Identification

Name
Baclofen
Accession Number
DB00181  (APRD00551)
Type
Small Molecule
Groups
Approved
Description

Baclofen 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
  • (+-)-Baclofen
  • 4-Amino-3-(4-chlorophenyl)butyric acid
  • Baclofen
  • Baclofène
  • Baclofeno
  • Baclofenum
  • beta-(4-Chlorophenyl)gaba
  • beta-(Aminomethyl)-4-chlorobenzenepropanoic acid
  • beta-(Aminomethyl)-p-chlorohydrocinnamic acid
  • beta-(p-Chlorophenyl)-gamma-aminobutyric acid
  • DL-4-Amino-3-p-chlorophenylbutanoic acid
  • DL-Baclofen
  • gamma-Amino-beta-(p-chlorophenyl)butyric acid
Product Ingredients
IngredientUNIICASInChI Key
Baclofen hydrochloride64OSE3996V28311-31-1WMNUVYYLMCMHLU-UHFFFAOYSA-N
Product Images
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
BaclofenTablet20 mgOralApotex Corporation1994-12-312014-08-23Canada
BaclofenTablet20 mgOralSanis Health Inc2010-02-25Not applicableCanada
BaclofenTablet20 mg/1OralCaraco Pharmaceutical Laboratories, Ltd.2007-03-30Not applicableUs
BaclofenTablet20 mg/1OralVintage Pharmaceuticals, LLC2007-05-172007-05-17Us
BaclofenTablet10 mgOralSanis Health Inc2010-02-25Not applicableCanada
BaclofenTablet10 mg/1OralCaraco Pharmaceutical Laboratories, Ltd.2007-03-30Not applicableUs
BaclofenTablet10 mg/1OralVintage Pharmaceuticals, LLC2007-05-172007-05-17Us
BaclofenTablet10 mgOralApotex Corporation1994-12-312014-08-23Canada
Baclofen InjectionSolution0.05 mgIntrathecalSterimax Inc2014-06-06Not applicableCanada
Baclofen InjectionSolution0.5 mgIntrathecalTeligent Ou2017-08-25Not applicableCanada
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Apo-baclofen Tablets - 10mgTablet10 mgOralApotex Corporation1994-12-31Not applicableCanada
Apo-baclofen Tablets - 20mgTablet20 mgOralApotex Corporation1994-12-31Not applicableCanada
Ava-baclofenTablet10 mgOralAvanstra Inc2011-10-112014-08-21Canada
Ava-baclofenTablet20 mgOralAvanstra Inc2011-10-112014-08-21Canada
BaclofenTablet10 mg/1OralPreferreed Pharmaceuticals Inc.2004-07-01Not applicableUs
BaclofenTablet20 mg/1OralAidarex Pharmaceuticals LLC2005-08-30Not applicableUs
BaclofenTablet10 mg/1OralCaremark L.L.C.2003-09-262011-07-31Us
BaclofenTablet20 mg/1OralClinical Solutions Wholsesale2010-10-202017-06-08Us00832 1025 00 nlmimage10 73233989
BaclofenTablet20 mg/1OralProficient Rx LP1988-07-21Not applicableUs
BaclofenTablet20 mg/1OralUpsher-Smith Laboratories, LLC2010-10-20Not applicableUs
Unapproved/Other Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Equipto - Baclofen External Cream Compounding KitBaclofen (1 g/1g)KitTopicalAlvix Laboratories2015-01-202018-03-08Us
Gapeam BudibacBaclofen (1 g/1g) + Amantadine hydrochloride (1 g/1g) + Bupivacaine hydrochloride (1 g/1g) + Cyclobenzaprine Hydrochloride (1 g/1g) + Diclofenac sodium (1 g/1g) + Gabapentin (1 g/1g) + Pentoxifylline (1 g/1g)KitTopicalAlvix Laboratories2014-12-052018-03-08Us
Innoprax-5Baclofen (3 g/3g) + Amantadine hydrochloride (8 g/8g) + Diclofenac sodium (3 g/3g) + Gabapentin (6 g/6g) + Lidocaine hydrochloride (5 g/5g)KitAccumix Pharmaceuticals2014-12-152015-07-17Us
International/Other Brands
Baclon (Uniao Quimica (Brazil)) / Kemstro (Schwarz (United States)) / Lioresal Intrathecal (Novartis Pharmaceuticals) / Nu-Baclofen (Nu-Pharm)
Categories
UNII
H789N3FKE8
CAS number
1134-47-0
Weight
Average: 213.661
Monoisotopic: 213.05565634
Chemical Formula
C10H12ClNO2
InChI Key
KPYSYYIEGFHWSV-UHFFFAOYSA-N
InChI
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)
IUPAC Name
4-amino-3-(4-chlorophenyl)butanoic acid
SMILES
NCC(CC(O)=O)C1=CC=C(Cl)C=C1

