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    Chemistry

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    Also known as: 95-25-0, Paraflex, Chloroxazone, Chlorzoxazon, 5-chloro-2-benzoxazolone, 5-chloro-2-benzoxazolinone
    Molecular Formula
    C7H4ClNO2
    Molecular Weight
    169.56  g/mol
    InChI Key
    TZFWDZFKRBELIQ-UHFFFAOYSA-N
    FDA UNII
    H0DE420U8G
    Chlorzoxazone
    A centrally acting central muscle relaxant with sedative properties. It is claimed to inhibit muscle spasm by exerting an effect primarily at the level of the spinal cord and subcortical areas of the brain. (From Martindale, The Extra Pharmacopoea, 30th ed, p1202)
    Chlorzoxazone is a Muscle Relaxant. The physiologic effect of chlorzoxazone is by means of Centrally-mediated Muscle Relaxation.
    1 2D Structure

    Chlorzoxazone

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    5-chloro-3H-1,3-benzoxazol-2-one
    2.1.2 InChI
    InChI=1S/C7H4ClNO2/c8-4-1-2-6-5(3-4)9-7(10)11-6/h1-3H,(H,9,10)
    2.1.3 InChI Key
    TZFWDZFKRBELIQ-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    C1=CC2=C(C=C1Cl)NC(=O)O2
    2.2 Other Identifiers
    2.2.1 UNII
    H0DE420U8G
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Paraflex

    2. Parafon

    3. Parafon Forte Dsc

    2.3.2 Depositor-Supplied Synonyms

    1. 95-25-0

    2. Paraflex

    3. Chloroxazone

    4. Chlorzoxazon

    5. 5-chloro-2-benzoxazolone

    6. 5-chloro-2-benzoxazolinone

    7. 2(3h)-benzoxazolone, 5-chloro-

    8. Biomioran

    9. Escoflex

    10. Myoflexin

    11. Myoflexine

    12. Pathorysin

    13. 5-chloro-2-hydroxybenzoxazole

    14. Mioran

    15. Miotran

    16. Neoflex

    17. Solaxin

    18. 5-chloro-2(3h)-benzoxazolone

    19. Parafon Forte Dsc

    20. 5-chlorobenzoxazolidone

    21. 5-chlorobenzo[d]oxazol-2(3h)-one

    22. 5-chloro-2-benzoxazolol

    23. Chlorzoxane

    24. 5-chloro-1,3-benzoxazol-2(3h)-one

    25. Usaf Ma-10

    26. 5-chlorobenzoxazol-2-one

    27. 5-chloro-3h-1,3-benzoxazol-2-one

    28. Strifon Forte Dsc

    29. Parafon

    30. 5-chlorobenzoxazolone

    31. 2-hydroxy-5-chlorobenzoxazole

    32. Chlorzoxazonum

    33. 5-chlorbenzoxazolin-2-on

    34. 5-chloro-3(h)-2-benzoxazolone

    35. 5-chlorobenzo[d]oxazol-2-ol

    36. 5-chlorobenzoksazolon-2

    37. 5-chlorobenzoksazolinon-2

    38. 5-chlorobenzoxazolin-2-one

    39. Strifon

    40. Nsc 26189

    41. 2-benzoxazolinone, 5-chloro-

    42. 5-chloro-3h-benzooxazol-2-one

    43. 5-chloro-1,3-benzoxazol-2-ol

    44. Chembl1371

    45. Mls000069380

    46. Chebi:3655

    47. H0de420u8g

    48. Chlorsoxazone

    49. Klorzoxazon

    50. Nyoflex

    51. Remofleks

    52. 5-chloro-2,3-dihydro-1,3-benzoxazol-2-one

    53. Parafon Forte

    54. Nsc-26189

    55. Cas-95-25-0

    56. Ncgc00015238-02

    57. Clorzoxazona

    58. Lorzone

    59. Smr000058269

    60. Dsstox_cid_2813

    61. Dsstox_rid_76739

    62. Dsstox_gsid_22813

    63. Clw

    64. Chlorzoxazonum [inn-latin]

    65. Clorzoxazona [inn-spanish]

    66. Chlorzoxazona

    67. 5-chlorobenzoksazolon-2 [polish]

    68. 5-chlorobenzoksazolinon-2 [polish]

