Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00594)
Name
Rilpivirine
Synonyms    Click to Show/Hide the Synonyms of This API
Rilpivirine; 500287-72-9; TMC278; Edurant; TMC 278; TMC-278; R278474; UNII-FI96A8X663; Rilpivirine free base; R 278474; 4-[[4-[[4-[(E)-2-Cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzonitrile; 4-{[4-({4-[(E)-2-Cyanoethenyl]-2,6-Dimethylphenyl}amino)pyrimidin-2-Yl]amino}benzonitrile; 4-{[4-({4-[(E)-2-cyanovinyl]-2,6-dimethylphenyl}amino)pyrimidin-2-yl]amino}benzonitrile; CHEBI:68606; FI96A8X663; Rilpivirine-d6; 500287-72-9 (free base); (E)-4-((4-((4-(2-cyanovinyl)-2,6-dimethylphenyl)amino)pyrimidin-2-yl)amino)benzonitrile; Rilpivirine [USAN:INN]; R-278474; HSDB 8153; (E)-4-(4-(4-(2-cyanovinyl)-2,6-dimethylphenylamino)pyrimidin-2-ylamino)benzonitrile; Edurant(TM); SCHEMBL384696; SCHEMBL385113; Rilpivirine (JAN/USAN/INN); CHEMBL175691; GTPL11387; DTXSID10198189; EX-A245; BDBM222178; AOB87760; BCP03563; ZINC1554274; MFCD11046372; STL484047; AKOS015901680; BCP9000016; CCG-268241; CS-0440; DB08864; KE-0036; R278474;TMC278; SB19133; 4-[[4-[4-[(E)-2-cyanovinyl]-2,6-dimethyl-anilino]pyrimidin-2-yl]amino]benzonitrile; NCGC00319175-03; Rilpivirine(R 278474, TMC 278); AC-30619; HY-10574; BCP0726000192; AB0027978; SW220232-1; A11542; D09720; W-5469; A827939; Q421547; W-202888; 4-[[4-[[4-(2-Cyanoethenyl)-2,6-dimethylphenyl]amino]pyrimidine-2-yl]amino]benzonitrile; 4-[[4-[4-[(E)-2-cyanoethenyl]-2,6-dimethylanilino]-2-pyrimidinyl]amino]benzonitrile; 4-{4-[4-((E)-2-Cyano-vinyl)-2,6-dimethyl-phenylamino]-pyrimidin-2-ylamino}-benzonitrile; (E)-3-{4-[2-(p-Cyanophenylamino)-4-pyrimidinylamino]-3,5-xylyl}acrylonitrile; 4-[[4-[[4-[(1E)-2-Cyanoethenyl]-2,6-dimethylphenyl]amino]-2-pyrimidinyl]amino]benzonitrile; 4-((4-((4-((1E)-2-Cyanoethenyl)-2,6-dimethylphenyl)amino)-2-pyrimidinyl)amino)benzonitrile; 4-[[4-[[4-[(E)-2-cyanoethenyl]-2,6-dimethyl-phenyl]amino]pyrimidin-2-yl]amino]benzenecarbonitrile; Benzonitrile, 4-((4-((4-((1E)-2-cyanoethenyl)-2,6-dimethylphenyl)amino)-2-pyrimidinyl)amino)-
Clinical Status
Approved
Disease Indication Human immunodeficiency virus infection ICD-11: 1C60 [1]
PubChem CID
6451164
Formula
C22H18N6
Canonical SMILES
CC1=CC(=CC(=C1NC2=NC(=NC=C2)NC3=CC=C(C=C3)C#N)C)/C=C/C#N
InChI
1S/C22H18N6/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)/b4-3+
InChIKey
YIBOMRUWOWDFLG-ONEGZZNKSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=6451164"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 366.4 Topological Polar Surface Area 97.4
XlogP 4.5 Complexity 607
Heavy Atom Count 28 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 6
Full List of Drug Formulations (DFMs) Containing This API
          Rilpivirine 25 mg tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Lactose monohydrate; Magnesium stearate; Titanium dioxide; Triacetin; Croscarmellose sodium; Polysorbate 20; Povidone k30; Silicon dioxide; Hypromellose 2910 (6 mpa.s); Microcrystalline cellulose; Polyethylene glycol 3000
                   Dosage Form Oral Tablet
                   Company Janssen Products
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Polysorbate 20 DIG Info Cytochrome P450 2E1 (IC50 = 64.1 uM) [2]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
Carmellose sodium DIG Info Albendazole monooxygenase (Protein expression upregulation) [3]
Silicon dioxide DIG Info Albendazole monooxygenase (Protein expression downregulation) [3]
          Rilpivirine Hydrochloride eq 25mg base tablet Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Croscarmellose Sodium, Lactose Monohydrate, Magnesium Stearate, Polysorbate 20, Povidone K30; Silicified Microcrystalline Cellulose; Hypromellose 2910 6 Mpa.S; Lactose Monohydrate; Peg 3000; Titanium Dioxide; Triacetin
                   Dosage Form Tablet
                   Company Janssen Prods
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Hypromellose DIG Info Cytochrome P450 3A5 (IC50 = 19.4 uM) [2]
References
1 FDA label for approved rilpivirine from the official website of the U.S. Food and Drug Administration.
2 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
3 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.

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