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Chemistry

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Also known as: 31677-93-7, Bupropion hcl, 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrochloride, Wellbutrin, Amfebutamone hydrochloride, Zyban
Molecular Formula
C13H19Cl2NO
Molecular Weight
276.20  g/mol
InChI Key
HEYVINCGKDONRU-UHFFFAOYSA-N
FDA UNII
ZG7E5POY8O

Bupropion Hydrochloride
A propiophenone-derived antidepressant and antismoking agent that inhibits the uptake of DOPAMINE.
1 2D Structure

Bupropion Hydrochloride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one;hydrochloride
2.1.2 InChI
InChI=1S/C13H18ClNO.ClH/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10;/h5-9,15H,1-4H3;1H
2.1.3 InChI Key
HEYVINCGKDONRU-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C(=O)C1=CC(=CC=C1)Cl)NC(C)(C)C.Cl
2.2 Other Identifiers
2.2.1 UNII
ZG7E5POY8O
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (+-)-1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone

2. Amfebutamone

3. Bupropion

4. Bupropion Hydrochloride, (+-)-isomer

5. Bupropion, (+-)-isomer

6. Quomen

7. Wellbutrin

8. Zyban (anti-smoking)

9. Zyban (bupropion)

10. Zyntabac

2.3.2 Depositor-Supplied Synonyms

1. 31677-93-7

2. Bupropion Hcl

3. 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one Hydrochloride

4. Wellbutrin

5. Amfebutamone Hydrochloride

6. Zyban

7. Wellbutrin Xl

8. Wellbutrin Sr

9. Budeprion

10. Forfivo Xl

11. Wellbatrin

12. Amfebutamone (bupropion) Hcl

13. Bw 323

14. Mysimba

15. Bupropion (hydrochloride)

16. Bupropion Sr

17. 2-(tert-butylamino)-3'-chloropropiophenone Hydrochloride

18. Zg7e5poy8o

19. Nsc-315851

20. 31677-93-7 (hcl)

21. Elontril

22. Bw-323

23. 234447-17-7

24. 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one;hydrochloride

25. 1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone Hydrochloride

26. 1-propanone, 1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-, Hydrochloride (1:1), (-)-

27. Dsstox_cid_24561

28. Dsstox_rid_80314

29. Dsstox_gsid_44561

30. Bupropion Hydrochloride 100 Microg/ml In Acetonitrile

31. Bupropion Hydrocloride

32. 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one Hcl

33. Zyban (pharmaceutical)

34. Voxra

35. Budeprion Xl

36. (+/-)-bupropion; Amfebutamon; Amfebutamone; Aplenzin; Bupropion Sr; Bupropion Xl

