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Technical details about Lisdexamfetamine Dimesylate, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
Also known as: Vyvanse, 608137-33-3, Nrp-104, Lisdexamfetamine mesilate, Spd489, Tyvense
Molecular Formula
C17H33N3O7S2
Molecular Weight
455.6  g/mol
InChI Key
CETWSOHVEGTIBR-FORAGAHYSA-N
FDA UNII
SJT761GEGS

A dextroamphetamine drug precursor that also functions as a CENTRAL NERVOUS SYSTEM STIMULANT and DOPAMINE UPTAKE INHIBITOR and is used in the treatment of ATTENTION DEFICIT HYPERACTIVITY DISORDER.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2S)-2,6-diamino-N-[(2S)-1-phenylpropan-2-yl]hexanamide;methanesulfonic acid
2.1.2 InChI
InChI=1S/C15H25N3O.2CH4O3S/c1-12(11-13-7-3-2-4-8-13)18-15(19)14(17)9-5-6-10-16;2*1-5(2,3)4/h2-4,7-8,12,14H,5-6,9-11,16-17H2,1H3,(H,18,19);2*1H3,(H,2,3,4)/t12-,14-;;/m0../s1
2.1.3 InChI Key
CETWSOHVEGTIBR-FORAGAHYSA-N
2.1.4 Canonical SMILES
CC(CC1=CC=CC=C1)NC(=O)C(CCCCN)N.CS(=O)(=O)O.CS(=O)(=O)O
2.1.5 Isomeric SMILES
C[C@@H](CC1=CC=CC=C1)NC(=O)[C@H](CCCCN)N.CS(=O)(=O)O.CS(=O)(=O)O
2.2 Other Identifiers
2.2.1 UNII
SJT761GEGS
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Dimesylate, Lis-dexamfetamine

2. Dimesylate, Lisdexamfetamine

3. Elvanse

4. Lis Dexamfetamine Dimesylate

5. Lis-dexamfetamine Dimesylate

6. Lisdexamfetamine

7. Nrp 104

8. Nrp-104

9. Nrp104

10. Vyvanse

2.3.2 Depositor-Supplied Synonyms

1. Vyvanse

2. 608137-33-3

3. Nrp-104

4. Lisdexamfetamine Mesilate

5. Spd489

6. Tyvense

7. Nrp104

8. Spd-489

9. Lisdexamfetamine Dimesylate [usan]

10. Lisdexamfetamine Dimesilate

11. Sjt761gegs

12. Lisdexamphetamine Dimesilate

13. L-lysine-d-amphetamine Dimesylate

14. Lisdexamfetamine Dimethanesulfonate

15. (2s)-2,6-diamino-n-[(1s)-1-methyl-2-phenylethyl]hexanamide Dimethanesulfonate

16. Lis-dexamfetamine Dimesylate

17. Lisdexamfetamine Mesilate (jan)

18. Lisdexamfetamine Dimesylate (usan)

19. Lisdexamfetamine Mesylate

20. Nrp 104

21. Lisdexamfetamine Mesilate [jan]

22. (2s)-2,6-diamino-n-[(2s)-1-phenylpropan-2-yl]hexanamide;methanesulfonic Acid

23. Unii-sjt761gegs

24. Venvanse

25. (2s)-2,6-diamino-n-((1s)-1-methyl-2-phenylethyl)hexanamide Dimethanesulfonate

26. Lys-amp

27. Spd 489

28. Lys-d-amp

29. Elvanse (tn)

30. Vyvanse (tn)

31. Schembl678421

32. Chembl1201178

33. Dtxsid60209653

34. Lisdexamfetamine Dimesylate Solution

35. Bcp24044

36. Akos030254940

37. Lisdexamfetamine Mesilate [mart.]

38. Ldx

39. Lisdexamfetamine Mesilate [who-dd]

40. Lisdexamfetamine Dimesylate [vandf]

41. D04747

42. Lisdexamfetamine Dimethanesulfonate [mi]

43. Lisdexamfetamine Dimesylate [orange Book]

44. 137l333

45. Q27289243

46. (2s)-2,6-diamino-n-((1s)-1-methyl-2-phenylethyl)hexanamide Dimethanesulphonate

