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1134-47-0 molecular structure
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4-amino-3-(4-chlorophenyl)butanoic acid

ChemBase ID: 66
Molecular Formular: C10H12ClNO2
Molecular Mass: 213.66078
Monoisotopic Mass: 213.05565631
SMILES and InChIs

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

Cite this record

CBID:66 http://www.chembase.cn/molecule-66.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
4-Amino-3-(4-chlorophenyl)butanoic acid
(±)-β-(Aminoethyl)-4-chlorobenzenepropanoic acid
(±)-β-(Aminomethyl)-4-chlorobenzenepropanoic acid
Lioresal
β-(Aminomethyl)-4-chloro-benzenepropanoic Acid
β-(Aminomethyl)-p-chlorohydrocinnamic Acid
β-(4-Chlorophenyl)-GABA
Ba-34647
Baclon
Baclofen
Clofen
(±)-BACLOFEN
(±)-Baclofen
CAS Number
1134-47-0
EC Number
214-486-9
MDL Number
MFCD00055143
PubChem SID
24278146
46508181
160963529
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

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 3.8868947  H Acceptors
H Donor LogD (pH = 5.5) -0.79014736 
LogD (pH = 7.4) -0.7832327  Log P -0.78240025 
Molar Refractivity 54.8292 cm3 Polarizability 21.613943 Å3
Polar Surface Area 63.32 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.82  LOG S -2.48 
Solubility (Water) 7.12e-01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1 M HCl: soluble50 mg/mL expand Show data source
2090 mg/L expand Show data source
Water expand Show data source
Apperance
Off-White Solid expand Show data source
white to very faintly yellow solid expand Show data source
Melting Point
207°C expand Show data source
208-210°C expand Show data source
Hydrophobicity(logP)
-0.62 expand Show data source
1.3 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
MW5084200 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
3 expand Show data source
III expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
61-25-36/37/38-42/43 expand Show data source
R:25-36/37/38 expand Show data source
Safety Statements
53-22-36/37/39-45 expand Show data source
S:28-29-36/37/39-45 expand Show data source
EU Classification
T2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS06 expand Show data source
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H301-H315-H317-H319-H334-H335-H360 expand Show data source
GHS Precautionary statements
P201-P261-P280-P301 + P310-P305 + P351 + P338-P308 + P313 expand Show data source
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 expand Show data source
RID/ADR
UN 2811 6.1/PG 3 expand Show data source
Storage Temperature
2-8°C expand Show data source
Admin Routes
Oral, intrathecal expand Show data source
Bioavailability
well absorbed expand Show data source
Excretion
renal (70-80%) expand Show data source
Half Life
1.5 to 4 hours expand Show data source
Metabolism
85% excreted in urine/faeces unchanged. 15% metabolised by deamination expand Show data source
Protein Bound
30% expand Show data source
Legal Status
Rx-only (US) expand Show data source
Pregnancy Category
C (US) expand Show data source
US Licence
Baclofen expand Show data source
Gene Information
human ... GABBR1(2550), GABBR2(9568)rat ... Gabbr1(81657), Gabra2(29706) expand Show data source
Purity
≥98% (TLC) expand Show data source
95% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source

DETAILS

DETAILS

Wikipedia Wikipedia DrugBank DrugBank MP Biomedicals MP Biomedicals Sigma Aldrich Sigma Aldrich TRC TRC
DrugBank - DB00181 external link
Item Information
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
MP Biomedicals - 02153629 external link
White solid; mp 192-193°C.
Store tightly sealed.
Soluble in water, dilute acid and base.
Sigma Aldrich - B5399 external link
Biochem/physiol Actions
GABAB receptor agonist; skeletal muscle relaxant; antispastic agent.
Toronto Research Chemicals - B108000 external link
Specific GABA-B receptor agonist. Muscle relaxant (skeletal).

REFERENCES

REFERENCES

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

PATENTS

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INTERNET

INTERNET

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