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    Chemistry

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    Also known as: 1134-47-0, Lioresal, 4-amino-3-(4-chlorophenyl)butanoic acid, Kemstro, Baclon, Dl-baclofen
    Molecular Formula
    C10H12ClNO2
    Molecular Weight
    213.66  g/mol
    InChI Key
    KPYSYYIEGFHWSV-UHFFFAOYSA-N
    FDA UNII
    H789N3FKE8
    Baclofen
    A GAMMA-AMINOBUTYRIC ACID derivative that is a specific agonist of GABA-B RECEPTORS. It is used in the treatment of MUSCLE SPASTICITY, especially that due to SPINAL CORD INJURIES. Its therapeutic effects result from actions at spinal and supraspinal sites, generally the reduction of excitatory transmission.
    Baclofen is a gamma-Aminobutyric Acid-ergic Agonist. The mechanism of action of baclofen is as a GABA A Agonist, and GABA B Agonist.
    1 2D Structure

    Baclofen

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    4-amino-3-(4-chlorophenyl)butanoic acid
    2.1.2 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)
    2.1.3 InChI Key
    KPYSYYIEGFHWSV-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC(=CC=C1C(CC(=O)O)CN)Cl
    2.2 Other Identifiers
    2.2.1 UNII
    H789N3FKE8
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Apo Baclofen

