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Chemistry

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Also known as: 112111-43-0, Nuvigil, (r)-modafinil, (-)-modafinil, (r)-(-)-modafinil, Cep-10953
Molecular Formula
C15H15NO2S
Molecular Weight
273.4  g/mol
InChI Key
YFGHCGITMMYXAQ-LJQANCHMSA-N
FDA UNII
V63XWA605I

Armodafinil
A benzhydryl acetamide compound, central nervous system stimulant, and CYP3A4 inducing agent that is used in the treatment of NARCOLEPSY and SLEEP WAKE DISORDERS.
1 2D Structure

Armodafinil

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-[(R)-benzhydrylsulfinyl]acetamide
2.1.2 InChI
InChI=1S/C15H15NO2S/c16-14(17)11-19(18)15(12-7-3-1-4-8-12)13-9-5-2-6-10-13/h1-10,15H,11H2,(H2,16,17)/t19-/m1/s1
2.1.3 InChI Key
YFGHCGITMMYXAQ-LJQANCHMSA-N
2.1.4 Canonical SMILES
C1=CC=C(C=C1)C(C2=CC=CC=C2)S(=O)CC(=O)N
2.1.5 Isomeric SMILES
C1=CC=C(C=C1)C(C2=CC=CC=C2)[S@](=O)CC(=O)N
2.2 Other Identifiers
2.2.1 UNII
V63XWA605I
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2 Benzhydrylsulfinylacetamide

2. 2-((diphenylmethyl)sulfinyl)acetamide

3. 2-((r)-(diphenylmethyl)sulfinyl)acetamide

4. 2-(benzhydrylsulfinyl)acetamide

5. 2-benzhydrylsulfinylacetamide

6. Alertec

7. Benzhydrylsulfinylacetamide

8. Crl 40476

9. Crl-40476

10. Modafinil

11. Modiodal

12. Nuvigil

13. Provigil

14. R Modafinil

15. R-modafinil

16. Sparlon

2.3.2 Depositor-Supplied Synonyms

1. 112111-43-0

2. Nuvigil

3. (r)-modafinil

4. (-)-modafinil

5. (r)-(-)-modafinil

6. Cep-10953

7. Crl 40982

8. Modafinil, (r)-

9. R-(-)-modafinil

10. 2-[(r)-(diphenylmethyl)sulfinyl]acetamide

11. (-)-(r)-modafinil

12. Cep 10953

13. Cep-10952

14. Crl-40982

15. V63xwa605i

16. Chembl1201192

17. Chebi:77590

18. Nsc-751850

19. Nsc-758711

20. (-)-2-((r)-(diphenylmethyl)sulfinyl)acetamide

21. Acetamide, 2-((diphenylmethyl)sulfinyl)-, (-)-

22. Armodafinil [inn]

23. (-)-2-[(r)-(diphenylmethyl)sulfinyl]acetamide

24. Armodafinil [usan:inn]

25. Armodafinilo

26. Armodafinilum

27. Unii-v63xwa605i

28. L-modafinil

29. (-) Modafinil

30. Nuvigil (tn)

31. Armodafinil (usan/inn)

32. Armodafinil [usan]

33. Armodafinil [vandf]

34. Armodafinil [mart.]

35. Schembl34489

36. Armodafinil [usp-rs]

37. Armodafinil [who-dd]

38. Zinc6156

39. Armodafinil, >=98% (hplc)

40. Armodafinil [orange Book]

41. Dtxsid90920667

42. 2-[(r)-benzhydrylsulfinyl]acetamide

43. Bdbm50336892

44. Akos030211019

45. At22562

46. Ccg-230228

47. Cs-0665

48. Db06413

49. Nsc 751850

50. Nsc 758711

51. 2-[(r)-diphenylmethanesulfinyl]acetamide

52. Hy-15201

53. (-)-2r-[(diphenylmethyl)sulfinyl]acetamide

54. S4645

55. D03215

56. Q418913

57. Acetamide, 2-((r)-(diphenylmethyl)sulfinyl)-

2.4 Create Date
2006-10-24
3 Chemical and Physical Properties
Molecular Weight 273.4 g/mol
Molecular Formula C15H15NO2S
XLogP31.7
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count3
Rotatable Bond Count5
Exact Mass273.08234989 g/mol
Monoisotopic Mass273.08234989 g/mol
Topological Polar Surface Area79.4 Ų
Heavy Atom Count19
Formal Charge0
Complexity302
Isotope Atom Count0
Defined Atom Stereocenter Count1
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 4  
Drug NameArmodafinil
PubMed HealthArmodafinil (By mouth)
Drug ClassesCNS Stimulant
Drug LabelNUVIGIL (armodafinil) is a wakefulness-promoting agent for oral administration. Armodafinil is the R-enantiomer of modafinil which is a mixture of the R- and S-enantiomers. The chemical name for armodafinil is 2-[(R)-(diphenylmethyl)sulfinyl]acetam...
Active IngredientArmodafinil
Dosage FormTablet
Routeoral; Oral
Strength2500mg; 200mg; 250mg; 100mg; 50mg; 150mg
Market StatusTentative Approval; Prescription
CompanyWatson Labs; Mylan Pharms; Teva Pharms Usa; Lupin