Pharmacology

Indication

For the alleviation of signs and symptoms of spasticity resulting from multiple sclerosis, particularly for the relief of flexor spasms and concomitant pain, clonus, and muscular rigidity.

Associated Conditions
Pharmacodynamics

Baclofen is a muscle relaxant and antispastic. Baclofen is useful for the alleviation of signs and symptoms of spasticity resulting from multiple sclerosis, particularly for the relief of flexor spasms and concomitant pain, clonus, and muscular rigidity. 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. In studies with animals, Baclofen has been shown to have general CNS depressant properties as indicated by the production of sedation with tolerance, somnolence, ataxia, and respiratory and cardiovascular depression. 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 intersubject variation in absorption and/or elimination.

Mechanism of action

Baclofen is a direct agonist at GABAB 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.

TargetActionsOrganism
AGamma-aminobutyric acid type B receptor subunit 1
agonist
Human
AGamma-aminobutyric acid type B receptor subunit 2
agonist
Human
Absorption

Rapidly and almost completely absorbed from the GI tract.

Volume of distribution
  • 59 L
Protein binding

30%

Metabolism

~ 15% of the dose is metabolized in the liver, primarily by deamination. 70-80% of the dose is excreted unchanged or as metabolites in urine and the remainder is excreted in feces.

Route of elimination

In a study using radiolabeled baclofen, approximately 85% of the dose was excreted unchanged in the urine and feces. Baclofen is excreted primarily by the kidney as unchanged drug; 70 - 80% of a dose appears in the urine as unchanged drug. The remainder is excreted as unchanged drug in the feces or as metabolites in the urine and feces.

Half life

2.5-4 hours

Clearance
  • 180 mL/min
Toxicity

LD50=45 mg/kg (male mice, IV); LD50=78 mg/kg (male rat, IV)

Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of adverse effects can be increased when Baclofen is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3,4-MethylenedioxyamphetamineThe risk or severity of adverse effects can be increased when Baclofen is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of adverse effects can be increased when Baclofen is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-MethoxyamphetamineThe risk or severity of adverse effects can be increased when Baclofen is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of adverse effects can be increased when Baclofen is combined with 5-methoxy-N,N-dimethyltryptamine.
7-NitroindazoleThe risk or severity of adverse effects can be increased when Baclofen is combined with 7-Nitroindazole.
AbacavirBaclofen may decrease the excretion rate of Abacavir which could result in a higher serum level.
AcarboseBaclofen may decrease the excretion rate of Acarbose which could result in a higher serum level.
AceclofenacAceclofenac may decrease the excretion rate of Baclofen which could result in a higher serum level.
AcemetacinAcemetacin may decrease the excretion rate of Baclofen which could result in a higher serum level.
Food Interactions
  • Avoid alcohol.
  • Take without regard to meals.

References

Synthesis Reference

Wayne Levadoux, Denis Groleau, Michael Trani, Robert Lortie, "Streptomyces microorganism useful for the preparation of (R)-baclofen from the racemic mixture." U.S. Patent US5843765, issued April, 1994.