    2. Apo-baclofen

    3. Apobaclofen

    4. Atrofen

    5. Awd, Baclofen

    6. Ba-34,647

    7. Ba-34647

    8. Ba34,647

    9. Ba34647

    10. Baclofne Irex

    11. Baclofne-irex

    12. Baclofneirex

    13. Baclofen Awd

    14. Baclophen

    15. Baclospas

    16. Beta-(aminomethyl)-4-chlorobenzenepropanoic Acid

    17. Beta-(p-chlorophenyl)-gamma-aminobutyric Acid

    18. Chlorophenyl Gaba

    19. Ciba-34,647-ba

    20. Ciba34,647ba

    21. Clofen

    22. Gaba, Chlorophenyl

    23. Gen Baclofen

    24. Gen-baclofen

    25. Genbaclofen

    26. Genpharm

    27. Lebic

    28. Liorsal

    29. Lioresal

    30. Nu Baclo

    31. Nu-baclo

    32. Nubaclo

    33. Pcp-gaba

    34. Pms Baclofen

    35. Pms-baclofen

    36. Pmsbaclofen

    2.3.2 Depositor-Supplied Synonyms

    1. 1134-47-0

    2. Lioresal

    3. 4-amino-3-(4-chlorophenyl)butanoic Acid

    4. Kemstro

    5. Baclon

    6. Dl-baclofen

    7. Gabalon

    8. (+-)-baclofen

    9. Baclofene

    10. Baclofeno

    11. Baclofenum

    12. (rs)-baclofen

    13. Beta-(4-chlorophenyl)gaba

    14. 4-amino-3-(4-chlorophenyl)butyric Acid

    15. Ba-34647

    16. Gablofen

    17. Ciba 34,647-ba

    18. (+/-)-baclofen

    19. Dl-4-amino-3-p-chlorophenylbutanoic Acid

    20. Beta-(aminomethyl)-4-chlorobenzenepropanoic Acid

    21. Ba-34,647

    22. Beta-(p-chlorophenyl)-gamma-aminobutyric Acid

    23. Baclofen (r,s)

    24. C 34647ba

    25. Ba 34647

    26. Beta-(aminomethyl)-p-chlorohydrocinnamic Acid

    27. Gamma-amino-beta-(p-chlorophenyl)butyric Acid

    28. Butanoic Acid, 4-amino-3-(4-chlorophenyl)-

    29. Mfcd00055143

    30. Chembl701

    31. Nsc-755906

    32. Benzenepropanoic Acid, Beta-(aminomethyl)-4-chloro-

    33. Chebi:2972

    34. H789n3fke8

    35. (+)-baclofen; (l)-baclofen

    36. Atrofen

    37. Baclophen

    38. Lioresal Intrathecal

    39. Apo-baclofen

    40. Ncgc00015156-11

    41. (rs)-amino-3-(4-chlorophenyl)butyric Acid

    42. Dsstox_cid_2641

    43. 4-amino-3(4-chlorophenyl)butyric Acid

    44. Baclofene [inn-french]

    45. Baclofenum [inn-latin]

    46. .beta.-(aminomethyl)-p-chlorohydrocinnamic Acid

    47. Dsstox_rid_76670

    48. Baclofeno [inn-spanish]

    49. Dsstox_gsid_22641

    50. .beta.-(aminomethyl)-4-chlorobenzenepropanoic Acid

    51. Lioresal (tn)

    52. Kemstro (tn)

    53. Ccris 3722

    54. Sr-01000000107

    55. Einecs 214-486-9

    56. Brn 2104494

    57. Unii-h789n3fke8

    58. Baclofen O

    59. Ipx056

    60. Mfcd01321057

    61. Ipx 056

    62. (y)-baclofen

    63. Prestwick_85

    64. Cas-1134-47-0

    65. (?)-baclofen

    66. Fleqsuvy

    67. Lyvispah

    68. Ozobax

    69. Baclofen [usan:usp:inn:ban:jan]

    70. (a+/-)-baclofen

    71. Spectrum_000066

    72. Baclofen [usan]

    73. Baclofen [inn]

    74. Baclofen [jan]

    75. Baclofen [mi]

    76. Baclofen [vandf]

    77. (.+/-.)-baclofen

    78. (.+/-.)-baklofen

    79. Prestwick0_000085

    80. Prestwick1_000085

    81. Prestwick2_000085

    82. Prestwick3_000085

    83. Spectrum2_000092

    84. Spectrum3_000310

    85. Spectrum4_000245

    86. Spectrum5_000852

    87. Baclofen-[d4] (major)

    88. Baclofen [mart.]

    89. Baclofen [usp-rs]

    90. Baclofen [who-dd]

    91. Biomol-nt_000251

    92. Upcmld-dp142

    93. (±)-baclofen

    94. B 5399

    95. Lopac0_000163

    96. Oprea1_440627

    97. Schembl19333

    98. Bspbio_000010

    99. Bspbio_001880

    100. Kbiogr_000650

    101. Kbioss_000466

    102. Mls000028480

    103. .beta.-(4-chlorophenyl)gaba

    104. Divk1c_000001

    105. Spectrum1500135

    106. Baclofen (jp17/usp/inn)

    107. Hydrocinnamic Acid, .beta.-(aminomethyl)-p-chloro-

    108. Spbio_000044

    109. Spbio_001949

    110. Baclofen [orange Book]

    111. Benzenepropanoic Acid, .beta.-(aminomethyl)-4-chloro-

    112. Bpbio1_000012

    113. Bpbio1_000750

    114. Gtpl1084

    115. Baclofen [ep Monograph]

    116. Baclofen [usp Monograph]

    117. Dtxsid5022641

    118. Hydrocinnamic Acid, Beta-(aminomethyl)-p-chloro-

    119. Upcmld-dp142:001

    120. Bdbm24182

    121. Hms500a03

    122. Kbio1_000001

    123. Kbio2_000466

    124. Kbio2_003034

    125. Kbio2_005602

    126. Kbio3_001380

    127. Baclofen 0.5 Mg/ml In Methanol

    128. Ninds_000001

    129. Hms1568a12

    130. Hms1920e21

    131. Hms2091m03

    132. Hms2095a12

    133. Hms3260b07

