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Chemistry

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Also known as: 80-77-3, Trancopal, Chlormethazanone, Chlormethazone, Chlormezanon, Clormetazanone
Molecular Formula
C11H12ClNO3S
Molecular Weight
273.74  g/mol
InChI Key
WEQAYVWKMWHEJO-UHFFFAOYSA-N
FDA UNII
4BU37OM8KL

Chlormezanone
A non-benzodiazepine that is used in the management of anxiety. It has been suggested for use in the treatment of muscle spasm.
1 2D Structure

Chlormezanone

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(4-chlorophenyl)-3-methyl-1,1-dioxo-1,3-thiazinan-4-one
2.1.2 InChI
InChI=1S/C11H12ClNO3S/c1-13-10(14)6-7-17(15,16)11(13)8-2-4-9(12)5-3-8/h2-5,11H,6-7H2,1H3
2.1.3 InChI Key
WEQAYVWKMWHEJO-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CN1C(S(=O)(=O)CCC1=O)C2=CC=C(C=C2)Cl
2.2 Other Identifiers
2.2.1 UNII
4BU37OM8KL
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Chlormethazanone

2.3.2 Depositor-Supplied Synonyms

1. 80-77-3

2. Trancopal

3. Chlormethazanone

4. Chlormethazone

5. Chlormezanon

6. Clormetazanone

7. Clormetazon

8. Phenarol

9. Dl-chlormezanone

10. Clorilax

11. Miorilax

12. Myolespen

13. Rilansyl

14. Rilaquil

15. Rilassol

16. Supotran

17. Trancote

18. Alinam

19. Banabin

20. Bisina

21. Tanafol

22. Rexan

23. Rilax

24. Banabin-sintyal

25. Muskel-trancopal

26. Mio-sed

27. Banabil-sintyal

28. 2-(4-chlorophenyl)-3-methyl-1,3-thiazinan-4-one 1,1-dioxide

29. Chlormezanonum

30. Dichloromezanone

31. Clormezanone [dcit]

32. Chlomedinon

33. Rillasol

34. Suprotan

35. Muskel

36. Lobak

37. (+-)-chlormezanone

38. Chlormezanonum [inn-latin]

39. Clormezanona [inn-spanish]

40. Dichloromethazanone

41. 2-(4-chlorophenyl)-3-methyl-1,1-dioxo-1,3-thiazinan-4-one

42. Win 4692

43. 2-(p-chlorophenyl)tetrahydro-3-methyl-4h-1,3-thiazin-4-one 1,1-dioxide

44. (+)-chlormezanone

45. (-)-chlormezanone

46. 4h-1,3-thiazin-4-one, 2-(4-chlorophenyl)tetrahydro-3-methyl-, 1,1-dioxide

47. 2-(4-chlorophenyl)-3-methyl-4-metathiazanone-1,1-dioxide

48. (+)-fenarol

49. (-)-fenarol

50. 2-(p-chlorphenyl)-3-methyl-1,3-perhydrothiazin-4-on-1,1-dioxide

51. Chlormezanone, (+)-

52. Chlormezanone, (-)-

53. Chlormezanone (trancopal)

54. Tranrilax

55. Nsc-169108

56. 4bu37om8kl

57. 4h-1,3-thiazin-4-one, Tetrahydro-2-(p-chlorophenyl)-3-methyl-, 1,1-dioxide

58. C14wb33y0s

59. Chebi:3619

60. Clormezanone

61. Gp568v9g19

62. 2-(4-chlorophenyl)tetrahydro-3-methyl-4h-1,3-thiazin-4-one 1,1-dioxide

63. Chlormezanone 100 Microg/ml In Ethanol

64. Ncgc00015191-06

65. Ncgc00015191-07

66. Clormezanona

67. Rilasol

68. Transanate

69. (+-)-fenarol

70. Dsstox_cid_2798

71. Dsstox_rid_76732

72. Dsstox_gsid_22798

73. Chlormezanona

74. Chlormezanone [ban:inn:jan]

75. Chlormezanone [inn:ban:jan]

76. Mfcd00143951

77. 2-(4-chlorophenyl)tetrahydro-3-methyl-4h-1,3-thiazin-4-one-1,1-dioxide

78. 4h-1,3-thiazin-4-one, 2-(4-chlorophenyl)tetrahydro-3-methyl-, 1,1-dioxide, (+)-

