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    Clomethiazole

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

    GLOBAL SALES INFORMATION

    PharmaCompass
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    2D Structure
    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

    2D Structure

    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 Weight 161.65 g/mol
    Molecular Formula C6H8ClNS
    XLogP32.1
    Hydrogen Bond Donor Count0
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count2
    Exact Mass161.0065981 g/mol
    Monoisotopic Mass161.0065981 g/mol
    Topological Polar Surface Area41.1 Ų
    Heavy Atom Count9
    Formal Charge0
    Complexity89.1
    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 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