBI
4-amino-3-(4-Chlorophenyl)butyric acidChEBI
BaclofeneChEBI
BaclofenoChEBI
BaclofenumChEBI
beta-(4-Chlorophenyl)gabaChEBI
beta-(Aminomethyl)-4-chlorobenzenepropanoic acidChEBI
beta-(Aminomethyl)-P-chlorohydrocinnamic acidChEBI
beta-(P-Chlorophenyl)-gamma-aminobutyric acidChEBI
DL-4-amino-3-P-Chlorophenylbutanoic acidChEBI
DL-BaclofenChEBI
gamma-amino-beta-(P-Chlorophenyl)butyric acidChEBI
4-amino-3-(4-Chlorophenyl)butyrateGenerator
b-(4-Chlorophenyl)gabaGenerator
β-(4-chlorophenyl)gabaGenerator
b-(Aminomethyl)-4-chlorobenzenepropanoateGenerator
b-(Aminomethyl)-4-chlorobenzenepropanoic acidGenerator
beta-(Aminomethyl)-4-chlorobenzenepropanoateGenerator
β-(aminomethyl)-4-chlorobenzenepropanoateGenerator
β-(aminomethyl)-4-chlorobenzenepropanoic acidGenerator
b-(Aminomethyl)-P-chlorohydrocinnamateGenerator
b-(Aminomethyl)-P-chlorohydrocinnamic acidGenerator
beta-(Aminomethyl)-P-chlorohydrocinnamateGenerator
β-(aminomethyl)-P-chlorohydrocinnamateGenerator
β-(aminomethyl)-P-chlorohydrocinnamic acidGenerator
b-(P-Chlorophenyl)-g-aminobutyrateGenerator
b-(P-Chlorophenyl)-g-aminobutyric acidGenerator
beta-(P-Chlorophenyl)-gamma-aminobutyrateGenerator
β-(P-chlorophenyl)-γ-aminobutyrateGenerator
β-(P-chlorophenyl)-γ-aminobutyric acidGenerator
DL-4-amino-3-P-ChlorophenylbutanoateGenerator
g-amino-b-(P-Chlorophenyl)butyrateGenerator
g-amino-b-(P-Chlorophenyl)butyric acidGenerator
gamma-amino-beta-(P-Chlorophenyl)butyrateGenerator
γ-amino-β-(P-chlorophenyl)butyrateGenerator
γ-amino-β-(P-chlorophenyl)butyric acidGenerator
ASTA medica brand OF baclofenMeSH
Alphapharm brand OF baclofenMeSH
Ashbourne brand OF baclofenMeSH
Baclofen athena brandMeSH
Baclofen irex brandMeSH
BaclospasMeSH
Chlorophenyl gabaMeSH
Ciba geigy brand OF baclofenMeSH
Gen baclofenMeSH
GenBaclofenMeSH
Isis brand OF baclofenMeSH
PCP-GABAMeSH
AWD, baclofenMeSH
Athena brand OF baclofenMeSH
AtrofenMeSH
Baclofen apotex brandMeSH
Baclofen isis brandMeSH
Baclofen medtronic brandMeSH
Baclofen nu-pharm brandMeSH
Baclofen pharmascience brandMeSH
NuBacloMeSH
PMS-BaclofenMeSH
PMSBaclofenMeSH
apo BaclofenMeSH
ApoBaclofenMeSH
Apotex brand OF baclofenMeSH
Baclofen awdMeSH
Baclofen ciba-geigy brandMeSH
Baclofen novartis brandMeSH
Baclofène irexMeSH
Baclofène-irexMeSH
BaclofèneIrexMeSH
CIBA-34,647-baMeSH
Gen-baclofenMeSH
Irex brand OF baclofenMeSH
LebicMeSH
LioresalMeSH
Nu bacloMeSH
Nu-bacloMeSH
Nu-pharm brand OF baclofenMeSH
PMS BaclofenMeSH
apo-BaclofenMeSH
Baclofen alphapharm brandMeSH
Baclofen ashbourne brandMeSH
BaclophenMeSH
CIBA34,647baMeSH
Ciba-geigy brand OF baclofenMeSH
ClofenMeSH
GABA, chlorophenylMeSH
GenpharmMeSH
LiorésalMeSH
Medtronic brand OF baclofenMeSH
Novartis brand OF baclofenMeSH
Nu pharm brand OF baclofenMeSH
Pharmascience brand OF baclofenMeSH
Chemical FormulaC10H12ClNO2
Average Molecular Weight213.661
Monoisotopic Molecular Weight213.05565634
IUPAC Name4-amino-3-(4-chlorophenyl)butanoic acid
Traditional Namebaclofen
CAS Registry Number1134-47-0
SMILES
NCC(CC(O)=O)C1=CC=C(Cl)C=C1
InChI Identifier
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)
InChI KeyKPYSYYIEGFHWSV-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentGamma amino acids and derivatives
Alternative Parents
Substituents
  • Gamma amino acid or derivatives
  • 3-phenylpropanoic-acid
  • Amino fatty acid
  • Chlorobenzene
  • Aralkylamine
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Fatty acyl
  • Benzenoid
  • Amino acid
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Organohalogen compound
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organooxygen compound
  • Primary amine
  • Hydrocarbon derivative
  • Amine
  • Carbonyl group
  • Organic oxide
  • Organopnictogen compound
  • Organic oxygen compound
  • Organochloride
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Route of exposure:

