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Chemistry

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Also known as: 14028-44-5, Asendin, Demolox, Moxadil, Amoxan, Desmethylloxapin
Molecular Formula
C17H16ClN3O
Molecular Weight
313.8  g/mol
InChI Key
QWGDMFLQWFTERH-UHFFFAOYSA-N
FDA UNII
R63VQ857OT

Amoxapine
The N-demethylated derivative of the antipsychotic agent LOXAPINE that works by blocking the reuptake of norepinephrine, serotonin, or both; it also blocks dopamine receptors. Amoxapine is used for the treatment of depression.
Amoxapine is a Tricyclic Antidepressant.
1 2D Structure

Amoxapine

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
8-chloro-6-piperazin-1-ylbenzo[b][1,4]benzoxazepine
2.1.2 InChI
InChI=1S/C17H16ClN3O/c18-12-5-6-15-13(11-12)17(21-9-7-19-8-10-21)20-14-3-1-2-4-16(14)22-15/h1-6,11,19H,7-10H2
2.1.3 InChI Key
QWGDMFLQWFTERH-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1CN(CCN1)C2=NC3=CC=CC=C3OC4=C2C=C(C=C4)Cl
2.2 Other Identifiers
2.2.1 UNII
R63VQ857OT
2.3 Synonyms
2.3.1 MeSH Synonyms

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

2. Asendin

3. Asendis

4. Cl 67,772

5. Cl-67,772

6. Cl67,772

7. Dfanyl

8. Demolox

9. Desmethylloxapine

2.3.2 Depositor-Supplied Synonyms

1. 14028-44-5

2. Asendin

3. Demolox

4. Moxadil

5. Amoxan

6. Desmethylloxapin

7. Amoxapina

8. Amoxapinum

9. Amoxepine

10. Cl-67772

11. Dibenz[b,f][1,4]oxazepine, 2-chloro-11-(1-piperazinyl)-

12. Cl 67772

13. 2-chloro-11-(1-piperazinyl)dibenz(b,f)(1,4)oxazepine

14. 8-chloro-6-piperazin-1-ylbenzo[b][1,4]benzoxazepine

15. Cl-67,772

16. Cl 67,772

17. 2-chloro-11-(piperazin-1-yl)dibenzo[b,f][1,4]oxazepine

18. Asendis

19. Nsc-759559

20. Dibenz(b,f)(1,4)oxazepine, 2-chloro-11-(1-piperazinyl)-

21. Chembl1113

22. 2-chloro-11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine

23. Mls000069371

24. Chebi:2675

25. R63vq857ot

26. 2-chloro-11-piperazin-1-yldibenzo[b,f][1,4]oxazepine

27. Ncgc00015004-09

28. Ascendin

29. Smr000058416

30. Cas-14028-44-5

31. Dsstox_cid_2598

32. Amoxapinum [inn-latin]

33. Dsstox_rid_76652

34. Amoxapina [inn-spanish]

35. Dsstox_gsid_22598

36. 13-chloro-10-(piperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3(8),4,6,9,12,14-heptaene

