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2D Structure
Also known as: 905818-69-1, Aplenzin, Bupropion hbr, Bupropion hydrobromide [usan], Bupropion (hydrobromide), 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrobromide
Molecular Formula
C13H19BrClNO
Molecular Weight
320.65  g/mol
InChI Key
WSTCENNATOVXKQ-UHFFFAOYSA-N
FDA UNII
E70G3G5863

Bupropion Hydrobromide is the hydrobromide salt of an aminoketone with antidepressant activity. The molecular mechanism of the antidepressant effect of bupropion is unknown. This agent does not inhibit monoamine oxidase and, compared to classical tricyclic antidepressants, is a weak blocker of the neuronal uptake of serotonin and norepinephrine. Buproprion also weakly inhibits the neuronal re-uptake of dopamine.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one;hydrobromide
2.1.2 InChI
InChI=1S/C13H18ClNO.BrH/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
WSTCENNATOVXKQ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(C(=O)C1=CC(=CC=C1)Cl)NC(C)(C)C.Br
2.2 Other Identifiers
2.2.1 UNII
E70G3G5863
2.3 Synonyms
2.3.1 Depositor-Supplied Synonyms

1. 905818-69-1

2. Aplenzin

3. Bupropion Hbr

4. Bupropion Hydrobromide [usan]

5. Bupropion (hydrobromide)

6. 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one Hydrobromide

7. Bvf-033

8. E70g3g5863

9. Bupropion Hydrobromide (usan)

10. Aplenzin Er

11. Unii-e70g3g5863

12. Aplenzin (tn)

13. Schembl636116

14. Chembl1201735

15. Dtxsid20920317

16. Bupropion Hydrobromide [mi]

17. 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one,hydrobromide

18. 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one;hydrobromide

19. Bupropion Hydrobromide [vandf]

20. Akos015917698

21. Bupropion Hydrobromide [mart.]

22. Bupropion Hydrobromide [usp-rs]

23. Bupropion Hydrobromide [who-dd]

24. Bupropion Hydrobromide [orange Book]

25. D07938

26. Q27276951

27. (2rs)-1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)propan-1-one Hbr

28. (2rs)-1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)propan-1-one Hydrobromide

29. 1-propanone, 1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-, Hbr (1:1)

30. 1-propanone, 1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-, Hydrobromide (1:1)

31. 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one--hydrogen Bromide (1/1)

2.4 Create Date
2007-01-10
3 Chemical and Physical Properties
Molecular Weight 320.65 g/mol
Molecular Formula C13H19BrClNO
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count4
Exact Mass319.03385 g/mol
Monoisotopic Mass319.03385 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 4  
Drug NameAplenzin
Active IngredientBupropion hydrobromide
Dosage FormTablet, extended release
RouteOral
Strength348mg; 522mg; 174mg
Market StatusPrescription
CompanyValeant Bermuda

2 of 4  
Drug NameBupropion hydrobromide
PubMed HealthBupropion (By mouth)
Drug ClassesAntidepressant, Smoking Cessation Agent
Active IngredientBupropion hydrobromide
Dosage FormTablet, extended release
Routeoral
Strength522mg; 174mg
Market StatusTentative Approval
CompanyWatson Labs

3 of 4  
Drug NameAplenzin
Active IngredientBupropion hydrobromide
Dosage FormTablet, extended release
RouteOral
Strength348mg; 522mg; 174mg
Market StatusPrescription
CompanyValeant Bermuda

4 of 4  
Drug NameBupropion hydrobromide
PubMed HealthBupropion (By mouth)
Drug ClassesAntidepressant, Smoking Cessation Agent
Active IngredientBupropion hydrobromide
Dosage FormTablet, extended release
Routeoral
Strength522mg; 174mg
Market StatusTentative Approval
CompanyWatson Labs

5 Pharmacology and Biochemistry
5.1 FDA Pharmacological Classification
5.1.1 Pharmacological Classes
Dopamine Uptake Inhibitors [MoA]; Increased Dopamine Activity [PE]; Increased Norepinephrine Activity [PE]; Norepinephrine Uptake Inhibitors [MoA]; Aminoketone [EPC]