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Chemistry

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Also known as: 533-45-9, Chlormethiazole, 5-(2-chloroethyl)-4-methylthiazole, Distraneurin, 5-(2-chloroethyl)-4-methyl-1,3-thiazole, Chlorethiazol

Molecular Formula

C₆H₈ClNS

Molecular Weight

161.65 g/mol

InChI Key

PCLITLDOTJTVDJ-UHFFFAOYSA-N

FDA UNII

0C5DBZ19HV

A sedative and anticonvulsant often used in the treatment of alcohol withdrawal. Chlormethiazole has also been proposed as a neuroprotective agent. The mechanism of its therapeutic activity is not entirely clear, but it does potentiate GAMMA-AMINOBUTYRIC ACID receptors response and it may also affect glycine receptors.

1 2D Structure

Clomethiazole

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-(2-chloroethyl)-4-methyl-1,3-thiazole

2.1.2 InChI

InChI=1S/C6H8ClNS/c1-5-6(2-3-7)9-4-8-5/h4H,2-3H2,1H3

2.1.3 InChI Key

PCLITLDOTJTVDJ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(SC=N1)CCCl

2.2 Other Identifiers

2.2.1 UNII

0C5DBZ19HV

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Chlormethiazole

2. Distraneurin

2.3.2 Depositor-Supplied Synonyms

1. 533-45-9

2. Chlormethiazole

3. 5-(2-chloroethyl)-4-methylthiazole

4. Distraneurin

5. 5-(2-chloroethyl)-4-methyl-1,3-thiazole

6. Chlorethiazol

7. Chlormethiazol

8. Clomethiazolum

9. Emineurina

10. Somnevrin

11. Thiazole, 5-(2-chloroethyl)-4-methyl-

12. Clomethiazole [inn]

13. Chloro-s.c.t.z.

14. Distraneurine

15. Wy 1485

16. Sctz [as Edisylate]

17. 0c5dbz19hv

18. Chlorethiazole

19. Clomethiazole (inn)

20. Ncgc00024842-02

21. Clometiazole

22. Dsstox_cid_2842

23. C6h8clns

24. Dsstox_rid_76753

25. Dsstox_gsid_22842

26. Clometiazolo [dcit]

27. Chloraethiazol

28. Clometiazol

29. Clometiazolo

30. Clometiazol [inn-spanish]

31. Clomethiazolum [inn-latin]

32. Cas-533-45-9

33. Einecs 208-565-7

34. Clomethiazole [inn:ban]

35. Unii-0c5dbz19hv

36. 4-methyl-5-(beta-chloroethyl)thiazole

37. Brn 0114244

38. Distraneurine (tn)

39. Sctz (salt/mix)

40. Tocris-0881

41. Heminevrin (salt/mix)

42. Clomethiazole [mi]

43. Biomol-nt_000260

44. Schembl35223

45. 4-27-00-00990 (beilstein Handbook Reference)

46. Mls004754487

47. Clomethiazole [mart.]

48. Clomethiazole [who-dd]

49. Bpbio1_000815

50. Chembl315795

51. Zinc1192

52. Dtxsid6022842

53. Chebi:92875

54. Bdbm234400

55. Clomethiazole [nflis-drug]

56. Tox21_110931

57. Mfcd00868012

58. 4-methyl-5-(2-chloroethyl)-thiazole

59. Akos011348416

60. Tox21_110931_1

61. Ab07565

62. Db06470

63. Sdccgsbi-0633688.p001

64. 5-(2-chloro-ethyl)-4-methyl-thiazole

65. Ncgc00024842-01

66. Ncgc00024842-03

67. Ncgc00024842-04

68. Ncgc00024842-05

69. 4-methyl-5-(.beta.-chloroethyl)thiazole

70. Ac-33175

71. As-13864

72. Smr002529479

73. Db-071667

74. Hy-129105

75. Cs-0103601

76. Ft-0659713

77. En300-60459

78. 33c459

79. 5-(2-chloroethyl)-4-methyl-1,3-thiazole #

80. D07330

81. Q417178

82. W-203012

83. Brd-k50422030-001-01-2

84. Brd-k50422030-003-01-8

85. Z1259086813

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₆H₈ClNS
Molecular Weight	161.65 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	161.0065981 g/mol
Monoisotopic Mass	161.0065981 g/mol
Topological Polar Surface Area	41.1 Å²
Heavy Atom Count	9
Formal Charge	0
Complexity	89.1
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Indication

Investigated for use/treatment in strokes.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anticonvulsants

Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

Neuroprotective Agents

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)

GABA Modulators

Substances that do not act as agonists or antagonists but do affect the GAMMA-AMINOBUTYRIC ACID receptor-ionophore complex. GABA-A receptors (RECEPTORS, GABA-A) appear to have at least three allosteric sites at which modulators act: a site at which BENZODIAZEPINES act by increasing the opening frequency of GAMMA-AMINOBUTYRIC ACID-activated chloride channels; a site at which BARBITURATES act to prolong the duration of channel opening; and a site at which some steroids may act. GENERAL ANESTHETICS probably act at least partly by potentiating GABAergic responses, but they are not included here. (See all compounds classified as GABA Modulators.)

Hypnotics and Sedatives

Drugs used to induce drowsiness or sleep or to reduce psychological excitement or anxiety. (See all compounds classified as Hypnotics and Sedatives.)

5.2 ATC Code

N - Nervous system

N05 - Psycholeptics

N05C - Hypnotics and sedatives

N05CM - Other hypnotics and sedatives

N05CM02 - Clomethiazole

5.3 Metabolism/Metabolites

Clomethiazole has known human metabolites that include NLA-715.

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

5.4 Mechanism of Action

clomethiazole interacts with the GABAA receptor complex. It inhibits the binding of [35S]butyl-bicyclophosphorothionate (TBPS), an effect indicative of GABAA receptor-channel activation, by increasing the rate of [35S]TBPS dissociation and decreasing the binding affinity. Gamma-aminobutyric acid (GABA), acting at GABAA receptors, is the main fast inhibitory neurotransmitter in mammalian central nervous system

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