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Armodafinil

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ACTIVE PHARMA INGREDIENTS

20 API Suppliers, 11 USDMF, 5 EU WC, 1 KDMF, 9 NDC API, 10 Listed Suppliers, $ API Reference Price

20 API Suppliers
11 USDMF
5 EU WC
1 KDMF
9 NDC API
10 Listed Suppliers
$ API Reference Price

INTERMEDIATES

3 Intermediates Suppliers

3 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

40 FDF Dossiers, 37 FDA Orange Book, 3 Australia

40 FDF Dossiers
37 FDA Orange Book
3 Australia

DRUG PRODUCT COMPOSITIONS

TABLET;ORAL - 100MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**, TABLET;ORAL - 150MG, TABLET;ORAL - 200MG, TABLET;ORAL - 250MG, TABLET;ORAL - 50MG

drugProductComposition
TABLET;ORAL - 100MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**
TABLET;ORAL - 150MG
TABLET;ORAL - 200MG
TABLET;ORAL - 250MG
TABLET;ORAL - 50MG

RELATED EXCIPIENT COMPANIES

1 Minakem, 5 SPI Pharma, 1 DKSH, 2 Jai Radhe Sales, 5 Faran Shimi Pharmaceutical, 4 Boai NKY Pharmaceuticals Ltd, 1 Chynops Pharma, 14 Gangwal Healthcare, 1 Nanjing Well Pharmaceutical, 1 ACG Worldwide, 1 Alcedo Pharmachem, 9 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 9 BASF, 10 Corel Pharma Chem, 7 DFE Pharma, 7 Gangwal Chemicals, 5 Ideal Cures Pvt Ltd, 4 Ingredion Pharma Solutions, 35 Kerry, 3 Kima Chemical, 6 Lonza Capsugel, 12 Microlex e.U, 1 NEWEDGE Overseas, 2 Novo Excipients, 4 Pharmatrans-Sanaq, 5 Pluviaendo, 5 Prachin Chemical, 1 Qianhao Chemical (Hebei) Co., Ltd, 1 Qualicaps, 16 Roquette, 7 Seppic, 6 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 1 Shanghai Welltone Material Technology Co., Ltd, 11 Sigachi Industries, 2 The Dow Chemical Company, 1 Ulanqab Kema New Material, 4 Vasa Pharmachem

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DIGITAL CONTENT

2 DATA COMPILATION #PharmaFlow, 7 NEWS #PharmaBuzz

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2 DATA COMPILATION #PharmaFlow
7 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

2 US Medicaid Prescriptions, 4 Annual Reports

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2 US Medicaid Prescriptions
4 Annual Reports

MARKET PLACE

2 APIs

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2 APIs

PATENTS & EXCLUSIVITIES

10 US Patents

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10 US Patents

REF. STANDARDS & IMPURITIES

1 Others

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1 Others

ANALYTICAL

1 BioAnalytical Methods

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1 BioAnalytical Methods

Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

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CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

Listed Suppliers

API REF. PRICE (USD/KG)

$ 425

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API

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FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

0 DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

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News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

15,398,881

Annual Reports (USD Million)

670

Finished Drug Prices

210 RELATED EXCIPIENT COMPANIES

328EXCIPIENTS BY APPLICATIONS

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

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 Formula	C₁₅H₁₅NO₂S
Molecular Weight	273.4 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	3
Rotatable Bond Count	5
Exact Mass	273.08234989 g/mol
Monoisotopic Mass	273.08234989 g/mol
Topological Polar Surface Area	79.4 Å²
Heavy Atom Count	19
Formal Charge	0
Complexity	302
Isotope Atom Count	0
Defined Atom Stereocenter Count	1
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Armodafinil
PubMed Health	Armodafinil (By mouth)
Drug Classes	CNS Stimulant
Drug Label	NUVIGIL (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 Ingredient	Armodafinil
Dosage Form	Tablet
Route	oral; Oral
Strength	2500mg; 200mg; 250mg; 100mg; 50mg; 150mg
Market Status	Tentative Approval; Prescription
Company	Watson Labs; Mylan Pharms; Teva Pharms Usa; Lupin

2 of 4
Drug Name	Nuvigil
PubMed Health	Armodafinil (By mouth)
Drug Classes	CNS Stimulant
Drug Label	NUVIGIL (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 Ingredient	Armodafinil
Dosage Form	Tablet
Route	Oral
Strength	200mg; 250mg; 150mg; 50mg
Market Status	Prescription
Company	Cephalon

3 of 4
Drug Name	Armodafinil
PubMed Health	Armodafinil (By mouth)
Drug Classes	CNS Stimulant
Drug Label	NUVIGIL (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 Ingredient	Armodafinil
Dosage Form	Tablet
Route	oral; Oral
Strength	2500mg; 200mg; 250mg; 100mg; 50mg; 150mg
Market Status	Tentative Approval; Prescription
Company	Watson Labs; Mylan Pharms; Teva Pharms Usa; Lupin

4 of 4
Drug Name	Nuvigil
PubMed Health	Armodafinil (By mouth)
Drug Classes	CNS Stimulant
Drug Label	NUVIGIL (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 Ingredient	Armodafinil
Dosage Form	Tablet
Route	Oral
Strength	200mg; 250mg; 150mg; 50mg
Market Status	Prescription
Company	Cephalon

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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API Reference Price

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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**