47. Hexanamide, 2,6-diamino-n-((1s)-1-methyl-2-phenylethyl), (2s), Dimethanesulfonate

48. Hexanamide, 2,6-diamino-n-((1s)-1-methyl-2-phenylethyl), (2s), Dimethanesulphonate

49. Ldx;lisdexamfetamine Mesilate;lisdexamfetamine Mesylate;nrp 104;nrp-104;spd 489

50. Lisdexamfetamine Dimesylate Solution, 1.0 Mg/ml In Methanol (as Free Base), Ampule Of 1 Ml, Certified Reference Material

2.4 Create Date
2006-10-26
3 Chemical and Physical Properties
Molecular Weight 455.6 g/mol
Molecular Formula C17H33N3O7S2
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count9
Rotatable Bond Count8
Exact Mass455.17599275 g/mol
Monoisotopic Mass455.17599275 g/mol
Topological Polar Surface Area207 Ų
Heavy Atom Count29
Formal Charge0
Complexity344
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Drug and Medication Information
4.1 Drug Information
1 of 4  
Drug NameLisdexamfetamine dimesylate
Drug LabelVyvanse (lisdexamfetamine dimesylate), a CNS stimulant,isa capsule for once-a-day oral administration. The chemical designation for lisdexamfetamine dimesylate is (2S)-2,6-diamino-N-[(1S)-1-methyl-2-phenylethyl] hexanamide dimethanesulfonate....
Active IngredientLisdexamfetamine dimesylate
Dosage FormCapsule
RouteOral
Strength30mg; 50mg; 60mg; 40mg; 70mg; 20mg
Market StatusTentative Approval
CompanyMylan Pharms; Amneal Pharms; Roxane

2 of 4  
Drug NameVyvanse
PubMed HealthAmphetamine (By mouth)
Drug ClassesAmphetamine
Drug LabelVyvanse (lisdexamfetamine dimesylate), a CNS stimulant,isa capsule for once-a-day oral administration. The chemical designation for lisdexamfetamine dimesylate is (2S)-2,6-diamino-N-[(1S)-1-methyl-2-phenylethyl] hexanamide dimethanesulfonate....
Active IngredientLisdexamfetamine dimesylate
Dosage FormCapsule
RouteOral
Strength30mg; 50mg; 60mg; 40mg; 20mg; 70mg
Market StatusPrescription
CompanyShire Development

3 of 4  
Drug NameLisdexamfetamine dimesylate
Drug LabelVyvanse (lisdexamfetamine dimesylate), a CNS stimulant,isa capsule for once-a-day oral administration. The chemical designation for lisdexamfetamine dimesylate is (2S)-2,6-diamino-N-[(1S)-1-methyl-2-phenylethyl] hexanamide dimethanesulfonate....
Active IngredientLisdexamfetamine dimesylate
Dosage FormCapsule
RouteOral
Strength30mg; 50mg; 60mg; 40mg; 70mg; 20mg
Market StatusTentative Approval
CompanyMylan Pharms; Amneal Pharms; Roxane

4 of 4  
Drug NameVyvanse
PubMed HealthAmphetamine (By mouth)
Drug ClassesAmphetamine
Drug LabelVyvanse (lisdexamfetamine dimesylate), a CNS stimulant,isa capsule for once-a-day oral administration. The chemical designation for lisdexamfetamine dimesylate is (2S)-2,6-diamino-N-[(1S)-1-methyl-2-phenylethyl] hexanamide dimethanesulfonate....
Active IngredientLisdexamfetamine dimesylate
Dosage FormCapsule
RouteOral
Strength30mg; 50mg; 60mg; 40mg; 20mg; 70mg
Market StatusPrescription
CompanyShire Development

4.2 Drug Indication

Treatment of Attention Deficit Hyperactivity Disorder (ADHD)


5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Central Nervous System Stimulants

A loosely defined group of drugs that tend to increase behavioral alertness, agitation, or excitation. They work by a variety of mechanisms, but usually not by direct excitation of neurons. The many drugs that have such actions as side effects to their main therapeutic use are not included here. (See all compounds classified as Central Nervous System Stimulants.)


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
Central Nervous System Stimulation [PE]; Central Nervous System Stimulant [EPC]
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