2 of 4  
Drug NameNuvigil
PubMed HealthArmodafinil (By mouth)
Drug ClassesCNS Stimulant
Drug LabelNUVIGIL (armodafinil) is a wakefulness-promoting agent for oral administration. Armodafinil is the R-enantiomer of modafinil which is a mixture of the R- and S-enantiomers. The chemical name for armodafinil is 2-[(R)-(diphenylmethyl)sulfinyl]acetam...
Active IngredientArmodafinil
Dosage FormTablet
RouteOral
Strength200mg; 250mg; 150mg; 50mg
Market StatusPrescription
CompanyCephalon

3 of 4  
Drug NameArmodafinil
PubMed HealthArmodafinil (By mouth)
Drug ClassesCNS Stimulant
Drug LabelNUVIGIL (armodafinil) is a wakefulness-promoting agent for oral administration. Armodafinil is the R-enantiomer of modafinil which is a mixture of the R- and S-enantiomers. The chemical name for armodafinil is 2-[(R)-(diphenylmethyl)sulfinyl]acetam...
Active IngredientArmodafinil
Dosage FormTablet
Routeoral; Oral
Strength2500mg; 200mg; 250mg; 100mg; 50mg; 150mg
Market StatusTentative Approval; Prescription
CompanyWatson Labs; Mylan Pharms; Teva Pharms Usa; Lupin

4 of 4  
Drug NameNuvigil
PubMed HealthArmodafinil (By mouth)
Drug ClassesCNS Stimulant
Drug LabelNUVIGIL (armodafinil) is a wakefulness-promoting agent for oral administration. Armodafinil is the R-enantiomer of modafinil which is a mixture of the R- and S-enantiomers. The chemical name for armodafinil is 2-[(R)-(diphenylmethyl)sulfinyl]acetam...
Active IngredientArmodafinil
Dosage FormTablet
RouteOral
Strength200mg; 250mg; 150mg; 50mg
Market StatusPrescription
CompanyCephalon

4.2 Drug Indication

Investigated for use/treatment in sleep disorders, obstructive sleep apnea, schizophrenia and schizoaffective disorders, depression, and bipolar disorders.


FDA Label


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.)


Cytochrome P-450 CYP3A Inducers

Drugs and compounds that induce the synthesis of CYTOCHROME P-450 CYP3A. (See all compounds classified as Cytochrome P-450 CYP3A Inducers.)


Wakefulness-Promoting Agents

A specific category of drugs that prevent sleepiness by specifically targeting sleep-mechanisms in the brain. They are used to treat DISORDERS OF EXCESSIVE SOMNOLENCE such as NARCOLEPSY. Note that this drug category does not include broadly-acting central nervous system stimulants such as AMPHETAMINES. (See all compounds classified as Wakefulness-Promoting Agents.)


5.2 ATC Code

N - Nervous system

N06 - Psychoanaleptics

N06B - Psychostimulants, agents used for adhd and nootropics

N06BA - Centrally acting sympathomimetics

N06BA13 - Armodafinil


5.3 Absorption, Distribution and Excretion

Absorption

Tmax is 2 hours when fasted and can be delayed approximately 2-4 hours by food, potentially affecting the onset of action.


Volume of Distribution

Apparent volume of distribution: 42L.


Clearance

The oral clearance of armodafinil is approximately 33 mL/min.


5.4 Metabolism/Metabolites

In vitro and in vivo data show that armodafinil undergoes hydrolytic deamidation, S-oxidation, and aromatic ring hydroxylation, with subsequent glucuronide conjugation of the hydroxylated products. Amide hydrolysis is the single most prominent metabolic pathway, with sulfone formation by cytochrome P450 (CYP) 3A4/5 being next in importance. The other oxidative products are formed too slowly in vitro to enable identification of the enzyme(s) responsible. Only two metabolites reach appreciable concentrations in plasma (i.e., R-modafinil acid and modafinil sulfone). Data specific to armodafinil disposition are not available.


5.5 Biological Half-Life

Terminal half-life is approximately 15 hours.


5.6 Mechanism of Action

Nuvigil (armodafinil) is a single-isomer of modafini. The exact mechanism of action is unknown. Armodafinil belongs to a class of drugs known as eugeroics, which are stimulants that provide long-lasting mental arousal. Pharmacologically, armodafinil does not bind to or inhibit several receptors and enzymes potentially relevant for sleep/wake regulation. Armodafinil is not a direct- or indirect-acting dopamine receptor agonist. However, in vitro, both armodafinil and modafinil bind to the dopamine transporter and inhibit dopamine reuptake. [Medilexicon]


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09-Oct-2023
27-Aug-2024
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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 - 21875

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