    134. Hms3712a12

    135. Pharmakon1600-01500135

    136. ( Inverted Question Mark)-baclofen

    137. Albb-014712

    138. Bcp11844

    139. Bcp32777

    140. Ex-a1378

    141. Hy-b0007

    142. Tox21_110090

    143. Tox21_500163

    144. Bbl010735

    145. Ccg-38910

    146. Cx1358

    147. Nsc329137

    148. Nsc755906

    149. S4840

    150. Stk535284

    151. Akos005174692

    152. Tox21_110090_1

    153. Ac-4530

    154. Db00181

    155. Hs-1001

    156. Lp00163

    157. Mb00475

    158. Nsc 755906

    159. Nsc-329137

    160. Sb67382

    161. Sdccgsbi-0050151.p005

    162. 4-amino-3-(4-chlorophenyl)butanoicacid

    163. 4-amino-3-(p-chlorophenyl)butyric Acid

    164. Idi1_000001

    165. Smp1_000036

    166. Ncgc00015156-04

    167. Ncgc00015156-05

    168. Ncgc00015156-06

    169. Ncgc00015156-07

    170. Ncgc00015156-08

    171. Ncgc00015156-12

    172. Ncgc00015156-13

    173. Ncgc00015156-15

    174. Ncgc00015156-26

    175. Ncgc00015156-28

    176. Ncgc00023843-03

    177. Ncgc00024579-03

    178. Ncgc00024579-04

    179. Ncgc00024579-05

    180. Ncgc00024579-06

    181. Ncgc00260848-01

    182. Bb166152

    183. Smr000058294

    184. Sy023865

    185. Sy052300

    186. Sbi-0050151.p004

    187. (+/-)-baclofen, >=98% (tlc), Solid

    188. 4-amino-3-(4-chlorophenyl)butanoic Acid #

    189. Ab00051921

    190. Eu-0100163

    191. Ft-0622547

    192. Ft-0662468

    193. Ft-0662469

    194. (rs)-4-amino-3-(4-chlorophenyl)butanoic Acid

    195. D00241

    196. Ab00051921_16

    197. .beta.-(p-chlorophenyl)-.gamma.-aminobutyric Acid

    198. .gamma.-amino-.beta.-(p-chlorophenyl)butyric Acid

    199. 134b470

    200. L000002

    201. Q413717

    202. J-002965

    203. Sr-01000000107-2

    204. Sr-01000000107-4

    205. Sr-01000000107-6

    206. Sr-01000000107-8

    207. Brd-a84174873-001-05-2

    208. (+/- )-beta-(aminomethyl)-4-chlorobenzenepropanoic Acid

    209. Baclofen, British Pharmacopoeia (bp) Reference Standard

    210. Baclofen, European Pharmacopoeia (ep) Reference Standard

    211. F2173-1127

    212. Stx209; Stx-209; Stx 209; D-baclofen; Arbaclofen

    213. Baclofen Lioresal 4-amino-3-(4-chlorophenyl)butyric Acid

    214. Baclofen, United States Pharmacopeia (usp) Reference Standard

    215. N-boc-(2s,3s)-2-hydroxy-3-amino-5-methylhexanoicacid

    216. Baclofen, Pharmaceutical Secondary Standard; Certified Reference Material

    217. Baclofen Solution, 500 Mug/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

    218. Baclofen Solution, 500 Mug/ml (90:10 Meoh:dmso), Certified Reference Material, Ampule Of 1 Ml

    219. Brivaracetam-d3 Solution, 100 Mug/ml In Methanol, Certified Reference Material, Ampule Of 1 Ml

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 213.66 g/mol
    Molecular Formula C10H12ClNO2
    XLogP3-1
    Hydrogen Bond Donor Count2
    Hydrogen Bond Acceptor Count3
    Rotatable Bond Count4
    Exact Mass213.0556563 g/mol
    Monoisotopic Mass213.0556563 g/mol
    Topological Polar Surface Area63.3 Ų
    Heavy Atom Count14
    Formal Charge0
    Complexity191
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 6  
    Drug NameBaclofen
    PubMed HealthBaclofen
    Drug ClassesAnalgesic, Skeletal Muscle Relaxant, Centrally Acting
    Drug LabelLIORESAL INTRATHECAL (baclofen injection) is a muscle relaxant and antispastic. Its chemical name is 4-amino-3-(4-chlorophenyl) butanoic acid, and its structural formula is: Baclofen is a white to off-white, odorless or practically odorless crystal...
    Active IngredientBaclofen
    Dosage FormTablet
    Routeoral; Oral
    Strength10mg; 20mg
    Market StatusPrescription
    CompanyWatson Labs; Vintage Pharms; Mylan Pharms; Ivax Sub Teva Pharms; Caraco; Lannett; Usl Pharma; Sun Pharm Inds; Northstar Hlthcare; Prosam Labs; Mylan; Impax Labs

    2 of 6  
    Drug NameGablofen
    PubMed HealthBaclofen
    Drug ClassesAnalgesic, Skeletal Muscle Relaxant, Centrally Acting
    Drug LabelGablofen (baclofen injection) is a muscle relaxant and antispastic. Baclofen's pharmacological class is a gamma-aminobutyric acid (GABA) ergic agonist. Baclofen's chemical name is 4-amino- 3-(4-chlorophenyl) butanoic acid, and its structural for
    Active IngredientBaclofen
    Dosage FormInjectable
    RouteIntrathecal
    Strength2mg/ml; 1mg/ml; 0.05mg/ml; 0.5mg/ml
    Market StatusPrescription
    CompanyMallinckrodt