  Parenteral:

  Enteral:

Role

Industrial application:

  Pharmaceutical industry:

Indirect biological role:

Physiological effect

Health effect:

  Health condition:

    Nervous system disorders:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point206 - 208 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.71 g/LNot Available
LogP1.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.71 g/LALOGPS
logP-0.82ALOGPS
logP-0.78ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)3.89ChemAxon
pKa (Strongest Basic)9.79ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area63.32 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.83 m³·mol⁻¹ChemAxon
Polarizability21.13 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001i-9600000000-6ae6d753213a9472b32cView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0ff0-9720000000-6949ab5f0b56c63b916aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03dr-0950000000-33d21cbb6740c1f1aee1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-1590000000-8a64733764308ba98f9aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0f6t-0900000000-6647c58db763b4df68a0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0udi-0900000000-72d6d878c9c2f29d846aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-1900000000-18f69033596a03ee643aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-014i-1900000000-997473c303f07afcdf4eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT , positivesplash10-0002-0900000000-d1da4625d180fe0af521View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-03di-0190000000-bd0fff49defde62ed0faView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0ik9-0790000000-1a50b0b7f24aaaf6a87eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ot-0930000000-4c6fbeef09787ebe54c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-016s-0900000000-904b104c639269bfe4f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000000-62cafb0d9fec846e47b9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03xr-0690000000-4dd9b649eccb58c3cef0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03xr-0940000000-08d03c01d7cee16a2833View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ikl-1900000000-69e953c6f51f0939e70cView in MoNA
MSMass Spectrum (Electron Ionization)splash10-000i-2900000000-963f049a4367a1d5a5f5View in MoNA
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00181 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00181 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiofluidValueOriginal ageOriginal sexOriginal conditionComments
Blood0-5 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0-2 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00181
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2197
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBaclofen
METLIN IDNot Available
PubChem Compound2284
PDB IDNot Available
ChEBI ID2972
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Mezler M, Muller T, Raming K: Cloning and functional expression of GABA(B) receptors from Drosophila. Eur J Neurosci. 2001 Feb;13(3):477-86. [PubMed:11168554 ]
  2. Dzitoyeva S, Dimitrijevic N, Manev H: Gamma-aminobutyric acid B receptor 1 mediates behavior-impairing actions of alcohol in Drosophila: adult RNA interference and pharmacological evidence. Proc Natl Acad Sci U S A. 2003 Apr 29;100(9):5485-90. Epub 2003 Apr 11. [PubMed:12692303 ]
  3. See S, Ginzburg R: Skeletal muscle relaxants. Pharmacotherapy. 2008 Feb;28(2):207-13. doi: 10.1592/phco.28.2.207. [PubMed:18225966 ]