79. 4h-1,3-thiazin-4-one, 2-(4-chlorophenyl)tetrahydro-3-methyl-, 1,1-dioxide, (-)-

80. 102818-66-6

81. 102818-67-7

82. Smr001456219

83. Hsdb 3300

84. Sr-01000075208

85. Trancopal (tn)

86. Einecs 201-307-4

87. Chlormezanone (jan/inn)

88. Nsc 169108

89. Fenaprim

90. Trancopa

91. 2-(4-chlorphenyl)-3-methyl-4-metathiazanon-1,1-dioxid

92. Unii-gp568v9g19

93. Cas-80-77-3

94. 4h-1,3-thiazin-4-one, 2-(p-chlorophenyl)tetrahydro-3-methyl-1,1-dioxide

95. Prestwick_736

96. 2-(para-chlorophenyl)tetrahydro-3-methyl-4h-1,3-thiazin-4-one, 1,1-dioxide

97. 4h-1,3-thiazin-4-one, 2-(4-chlorophenyl)tetrahydro-3-methyl-1,1-dioxide

98. (+/-)-chlormezanone

99. Spectrum_000414

100. (.+/-.)-fenarol

101. Prestwick0_000336

102. Prestwick1_000336

103. Prestwick2_000336

104. Prestwick3_000336

105. Spectrum2_001807

106. Spectrum3_001084

107. Spectrum4_001237

108. Spectrum5_001364

109. C-192

110. Chlormezanone [mi]

111. (.+/-.)-chlormezanone

112. Biomol-nt_000277

113. Unii-4bu37om8kl

114. Chlormezanone [inn]

115. Chlormezanone [jan]

116. Chlormezanone [hsdb]

117. Unii-c14wb33y0s

118. Lopac0_000383

119. Oprea1_275911

120. Bspbio_000371

121. Bspbio_002728

122. Chlormezanone [vandf]

123. Kbiogr_001734

124. Kbioss_000894

125. Chlormezanone Trancopal

126. Mls003876813

127. Mls004773972

128. Chlormezanone [mart.]

129. Divk1c_000886

130. Schembl217864

131. Spectrum2300062

132. Spbio_001793

133. Spbio_002292

134. Chlormezanone [who-dd]

135. Bpbio1_000409

136. Bpbio1_001189

137. Gtpl7323

138. Chembl1200714

139. Dtxsid3022798

140. Hms502m08

141. Kbio1_000886

142. Kbio2_000894

143. Kbio2_003462

144. Kbio2_006030

145. Kbio3_001948

146. Weqayvwkmwhejo-uhfffaoysa-

147. Ninds_000886

148. Hms1569c13

149. Hms2096c13

150. Hms3261m07

151. Hms3266a22

152. Hms3411m15

153. Hms3655n09

154. Hms3675m15

155. Hms3713c13

156. Hms3884e20

157. Pharmakon1600-02300062

158. Chlormezanone [orange Book]

159. Bcp14385

160. Hy-b0353

161. Wln: T6vn Dswtj B1 Cr Dg

162. Tox21_110093

163. Tox21_113151

164. Tox21_302197

165. Tox21_500383

166. Ccg-39616

167. Nsc169108

168. Nsc759569

169. S2021

170. Chlormezanone 1.0 Mg/ml In Methanol

171. 4h-1,3-thiazin-4-one, 2-(p-chlorophenyl)tetrahydro-3-methyl-, 1,1-dioxide

172. Akos000121464

173. Akos016844064

174. Tox21_110093_1

175. Db01178

176. Lp00383

177. Nsc-759569

178. Sdccgsbi-0050370.p004

179. Idi1_000886

180. Ncgc00015191-03

181. Ncgc00015191-04

182. Ncgc00015191-05

183. Ncgc00015191-08

184. Ncgc00015191-09

185. Ncgc00015191-10

186. Ncgc00015191-13

187. Ncgc00015191-22

188. Ncgc00024597-02

189. Ncgc00024597-03

190. Ncgc00024597-04

191. Ncgc00024597-05

192. Ncgc00024597-06

193. Ncgc00255305-01

194. Ncgc00261068-01

195. 2-(p-chlorphenyl)-3-methyl-1,1-dioxide

196. Sbi-0050370.p003

197. Ab00052410

198. Eu-0100383

199. Ft-0623609

200. Sw196880-3

201. C76585

202. D00268

203. Ab00052410_04

204. Ab00052410_05

205. Q5102983

206. Sr-01000075208-1

207. Sr-01000075208-3

208. Sr-01000075208-5

209. Sr-01000075208-6

210. Brd-a20348246-001-05-9

211. Brd-a20348246-001-08-3

212. 2-(p-chlorophenyl)tetrahydro-3-methyl-4h-1,1-dioxide