    3 of 6  
    Drug NameLioresal
    PubMed HealthBaclofen (By mouth)
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting
    Drug LabelLIORESAL INTRATHECAL (baclofen injection) is a muscle relaxant and antispastic. Its chemical name is 4-amino-3-(4-chlorophenyl) butanoic acid, and its structural formula is: Baclofen is a white to off-white, odorless or practically odorless crystal...
    Active IngredientBaclofen
    Dosage FormInjectable
    RouteIntrathecal
    Strength2mg/ml; 0.05mg/ml; 0.5mg/ml
    Market StatusPrescription
    CompanyMedtronic Neuro

    4 of 6  
    Drug NameBaclofen
    PubMed HealthBaclofen
    Drug ClassesAnalgesic, Skeletal Muscle Relaxant, Centrally Acting
    Drug LabelLIORESAL INTRATHECAL (baclofen injection) is a muscle relaxant and antispastic. Its chemical name is 4-amino-3-(4-chlorophenyl) butanoic acid, and its structural formula is: Baclofen is a white to off-white, odorless or practically odorless crystal...
    Active IngredientBaclofen
    Dosage FormTablet
    Routeoral; Oral
    Strength10mg; 20mg
    Market StatusPrescription
    CompanyWatson Labs; Vintage Pharms; Mylan Pharms; Ivax Sub Teva Pharms; Caraco; Lannett; Usl Pharma; Sun Pharm Inds; Northstar Hlthcare; Prosam Labs; Mylan; Impax Labs

    5 of 6  
    Drug NameGablofen
    PubMed HealthBaclofen
    Drug ClassesAnalgesic, Skeletal Muscle Relaxant, Centrally Acting
    Drug LabelGablofen (baclofen injection) is a muscle relaxant and antispastic. Baclofen's pharmacological class is a gamma-aminobutyric acid (GABA) ergic agonist. Baclofen's chemical name is 4-amino- 3-(4-chlorophenyl) butanoic acid, and its structural for
    Active IngredientBaclofen
    Dosage FormInjectable
    RouteIntrathecal
    Strength2mg/ml; 1mg/ml; 0.05mg/ml; 0.5mg/ml
    Market StatusPrescription
    CompanyMallinckrodt

    6 of 6  
    Drug NameLioresal
    PubMed HealthBaclofen (By mouth)
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting
    Drug LabelLIORESAL INTRATHECAL (baclofen injection) is a muscle relaxant and antispastic. Its chemical name is 4-amino-3-(4-chlorophenyl) butanoic acid, and its structural formula is: Baclofen is a white to off-white, odorless or practically odorless crystal...
    Active IngredientBaclofen
    Dosage FormInjectable
    RouteIntrathecal
    Strength2mg/ml; 0.05mg/ml; 0.5mg/ml
    Market StatusPrescription
    CompanyMedtronic Neuro

    4.2 Drug Indication

    Baclofen is indicated for the treatment of spasticity resulting from multiple sclerosis and is particularly useful for the relief of flexor spasms and concomitant pain, clonus, and muscular rigidity. It may also be of value in the treatment of patients with spinal cord injuries or diseases. Baclofen is also indicated as an intrathecal injection for the management of severe spasticity of cerebral or spinal original in patients 4 years of age and older. Patients who respond to bolus intrathecal doses of baclofen, and who require chronic therapy, can use an implantable intrathecal pump to administer baclofen via long-term infusion.

    FDA Label

    Treatment of alcohol dependence

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    In neurological diseases associated with spasm of the skeletal muscles, the clinical effects of baclofen occur due to baclofen action on reflex muscle contractions and of significant relief from painful spasm, automatism, as well as clonus. Baclofen, when used as indicated, improves mobility, increasing levels of independence, and facilitates both passive and active physiotherapy. Baclofen also stimulates gastric acid secretion. GABA-B receptor activation by baclofen may produce protective neurological effects. Baclofen also possesses anti-inflammatory properties that may be of interest in the study of addiction treatment. Preclinical studies have shown that GABA-B receptors have roles in memory storage and retrieval, reward, motivation, mood, as well as anxiety. Neuroimaging studies in humans indicate that baclofen produces region-specific alterations in brain activity.

    5.2 MeSH Pharmacological Classification

    GABA-B Receptor Agonists

    Endogenous compounds and drugs that bind to and activate GABA-B RECEPTORS. (See all compounds classified as GABA-B Receptor Agonists.)