US5843765
General References
  1. 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]
  2. 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]
  3. See S, Ginzburg R: Skeletal muscle relaxants. Pharmacotherapy. 2008 Feb;28(2):207-13. doi: 10.1592/phco.28.2.207. [PubMed:18225966]
External Links
Human Metabolome Database
HMDB0014327
KEGG Drug
D00241
PubChem Compound
2284
PubChem Substance
46508181
ChemSpider
2197
BindingDB
24182
ChEBI
2972
ChEMBL
CHEMBL701
Therapeutic Targets Database
DAP000257
PharmGKB
PA448533
IUPHAR
1084
Guide to Pharmacology
GtP Drug Page
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Baclofen
ATC Codes
M03BX01 — Baclofen
AHFS Codes
  • 12:20.12 — Gaba-derivative Skeletal Muscle Relaxants
FDA label
Download (135 KB)
MSDS
Download (73.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
0CompletedTreatmentAtaxia Telangiectasia (AT)1
0Not Yet RecruitingTreatmentOsteoarthritis of the Hands1
0RecruitingTreatmentSubstance Abuse1
1CompletedNot AvailableHealthy Volunteers / Obese, Otherwise Healthy Volunteers1
1CompletedBasic ScienceAlcohol Dependence1
1CompletedTreatmentAlcohol Dependence1
1CompletedTreatmentBaclofen Withdrawal Syndrome1
1CompletedTreatmentCheyne Stokes Respiration1
1CompletedTreatmentHealthy Volunteers1
1CompletedTreatmentSafety and Pharmacokinetics of Intravenous Baclofen1
1, 2CompletedTreatmentCerebral Palsy (CP) / Spasticity1
1, 2CompletedTreatmentLiver Cirrhosis, Alcoholic1
1, 2Not Yet RecruitingTreatmentIntravenous Baclofen1
1, 2RecruitingPreventionLow Birthweight, Extremely (999 Grams or Less) / Prematurity; Extreme1
2CompletedBasic ScienceMarijuana Dependence1
2CompletedOtherAlcohol Dependence / Alcohol Drinking / Alcohol Drinking Related Problems / Anxiety Disorders1
2CompletedTreatmentAlcohol Dependence2
2CompletedTreatmentCocaine-Related Disorders3
2CompletedTreatmentDisseminated Sclerosis / Spasticity1
2CompletedTreatmentLiver Cirrhosis / Muscle Cramps1
2CompletedTreatmentMarijuana Dependence1
2CompletedTreatmentNicotine Dependence1
2CompletedTreatmentSpastic Diplegic Cerebral Palsy1
2RecruitingTreatmentAlcohol Use Disorder (AUD)1
2TerminatedPreventionAlcohol Dependence / Alcohol Withdrawal Syndrome(AWS)1
2TerminatedTreatmentCerebral Anoxia / Comatose / Dysautonomia / Hypertonia / Traumatic Brain Injury (TBI)1
2TerminatedTreatmentNicotine Dependence1
2TerminatedTreatmentNicotine Dependence / Nicotine Use Disorder / Smoking / Tobacco Use Disorders1
2WithdrawnTreatmentDependence, Cocaine1
2WithdrawnTreatmentHepatocellular,Carcinoma1
2, 3CompletedTreatmentAlcohol Dependence3
2, 3CompletedTreatmentFemale Genital Diseases1
3CompletedSupportive CareChronic Myeloproliferative Disorders / Leukemias / Lymphoproliferative Disorders / Malignant Lymphomas / Multiple Myeloma and Plasma Cell Neoplasm / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Neoplasms / Neurologic toxicity / Pain NOS / Unspecified Adult Solid Tumor, Protocol Specific1
3CompletedTreatmentAlcohol Dependence1
3CompletedTreatmentAlcohol Dependence / Severe alcoholic liver disease1
3CompletedTreatmentCerebral Palsy (CP) / Spasticity1
3CompletedTreatmentDisseminated Sclerosis2
3CompletedTreatmentDisseminated Sclerosis / Spasticity1
3CompletedTreatmentGastro-esophageal Reflux Disease (GERD)1
3CompletedTreatmentSevere Spasticity1
3RecruitingTreatmentAlcohol Dependence1
3TerminatedTreatmentAlcohol Withdrawal Syndrome(AWS)1
4CompletedTreatmentAlcohol Dependence1
4CompletedTreatmentAlcohol Use Disorders (AUD) / Hepatitis C Viral Infection1
4CompletedTreatmentBack Pain Lower Back1
4CompletedTreatmentPostoperative pain1
4CompletedTreatmentRecurrent Crying Spells1
4CompletedTreatmentRumination Disorders / Supra-gastric Belching1
4Not Yet RecruitingTreatmentPain NOS1
4RecruitingOtherAlcohol Use Disorder (AUD)1
4RecruitingSupportive CareMuscle Spasticity1
4RecruitingTreatmentAlcohol Use Disorder (AUD) / Alcohol Withdrawal Syndrome(AWS)1
4RecruitingTreatmentSickle Cell Anemia Crisis1
4SuspendedTreatmentSleep1
4TerminatedBasic ScienceLower Urinary Tract Symptoms (LUTS) / Occasional Constipation / Urinary Bladder, Overactive1
4Unknown StatusSupportive CareCerebral Palsy (CP)1
4WithdrawnTreatmentCerebral Palsy (CP) / Gastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedNot AvailableAcute Gouty Arthritis / Arthritis / Headaches / Migraines / Muscle Spasms / Radicular syndrome / Synovitis / Tendonitis1
Not AvailableCompletedBasic ScienceBrain GABA-B Function / No Conditions1
Not AvailableCompletedDiagnosticGastro-esophageal Reflux Disease (GERD)1
Not AvailableCompletedPreventionAlcohol Withdrawal Delirium1
Not AvailableCompletedTreatmentBulimia Nervosa (BN) / Eating Disorders1
Not AvailableCompletedTreatmentSpinal Cord Injuries (SCI)1
Not AvailableNot Yet RecruitingTreatmentPelvic Floor Dyssynergia1
Not AvailableRecruitingTreatmentGynecologic Diseases / Postoperative pain1
Not AvailableTerminatedTreatmentNon-Cardiac Chest Pain1
Not AvailableUnknown StatusTreatmentLiver Cirrhosis / Muscle Cramps1
Not AvailableWithdrawnTreatmentAutism Spectrum Conditions/Disorders / Tactile Defensiveness1