213. Z271004890

214. 4h-1, 2-(4-chlorophenyl)tetrahydro-3-methyl-, 1,1-dioxide

215. 4h-1, 2-(p-chlorophenyl)tetrahydro-3-methyl-, 1,1-dioxide

216. 2-(4-chlorophenyl)-3-methyl-1lambda6,3-thiazinane-1,1,4-trione

217. 2-(p-chlorphenyl)-3-methyl-1,3-perhydrothiazin-4-one, 1,1-dioxide

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 273.74 g/mol
Molecular Formula C11H12ClNO3S
XLogP31.1
Hydrogen Bond Donor Count0
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass273.0226421 g/mol
Monoisotopic Mass273.0226421 g/mol
Topological Polar Surface Area62.8 Ų
Heavy Atom Count17
Formal Charge0
Complexity395
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 Therapeutic Uses

Anti-Anxiety Agents; Muscle Relaxants, Central

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


...ADMIN IV HAVE ESTABLISHED VALUE IN TREATING ACUTE MUSCLE SPASMS ASSOC WITH TRAUMA & INFLAMMATION. ...ALSO BENEFICIAL IN PRODUCING MUSCLE RELAXATION FOR CERTAIN ORTHOPEDIC MANIPULATIONS. ...MAY TEMPORARILY ABATE SOME OF SYMPTOMS OF CEREBRAL PALSY... /CENTRALLY ACTING MUSCLE RELAXANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 241


MANY AGENTS WITH MUSCLE RELAXANT PROPERTIES PRODUCE NOTABLE SEDATION IN ORDINARY ORAL DOSES. SUCH AGENTS ENJOY PARTICULARLY WIDE USE IN TREATMENT OF MUSCLE TENSION & PAINS ASSOC WITH ANXIETY STATES & PSYCHOSOMATIC DISORDERS. /CENTRALLY ACTING MUSCLE RELAXANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 241


MUSCLE RELAXANTS CAUSE SKELETAL MUSCULAR RELAXATION, WITHOUT LOSS OF CONSCIOUSNESS, AS RESULT OF SELECTIVE ACTION UPON CNS. ... ALL TYPES OF EXPTL HYPERTONIA & HYPERREFLEXIA...PRODUCED BY SPINAL OR SUPRASPINAL LESIONS, ARE DIMINISHED... ALSO...PROTECTION AGAINST...CONVULSIVE AGENTS... /CENTRALLY ACTING MUSCLE RELAXANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 239


...AS EFFECTIVE AS CHLORDIAZEPOXIDE IN TREATING MILD ANXIETY. MUSCULOSKELETAL DISORDERS IN WHICH ANXIETY & TENSION INTENSIFY SYMPTOMS MAY RESPOND TO ITS SEDATIVE EFFECT...DOES NOT APPEAR TO HAVE ANY SPECIFIC EFFECT ON SPASTICITY OR RIGIDITY ASSOC WITH ORG NEUROLOGIC DISORDERS.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 418


4.2 Drug Warning

SOMETIMES METABOLITE DISCOLORS URINE.

Osol, A. and J.E. Hoover, et al. (eds.). Remington's Pharmaceutical Sciences. 15th ed. Easton, Pennsylvania: Mack Publishing Co., 1975., p. 860


UNTOWARD EFFECTS ARE GENERALLY MILD & OCCUR RELATIVELY INFREQUENTLY BUT, IN 2 CONTROLLED STUDIES, REACTIONS WERE MORE COMMON...THAN WITH CHLORDIAZEPOXIDE.

American Medical Association, AMA Department of Drugs, AMA Drug Evaluations. 3rd ed. Littleton, Massachusetts: PSG Publishing Co., Inc., 1977., p. 419


...PRODUCE SOME SEDATION, @ LEAST @ HIGHEST DOSES EMPLOYED CLINICALLY. /CENTRALLY ACTING MUSCLE RELAXANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 241


4.3 Drug Indication

Used in the management of anxiety and in the treatment of muscle spasm.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Chlormezanone is a non-benzodiazepine muscle relaxant. It was discontinued worldwide in 1996 by its manufacturer due to confirmed serious and rare cutaneous reactions (toxic epidermal necrolysis).


