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2-chloro-11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]thiazepine

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Chemistry

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Also known as: Clotiapine, 2058-52-8, Entumin, Etumine, Hf 2159, Clothiapine [usan]

Molecular Formula

C₁₈H₁₈ClN₃S

Molecular Weight

343.9 g/mol

InChI Key

KAAZGXDPUNNEFN-UHFFFAOYSA-N

FDA UNII

Z05HCY0X1T

Clothiapine has been approved in European countries and is an atypical antipsychotic, shown to be useful in some treatment-resistant patients.

1 2D Structure

Clothiapine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzothiazepine

2.1.2 InChI

InChI=1S/C18H18ClN3S/c1-21-8-10-22(11-9-21)18-14-12-13(19)6-7-16(14)23-17-5-3-2-4-15(17)20-18/h2-7,12H,8-11H2,1H3

2.1.3 InChI Key

KAAZGXDPUNNEFN-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1CCN(CC1)C2=NC3=CC=CC=C3SC4=C2C=C(C=C4)Cl

2.2 Other Identifiers

2.2.1 UNII

Z05HCY0X1T

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Clotiapine

2. Entumine

2.3.2 Depositor-Supplied Synonyms

1. Clotiapine

2. 2058-52-8

3. Entumin

4. Etumine

5. Hf 2159

6. Clothiapine [usan]

7. S-805c

8. Clotiapine [inn]

9. Dibenzo(b,f)(1,4)thiazepine, 2-chloro-11-(4-methyl-1-piperazinyl)-

10. Hf-2159

11. Lw 2159

12. 8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzothiazepine

13. 2-chloro-11-(4-methyl-1-piperazinyl)dibenzo(b,f)(1,4)thiazepine

14. Dibenzo[b,f][1,4]thiazepine, 2-chloro-11-(4-methyl-1-piperazinyl)-

15. Z05hcy0x1t

16. Chembl304902

17. Entumine

18. 2-chloro-11-(4-methylpiperazino)dibenzo(b,f)(1,4)thiazepine

19. 2-chloro-11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]thiazepine

20. Clothiapine (usan)

21. Ncgc00160387-01

22. 2-chloro-11-(4-methyl-1-piperazinyl)dibenzo[b,f][1,4]thiazepine

23. Dsstox_cid_2851

24. Dsstox_rid_76758

25. Dsstox_gsid_22851

26. Clotiapina

27. Clotiapinum

28. Clotiapinum [inn-latin]

29. Clotiapina [inn-spanish]

30. Cas-2058-52-8

31. Einecs 218-162-8

32. Unii-z05hcy0x1t

33. Brn 0568276

34. Entumin (tn)

35. Kinetinriboside

36. Clotiapine (jan/inn)

37. Clothiapine [mi]

38. Clotiapine [jan]

39. W 130

40. Biomol-nt_000008

41. Clotiapine [mart.]

42. Clotiapine [who-dd]

43. Schembl122941

44. Bpbio1_001137

45. Dtxsid5022851

46. Chebi:31424

47. Chebi:108591

48. Hms2089l15

49. Bcp06511

50. Tox21_111779

51. Bdbm50040237

52. Hf2159

53. Pdsp1_000469

54. Pdsp2_000467

55. Zinc26185346

56. Akos005065858

57. Tox21_111779_1

58. Db13256

59. Mrf-0000024

60. Ncgc00160387-02

61. Ncgc00160387-03

62. Ncgc00160387-04

63. Db-045296

64. Hy-117083

65. Cs-0063673

66. Ft-0603194

67. D01597

68. Ab01275460-01

69. Sr-05000001467

70. J-013441

71. Q3661095

72. Sr-05000001467-1

73. Brd-k10990317-001-01-1

74. Brd-k10990317-001-02-9

75. 8-chloro-6-(4-methyl-1-piperazinyl)benzo[b][1,4]benzothiazepine

76. (e)-2-chloro-11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]thiazepine

77. 2-chloro-11-(4-methyl-piperazin-1-yl)-dibenzo[b,f][1,4]thiazepine

78. 2-chloro-11-(4-methyl-piperazin-1-yl)-dibenzo[b,f][1,4]thiazepine(clothiapine)

2.4 Create Date

2005-03-27

3 Chemical and Physical Properties

Molecular Formula	C₁₈H₁₈ClN₃S
Molecular Weight	343.9 g/mol
XLogP3	3.6
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	1
Exact Mass	343.0909965 g/mol
Monoisotopic Mass	343.0909965 g/mol
Topological Polar Surface Area	44.1 Å²
Heavy Atom Count	23
Formal Charge	0
Complexity	450
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 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Antipsychotic Agents

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus. (See all compounds classified as Antipsychotic Agents.)

4.2 ATC Code

N - Nervous system

N05 - Psycholeptics

N05A - Antipsychotics

N05AH - Diazepines, oxazepines, thiazepines and oxepines

N05AH06 - Clotiapine

FDF Dossiers