Pharmacoeconomics

Manufacturers
  • Medtronic inc
  • Schwarz pharma inc
  • Actavis totowa llc
  • Caraco pharmaceutical laboratories ltd
  • Impax laboratories inc
  • Ivax pharmaceuticals inc sub teva pharmaceuticals usa
  • Lannett holdings inc
  • Matrix laboratories ltd
  • Mylan pharmaceuticals inc
  • Northstar healthcare holdings ltd
  • Teva pharmaceuticals usa inc
  • Usl pharma inc
  • Vintage pharmaceuticals inc
  • Watson laboratories inc
  • Novartis pharmaceuticals corp
Packagers
  • Actavis Group
  • Advanced Pharmaceutical Services Inc.
  • Aidarex Pharmacuticals LLC
  • Alphapharm Party Ltd.
  • Amerisource Health Services Corp.
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Bryant Ranch Prepack
  • Caraco Pharmaceutical Labs
  • Cardinal Health
  • Caremark LLC
  • Comprehensive Consultant Services Inc.
  • Corepharma LLC
  • Direct Dispensing Inc.
  • Dispensing Solutions
  • Diversified Healthcare Services Inc.
  • Genpharm LP
  • Heartland Repack Services LLC
  • Innoviant Pharmacy Inc.
  • Ivax Pharmaceuticals
  • Keltman Pharmaceuticals Inc.
  • Lake Erie Medical and Surgical Supply
  • Lannett Co. Inc.
  • Major Pharmaceuticals
  • Mckesson Corp.
  • Medisca Inc.
  • Medtronic
  • Murfreesboro Pharmaceutical Nursing Supply
  • Mylan
  • Northstar Rx LLC
  • Novartis AG
  • Nucare Pharmaceuticals Inc.
  • Palmetto Pharmaceuticals Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmaceutical Packaging Center
  • Physicians Total Care Inc.
  • Piramal Healthcare
  • Preferred Pharmaceuticals Inc.
  • Prepak Systems Inc.
  • Prescription Dispensing Service Inc.
  • Qualitest
  • Rebel Distributors Corp.
  • Remedy Repack
  • Resource Optimization and Innovation LLC
  • Sandhills Packaging Inc.
  • Southwood Pharmaceuticals
  • St Mary's Medical Park Pharmacy
  • Stat Rx Usa
  • UDL Laboratories
  • United Research Laboratories Inc.
  • USL Pharma Inc.
  • Vangard Labs Inc.
  • Vintage Pharmaceuticals Inc.
  • Watson Pharmaceuticals
Dosage forms
FormRouteStrength
InjectionIntrathecal0.05 mg/1mL
InjectionIntrathecal10 mg/20mL
InjectionIntrathecal40 mg/20mL
Injection, solutionIntrathecal10 mg/20mL
Injection, solutionIntrathecal40 mg/20mL
TabletOral5 mg/1
SolutionIntrathecal10 mg
KitTopical1 g/1g
InjectionIntrathecal1000 ug/1mL
InjectionIntrathecal2000 ug/1mL
InjectionIntrathecal50 ug/1mL
InjectionIntrathecal500 ug/1mL
Injection, solutionIntrathecal1000 ug/1mL
Injection, solutionIntrathecal2000 ug/1mL
Injection, solutionIntrathecal50 ug/1mL
Injection, solutionIntrathecal500 ug/1mL
KitTopical
Kit
Tablet, orally disintegratingOral10 mg/1
Tablet, orally disintegratingOral20 mg/1
InjectionIntrathecal0.5 mg/1mL
InjectionIntrathecal2 mg/1mL
TabletOral10 mg/1
TabletOral20 mg/1
InjectionIntrathecal10 mg/5mL
SolutionIntrathecal0.05 mg
SolutionIntrathecal0.5 mg
SolutionIntrathecal2 mg
TabletOral10 mg
TabletOral20 mg
Prices
Unit descriptionCostUnit
Lioresal it 0.05 mg/1 ml amp84.0USD ml
Lioresal it 10 mg/5 ml kit51.6USD ml
Lioresal Intrathecal 2 mg/ml44.64USD ml
Lioresal Intrathecal 0.05 mg/ml14.89USD ml
Baclofen powder14.38USD g
Lioresal it 10 mg/20 ml kit12.9USD ml
Lioresal Intrathecal 0.5 mg/ml11.16USD ml
Lioresal D.S. 20 mg Tablet1.4USD tablet
Baclofen 20 mg tablet0.92USD tablet
Lioresal 10 mg Tablet0.72USD tablet
Apo-Baclofen 20 mg Tablet0.59USD tablet
Mylan-Baclofen 20 mg Tablet0.59USD tablet
Nu-Baclo 20 mg Tablet0.59USD tablet
Phl-Baclofen 20 mg Tablet0.59USD tablet
Pms-Baclofen 20 mg Tablet0.59USD tablet
Ratio-Baclofen 20 mg Tablet0.59USD tablet
Baclofen 10 mg tablet0.51USD tablet
Apo-Baclofen 10 mg Tablet0.3USD tablet
Mylan-Baclofen 10 mg Tablet0.3USD tablet
Nu-Baclo 10 mg Tablet0.3USD tablet
Phl-Baclofen 10 mg Tablet0.3USD tablet
Pms-Baclofen 10 mg Tablet0.3USD tablet
Ratio-Baclofen 10 mg Tablet0.3USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US6221392No2001-04-242018-04-09Us
US6024981No2000-02-152018-04-09Us

