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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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BOX 979,FI-20101 TURKU,., FINLAND","customerAddress":"430, DLF TOWERS,"}]
07-Jan-2021
31-Aug-2024
KGS
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DOSAGE - SOLUTION;ORAL - 10MG/5ML

USFDA APPLICATION NUMBER - 208193

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DOSAGE - SOLUTION;ORAL - 5MG/5ML

USFDA APPLICATION NUMBER - 208193

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DOSAGE - INJECTABLE;INTRATHECAL - 0.05MG/ML

USFDA APPLICATION NUMBER - 22462

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DOSAGE - INJECTABLE;INTRATHECAL - 0.5MG/ML

USFDA APPLICATION NUMBER - 22462

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DOSAGE - INJECTABLE;INTRATHECAL - 1MG/ML

USFDA APPLICATION NUMBER - 22462

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DOSAGE - INJECTABLE;INTRATHECAL - 2MG/ML

USFDA APPLICATION NUMBER - 22462

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