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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

    API Reference Price

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    05-Jan-2021
    30-Oct-2024
    KGS
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    Average Price (USD/KGS)

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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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