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)206-208 °CKeberle, H., Faigle, J.W. and Wilhelm, M.; U.S. Patent 3,471,548; October 7, 1969; assigned to Ciba Corporation. Keberle, H., Faigle, J.W. and Wilhelm, M.; U.S. Patent 3,634,428; January 11, 1972; assigned to Ciba Corporation.
water solubility2090 mg/LNot Available
logP1.3Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.712 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.83 m3·mol-1ChemAxon
Polarizability21.13 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.978
Blood Brain Barrier+0.9339
Caco-2 permeable+0.5668
P-glycoprotein substrateNon-substrate0.7373
P-glycoprotein inhibitor INon-inhibitor0.9825
P-glycoprotein inhibitor IINon-inhibitor0.9842
Renal organic cation transporterNon-inhibitor0.8435
CYP450 2C9 substrateNon-substrate0.8746
CYP450 2D6 substrateNon-substrate0.8426
CYP450 3A4 substrateNon-substrate0.7618
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.736
CYP450 2C19 inhibitorNon-inhibitor0.8215
CYP450 3A4 inhibitorNon-inhibitor0.8309
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9204
Ames testNon AMES toxic0.8621
CarcinogenicityNon-carcinogens0.7401
BiodegradationNot ready biodegradable0.7362
Rat acute toxicity3.1364 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9478
hERG inhibition (predictor II)Non-inhibitor0.8578
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Mass Spectrum (Electron Ionization)MSsplash10-000i-2900000000-963f049a4367a1d5a5f5
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-QTOF , negativeLC-MS/MSsplash10-03dr-0950000000-33d21cbb6740c1f1aee1
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-03di-1590000000-8a64733764308ba98f9a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0f6t-0900000000-6647c58db763b4df68a0
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-0udi-0900000000-72d6d878c9c2f29d846a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-1900000000-18f69033596a03ee643a
LC-MS/MS Spectrum - LC-ESI-QQ , positiveLC-MS/MSsplash10-014i-1900000000-997473c303f07afcdf4e
LC-MS/MS Spectrum - LC-ESI-IT , positiveLC-MS/MSsplash10-0002-0900000000-d1da4625d180fe0af521
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-03di-0190000000-bd0fff49defde62ed0fa
LC-MS/MS Spectrum - LC-ESI-QTOF , positiveLC-MS/MSsplash10-0ik9-0790000000-1a50b0b7f24aaaf6a87e