37. Smr000058423

38. Budeprion Xl 300

39. Nsc315851

40. Amfebutamon Hydrochloride

41. Sr-01000002989

42. Einecs 250-759-9

43. Unii-zg7e5poy8o

44. Nsc 315851

45. Quomem

46. Bupropion Hydrochloride [usan]

47. Wellbutrin Xr

48. Wellbutrin Retard

49. Wellbutrin (tn)

50. Bupropion D9 Hcl

51. Prestwick_668

52. Einecs 252-243-9

53. Mfcd00055209

54. Zyban (tn)

55. M-chloro-alpha-tert-butylaminopropiophenone Hydrochloride

56. Alpha-(tert-butylamino)-m-chloropropiophenone Hydrochloride

57. M-chloro-alpha-tert-butylaminopropionphenone Hydrochloride

58. Bupropion Hydrochloride [usan:usp:jan]

59. (+-)-2-(tert-butylamino)-3'-chloropropiophenone Hydrochloride

60. (+-)-alpha-tert-butylamino-3-chloropropiophenone Hydrochloride

61. Amfebutamone (bupropion)

62. Ncgc00016807-01

63. Cas-31677-93-7

64. Chembl1698

65. Schembl41602

66. Mls000069376

67. Mls001401370

68. Mls002320678

69. Spectrum1504174

70. Bupropion Hydrochloride- Bio-x

71. Bupropion Hydrochloride Solution

72. Chebi:3220

73. Dtxsid6044561

74. Hy-b0403a

75. Bvf 033

76. Bw 322u

77. Cpi-300

78. Hms1568b20

79. Hms1922f09

80. Pharmakon1600-01504174

81. Bupropion Hydrochloride (jan/usp)

82. Bcp22394

83. Bupropion Hydrochloride [mi]

84. Tox21_110621

85. Tox21_301844

86. Tox21_500166

87. Ac-196

88. Amfebutamone-hydrochloride(bupropion)

89. Bupropion Hydrochloride [jan]

90. Bw-323u66

91. Ccg-39085

92. Nsc758686

93. Propiophenone, 2-(tert-butylamino)-3'-chloro-, Hydrochloride, (+-)-

94. Bupropion Hydrochloride [hsdb]

95. Akos015844544

96. Tox21_110621_1

97. Ab02273

98. Bcp9000462

99. Bupropion Hydrochloride [mart.]

100. Bupropion Hydrochloride [vandf]

101. Ccg-100911

102. Ks-1034

103. Lp00166

104. Nc00161

105. 1-propanone, 1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-, Hydrochloride, (+-)-

106. Bupropion Hydrochloride [usp-rs]

107. Bupropion Hydrochloride [who-dd]

108. Ncgc00015122-11

109. Ncgc00093650-01

110. Ncgc00093650-02

111. Ncgc00093650-03

112. Ncgc00093650-04

113. Ncgc00093650-05

114. Ncgc00180895-01

115. Ncgc00180895-02

116. Ncgc00255927-01

117. Ncgc00260851-01

118. Propiophenone, Hydrochloride, (.+-.)-

119. Bb164268

120. Smr001338824

121. Bcp0726000049

122. Am20060780

123. B-102

124. B3649

125. Bupropion Hydrochloride [orange Book]

126. Eu-0100166

127. S2452

128. Sw196823-6

129. Bupropion Hydrochloride [usp Impurity]

130. 77b937

131. Bupropion Hydrochloride [usp Monograph]

132. D00817

133. Bupropion Hydrochloride, >=98% (hplc), Solid

134. Contrave Component Bupropion Hydrochloride

135. A820950

136. Bupropion Hydrochloride Component Of Contrave

137. Sr-01000002989-2

138. Q27295463

139. Sr-01000002989-10

140. (+/-)-2-(t-butylamino)-3'-chloropropiophenone Hydrochloride

141. 1-propanone,1-dimethylethyl)amino]-, Hydrochloride, (.+-.)-

142. Bupropion Hydrochloride 1.0 Mg/ml In Methanol (as Free Base)

143. (+/-)-2-(tert-butylamino)-3'-chloropropiophenone Hydrochloride

144. (.+-.)-2-(tert-butylamino)-3'-chloropropiophenone Hydrochloride

145. 2-(tert-butylamino)-1-(3-chlorophenyl)-1-propanone Hydrochloride

146. Bupropion Hydrochloride, United States Pharmacopeia (usp) Reference Standard

147. 1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propane, Monohydrochloride

148. 1-propanone, 1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-, Hydrochloride (1:1)

149. 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one Hydrochloride;bupropion Hcl

150. Bupropion Hydrochloride, Pharmaceutical Secondary Standard; Certified Reference Material

151. ( Inverted Question Mark)-1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone Hydrochloride

152. 1-propanone, 1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-, Hydrochloride, (+/-)-

153. Bupropion Hydrochloride Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.3.3 Other Synonyms

1. Amfebutamon

2. Amfebutamona

3. Amfebutamonum

4. Aplenzin

5. Bupropion

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 276.20 g/mol
Molecular Formula C13H19Cl2NO
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count4
Exact Mass275.0843696 g/mol
Monoisotopic Mass275.0843696 g/mol
Topological Polar Surface Area29.1 Ų
Heavy Atom Count17
Formal Charge0
Complexity247
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 12  
Drug NameBupropion hydrochloride
PubMed HealthBupropion (By mouth)
Drug ClassesAntidepressant, Smoking Cessation Agent
Drug Labelhydrochloride. The molecular weight is 276.2. The molecular formula is C13H18ClNOHCl. Bupropion hydrochloride powder is white, crystalline, and highly soluble in water. It has a bitter taste and produces the sensation of local anesthesia on the oral...
Active IngredientBupropion hydrochloride
Dosage FormTablet, extended release; Tablet
RouteOral
Strength300mg; 75mg; 200mg; 100mg; 150mg
Market StatusPrescription
CompanyWatson Labs; Wockhardt; Anchen Pharms; Jubilant Generics; Actavis Labs Fl; Apotex; Zydus Pharms Usa; Sandoz; Sun Pharma Global; Mylan; Actavis; Impax Labs

