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Loxapine Succinate

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Also known as: 27833-64-3, Loxapine succinate salt, Loxapac, Cloxazepin, Daxolin, Loxapine (succinate)

Molecular Formula

C₂₂H₂₄ClN₃O₅

Molecular Weight

445.9 g/mol

InChI Key

YQZBAXDVDZTKEQ-UHFFFAOYSA-N

FDA UNII

X59SG0MRYU

An antipsychotic agent used in schizophrenia.

1 2D Structure

Loxapine Succinate

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

butanedioic acid;8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzoxazepine

2.1.2 InChI

InChI=1S/C18H18ClN3O.C4H6O4/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;5-3(6)1-2-4(7)8/h2-7,12H,8-11H2,1H3;1-2H2,(H,5,6)(H,7,8)

2.1.3 InChI Key

YQZBAXDVDZTKEQ-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CN1CCN(CC1)C2=NC3=CC=CC=C3OC4=C2C=C(C=C4)Cl.C(CC(=O)O)C(=O)O

2.2 Other Identifiers

2.2.1 UNII

X59SG0MRYU

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 2-chloro-11-(4-methyl-1-piperazinyl)-dibenz(b,f)(1,4)oxazepine

2. Cl 71,563

3. Cl-71,563

4. Cl71,563

5. Cloxazepine

6. Hydrochloride, Loxapine

7. Loxapine

8. Loxapine Hydrochloride

9. Loxapine Monohydrochloride

10. Loxapinsuccinate

11. Loxipine Maleate

12. Loxipine Succinate

13. Loxitane

14. Maleate, Loxipine

15. Oxilapine

16. Succinate, Loxapine

2.3.2 Depositor-Supplied Synonyms

1. 27833-64-3

2. Loxapine Succinate Salt

3. Loxapac

4. Cloxazepin

5. Daxolin

6. Loxapine (succinate)

7. Loxapine, Succinate

8. Cl 71563

9. Loxapine,succinate

10. X59sg0mryu

11. Nsc-759578

12. Cl-71563

13. Cpd000058470

14. Mls000069383

15. Butanedioic Acid, Compd. With 2-chloro-11-(4-methyl-1-piperazinyl)dibenz[b,f][1,4]oxazepine (1:1)

16. Ncgc00016160-02

17. Lederle

18. Smr000058470

19. Cas-27833-64-3

20. Dsstox_cid_25227

21. Dsstox_rid_80764

22. Dsstox_gsid_45227

23. 2-chloro-11-(4-methyl-1-piperazinyl)dibenz(b,f)(1,4)oxazepine Succinate (1:1)