Enzymes

General function:
Involved in G-protein coupled receptor activity
Specific function:
Isoform 1E function may be to regulate the availability of functional GABA-B-R1A/GABA-B-R2 heterodimers by competing for GABA-B-R2 dimerization. This could explain the observation that certain small molecule ligands exhibit differential affinity for central versus peripheral sites
Gene Name:
GABBR1
Uniprot ID:
Q9UBS5
Molecular weight:
108319.4
References
  1. Bowery NG: GABAB receptor pharmacology. Annu Rev Pharmacol Toxicol. 1993;33:109-47. [PubMed:8388192 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
  3. Garcia-Gil L, de Miguel R, Romero J, Perez A, Ramos JA, Fernandez-Ruiz JJ: Perinatal delta9-tetrahydrocannabinol exposure augmented the magnitude of motor inhibition caused by GABA(B), but not GABA(A), receptor agonists in adult rats. Neurotoxicol Teratol. 1999 May-Jun;21(3):277-83. [PubMed:10386831 ]
  4. Lehmann A: GABAB receptors as drug targets to treat gastroesophageal reflux disease. Pharmacol Ther. 2009 Jun;122(3):239-45. doi: 10.1016/j.pharmthera.2009.02.008. Epub 2009 Mar 19. [PubMed:19303900 ]
  5. Motalli R, Louvel J, Tancredi V, Kurcewicz I, Wan-Chow-Wah D, Pumain R, Avoli M: GABA(B) receptor activation promotes seizure activity in the juvenile rat hippocampus. J Neurophysiol. 1999 Aug;82(2):638-47. [PubMed:10444662 ]
  6. Mott DD, Li Q, Okazaki MM, Turner DA, Lewis DV: GABAB-Receptor-mediated currents in interneurons of the dentate-hilus border. J Neurophysiol. 1999 Sep;82(3):1438-50. [PubMed:10482760 ]
  7. Ogasawara T, Itoh Y, Tamura M, Mushiroi T, Ukai Y, Kise M, Kimura K: Involvement of cholinergic and GABAergic systems in the reversal of memory disruption by NS-105, a cognition enhancer. Pharmacol Biochem Behav. 1999 Sep;64(1):41-52. [PubMed:10494996 ]
  8. Pittman QJ: The action is at the terminal. J Physiol. 1999 Nov 1;520 Pt 3:629. [PubMed:10545129 ]
  9. Stringer JL, Lorenzo N: The reduction in paired-pulse inhibition in the rat hippocampus by gabapentin is independent of GABA(B) receptor receptor activation. Epilepsy Res. 1999 Feb;33(2-3):169-76. [PubMed:10094428 ]
General function:
Involved in G-protein coupled receptor activity
Specific function:
Receptor for GABA. The activity of this receptor is mediated by G-proteins that inhibit adenylyl cyclase activity, stimulates phospholipase A2, activates potassium channels, inactivates voltage-dependent calcium-channels and modulates inositol phospholipids hydrolysis. Plays a critical role in the fine-tuning of inhibitory synaptic transmission. Pre-synaptic GABA-B-R inhibit neurotransmitter release by down-regulating high- voltage activated calcium channels, whereas postsynaptic GABA-B-R decrease neuronal excitability by activating a prominent inwardly rectifying potassium (Kir) conductance that underlies the late inhibitory postsynaptic potentials. Not only implicated in synaptic inhibition but also in hippocampal long-term potentiation, slow wave sleep, muscle relaxation and antinociception
Gene Name:
GABBR2
Uniprot ID:
O75899
Molecular weight:
105820.5
References
  1. Belley M, Sullivan R, Reeves A, Evans J, O'Neill G, Ng GY: Synthesis of the nanomolar photoaffinity GABA(B) receptor ligand CGP 71872 reveals diversity in the tissue distribution of GABA(B) receptor forms. Bioorg Med Chem. 1999 Dec;7(12):2697-704. [PubMed:10658574 ]
  2. Braun M, Wendt A, Buschard K, Salehi A, Sewing S, Gromada J, Rorsman P: GABAB receptor activation inhibits exocytosis in rat pancreatic beta-cells by G-protein-dependent activation of calcineurin. J Physiol. 2004 Sep 1;559(Pt 2):397-409. Epub 2004 Jul 2. [PubMed:15235087 ]
  3. Bowery NG: GABAB receptor pharmacology. Annu Rev Pharmacol Toxicol. 1993;33:109-47. [PubMed:8388192 ]
  4. Filippov AK, Couve A, Pangalos MN, Walsh FS, Brown DA, Moss SJ: Heteromeric assembly of GABA(B)R1 and GABA(B)R2 receptor subunits inhibits Ca(2+) current in sympathetic neurons. J Neurosci. 2000 Apr 15;20(8):2867-74. [PubMed:10751439 ]
  5. Lehmann A: GABAB receptors as drug targets to treat gastroesophageal reflux disease. Pharmacol Ther. 2009 Jun;122(3):239-45. doi: 10.1016/j.pharmthera.2009.02.008. Epub 2009 Mar 19. [PubMed:19303900 ]
  6. Martin SC, Russek SJ, Farb DH: Molecular identification of the human GABABR2: cell surface expression and coupling to adenylyl cyclase in the absence of GABABR1. Mol Cell Neurosci. 1999 Mar;13(3):180-91. [PubMed:10328880 ]
  7. Pittman QJ: The action is at the terminal. J Physiol. 1999 Nov 1;520 Pt 3:629. [PubMed:10545129 ]