Taxonomy

Description
This compound belongs to the class of organic compounds known as gamma amino acids and derivatives. These are amino acids having a (-NH2) group attached to the gamma carbon atom.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Gamma amino acids and derivatives
Alternative Parents
Phenylpropanoic acids / Chlorobenzenes / Aralkylamines / Amino fatty acids / Aryl chlorides / Amino acids / Monocarboxylic acids and derivatives / Carboxylic acids / Organopnictogen compounds / Organochlorides
show 4 more
Substituents
Gamma amino acid or derivatives / 3-phenylpropanoic-acid / Amino fatty acid / Chlorobenzene / Aralkylamine / Halobenzene / Aryl chloride / Aryl halide / Monocyclic benzene moiety / Fatty acyl
show 18 more
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
monocarboxylic acid, primary amino compound, monochlorobenzenes, gamma-amino acid (CHEBI:2972)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled gaba receptor activity
Specific Function
Component of a heterodimeric G-protein coupled receptor for GABA, formed by GABBR1 and GABBR2. Within the heterodimeric GABA receptor, only GABBR1 seems to bind agonists, while GABBR2 mediates coup...
Gene Name
GABBR1
Uniprot ID
Q9UBS5
Uniprot Name
Gamma-aminobutyric acid type B receptor subunit 1
Molecular Weight
108319.4 Da
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]
Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
G-protein coupled gaba receptor activity
Specific Function
Component of a heterodimeric G-protein coupled receptor for GABA, formed by GABBR1 and GABBR2. Within the heterodimeric GABA receptor, only GABBR1 seems to bind agonists, while GABBR2 mediates coup...
Gene Name
GABBR2
Uniprot ID
O75899
Uniprot Name
Gamma-aminobutyric acid type B receptor subunit 2
Molecular Weight
105820.52 Da
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. Jones KA, Tamm JA, Craig DA, Ph D, Yao W, Panico R: Signal transduction by GABA(B) receptor heterodimers. Neuropsychopharmacology. 2000 Oct;23(4 Suppl):S41-9. [PubMed:11008066]
  6. 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]
  7. 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]
  8. Pittman QJ: The action is at the terminal. J Physiol. 1999 Nov 1;520 Pt 3:629. [PubMed:10545129]

Transporters

Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Sodium-independent organic anion transmembrane transporter activity
Specific Function
Plays an important role in the excretion/detoxification of endogenous and exogenous organic anions, especially from the brain and kidney. Involved in the transport basolateral of steviol, fexofenad...
Gene Name
SLC22A8
Uniprot ID
Q8TCC7
Uniprot Name
Solute carrier family 22 member 8
Molecular Weight
59855.585 Da
References
  1. Ohtsuki S, Asaba H, Takanaga H, Deguchi T, Hosoya K, Otagiri M, Terasaki T: Role of blood-brain barrier organic anion transporter 3 (OAT3) in the efflux of indoxyl sulfate, a uremic toxin: its involvement in neurotransmitter metabolite clearance from the brain. J Neurochem. 2002 Oct;83(1):57-66. [PubMed:12358729]
  2. Mori S, Takanaga H, Ohtsuki S, Deguchi T, Kang YS, Hosoya K, Terasaki T: Rat organic anion transporter 3 (rOAT3) is responsible for brain-to-blood efflux of homovanillic acid at the abluminal membrane of brain capillary endothelial cells. J Cereb Blood Flow Metab. 2003 Apr;23(4):432-40. [PubMed:12679720]

Drug created on June 13, 2005 07:24 / Updated on December 16, 2018 06:36