2 of 12  
Drug NameForfivo xl
Drug LabelFORFIVO XL (bupropion hydrochloride), an antidepressant of the aminoketone class, is chemically unrelated to tricyclic, tetracyclic, selective serotonin re-uptake inhibitor, or other known antidepressant agents. Its structure closely resembles that o...
Active IngredientBupropion hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength450mg
Market StatusPrescription
CompanyEdgemont Pharms

3 of 12  
Drug NameWellbutrin
PubMed HealthBupropion (By mouth)
Drug ClassesAntidepressant, Smoking Cessation Agent
Drug LabelDESCRIPTIONWELLBUTRINXL (bupropion hydrochloride), an antidepressant of the aminoketone class, is chemically unrelated to tricyclic, tetracyclic, selective serotonin re-uptake inhibitor, or other known antidepressant agents. Its structure closely r...
Active IngredientBupropion hydrochloride
Dosage FormTablet
RouteOral
Strength75mg; 100mg
Market StatusPrescription
CompanyGlaxosmithkline

4 of 12  
Drug NameWellbutrin sr
PubMed HealthBupropion (By mouth)
Drug ClassesAntidepressant, Smoking Cessation Agent
Drug LabelWELLBUTRINSR (bupropion hydrochloride), an antidepressant of the aminoketone class, is chemically unrelated to tricyclic, tetracyclic, selective serotonin reuptake inhibitor, or other known antidepressant agents. Its structure closely resembles...
Active IngredientBupropion hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength200mg; 150mg; 100mg
Market StatusPrescription
CompanyGlaxosmithkline

5 of 12  
Drug NameWellbutrin xl
Drug LabelDESCRIPTIONWELLBUTRINXL (bupropion hydrochloride), an antidepressant of the aminoketone class, is chemically unrelated to tricyclic, tetracyclic, selective serotonin re-uptake inhibitor, or other known antidepressant agents. Its structure closely r...
Active IngredientBupropion hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength150mg; 300mg
Market StatusPrescription
CompanyValeant Intl

6 of 12  
Drug NameZyban
PubMed HealthBupropion (By mouth)
Drug ClassesAntidepressant, Smoking Cessation Agent
Drug LabelZYBAN (bupropion hydrochloride) SustainedRelease Tablets are a nonnicotine aid to smoking cessation. ZYBAN is chemically unrelated to nicotine or other agents currently used in the treatment of nicotine addiction. Initially developed and market...
Active IngredientBupropion hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength150mg
Market StatusPrescription
CompanyGlaxosmithkline

7 of 12  
Drug NameBupropion hydrochloride
PubMed HealthBupropion (By mouth)
Drug ClassesAntidepressant, Smoking Cessation Agent
Drug Labelhydrochloride. The molecular weight is 276.2. The molecular formula is C13H18ClNOHCl. Bupropion hydrochloride powder is white, crystalline, and highly soluble in water. It has a bitter taste and produces the sensation of local anesthesia on the oral...
Active IngredientBupropion hydrochloride
Dosage FormTablet, extended release; Tablet
RouteOral
Strength300mg; 75mg; 200mg; 100mg; 150mg
Market StatusPrescription
CompanyWatson Labs; Wockhardt; Anchen Pharms; Jubilant Generics; Actavis Labs Fl; Apotex; Zydus Pharms Usa; Sandoz; Sun Pharma Global; Mylan; Actavis; Impax Labs

8 of 12  
Drug NameForfivo xl
Drug LabelFORFIVO XL (bupropion hydrochloride), an antidepressant of the aminoketone class, is chemically unrelated to tricyclic, tetracyclic, selective serotonin re-uptake inhibitor, or other known antidepressant agents. Its structure closely resembles that o...
Active IngredientBupropion hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength450mg
Market StatusPrescription
CompanyEdgemont Pharms

9 of 12  
Drug NameWellbutrin
PubMed HealthBupropion (By mouth)
Drug ClassesAntidepressant, Smoking Cessation Agent
Drug LabelDESCRIPTIONWELLBUTRINXL (bupropion hydrochloride), an antidepressant of the aminoketone class, is chemically unrelated to tricyclic, tetracyclic, selective serotonin re-uptake inhibitor, or other known antidepressant agents. Its structure closely r...
Active IngredientBupropion hydrochloride
Dosage FormTablet
RouteOral
Strength75mg; 100mg
Market StatusPrescription
CompanyGlaxosmithkline