24. Chebi:6549

25. Loxapine Succinate [usan]

26. Butanedioic Acid;8-chloro-6-(4-methylpiperazin-1-yl)benzo[b][1,4]benzoxazepine

27. Butanedioic Acid, Compd. With 2-chloro-11-(4-methyl-1-piperazinyl)dibenz(b,f)(1,4)oxazepine (1:1)

28. Ccris 1917

29. Az-004

30. Sr-01000002971

31. Einecs 248-682-0

32. Unii-x59sg0mryu

33. Loxapine Succinate [usan:usp]

34. Staccato-loxapine

35. Loxitane (tn)

36. Prestwick_304

37. Mfcd00069298

38. Lopac-l-106

39. Opera_id_1518

40. Loxapine Succinate (usp)

41. 2-chloro-11-(4-methyl-1-piperazinyl)dibenzo[b,f][1,4]oxazepine Succinate

42. Schembl41643

43. Maprotilinehydrochloride

44. Mls000758291

45. Mls001146961

46. Mls001401432

47. Mls002222201

48. Spectrum2300242

49. Loxapine Succinate Salt, Solid

50. Regid_for_cid_71399

51. Loxapine Succinate [mi]

52. Chembl1201155

53. Dtxsid3045227

54. Hms1568k06

55. Hms1922l14

56. Hms2051e05

57. Hms2093n20

58. Hms2095k06

59. Hms2232n05

60. Hms3262o21

61. Hms3374f02

62. Hms3393e05

63. Hms3652o10

64. Hms3712k06

65. Hms3885h03

66. Loxapine Succinate [vandf]

67. Pharmakon1600-02300242

68. Loxapine Succinate [mart.]

69. Loxapine Succinate [usp-rs]

70. Loxapine Succinate [who-dd]

71. Tox21_110311

72. Tox21_500720

73. Az-104

74. Ccg-39497

75. Hy-17390a

76. Nsc759578

77. S4086

78. Akos015994711

79. Tox21_110311_1

80. Cs-4285

81. Ks-1083

82. Lp00720

83. Nc00011

84. Nsc 759578

85. Loxapine Succinate [orange Book]

86. Ncgc00016160-01

87. Ncgc00016160-03

88. Ncgc00016160-04

89. Ncgc00016160-05

90. Ncgc00021145-11

91. Ncgc00094068-01

92. Ncgc00094068-02

93. Ncgc00094068-03

94. Ncgc00261405-01

95. Loxapine Succinate [usp Monograph]

96. Succinic Acid, Compd. With 2-chloro-11-(4-methyl-1-piperazinyl)dibenz(b,f)(1,4)oxazepine (1:1)

97. Succinic Acid, Compound With 2-chloro-11-(4-methylpiperazin-1-yl)dibenz(b,f)(1,4)oxazepine (1:1)

98. Eu-0100720

99. Ft-0653022

100. Sw196603-4

101. Vu0239541-8

102. D00794

103. F14786

104. 833l643

105. Sr-01000002971-2

106. Sr-01000002971-6

107. Sr-01000002971-9

108. W-107092

109. Q27107236

110. 2-chloro-11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]oxazepine Succinate

111. 2-chloro-11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]oxazepinesuccinate

112. Loxapine Succinate, United States Pharmacopeia (usp) Reference Standard

113. (e)-2-chloro-11-(4-methylpiperazin-1-yl)dibenzo[b,f][1,4]oxazepine Succinate

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₂₄ClN₃O₅
Molecular Weight	445.9 g/mol
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	7
Rotatable Bond Count	4
Exact Mass	445.1404486 g/mol
Monoisotopic Mass	445.1404486 g/mol
Topological Polar Surface Area	103 Å²
Heavy Atom Count	31
Formal Charge	0
Complexity	542
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	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Loxapine succinate
Drug Label	Loxapine, a dibenzoxazepine compound, represents a subclass of tricyclic antipsychotic agents, chemically distinct from the thioxanthenes, butyrophenones, and phenothiazines. Chemically, it is 2-Chloro-11-(4-methyl-1-piperazinyl)dibenz[b,f][1,4]oxaze...
Active Ingredient	Loxapine succinate
Dosage Form	Capsule
Route	Oral
Strength	eq 5mg base; eq 50mg base; eq 10mg base; eq 25mg base
Market Status	Prescription
Company	Lannett Holdings; Watson Labs; Mikah Pharma; Mylan

2 of 2
Drug Name	Loxapine succinate
Drug Label	Loxapine, a dibenzoxazepine compound, represents a subclass of tricyclic antipsychotic agents, chemically distinct from the thioxanthenes, butyrophenones, and phenothiazines. Chemically, it is 2-Chloro-11-(4-methyl-1-piperazinyl)dibenz[b,f][1,4]oxaze...
Active Ingredient	Loxapine succinate
Dosage Form	Capsule
Route	Oral
Strength	eq 5mg base; eq 50mg base; eq 10mg base; eq 25mg base
Market Status	Prescription
Company	Lannett Holdings; Watson Labs; Mikah Pharma; Mylan

5 Pharmacology and Biochemistry

5.1 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.)

Dopamine Antagonists

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME. (See all compounds classified as Dopamine Antagonists.)

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