5.2 MeSH Pharmacological Classification

Anti-Anxiety Agents

Agents that alleviate ANXIETY, tension, and ANXIETY DISORDERS, promote sedation, and have a calming effect without affecting clarity of consciousness or neurologic conditions. ADRENERGIC BETA-ANTAGONISTS are commonly used in the symptomatic treatment of anxiety but are not included here. (See all compounds classified as Anti-Anxiety Agents.)


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 ATC Code

M - Musculo-skeletal system

M03 - Muscle relaxants

M03B - Muscle relaxants, centrally acting agents

M03BB - Oxazol, thiazine, and triazine derivatives

M03BB02 - Chlormezanone


5.4 Absorption, Distribution and Excretion

RAPIDLY ABSORBED FROM GI TRACT...EFFECT WITHIN 15 TO 30 MIN...DURATION OF ACTION OF 4 TO 6 HR...FREE DRUG & /4-CHLOROHIPPURIC ACID/ EXCRETED IN URINE /HUMAN, ORAL/...PRESENT IN HIGH CONCN IN KIDNEY, LIVER, MUSCLE, HEART, & BODY FAT, & IN LESSER CONCN IN LUNG & PLASMA /RATS, ORAL/.

American Society of Hospital Pharmacists. Data supplied on contract from American Hospital Formulary Service and other current ASHP sources., p. 1969


AFTER ORAL ADMIN OF (14)C-CHLORMEZANONE, ABOUT 74% OF DOSE WAS EXCRETED INTO URINE OF RATS WITHIN 24 HR & 21% INTO URINE OF MICE WITHIN 2 HR. BILIARY EXCRETION OF RADIOACTIVITY WAS ABOUT 10% OF DOSE IN RATS.

HAKUSUI H ET AL; XENOBIOTICA 8 (4) 229-38 (1978)


5.5 Metabolism/Metabolites

CHLORMEZANONE...IS EXCRETED UNCHANGED IN HUMAN URINE & DOG BILE. FORMATION OF 4-CHLOROHIPPURIC ACID, MAJOR URINARY METABOLITE IN MAN, INVOLVES NON-ENZYMIC HYDROLYSIS, FOLLOWED BY OXIDATION & CONJUGATION OF 4-CHLOROBENZALDEHYDE PRODUCT OF HYDROLYSIS.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 1: A Review of the Literature Published Between 1960 and 1969. London: The Chemical Society, 1970., p. 181


(14)C-CHLORMEZANONE, METABOLITES IN URINE OF RATS & MICE WERE P-CHLOROBENZOIC ACID, P-CHLOROHIPPURIC ACID, N-METHYL-P-CHLOROBENZAMIDE, 2-[N-METHYL-N-(P-CHLOROBENZOYL)]CARBAMOYLETHYLSULFONIC ACID, 3-SULFOPROPIONIC ACID & GLUCURONIDE OF P-CHLOROBENZOIC ACID.

HAKUSUI H ET AL; XENOBIOTICA 8 (4) 229-38 (1978)


5.6 Mechanism of Action

Chlormezanone binds to central benzodiazepine receptors which interact allosterically with GABA receptors. This potentiates the effects of the inhibitory neurotransmitter GABA, increasing the inhibition of the ascending reticular activating system and blocking the cortical and limbic arousal that occurs following stimulation of the reticular pathways.


NEURONAL CONDUCTION, NEUROMUSCULAR TRANSMISSION, & MUSCLE EXCITABILITY ARE NOT DEPRESSED EXCEPT AFTER NEARLY LETHAL DOSES. PROMINENT EFFECT...IS TO DEPRESS SPINAL POLYSYNAPTIC REFLEXES PREFERENTIALLY OVER MONOSYNAPTIC REFLEXES. /CENTRALLY ACTING MUSCLE RELAXANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 240


IN ABSENCE OF DEFINITIVE STUDIES IT APPEARS REASONABLE TO ASCRIBE BENEFICIAL EFFECTS...TO THEIR SEDATIVE PROPERTIES. /CENTRALLY ACTING MUSCLE RELAXANTS/

Goodman, L.S., and A. Gilman. (eds.) The Pharmacological Basis of Therapeutics. 5th ed. New York: Macmillan Publishing Co., Inc., 1975., p. 241


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