10 of 12  
Drug NameWellbutrin sr
PubMed HealthBupropion (By mouth)
Drug ClassesAntidepressant, Smoking Cessation Agent
Drug LabelWELLBUTRINSR (bupropion hydrochloride), an antidepressant of the aminoketone class, is chemically unrelated to tricyclic, tetracyclic, selective serotonin reuptake inhibitor, or other known antidepressant agents. Its structure closely resembles...
Active IngredientBupropion hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength200mg; 150mg; 100mg
Market StatusPrescription
CompanyGlaxosmithkline

11 of 12  
Drug NameWellbutrin xl
Drug LabelDESCRIPTIONWELLBUTRINXL (bupropion hydrochloride), an antidepressant of the aminoketone class, is chemically unrelated to tricyclic, tetracyclic, selective serotonin re-uptake inhibitor, or other known antidepressant agents. Its structure closely r...
Active IngredientBupropion hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength150mg; 300mg
Market StatusPrescription
CompanyValeant Intl

12 of 12  
Drug NameZyban
PubMed HealthBupropion (By mouth)
Drug ClassesAntidepressant, Smoking Cessation Agent
Drug LabelZYBAN (bupropion hydrochloride) SustainedRelease Tablets are a nonnicotine aid to smoking cessation. ZYBAN is chemically unrelated to nicotine or other agents currently used in the treatment of nicotine addiction. Initially developed and market...
Active IngredientBupropion hydrochloride
Dosage FormTablet, extended release
RouteOral
Strength150mg
Market StatusPrescription
CompanyGlaxosmithkline

4.2 Drug Indication

Mysimba is indicated, as an adjunct to a reduced-calorie diet and increased physical activity, for the management of weight in adult patients (18 years) with an initial Body Mass Index (BMI) of

- 30 kg/m2 (obese), or

- 27 kg/m2 to < 30 kg/m2 (overweight) in the presence of one or more weight-related co morbidities (e. g. , type 2 diabetes, dyslipidaemia, or controlled hypertension)

Treatment with Mysimba should be discontinued after 16 weeks if patients have not lost at least 5% of their initial body weight.


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antidepressive Agents, Second-Generation

A structurally and mechanistically diverse group of drugs that are not tricyclics or monoamine oxidase inhibitors. The most clinically important appear to act selectively on serotonergic systems, especially by inhibiting serotonin reuptake. (See all compounds classified as Antidepressive Agents, Second-Generation.)


Smoking Cessation Agents

Substances that facilitate the cessation of tobacco smoking. (See all compounds classified as Smoking Cessation Agents.)


Cytochrome P-450 CYP2D6 Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP2D6. (See all compounds classified as Cytochrome P-450 CYP2D6 Inhibitors.)


Dopamine Uptake Inhibitors

Drugs that block the transport of DOPAMINE into axon terminals or into storage vesicles within terminals. Most of the ADRENERGIC UPTAKE INHIBITORS also inhibit dopamine uptake. (See all compounds classified as Dopamine Uptake Inhibitors.)


5.2 FDA Pharmacological Classification
5.2.1 Pharmacological Classes
Dopamine Uptake Inhibitors [MoA]; Increased Dopamine Activity [PE]; Increased Norepinephrine Activity [PE]; Norepinephrine Uptake Inhibitors [MoA]; Aminoketone [EPC]
5.3 ATC Code

A08AA


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05-Jan-2021
23-Sep-2024
KGS
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Quantity (KGS) & Unit rate (USD/KGS) over time

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - TABLET;ORAL - 100MG **Federal Regist...DOSAGE - TABLET;ORAL - 100MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 18644

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DOSAGE - TABLET;ORAL - 50MG **Federal Registe...DOSAGE - TABLET;ORAL - 50MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 18644

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DOSAGE - TABLET;ORAL - 75MG **Federal Registe...DOSAGE - TABLET;ORAL - 75MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 18644

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 90MG...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 90MG;8MG

USFDA APPLICATION NUMBER - 200063

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 100M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 100MG

USFDA APPLICATION NUMBER - 20358

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 150M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 150MG

USFDA APPLICATION NUMBER - 20358

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 200M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 200MG

USFDA APPLICATION NUMBER - 20358

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 150M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 150MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 20711

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 150M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 150MG

USFDA APPLICATION NUMBER - 21515

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 300M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 300MG

USFDA APPLICATION NUMBER - 21515

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DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 450M...DOSAGE - TABLET, EXTENDED RELEASE;ORAL - 450MG

USFDA APPLICATION NUMBER - 22497

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