37. (e)-2-chloro-11-(piperazin-1-yl)dibenzo[b,f][1,4]oxazepine

38. Asendin (tn)

39. Sr-01000003001

40. Einecs 237-867-1

41. Mfcd00069210

42. Amoxipine

43. Brn 0832057

44. Unii-r63vq857ot

45. 2-chlor-11-(1-piperazinyl)dibenz(b,f)(1,4)oxazepin

46. Amoxapine-[d8]

47. Prestwick_503

48. Amoxapine [usan:usp:inn:ban:jan]

49. Ks-1197

50. 2-chloro-11-(1-piperazinyl)dibenzo[b,f][1,4]oxazepine

51. Opera_id_33

52. Spectrum_000446

53. Cpd000058416

54. Amoxapine [inn]

55. Amoxapine [jan]

56. Amoxapine [mi]

57. Lopac-a-129

58. Amoxapine [usan]

59. Prestwick0_000102

60. Prestwick1_000102

61. Prestwick2_000102

62. Prestwick3_000102

63. Spectrum2_001245

64. Spectrum3_001067

65. Spectrum4_001218

66. Spectrum5_001284

67. Amoxapine [vandf]

68. A-129

69. Amoxapine [mart.]

70. Amoxapine [usp-rs]

71. Amoxapine [who-dd]

72. Lopac0_000116

73. Regid_for_cid_2170

74. Schembl33950

75. Bspbio_000084

76. Bspbio_002654

77. Gtpl201

78. Kbiogr_001656

79. Kbioss_000926

80. Zinc931

81. Maleicacidmonosodiumsalt

82. Divk1c_000236

83. Spectrum2300161

84. Spbio_001150

85. Spbio_002023

86. Amoxapine (jp17/usp/inn)

87. Bpbio1_000094

88. Amoxapine [orange Book]

89. 8-chloro-6-piperazin-1-yl-benzo[b][1,4]benzoxazepine

90. Amoxapine [usp Impurity]

91. Dtxsid7022598

92. Bdbm22870

93. Hms500l18

94. Kbio1_000236

95. Kbio2_000926

96. Kbio2_003494

97. Kbio2_006062

98. Kbio3_001874

99. Amoxapine [usp Monograph]

100. Ninds_000236

101. Hms1568e06

102. Hms2089g10

103. Hms2093n08

104. Hms2095e06

105. Hms2231e13

106. Hms3259g08

107. Hms3260g14

108. Hms3370p03

109. Hms3712e06

110. Pharmakon1600-02300161

111. Hy-b0991

112. Tox21_110064

113. Tox21_302352

114. Tox21_500116

115. Ccg-39135

116. Nsc759559

117. Pdsp1_001609

118. Pdsp2_001593

119. S4218

120. Akos015895092

121. Tox21_110064_1

122. Ac-5495

123. Cs-4485

124. Db00543

125. Lp00116

126. Nc00546

127. Nsc 759559

128. Sdccgsbi-0050104.p004

129. Idi1_000236

130. Ncgc00015004-01

131. Ncgc00015004-02

132. Ncgc00015004-03

133. Ncgc00015004-04

134. Ncgc00015004-05

135. Ncgc00015004-06

136. Ncgc00015004-07

137. Ncgc00015004-08

138. Ncgc00015004-10

139. Ncgc00015004-11

140. Ncgc00015004-13

141. Ncgc00015004-16

142. Ncgc00015004-22

143. Ncgc00023887-03

144. Ncgc00023887-04

145. Ncgc00023887-05

146. Ncgc00023887-06

147. Ncgc00255124-01

148. Ncgc00260801-01

149. Ba164170

150. Sbi-0050104.p003

151. Eu-0100116

152. Ft-0659871

153. Ft-0662122

154. A16406

155. D00228

156. Q58356

157. T70258

158. Ab00052421-13

159. Ab00052421_14

160. Ab00052421_15

161. 028a445

162. A807639

163. L001293

164. J-007373

165. Sr-01000003001-2

166. Sr-01000003001-4

167. Sr-01000003001-6

168. 8-chloro-6-piperazin-1-ylbenzo[b][1,5]benzoxazepine

169. Brd-k02265150-001-05-9

170. Brd-k02265150-001-15-8

171. 2-chloro-11-(1-piperazinyl)dibenz[b,f]-1,4-oxazepine

172. 2-chloro-11-(1-piperazinyl)dibenzo[b,f]-1,4-oxazepine

173. 2-chloro-11-piperazin-1-yl-dibenzo[b,f][1,4]oxazepine

174. 8-chloro-6-(1-piperazinyl)benzo[b][1,4]benzoxazepine

175. Z1551429736

176. 2-chloro-11-(1-piperazinyl)dibenzo[b,f][1,4]oxazepine #

177. 8-chloranyl-6-piperazin-1-yl-benzo[b][1,4]benzoxazepine

178. Amoxapine, 1.0 Mg/ml In Methanol, Certified Reference Material

179. Amoxapine, United States Pharmacopeia (usp) Reference Standard

180. Dibenzo[b,f][1,4]oxazepine, 2-chloro-11-(1-piperazinyl)-

181. Loxapine Succinate Impurity, Amoxapine- [usp Impurity]

182. Amoxapine, Pharmaceutical Secondary Standard; Certified Reference Material

183. 13-chloro-10-(piperazin-1-yl)-2-oxa-9-azatricyclo[9.4.0.0^{3,8}]pentadeca-1(11),3,5,7,9,12,14-heptaene

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 313.8 g/mol
Molecular Formula C17H16ClN3O
XLogP32.6
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count1
Exact Mass313.0981898 g/mol
Monoisotopic Mass313.0981898 g/mol
Topological Polar Surface Area36.9 Ų
Heavy Atom Count22
Formal Charge0
Complexity424
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 Information
1 of 2  
Drug NameAmoxapine
PubMed HealthAmoxapine (By mouth)
Drug ClassesAntidepressant
Drug LabelAmoxapine is an antidepressant of the dibenzoxazepine class, chemically distinct from the dibenzazepines, dibenzocycloheptenes, and dibenzoxepines.It is designated chemically as 2-Chloro-11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine. The structural for...
Active IngredientAmoxapine
Dosage FormTablet
RouteOral
Strength100mg; 25mg; 50mg; 150mg
Market StatusPrescription
CompanyWatson Labs