    Muscle Relaxants, Central

    A heterogeneous group of drugs used to produce muscle relaxation, excepting the neuromuscular blocking agents. They have their primary clinical and therapeutic uses in the treatment of muscle spasm and immobility associated with strains, sprains, and injuries of the back and, to a lesser degree, injuries to the neck. They have been used also for the treatment of a variety of clinical conditions that have in common only the presence of skeletal muscle hyperactivity, for example, the muscle spasms that can occur in MULTIPLE SCLEROSIS. (From Smith and Reynard, Textbook of Pharmacology, 1991, p358) (See all compounds classified as Muscle Relaxants, Central.)

    5.3 FDA Pharmacological Classification
    5.3.1 Active Moiety
    BACLOFEN
    5.3.2 FDA UNII
    H789N3FKE8
    5.3.3 Pharmacological Classes
    GABA B Agonists [MoA]; gamma-Aminobutyric Acid-ergic Agonist [EPC]; GABA A Agonists [MoA]
    5.4 ATC Code

    M03BX01

    S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

    M - Musculo-skeletal system

    M03 - Muscle relaxants

    M03B - Muscle relaxants, centrally acting agents

    M03BX - Other centrally acting agents

    M03BX01 - Baclofen

    5.5 Absorption, Distribution and Excretion

    Absorption

    Rapidly and almost completely absorbed from the gastrointestinal tract. Absorption may be dose-dependent, being reduced with increased doses. Baclofen, when introduced directly into the intrathecal space, allows for effective CSF concentrations to be achieved with resulting plasma concentrations 100 times less than concentrations occurring with oral administration,.

    Route of Elimination

    Baclofen is rapidly and extensively eliminated from the body. There is significant intersubject variation in elimination rates. Baclofen is excreted mainly by the kidney as unchanged drug. Seventy to eighty (70 - 80%) of a dose is measured in the urine as unchanged drug. The remainder of the dose is excreted as unchanged drug in the feces or as metabolites in the urine and feces. Excretion is complete within 72 hours after administration.

    Volume of Distribution

    **Apparent volume of distribution**: 59 liters. Baclofen does not readily cross the blood-brain barrier.

    Clearance

    **Total systemic clearance**: 180 mL/min **Renal clearance**: 103 mL/min Baclofen is primarily excreted unchanged by the kidneys. It should be administered cautiously, and it may be necessary to reduce the dosage in patients with reduced renal function.

    5.6 Metabolism/Metabolites

    Approximately 15% of the dose is metabolized in the liver, mainly by deamination. In a clinical study with radiolabeled baclofen, approximately 85% of the dose was excreted unchanged in the urine and feces. The -hydroxy metabolite, 3-(p-chlorophenyl)-4-hydroxybutyric acid, is formed by the deamination of baclofen. Because baclofen is partially metabolized in the liver, patients with impaired liver function should be regularly monitored with liver function tests.

    5.7 Biological Half-Life

    Elimination half-life: Approximately 5.5 hours.

    5.8 Mechanism of Action

    The exact mechanism of action of baclofen is not fully understood at this time,. Many studies indicate that baclofen is a GABA-B receptor agonist,,,,. Despite this, there is no conclusive evidence that the effects of baclofen on GABA systems are involved in the production of its clinical effects. Baclofen is an effective and widely used antispastic agent with a spinal site of action. Its mechanism of action and pharmacological properties are different from the effects of other antispastic agents. In addition, baclofen has central sites of action, shown by its adverse event profile and general CNS depressant properties. GABA-B receptors interact with signal transduction pathways and neurotransmitter systems. Baclofen exerts an antinociceptive effect. The clinical significance of this warrants further research data for clarification. Baclofen depresses monosynaptic and polysynaptic reflex transmission, by various actions, and possibly including the stimulation of GABA-receptors. This stimulation results in the inhibition of excitatory neurotransmitter (glutamate and aspartate) release, which may normally contribute to pain and spasticity. Although baclofen is an analog of the inhibitory neurotransmitter gamma-amino-butyric acid (GABA), there are no conclusive data indicating GABA systems are involved in its clinical effects.

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    07-Jan-2021
    27-Aug-2024
    KGS
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    Average Price (USD/KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

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    (KGS)    		 Average Price
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    DOSAGE - SOLUTION;ORAL - 10MG/5ML

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    DOSAGE - INJECTABLE;INTRATHECAL - 0.05MG/ML

    USFDA APPLICATION NUMBER - 22462

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    DOSAGE - INJECTABLE;INTRATHECAL - 0.5MG/ML

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    DOSAGE - INJECTABLE;INTRATHECAL - 1MG/ML

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