    69. Paraflex (tn)

    70. Sr-01000075207

    71. Einecs 202-403-9

    72. Mfcd00005717

    73. Component Of Parafon Forte

    74. Unii-h0de420u8g

    75. Ai3-63119

    76. Chlorzoxazone (jan/usp/inn)

    77. Prestwick_62

    78. Chlorzoxazone,(s)

    79. Chlorzoxazone [usp:inn:ban:jan]

    80. 5-chlorobenzoxazolinone

    81. Spectrum_000148

    82. Opera_id_1659

    83. Prestwick0_000163

    84. Prestwick1_000163

    85. Prestwick2_000163

    86. Prestwick3_000163

    87. Spectrum2_001149

    88. Spectrum3_000350

    89. Spectrum4_000287

    90. Spectrum5_000745

    91. Lopac-c-4397

    92. Chlorzoxazone [mi]

    93. C 4397

    94. Chlorzoxazone [inn]

    95. Chlorzoxazone [jan]

    96. 5-chloro-benzooxazol-2-ol

    97. 5-chloro-benzoxazolin-2-one

    98. Lopac0_000253

    99. Schembl35177

    100. Bspbio_000025

    101. Bspbio_002019

    102. Chlorzoxazone [vandf]

    103. Kbiogr_000814

    104. Kbioss_000628

    105. Wln: T56 Bmvoj Hg

    106. Chlorzoxazone [mart.]

    107. Divk1c_000895

    108. Spectrum1500188

    109. Spbio_001077

    110. Spbio_001946

    111. Chlorzoxazone [usp-rs]

    112. Chlorzoxazone [who-dd]

    113. Bpbio1_000029

    114. Gtpl2322

    115. Dtxsid9022813

    116. Hms502m17

    117. Kbio1_000895

    118. Kbio2_000628

    119. Kbio2_003196

    120. Kbio2_005764

    121. Kbio3_001239

    122. Ninds_000895

    123. Chlorzoxazone-[13c,15n,18o]

    124. Hms1568b07

    125. Hms1920o07

    126. Hms2091e14

    127. Hms2095b07

    128. Hms2235i19

    129. Hms3259i15

    130. Hms3260d08

    131. Hms3373p17

    132. Hms3652k22

    133. Hms3712b07

    134. Hms3885n07

    135. Pharmakon1600-01500188

    136. 5-chloro-2-hydroxybenzo[d]oxazole

    137. Chlorzoxazone [orange Book]

    138. Act08248

    139. Albb-012641

    140. Bcp07916

    141. Hy-b1462

    142. Nsc26189

    143. Str00805

    144. Chlorzoxazone [usp Impurity]

    145. Tox21_110105

    146. Tox21_500253

    147. Bdbm50290811

    148. Ccg-40323

    149. Chlorzoxazone [usp Monograph]

    150. Nsc756693

    151. S4155

    152. Stk071582

    153. Zinc84843283

    154. Akos000404381

    155. Tox21_110105_1

    156. Component Of Parafon Forte (salt/mix)

    157. Cs-5155

    158. Db00356

    159. Hg-0202

    160. Lp00253

    161. Nc00499

    162. Nsc-756693

    163. Sdccgsbi-0050241.p005

    164. 5-chloranyl-3h-1,3-benzoxazol-2-one

    165. 5-chloro-1,3-benzoxazole-2(3h)-one

    166. Idi1_000895

    167. Chlorzoxazone 1.0 Mg/ml In Acetonitrile

    168. Ncgc00015238-01

    169. Ncgc00015238-03

    170. Ncgc00015238-04

    171. Ncgc00015238-05

    172. Ncgc00015238-06

    173. Ncgc00015238-07

    174. Ncgc00015238-08

    175. Ncgc00015238-09

    176. Ncgc00015238-10

    177. Ncgc00015238-13

    178. Ncgc00015238-24

    179. Ncgc00093714-01

    180. Ncgc00093714-02

    181. Ncgc00093714-03

    182. Ncgc00093714-04

    183. Ncgc00260938-01

    184. 5-chloro-1,3-benzoxazol-2(3h)-one #

    185. Ac-12192

    186. Bp-11613

    187. Meso-butane-1,2,3,4-tetracarboxylicacid

    188. Sbi-0050241.p004

    189. Db-057571

    190. Ab00051947

    191. Eu-0100253

    192. Ft-0620220

    193. Sw196377-3

    194. En300-31026

    195. A16449

    196. C07931

    197. D00771

    198. D78096

    199. Ab00051947_05

    200. Ab00051947_06

    201. A845253

    202. Q3294630

    203. Sr-01000075207-1

    204. Sr-01000075207-3

    205. Sr-01000075207-5

    206. W-100168

    207. Brd-k98174813-001-05-7

    208. Brd-k98174813-001-08-1

    209. Z57183224

    210. Chlorzoxazone, United States Pharmacopeia (usp) Reference Standard

    2.4 Create Date
    2005-03-25
    3 Chemical and Physical Properties
    Molecular Weight 169.56 g/mol
    Molecular Formula C7H4ClNO2
    XLogP31.8
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count0
    Exact Mass168.9930561 g/mol
    Monoisotopic Mass168.9930561 g/mol
    Topological Polar Surface Area38.3 Ų
    Heavy Atom Count11
    Formal Charge0
    Complexity185
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameChlorzoxazone
    PubMed HealthChlorzoxazone (By mouth)
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting
    Drug LabelChlorzoxazone USP is a centrally acting skeletal muscle relaxant, available as tablets of 500 mg for oral administration. Its chemical name is 5-Chloro-2-benzoxazolinone, and its structural formula is: Chlorzoxazone Structural FormulaC7H4CINO2 MW 1...
    Active IngredientChlorzoxazone
    Dosage FormTablet
    RouteOral
    Strength750mg; 375mg; 500mg
    Market StatusPrescription
    CompanyWatson Labs; Mikart; Barr