2 of 2  
Drug NameAmoxapine
PubMed HealthAmoxapine (By mouth)
Drug ClassesAntidepressant
Drug LabelAmoxapine is an antidepressant of the dibenzoxazepine class, chemically distinct from the dibenzazepines, dibenzocycloheptenes, and dibenzoxepines.It is designated chemically as 2-Chloro-11-(1-piperazinyl)dibenz[b,f][1,4]oxazepine. The structural for...
Active IngredientAmoxapine
Dosage FormTablet
RouteOral
Strength100mg; 25mg; 50mg; 150mg
Market StatusPrescription
CompanyWatson Labs

4.2 Drug Indication

For the relief of symptoms of depression in patients with neurotic or reactive depressive disorders as well as endogenous and psychotic depressions. May also be used to treat depression accompanied by anxiety or agitation.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Amoxapine is a tricyclic antidepressant of the dibenzoxazepine class, chemically distinct from the dibenzodiazepines, dibenzocycloheptenes, and dibenzoxepines. It has a mild sedative component to its action. The mechanism of its clinical action in man is not well understood. In animals, amoxapine reduced the uptake of nor-epinephirine and serotonin and blocked the response of dopamine receptors to dopamine. Amoxapine is not a monoamine oxidase inhibitor. Clinical studies have demonstrated that amoxapine has a more rapid onset of action than either amitriptyline or imipramine


5.2 MeSH Pharmacological Classification

Adrenergic Uptake Inhibitors

Drugs that block the transport of adrenergic transmitters into axon terminals or into storage vesicles within terminals. The tricyclic antidepressants (ANTIDEPRESSIVE AGENTS, TRICYCLIC) and amphetamines are among the therapeutically important drugs that may act via inhibition of adrenergic transport. Many of these drugs also block transport of serotonin. (See all compounds classified as Adrenergic Uptake Inhibitors.)


Antidepressive Agents, Tricyclic

Substances that contain a fused three-ring moiety and are used in the treatment of depression. These drugs block the uptake of norepinephrine and serotonin into axon terminals and may block some subtypes of serotonin, adrenergic, and histamine receptors. However, the mechanism of their antidepressant effects is not clear because the therapeutic effects usually take weeks to develop and may reflect compensatory changes in the central nervous system. (See all compounds classified as Antidepressive Agents, Tricyclic.)


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.)


Neurotransmitter Uptake Inhibitors

Drugs that inhibit the transport of neurotransmitters into axon terminals or into storage vesicles within terminals. For many transmitters, uptake determines the time course of transmitter action so inhibiting uptake prolongs the activity of the transmitter. Blocking uptake may also deplete available transmitter stores. Many clinically important drugs are uptake inhibitors although the indirect reactions of the brain rather than the acute block of uptake itself is often responsible for the therapeutic effects. (See all compounds classified as Neurotransmitter Uptake Inhibitors.)


Selective Serotonin Reuptake Inhibitors

Compounds that specifically inhibit the reuptake of serotonin in the brain. (See all compounds classified as Selective Serotonin Reuptake Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
AMOXAPINE
5.3.2 FDA UNII
R63VQ857OT
5.3.3 Pharmacological Classes
Tricyclic Antidepressant [EPC]
5.4 ATC Code

N - Nervous system

N06 - Psychoanaleptics

N06A - Antidepressants

N06AA - Non-selective monoamine reuptake inhibitors

N06AA17 - Amoxapine


5.5 Absorption, Distribution and Excretion

Absorption

Rapidly and almost completely absorbed from the GI tract. Peak plasma concentrations occur within 1-2 hours of oral administration of a single dose.


Route of Elimination

60-69% of a single orally administered dose of amoxapine is excreted in urine, principally as conjugated metabolites. 7-18% of the dose is excrete feces mainly as unconjugated metabolites. Less than 5% of the dose is excreted as unchanged drug in urine.


Volume of Distribution

Widely distributed in body tissues with highest concentrations found in lungs, spleen, kidneys, heart, and brain. Lower concentrations can be detected in testes and muscle.


5.6 Metabolism/Metabolites

Amoxapine is almost completely metabolized in the liver to its major metabolite, 8-hydroxyamoxapine, and a minor metabolite, 7-hydroxyamoxapine. Both metabolites are phamacologically inactive and have half-lives of approximately 30 and 6.5 hours, respectively.


5.7 Biological Half-Life

8 hours


5.8 Mechanism of Action

Amoxapine acts by decreasing the reuptake of norepinephrine and serotonin (5-HT).


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