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Edurant

Synopsis, Chemistry

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2 Drug(s) in Development

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DRUG PRODUCT COMPOSITION

TABLET;ORAL - 200MG;EQ 25MG BASE;300MG, TABLET;ORAL - 200MG;EQ 25MG BASE;EQ 25MG BASE

TABLET;ORAL - 200MG;EQ 25MG BASE;300MG
TABLET;ORAL - 200MG;EQ 25MG BASE;EQ 25MG BASE

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REF STANDARD

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Also known as: Rilpivirine hcl, 700361-47-3, Tmc278 hydrochloride, Edurant, Rilpivirine hydrochloride [usan], 212wax8kdd

Molecular Formula

C₂₂H₁₉ClN₆

Molecular Weight

402.9 g/mol

InChI Key

KZVVGZKAVZUACK-BJILWQEISA-N

FDA UNII

212WAX8KDD

A diarylpyrimidine derivative and REVERSE TRANSCRIPTASE INHIBITOR with antiviral activity against HIV-1 that is used in the treatment of HIV INFECTIONS. It is also used in combination with other ANTI-HIV AGENTS, since ANTIVIRAL DRUG RESISTANCE emerges rapidly when it is used alone.

1 2D Structure

Edurant

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile;hydrochloride

2.1.2 InChI

InChI=1S/C22H18N6.ClH/c1-15-12-18(4-3-10-23)13-16(2)21(15)27-20-9-11-25-22(28-20)26-19-7-5-17(14-24)6-8-19;/h3-9,11-13H,1-2H3,(H2,25,26,27,28);1H/b4-3+;

2.1.3 InChI Key

KZVVGZKAVZUACK-BJILWQEISA-N

2.1.4 Canonical SMILES

CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)C=CC#N.Cl

2.1.5 Isomeric SMILES

CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)/C=C/C#N.Cl

2.2 Other Identifiers

2.2.1 UNII

212WAX8KDD

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 278, Tmc

2. Hcl, Rilpivirine

3. Hydrochloride, Rilpivirine

4. R278474

5. Rilpivirine

6. Rilpivirine Hcl

7. Tmc 278

8. Tmc-278

9. Tmc278

2.3.2 Depositor-Supplied Synonyms

1. Rilpivirine Hcl

2. 700361-47-3

3. Tmc278 Hydrochloride

4. Edurant

5. Rilpivirine Hydrochloride [usan]

6. 212wax8kdd

7. Rilpivirine (as Hydrochloride)

8. 700361-47-3 (hcl)

9. Chebi:68602

10. (e)-4-((4-((4-(2-cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile Hydrochloride

11. Benzonitrile, 4-((4-((4-((1e)-2-cyanoethenyl)-2,6-dimethylphenyl)amino)-2-pyrimidinyl)amino)-, Hydrochloride (1:1)

12. 4-[[4-[4-[(e)-2-cyanoethenyl]-2,6-dimethylanilino]pyrimidin-2-yl]amino]benzonitrile;hydrochloride

13. Unii-212wax8kdd

14. Endurant

15. Edurant (tn)

16. Rilpivirine Monohydrochloride

17. Tmc-278 Hydrochloride

18. Schembl1831067

19. Tmc-278-la

20. Tmc 278. Trade Name Edurant

21. Chembl1628504

22. Dtxsid80220320

23. Bcp13350

24. Rilpivirine Hydrochloride (jan/usan)

25. Rilpivirine Hydrochloride [mi]

26. Akos025149454

27. Rilpivirine Hydrochloride [jan]

28. 4-((4-((4-((1e)-2-cyanoethenyl)-2,6-dimethylphenyl)amino)pyrimidin-2- Yl)amino)benzonitrile

29. Rilpivirine Hydrochloride [vandf]

30. Ac-30620

31. Rilpivirine Hydrochloride [who-dd]

32. D09958

33. Rilpivirine Hydrochloride [orange Book]

34. Juluca Component Rilpivirine Hydrochloride

35. Eviplera Component Rilpivirine Hydrochloride

36. Odefsey Component Rilpivirine Hydrochloride

37. Rilpivirine Hydrochloride Component Of Juluca

38. Q27137040

39. Rilpivirine Hydrochloride Component Of Eviplera

40. Rilpivirine Hydrochloride Component Of Odefsey

41. 4-[[4-[[4-[(e)-2-cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile Monohydrochloride

42. 4-{[4-({4-[(e)-2-cyanoethenyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile Hydrochloride

43. 4-{[4-({4-[(e)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile Hydrochloride

44. Benzonitrile, 4-((4-((4-((1e)-2-cyanoethenyl)-2,6-dimethylphenyl)amino)-2- Pyrimidinyl)amino)-, Hydrochloride (1:1)

2.4 Create Date

2006-10-26

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₁₉ClN₆
Molecular Weight	402.9 g/mol
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	5
Exact Mass	402.1359723 g/mol
Monoisotopic Mass	402.1359723 g/mol
Topological Polar Surface Area	97.4 Å²
Heavy Atom Count	29
Formal Charge	0
Complexity	607
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	Edurant
PubMed Health	Rilpivirine (By mouth)
Drug Classes	Antiretroviral Agent
Active Ingredient	Rilpivirine hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	eq 25mg base
Market Status	Prescription
Company	Janssen Prods

2 of 2
Drug Name	Edurant
PubMed Health	Rilpivirine (By mouth)
Drug Classes	Antiretroviral Agent
Active Ingredient	Rilpivirine hydrochloride
Dosage Form	Tablet
Route	Oral
Strength	eq 25mg base
Market Status	Prescription
Company	Janssen Prods

4.2 Drug Indication

Edurant, in combination with other antiretroviral medicinal products, is indicated for the treatment of human immunodeficiency virus type 1 (HIV1) infection in antiretroviral treatmentnave patients 12 years of age and older with a viral load 100,000 HIV1 RNA copies/ml.

As with other antiretroviral medicinal products, genotypic resistance testing should guide the use of Edurant.

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Anti-HIV Agents

Agents used to treat AIDS and/or stop the spread of the HIV infection. These do not include drugs used to treat symptoms or opportunistic infections associated with AIDS. (See all compounds classified as Anti-HIV Agents.)

Reverse Transcriptase Inhibitors

Inhibitors of reverse transcriptase (RNA-DIRECTED DNA POLYMERASE), an enzyme that synthesizes DNA on an RNA template. (See all compounds classified as Reverse Transcriptase Inhibitors.)

5.2 FDA Pharmacological Classification

5.2.1 Pharmacological Classes

Non-Nucleoside Analog [EXT]; Non-Nucleoside Reverse Transcriptase Inhibitors [MoA]; Human Immunodeficiency Virus 1 Non-Nucleoside Analog Reverse Transcriptase Inhibitor [EPC]

5.3 ATC Code

J05AG05

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