    2 of 4  
    Drug NameParafon forte dsc
    PubMed HealthChlorzoxazone (By mouth)
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting
    Drug LabelEach caplet (capsule shaped tablet) contains:*5-chlorobenzoxazolinoneChlorzoxazone*500 mgInactive ingredients: FD&C Blue No. 1, microcrystalline cellulose, docusate sodium, lactose (hydrous), magnesium stearate, sodium benzoate, sodium star...
    Active IngredientChlorzoxazone
    Dosage FormTablet
    RouteOral
    Strength500mg
    Market StatusPrescription
    CompanyJanssen R And D

    3 of 4  
    Drug NameChlorzoxazone
    PubMed HealthChlorzoxazone (By mouth)
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting
    Drug LabelChlorzoxazone USP is a centrally acting skeletal muscle relaxant, available as tablets of 500 mg for oral administration. Its chemical name is 5-Chloro-2-benzoxazolinone, and its structural formula is: Chlorzoxazone Structural FormulaC7H4CINO2 MW 1...
    Active IngredientChlorzoxazone
    Dosage FormTablet
    RouteOral
    Strength750mg; 375mg; 500mg
    Market StatusPrescription
    CompanyWatson Labs; Mikart; Barr

    4 of 4  
    Drug NameParafon forte dsc
    PubMed HealthChlorzoxazone (By mouth)
    Drug ClassesSkeletal Muscle Relaxant, Centrally Acting
    Drug LabelEach caplet (capsule shaped tablet) contains:*5-chlorobenzoxazolinoneChlorzoxazone*500 mgInactive ingredients: FD&C Blue No. 1, microcrystalline cellulose, docusate sodium, lactose (hydrous), magnesium stearate, sodium benzoate, sodium star...
    Active IngredientChlorzoxazone
    Dosage FormTablet
    RouteOral
    Strength500mg
    Market StatusPrescription
    CompanyJanssen R And D

    4.2 Drug Indication

    For the relief of discomfort associated with acute painful musculoskeletal conditions.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Chlorzoxazone is a centrally-acting agent for painful musculoskeletal conditions. Data available from animal experiments as well as human study indicate that chlorzoxazone acts primarily at the level of the spinal cord and subcortical areas of the brain where it inhibits multisynaptic reflex a.c. involved in producing and maintaining skeletal muscle spasm of varied etiology. The clinical result is a reduction of the skeletal muscle spasm with relief of pain and increased mobility of the involved muscles.

    5.2 MeSH Pharmacological Classification

    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
    CHLORZOXAZONE
    5.3.2 FDA UNII
    H0DE420U8G
    5.3.3 Pharmacological Classes
    Muscle Relaxant [EPC]; Centrally-mediated Muscle Relaxation [PE]
    5.4 ATC Code

    M - Musculo-skeletal system

    M03 - Muscle relaxants

    M03B - Muscle relaxants, centrally acting agents

    M03BB - Oxazol, thiazine, and triazine derivatives

    M03BB03 - Chlorzoxazone

    5.5 Absorption, Distribution and Excretion

    Route of Elimination

    Chlorzoxazone is rapidly metabolized and is excreted in the urine, primarily in a conjugated form as the glucuronide.

    5.6 Metabolism/Metabolites

    Chlorzoxazone is rapidly metabolized in the liver and is excreted in the urine, primarily in a conjugated form as the glucuronide.

    Chlorzoxazone has known human metabolites that include 6-Hydroxychlorzoxazone.

    S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

    5.7 Mechanism of Action

    Chlorzoxazone inhibits degranulation of mast cells, subsequently preventing the release of histamine and slow-reacting substance of anaphylaxis (SRS-A), mediators of type I allergic reactions. Chlorzoxazone also may reduce the release of inflammatory leukotrienes. Chlorzoxazone may act by inhibiting calcium and potassium influx which would lead to neuronal inhibition and muscle relaxation. Data available from animal experiments as well as human study indicate that chlorzoxazone acts primarily at the level of the spinal cord and subcortical areas of the brain where it inhibits multisynaptic reflex arcs involved in producing and maintaining skeletal muscle spasm

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    07-Jan-2021
    30-Aug-2024
    KGS
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