4-amino-3-(4-chlorophenyl)butanoic acid

• ChemBase ID: 66
• Molecular Formular: C10H12ClNO2
• Molecular Mass: 213.66078
• Monoisotopic Mass: 213.05565631
• SMILES: Clc1ccc(C(CC(=O)O)CN)cc1
• Canonical SMILES: NCC(c1ccc(cc1)Cl)CC(=O)O
• 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)
• InChIKey: KPYSYYIEGFHWSV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-3-(4-chlorophenyl)butanoic acid
• IUPAC Traditional name: baclofen
• Brand Name: Baclon; Kemstro; Lioresal; Lioresal Intrathecal; Nu-Baclofen; Pms-Baclofen; Lioresal, Liofen
• Synonyms: β-(Aminomethyl)-4-chloro-benzenepropanoic Acid; β-(Aminomethyl)-p-chlorohydrocinnamic Acid; β-(4-Chlorophenyl)-GABA; Ba-34647; Baclon; Clofen; 4-Amino-3-(4-chlorophenyl)butanoic acid; Baclofen; (±)-β-(Aminomethyl)-4-chlorobenzenepropanoic acid; Lioresal; (±)-Baclofen; (±)-β-(Aminoethyl)-4-chlorobenzenepropanoic acid; (±)-BACLOFEN

Database IDs

• CAS Number: 1134-47-0
• EC Number: 214-486-9
• MDL Number: MFCD00055143
• PubChem SID: 160963529; 46508181; 24278146
• PubChem CID: 2284
• CHEBI ID: 2972
• ATC CODE: M03BX01
• CHEMBL: 701
• Chemspider ID: 2197
• DrugBank ID: DB00181
• IUPHAR ligand ID: 1084
• KEGG ID: D00241
• Unique Ingredient Identifier: H789N3FKE8
• Wikipedia Title: Baclofen

CALCULATED PROPERTIES

JChem

• Acid pKa: 3.8868947
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.79014736
• LogD (pH = 7.4): -0.7832327
• Log P: -0.78240025
• Molar Refractivity: 54.8292 cm^3
• Polarizability: 21.613943 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: -0.82
• LOG S: -2.48
• Solubility (Water): 7.12e-01 g/l

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble50 mg/mL; 2090 mg/L; Water
• Apperance: Off-White Solid; white to very faintly yellow solid
• Melting Point: 207°C; 208-210°C
• Hydrophobicity(logP): -0.62; 1.3

Safety Information

• Storage Condition: -20°C Freezer; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: MW5084200
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3; III
• Australian Hazchem: 2X
• Risk Statements: 61-25-36/37/38-42/43; R:25-36/37/38
• Safety Statements: 53-22-36/37/39-45; S:28-29-36/37/39-45
• EU Classification: T2
• EU Hazard Identification Number: 6.1B
• Emergency Response Guidebook(ERG) Number: 154
• TSCA Listed: false
• GHS Pictograms: GHS06; GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H301-H315-H317-H319-H334-H335-H360
• GHS Precautionary statements: P201-P261-P280-P301 + P310-P305 + P351 + P338-P308 + P313
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Admin Routes: Oral, intrathecal
• Bioavailability: well absorbed
• Excretion: renal (70-80%)
• Half Life: 1.5 to 4 hours
• Metabolism: 85% excreted in urine/faeces unchanged. 15% metabolised by deamination
• Protein Bound: 30%
• Legal Status: Rx-only (US)
• Pregnancy Category: C (US)
• US Licence: Baclofen
• Gene Information: human ... GABBR1(2550), GABBR2(9568)rat ... Gabbr1(81657), Gabra2(29706)

Product Information

• Purity: ≥98% (TLC); 95%

DETAILS

MP Biomedicals - 02153629

White solid; mp 192-193°C.
Store tightly sealed.
Soluble in water, dilute acid and base.

DrugBank - DB00181

• Drug 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.
• 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.
• Pharmacology: 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.
• Toxicity: LD₅₀=45 mg/kg (male mice, IV); LD₅₀=78 mg/kg (male rat, IV)
• Affected Organisms: Humans and other mammals
• Biotransformation: ~ 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.
• Absorption: Rapidly and almost completely absorbed from the GI tract.
• Half Life: 2.5-4 hours
• Protein Binding: 30%
• 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.
• Distribution: * 59 L
• Clearance: * 180 mL/min
• References: 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] ; 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] ; See S, Ginzburg R: Skeletal muscle relaxants. Pharmacotherapy. 2008 Feb;28(2):207-13. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - B5399

Biochem/physiol Actions
GABAB receptor agonist; skeletal muscle relaxant; antispastic agent.

Toronto Research Chemicals - B108000

Specific GABA-B receptor agonist. Muscle relaxant (skeletal).

REFERENCES

• 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
• 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
• See S, Ginzburg R: Skeletal muscle relaxants. Pharmacotherapy. 2008 Feb;28(2):207-13. Pubmed
• Ahuja, S., et al.: Anal. Profiles Drug Subs., 14, 527 (1985)
• Brogden, R.N., et al.: Drugs, 8,1 (1974)